Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility

Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poo...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Fan, Jie-Ping [verfasserIn] Lai, Xiao-Hui [verfasserIn] Zhang, Xue-Hong [verfasserIn] Yang, Lu [verfasserIn] Yuan, Tian-Tao [verfasserIn] Chen, Hui-Ping [verfasserIn] Liang, Xianrui [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2021

Schlagwörter:	Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity

Übergeordnetes Werk:	Enthalten in: Journal of molecular liquids - New York, NY [u.a.] : Elsevier, 1983, 332
Übergeordnetes Werk:	volume:332

DOI / URN:	10.1016/j.molliq.2021.115837

Katalog-ID:	ELV005916011

Internformat


LEADER	01000caa a22002652 4500
001	ELV005916011
003	DE-627
005	20230524151250.0
007	cr uuu---uuuuu
008	230504s2021 xx \|\|\|\|\|o 00\| \|\|eng c
024	7		\|a 10.1016/j.molliq.2021.115837 \|2 doi
035			\|a (DE-627)ELV005916011
035			\|a (ELSEVIER)S0167-7322(21)00562-6
040			\|a DE-627 \|b ger \|c DE-627 \|e rda
041			\|a eng
082	0	4	\|a 540 \|q DE-600
084			\|a 35.21 \|2 bkl
100	1		\|a Fan, Jie-Ping \|e verfasserin \|4 aut
245	1	0	\|a Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
264		1	\|c 2021
336			\|a nicht spezifiziert \|b zzz \|2 rdacontent
337			\|a Computermedien \|b c \|2 rdamedia
338			\|a Online-Ressource \|b cr \|2 rdacarrier
520			\|a Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.
650		4	\|a Oleanolic acid
650		4	\|a Ursolic acid
650		4	\|a Ionic derivatives
650		4	\|a Solubility
650		4	\|a Apparent 1-octanol/water partition coefficients
650		4	\|a Cytotoxicity
700	1		\|a Lai, Xiao-Hui \|e verfasserin \|4 aut
700	1		\|a Zhang, Xue-Hong \|e verfasserin \|4 aut
700	1		\|a Yang, Lu \|e verfasserin \|4 aut
700	1		\|a Yuan, Tian-Tao \|e verfasserin \|4 aut
700	1		\|a Chen, Hui-Ping \|e verfasserin \|4 aut
700	1		\|a Liang, Xianrui \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Journal of molecular liquids \|d New York, NY [u.a.] : Elsevier, 1983 \|g 332 \|h Online-Ressource \|w (DE-627)302469664 \|w (DE-600)1491496-7 \|w (DE-576)259483915 \|x 1873-3166 \|7 nnns
773	1	8	\|g volume:332
912			\|a GBV_USEFLAG_U
912			\|a SYSFLAG_U
912			\|a GBV_ELV
912			\|a SSG-OLC-PHA
912			\|a GBV_ILN_20
912			\|a GBV_ILN_22
912			\|a GBV_ILN_23
912			\|a GBV_ILN_24
912			\|a GBV_ILN_31
912			\|a GBV_ILN_32
912			\|a GBV_ILN_40
912			\|a GBV_ILN_60
912			\|a GBV_ILN_62
912			\|a GBV_ILN_63
912			\|a GBV_ILN_65
912			\|a GBV_ILN_69
912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_74
912			\|a GBV_ILN_90
912			\|a GBV_ILN_95
912			\|a GBV_ILN_100
912			\|a GBV_ILN_101
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_150
912			\|a GBV_ILN_151
912			\|a GBV_ILN_224
912			\|a GBV_ILN_370
912			\|a GBV_ILN_374
912			\|a GBV_ILN_602
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2003
912			\|a GBV_ILN_2004
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2056
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2122
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2143
912			\|a GBV_ILN_2147
912			\|a GBV_ILN_2148
912			\|a GBV_ILN_2152
912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_2807
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
936	b	k	\|a 35.21 \|j Lösungen \|j Flüssigkeiten \|x Physikalische Chemie
951			\|a AR
952			\|d 332

Indexfelder

author_variant	j p f jpf x h l xhl x h z xhz l y ly t t y tty h p c hpc x l xl
matchkey_str	article:18733166:2021----::yteiadvlainfhcneclgotihbtratvtoteoidrvtvsflaoiaia
hierarchy_sort_str	2021
bklnumber	35.21
publishDate	2021
allfields	10.1016/j.molliq.2021.115837 doi (DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6 DE-627 ger DE-627 rda eng 540 DE-600 35.21 bkl Fan, Jie-Ping verfasserin aut Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells. Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity Lai, Xiao-Hui verfasserin aut Zhang, Xue-Hong verfasserin aut Yang, Lu verfasserin aut Yuan, Tian-Tao verfasserin aut Chen, Hui-Ping verfasserin aut Liang, Xianrui verfasserin aut Enthalten in Journal of molecular liquids New York, NY [u.a.] : Elsevier, 1983 332 Online-Ressource (DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915 1873-3166 nnns volume:332 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.21 Lösungen Flüssigkeiten Physikalische Chemie AR 332
spelling	10.1016/j.molliq.2021.115837 doi (DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6 DE-627 ger DE-627 rda eng 540 DE-600 35.21 bkl Fan, Jie-Ping verfasserin aut Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells. Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity Lai, Xiao-Hui verfasserin aut Zhang, Xue-Hong verfasserin aut Yang, Lu verfasserin aut Yuan, Tian-Tao verfasserin aut Chen, Hui-Ping verfasserin aut Liang, Xianrui verfasserin aut Enthalten in Journal of molecular liquids New York, NY [u.a.] : Elsevier, 1983 332 Online-Ressource (DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915 1873-3166 nnns volume:332 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.21 Lösungen Flüssigkeiten Physikalische Chemie AR 332
allfields_unstemmed	10.1016/j.molliq.2021.115837 doi (DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6 DE-627 ger DE-627 rda eng 540 DE-600 35.21 bkl Fan, Jie-Ping verfasserin aut Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells. Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity Lai, Xiao-Hui verfasserin aut Zhang, Xue-Hong verfasserin aut Yang, Lu verfasserin aut Yuan, Tian-Tao verfasserin aut Chen, Hui-Ping verfasserin aut Liang, Xianrui verfasserin aut Enthalten in Journal of molecular liquids New York, NY [u.a.] : Elsevier, 1983 332 Online-Ressource (DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915 1873-3166 nnns volume:332 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.21 Lösungen Flüssigkeiten Physikalische Chemie AR 332
allfieldsGer	10.1016/j.molliq.2021.115837 doi (DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6 DE-627 ger DE-627 rda eng 540 DE-600 35.21 bkl Fan, Jie-Ping verfasserin aut Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells. Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity Lai, Xiao-Hui verfasserin aut Zhang, Xue-Hong verfasserin aut Yang, Lu verfasserin aut Yuan, Tian-Tao verfasserin aut Chen, Hui-Ping verfasserin aut Liang, Xianrui verfasserin aut Enthalten in Journal of molecular liquids New York, NY [u.a.] : Elsevier, 1983 332 Online-Ressource (DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915 1873-3166 nnns volume:332 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.21 Lösungen Flüssigkeiten Physikalische Chemie AR 332
allfieldsSound	10.1016/j.molliq.2021.115837 doi (DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6 DE-627 ger DE-627 rda eng 540 DE-600 35.21 bkl Fan, Jie-Ping verfasserin aut Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells. Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity Lai, Xiao-Hui verfasserin aut Zhang, Xue-Hong verfasserin aut Yang, Lu verfasserin aut Yuan, Tian-Tao verfasserin aut Chen, Hui-Ping verfasserin aut Liang, Xianrui verfasserin aut Enthalten in Journal of molecular liquids New York, NY [u.a.] : Elsevier, 1983 332 Online-Ressource (DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915 1873-3166 nnns volume:332 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.21 Lösungen Flüssigkeiten Physikalische Chemie AR 332
language	English
source	Enthalten in Journal of molecular liquids 332 volume:332
sourceStr	Enthalten in Journal of molecular liquids 332 volume:332
format_phy_str_mv	Article
bklname	Lösungen Flüssigkeiten
institution	findex.gbv.de
topic_facet	Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity
dewey-raw	540
isfreeaccess_bool	false
container_title	Journal of molecular liquids
authorswithroles_txt_mv	Fan, Jie-Ping @@aut@@ Lai, Xiao-Hui @@aut@@ Zhang, Xue-Hong @@aut@@ Yang, Lu @@aut@@ Yuan, Tian-Tao @@aut@@ Chen, Hui-Ping @@aut@@ Liang, Xianrui @@aut@@
publishDateDaySort_date	2021-01-01T00:00:00Z
hierarchy_top_id	302469664
dewey-sort	3540
id	ELV005916011
language_de	englisch
fullrecord	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">ELV005916011</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230524151250.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">230504s2021 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.molliq.2021.115837</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)ELV005916011</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(ELSEVIER)S0167-7322(21)00562-6</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rda</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">540</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.21</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Fan, Jie-Ping</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2021</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oleanolic acid</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Ursolic acid</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Ionic derivatives</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Solubility</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Apparent 1-octanol/water partition coefficients</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytotoxicity</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lai, Xiao-Hui</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Zhang, Xue-Hong</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Yang, Lu</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Yuan, Tian-Tao</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Chen, Hui-Ping</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Liang, Xianrui</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Journal of molecular liquids</subfield><subfield code="d">New York, NY [u.a.] : Elsevier, 1983</subfield><subfield code="g">332</subfield><subfield code="h">Online-Ressource</subfield><subfield code="w">(DE-627)302469664</subfield><subfield code="w">(DE-600)1491496-7</subfield><subfield code="w">(DE-576)259483915</subfield><subfield code="x">1873-3166</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:332</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_31</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_90</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_100</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_101</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_150</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_370</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_374</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2003</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2004</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2015</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2025</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2034</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2038</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2044</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2048</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2049</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2050</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2056</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2059</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2061</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2064</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2065</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2068</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2113</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2118</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2122</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2129</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2143</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2147</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2148</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2152</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2153</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2336</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2507</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2522</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2807</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4242</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4251</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4326</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4333</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4334</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4335</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4393</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.21</subfield><subfield code="j">Lösungen</subfield><subfield code="j">Flüssigkeiten</subfield><subfield code="x">Physikalische Chemie</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">332</subfield></datafield></record></collection>
author	Fan, Jie-Ping
spellingShingle	Fan, Jie-Ping ddc 540 bkl 35.21 misc Oleanolic acid misc Ursolic acid misc Ionic derivatives misc Solubility misc Apparent 1-octanol/water partition coefficients misc Cytotoxicity Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
authorStr	Fan, Jie-Ping
ppnlink_with_tag_str_mv	@@773@@(DE-627)302469664
format	electronic Article
dewey-ones	540 - Chemistry & allied sciences
delete_txt_mv	keep
author_role	aut aut aut aut aut aut aut
collection	elsevier
remote_str	true
illustrated	Not Illustrated
issn	1873-3166
topic_title	540 DE-600 35.21 bkl Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility Oleanolic acid Ursolic acid Ionic derivatives Solubility Apparent 1-octanol/water partition coefficients Cytotoxicity
topic	ddc 540 bkl 35.21 misc Oleanolic acid misc Ursolic acid misc Ionic derivatives misc Solubility misc Apparent 1-octanol/water partition coefficients misc Cytotoxicity
topic_unstemmed	ddc 540 bkl 35.21 misc Oleanolic acid misc Ursolic acid misc Ionic derivatives misc Solubility misc Apparent 1-octanol/water partition coefficients misc Cytotoxicity
topic_browse	ddc 540 bkl 35.21 misc Oleanolic acid misc Ursolic acid misc Ionic derivatives misc Solubility misc Apparent 1-octanol/water partition coefficients misc Cytotoxicity
format_facet	Elektronische Aufsätze Aufsätze Elektronische Ressource
format_main_str_mv	Text Zeitschrift/Artikel
carriertype_str_mv	cr
hierarchy_parent_title	Journal of molecular liquids
hierarchy_parent_id	302469664
dewey-tens	540 - Chemistry
hierarchy_top_title	Journal of molecular liquids
isfreeaccess_txt	false
familylinks_str_mv	(DE-627)302469664 (DE-600)1491496-7 (DE-576)259483915
title	Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
ctrlnum	(DE-627)ELV005916011 (ELSEVIER)S0167-7322(21)00562-6
title_full	Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
author_sort	Fan, Jie-Ping
journal	Journal of molecular liquids
journalStr	Journal of molecular liquids
lang_code	eng
isOA_bool	false
dewey-hundreds	500 - Science
recordtype	marc
publishDateSort	2021
contenttype_str_mv	zzz
author_browse	Fan, Jie-Ping Lai, Xiao-Hui Zhang, Xue-Hong Yang, Lu Yuan, Tian-Tao Chen, Hui-Ping Liang, Xianrui
container_volume	332
class	540 DE-600 35.21 bkl
format_se	Elektronische Aufsätze
author-letter	Fan, Jie-Ping
doi_str_mv	10.1016/j.molliq.2021.115837
dewey-full	540
author2-role	verfasserin
title_sort	synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
title_auth	Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
abstract	Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.
abstractGer	Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.
abstract_unstemmed	Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.
collection_details	GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_374 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2807 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393
title_short	Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility
remote_bool	true
author2	Lai, Xiao-Hui Zhang, Xue-Hong Yang, Lu Yuan, Tian-Tao Chen, Hui-Ping Liang, Xianrui
author2Str	Lai, Xiao-Hui Zhang, Xue-Hong Yang, Lu Yuan, Tian-Tao Chen, Hui-Ping Liang, Xianrui
ppnlink	302469664
mediatype_str_mv	c
isOA_txt	false
hochschulschrift_bool	false
doi_str	10.1016/j.molliq.2021.115837
up_date	2024-07-06T19:36:07.849Z
_version_	1803859596777881600
fullrecord_marcxml	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">ELV005916011</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230524151250.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">230504s2021 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1016/j.molliq.2021.115837</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)ELV005916011</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(ELSEVIER)S0167-7322(21)00562-6</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rda</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">540</subfield><subfield code="q">DE-600</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.21</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Fan, Jie-Ping</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2021</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Formation of ionic derivatives from drugs provided a simple tool to tune physical properties including water solubility and biological activity of the drugs. Oleanolic acid (OA) and ursolic acid (UA) are two ubiquitous isomeric triterpene phytochemicals with many pharmacological effects. But the poor water solubility greatly limits their clinical application. In order to improve the solubility of OA and UA, this research exploited a non-covalent synthetic approach to prepare a series of novel ionic derivatives of OA and UA by a simple acid-base neutralization method for converting them into simple organic salts. The OA/UA based ionic derivatives were characterized by HRMS, FTIR, NMR, XRPD, and TGA-DSC, their solubilities and apparent 1-octanol/water partition coefficients were measured under different conditions. The solubility of the ionic derivatives turned out to be higher than that of OA/UA under most of experiment conditions, which indicated our aim to improve the solubility was attained. The apparent 1-octanol/water partition coefficients indicated that the ionic derivatives of OA/UA had higher hydrophilicity than OA/UA under most of the experiment conditions. Moreover, the human hepatoma cell lines (HepG2) growth inhibitory activity of the derivatives was also evaluated by MTT assay. The results suggested that UA based ionic derivatives exhibited significantly lower IC50 values than OA based ionic derivatives under the same conditions, indicating stronger inhibitory effect on the growth of HepG2 cells.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Oleanolic acid</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Ursolic acid</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Ionic derivatives</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Solubility</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Apparent 1-octanol/water partition coefficients</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Cytotoxicity</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lai, Xiao-Hui</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Zhang, Xue-Hong</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Yang, Lu</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Yuan, Tian-Tao</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Chen, Hui-Ping</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Liang, Xianrui</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Journal of molecular liquids</subfield><subfield code="d">New York, NY [u.a.] : Elsevier, 1983</subfield><subfield code="g">332</subfield><subfield code="h">Online-Ressource</subfield><subfield code="w">(DE-627)302469664</subfield><subfield code="w">(DE-600)1491496-7</subfield><subfield code="w">(DE-576)259483915</subfield><subfield code="x">1873-3166</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:332</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_U</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ELV</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SSG-OLC-PHA</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_31</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_90</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_100</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_101</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_150</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_370</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_374</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2003</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2004</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2015</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2025</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2034</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2038</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2044</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2048</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2049</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2050</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2056</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2059</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2061</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2064</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2065</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2068</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2113</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2118</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2122</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2129</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2143</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2147</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2148</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2152</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2153</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2336</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2507</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2522</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2807</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4242</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4251</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4326</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4333</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4334</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4335</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4393</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.21</subfield><subfield code="j">Lösungen</subfield><subfield code="j">Flüssigkeiten</subfield><subfield code="x">Physikalische Chemie</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">332</subfield></datafield></record></collection>
score	7.3992815

Nicht das Richtige dabei?

Schreiben Sie uns!

Synthesis and evaluation of the cancer cell growth inhibitory activity of the ionic derivatives of oleanolic acid and ursolic acid with improved solubility

Nicht das Richtige dabei?

Zugang & Verfügbarkeit

Vorhandene Bände

Nicht das Richtige dabei?