Synthesis and comparison of antileishmanial and cytotoxic activities of

In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-bas...
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Autor*in:	Almeida Batista, Sabrina A. [verfasserIn] Vandresen, Fábio [verfasserIn] Falzirolli, Hugo [verfasserIn] Britta, Elizandra [verfasserIn] de Oliveira, Diogo N. [verfasserIn] Catharino, Rodrigo R. [verfasserIn] Gonçalves, Mateus A. [verfasserIn] Ramalho, Teodorico C. [verfasserIn] La Porta, Felipe A. [verfasserIn] Nakamura, Celso V. [verfasserIn] da Silva, Cleuza C. [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	Thiosemicarbazide Thiosemicarbazones QTAIM

Übergeordnetes Werk:	Enthalten in: Journal of molecular structure - New York, NY [u.a.] : Elsevier, 1967, 1179, Seite 252-262
Übergeordnetes Werk:	volume:1179 ; pages:252-262

DOI / URN:	10.1016/j.molstruc.2018.11.017

Katalog-ID:	ELV001267183

Internformat


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100	1		\|a Almeida Batista, Sabrina A. \|e verfasserin \|4 aut
245	1	0	\|a Synthesis and comparison of antileishmanial and cytotoxic activities of
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337			\|a Computermedien \|b c \|2 rdamedia
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520			\|a In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.
650		4	\|a Thiosemicarbazide
650		4	\|a Thiosemicarbazones
650		4	\|a QTAIM
700	1		\|a Vandresen, Fábio \|e verfasserin \|4 aut
700	1		\|a Falzirolli, Hugo \|e verfasserin \|4 aut
700	1		\|a Britta, Elizandra \|e verfasserin \|4 aut
700	1		\|a de Oliveira, Diogo N. \|e verfasserin \|4 aut
700	1		\|a Catharino, Rodrigo R. \|e verfasserin \|4 aut
700	1		\|a Gonçalves, Mateus A. \|e verfasserin \|4 aut
700	1		\|a Ramalho, Teodorico C. \|e verfasserin \|4 aut
700	1		\|a La Porta, Felipe A. \|e verfasserin \|4 aut
700	1		\|a Nakamura, Celso V. \|e verfasserin \|4 aut
700	1		\|a da Silva, Cleuza C. \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Journal of molecular structure \|d New York, NY [u.a.] : Elsevier, 1967 \|g 1179, Seite 252-262 \|h Online-Ressource \|w (DE-627)302469745 \|w (DE-600)1491504-2 \|w (DE-576)255266626 \|x 0022-2860 \|7 nnns
773	1	8	\|g volume:1179 \|g pages:252-262
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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_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_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 35.00 \|j Chemie: Allgemeines
951			\|a AR
952			\|d 1179 \|h 252-262

Indexfelder

author_variant	b s a a bsa bsaa f v fv h f hf e b eb o d n d odn odnd r r c rr rrc m a g ma mag t c r tc tcr p f a l pfa pfal c v n cv cvn s c c d scc sccd
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publishDate	2018
allfields	10.1016/j.molstruc.2018.11.017 doi (DE-627)ELV001267183 (ELSEVIER)S0022-2860(18)31321-8 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Almeida Batista, Sabrina A. verfasserin aut Synthesis and comparison of antileishmanial and cytotoxic activities of 2018 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis. Thiosemicarbazide Thiosemicarbazones QTAIM Vandresen, Fábio verfasserin aut Falzirolli, Hugo verfasserin aut Britta, Elizandra verfasserin aut de Oliveira, Diogo N. verfasserin aut Catharino, Rodrigo R. verfasserin aut Gonçalves, Mateus A. verfasserin aut Ramalho, Teodorico C. verfasserin aut La Porta, Felipe A. verfasserin aut Nakamura, Celso V. verfasserin aut da Silva, Cleuza C. verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1179, Seite 252-262 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1179 pages:252-262 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_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_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 35.00 Chemie: Allgemeines AR 1179 252-262
spelling	10.1016/j.molstruc.2018.11.017 doi (DE-627)ELV001267183 (ELSEVIER)S0022-2860(18)31321-8 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Almeida Batista, Sabrina A. verfasserin aut Synthesis and comparison of antileishmanial and cytotoxic activities of 2018 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis. Thiosemicarbazide Thiosemicarbazones QTAIM Vandresen, Fábio verfasserin aut Falzirolli, Hugo verfasserin aut Britta, Elizandra verfasserin aut de Oliveira, Diogo N. verfasserin aut Catharino, Rodrigo R. verfasserin aut Gonçalves, Mateus A. verfasserin aut Ramalho, Teodorico C. verfasserin aut La Porta, Felipe A. verfasserin aut Nakamura, Celso V. verfasserin aut da Silva, Cleuza C. verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1179, Seite 252-262 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1179 pages:252-262 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_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_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 35.00 Chemie: Allgemeines AR 1179 252-262
allfields_unstemmed	10.1016/j.molstruc.2018.11.017 doi (DE-627)ELV001267183 (ELSEVIER)S0022-2860(18)31321-8 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Almeida Batista, Sabrina A. verfasserin aut Synthesis and comparison of antileishmanial and cytotoxic activities of 2018 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis. Thiosemicarbazide Thiosemicarbazones QTAIM Vandresen, Fábio verfasserin aut Falzirolli, Hugo verfasserin aut Britta, Elizandra verfasserin aut de Oliveira, Diogo N. verfasserin aut Catharino, Rodrigo R. verfasserin aut Gonçalves, Mateus A. verfasserin aut Ramalho, Teodorico C. verfasserin aut La Porta, Felipe A. verfasserin aut Nakamura, Celso V. verfasserin aut da Silva, Cleuza C. verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1179, Seite 252-262 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1179 pages:252-262 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_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_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 35.00 Chemie: Allgemeines AR 1179 252-262
allfieldsGer	10.1016/j.molstruc.2018.11.017 doi (DE-627)ELV001267183 (ELSEVIER)S0022-2860(18)31321-8 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Almeida Batista, Sabrina A. verfasserin aut Synthesis and comparison of antileishmanial and cytotoxic activities of 2018 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis. Thiosemicarbazide Thiosemicarbazones QTAIM Vandresen, Fábio verfasserin aut Falzirolli, Hugo verfasserin aut Britta, Elizandra verfasserin aut de Oliveira, Diogo N. verfasserin aut Catharino, Rodrigo R. verfasserin aut Gonçalves, Mateus A. verfasserin aut Ramalho, Teodorico C. verfasserin aut La Porta, Felipe A. verfasserin aut Nakamura, Celso V. verfasserin aut da Silva, Cleuza C. verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1179, Seite 252-262 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1179 pages:252-262 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_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_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 35.00 Chemie: Allgemeines AR 1179 252-262
allfieldsSound	10.1016/j.molstruc.2018.11.017 doi (DE-627)ELV001267183 (ELSEVIER)S0022-2860(18)31321-8 DE-627 ger DE-627 rda eng 540 DE-600 35.00 bkl Almeida Batista, Sabrina A. verfasserin aut Synthesis and comparison of antileishmanial and cytotoxic activities of 2018 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis. Thiosemicarbazide Thiosemicarbazones QTAIM Vandresen, Fábio verfasserin aut Falzirolli, Hugo verfasserin aut Britta, Elizandra verfasserin aut de Oliveira, Diogo N. verfasserin aut Catharino, Rodrigo R. verfasserin aut Gonçalves, Mateus A. verfasserin aut Ramalho, Teodorico C. verfasserin aut La Porta, Felipe A. verfasserin aut Nakamura, Celso V. verfasserin aut da Silva, Cleuza C. verfasserin aut Enthalten in Journal of molecular structure New York, NY [u.a.] : Elsevier, 1967 1179, Seite 252-262 Online-Ressource (DE-627)302469745 (DE-600)1491504-2 (DE-576)255266626 0022-2860 nnns volume:1179 pages:252-262 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_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_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 35.00 Chemie: Allgemeines AR 1179 252-262
language	English
source	Enthalten in Journal of molecular structure 1179, Seite 252-262 volume:1179 pages:252-262
sourceStr	Enthalten in Journal of molecular structure 1179, Seite 252-262 volume:1179 pages:252-262
format_phy_str_mv	Article
bklname	Chemie: Allgemeines
institution	findex.gbv.de
topic_facet	Thiosemicarbazide Thiosemicarbazones QTAIM
dewey-raw	540
isfreeaccess_bool	false
container_title	Journal of molecular structure
authorswithroles_txt_mv	Almeida Batista, Sabrina A. @@aut@@ Vandresen, Fábio @@aut@@ Falzirolli, Hugo @@aut@@ Britta, Elizandra @@aut@@ de Oliveira, Diogo N. @@aut@@ Catharino, Rodrigo R. @@aut@@ Gonçalves, Mateus A. @@aut@@ Ramalho, Teodorico C. @@aut@@ La Porta, Felipe A. @@aut@@ Nakamura, Celso V. @@aut@@ da Silva, Cleuza C. @@aut@@
publishDateDaySort_date	2018-01-01T00:00:00Z
hierarchy_top_id	302469745
dewey-sort	3540
id	ELV001267183
language_de	englisch
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author	Almeida Batista, Sabrina A.
spellingShingle	Almeida Batista, Sabrina A. ddc 540 bkl 35.00 misc Thiosemicarbazide misc Thiosemicarbazones misc QTAIM Synthesis and comparison of antileishmanial and cytotoxic activities of
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topic_title	540 DE-600 35.00 bkl Synthesis and comparison of antileishmanial and cytotoxic activities of Thiosemicarbazide Thiosemicarbazones QTAIM
topic	ddc 540 bkl 35.00 misc Thiosemicarbazide misc Thiosemicarbazones misc QTAIM
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title	Synthesis and comparison of antileishmanial and cytotoxic activities of
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title_full	Synthesis and comparison of antileishmanial and cytotoxic activities of
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author_browse	Almeida Batista, Sabrina A. Vandresen, Fábio Falzirolli, Hugo Britta, Elizandra de Oliveira, Diogo N. Catharino, Rodrigo R. Gonçalves, Mateus A. Ramalho, Teodorico C. La Porta, Felipe A. Nakamura, Celso V. da Silva, Cleuza C.
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title_sort	synthesis and comparison of antileishmanial and cytotoxic activities of
title_auth	Synthesis and comparison of antileishmanial and cytotoxic activities of
abstract	In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.
abstractGer	In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.
abstract_unstemmed	In this study, we explore a series of novel potential antiprotozoal S-(−)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.
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title_short	Synthesis and comparison of antileishmanial and cytotoxic activities of
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author2	Vandresen, Fábio Falzirolli, Hugo Britta, Elizandra de Oliveira, Diogo N. Catharino, Rodrigo R. Gonçalves, Mateus A. Ramalho, Teodorico C. La Porta, Felipe A. Nakamura, Celso V. da Silva, Cleuza C.
author2Str	Vandresen, Fábio Falzirolli, Hugo Britta, Elizandra de Oliveira, Diogo N. Catharino, Rodrigo R. Gonçalves, Mateus A. Ramalho, Teodorico C. La Porta, Felipe A. Nakamura, Celso V. da Silva, Cleuza C.
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doi_str	10.1016/j.molstruc.2018.11.017
up_date	2024-07-06T20:47:42.072Z
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Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(−)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Thiosemicarbazide</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Thiosemicarbazones</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">QTAIM</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Vandresen, Fábio</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Falzirolli, Hugo</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Britta, Elizandra</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">de Oliveira, Diogo N.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Catharino, Rodrigo R.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Gonçalves, Mateus A.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Ramalho, Teodorico C.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">La Porta, Felipe A.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" 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