Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA

The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discriminati...
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Autor*in:	Zhu, Yiwen [verfasserIn] Hou, Jinqiang [verfasserIn] Huang, Xuan-He [verfasserIn] Zhong, Dong-Xiao [verfasserIn] Long, Wei [verfasserIn] Liu, Wenjie [verfasserIn] Lu, Yu-Jing [verfasserIn] Zhang, Kun [verfasserIn] Wong, Wing-Leung [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2020

Schlagwörter:	Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking

Übergeordnetes Werk:	Enthalten in: Journal of luminescence - New York, NY [u.a.] : Elsevier, 1970, 226
Übergeordnetes Werk:	volume:226

DOI / URN:	10.1016/j.jlumin.2020.117488

Katalog-ID:	ELV004479726

Internformat


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520			\|a The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined.
650		4	\|a Fluorescent binding ligand
650		4	\|a Ligand-DNA interaction
650		4	\|a G-quadruplex DNA recognition
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700	1		\|a Hou, Jinqiang \|e verfasserin \|4 aut
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700	1		\|a Long, Wei \|e verfasserin \|4 aut
700	1		\|a Liu, Wenjie \|e verfasserin \|4 aut
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700	1		\|a Zhang, Kun \|e verfasserin \|4 aut
700	1		\|a Wong, Wing-Leung \|e verfasserin \|4 aut
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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
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912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
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912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
936	b	k	\|a 33.00 \|j Physik: Allgemeines
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publishDate	2020
allfields	10.1016/j.jlumin.2020.117488 doi (DE-627)ELV004479726 (ELSEVIER)S0022-2313(20)30992-3 DE-627 ger DE-627 rda eng 530 DE-600 33.00 bkl Zhu, Yiwen verfasserin aut Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined. Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking Hou, Jinqiang verfasserin aut Huang, Xuan-He verfasserin aut Zhong, Dong-Xiao verfasserin aut Long, Wei verfasserin aut Liu, Wenjie verfasserin aut Lu, Yu-Jing verfasserin aut Zhang, Kun verfasserin aut Wong, Wing-Leung verfasserin aut Enthalten in Journal of luminescence New York, NY [u.a.] : Elsevier, 1970 226 Online-Ressource (DE-627)302468749 (DE-600)1491401-3 (DE-576)120883473 0022-2313 nnns volume:226 GBV_USEFLAG_U SYSFLAG_U GBV_ELV 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 33.00 Physik: Allgemeines AR 226
spelling	10.1016/j.jlumin.2020.117488 doi (DE-627)ELV004479726 (ELSEVIER)S0022-2313(20)30992-3 DE-627 ger DE-627 rda eng 530 DE-600 33.00 bkl Zhu, Yiwen verfasserin aut Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined. Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking Hou, Jinqiang verfasserin aut Huang, Xuan-He verfasserin aut Zhong, Dong-Xiao verfasserin aut Long, Wei verfasserin aut Liu, Wenjie verfasserin aut Lu, Yu-Jing verfasserin aut Zhang, Kun verfasserin aut Wong, Wing-Leung verfasserin aut Enthalten in Journal of luminescence New York, NY [u.a.] : Elsevier, 1970 226 Online-Ressource (DE-627)302468749 (DE-600)1491401-3 (DE-576)120883473 0022-2313 nnns volume:226 GBV_USEFLAG_U SYSFLAG_U GBV_ELV 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 33.00 Physik: Allgemeines AR 226
allfields_unstemmed	10.1016/j.jlumin.2020.117488 doi (DE-627)ELV004479726 (ELSEVIER)S0022-2313(20)30992-3 DE-627 ger DE-627 rda eng 530 DE-600 33.00 bkl Zhu, Yiwen verfasserin aut Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined. Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking Hou, Jinqiang verfasserin aut Huang, Xuan-He verfasserin aut Zhong, Dong-Xiao verfasserin aut Long, Wei verfasserin aut Liu, Wenjie verfasserin aut Lu, Yu-Jing verfasserin aut Zhang, Kun verfasserin aut Wong, Wing-Leung verfasserin aut Enthalten in Journal of luminescence New York, NY [u.a.] : Elsevier, 1970 226 Online-Ressource (DE-627)302468749 (DE-600)1491401-3 (DE-576)120883473 0022-2313 nnns volume:226 GBV_USEFLAG_U SYSFLAG_U GBV_ELV 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 33.00 Physik: Allgemeines AR 226
allfieldsGer	10.1016/j.jlumin.2020.117488 doi (DE-627)ELV004479726 (ELSEVIER)S0022-2313(20)30992-3 DE-627 ger DE-627 rda eng 530 DE-600 33.00 bkl Zhu, Yiwen verfasserin aut Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined. Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking Hou, Jinqiang verfasserin aut Huang, Xuan-He verfasserin aut Zhong, Dong-Xiao verfasserin aut Long, Wei verfasserin aut Liu, Wenjie verfasserin aut Lu, Yu-Jing verfasserin aut Zhang, Kun verfasserin aut Wong, Wing-Leung verfasserin aut Enthalten in Journal of luminescence New York, NY [u.a.] : Elsevier, 1970 226 Online-Ressource (DE-627)302468749 (DE-600)1491401-3 (DE-576)120883473 0022-2313 nnns volume:226 GBV_USEFLAG_U SYSFLAG_U GBV_ELV 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 33.00 Physik: Allgemeines AR 226
allfieldsSound	10.1016/j.jlumin.2020.117488 doi (DE-627)ELV004479726 (ELSEVIER)S0022-2313(20)30992-3 DE-627 ger DE-627 rda eng 530 DE-600 33.00 bkl Zhu, Yiwen verfasserin aut Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined. Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking Hou, Jinqiang verfasserin aut Huang, Xuan-He verfasserin aut Zhong, Dong-Xiao verfasserin aut Long, Wei verfasserin aut Liu, Wenjie verfasserin aut Lu, Yu-Jing verfasserin aut Zhang, Kun verfasserin aut Wong, Wing-Leung verfasserin aut Enthalten in Journal of luminescence New York, NY [u.a.] : Elsevier, 1970 226 Online-Ressource (DE-627)302468749 (DE-600)1491401-3 (DE-576)120883473 0022-2313 nnns volume:226 GBV_USEFLAG_U SYSFLAG_U GBV_ELV 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 33.00 Physik: Allgemeines AR 226
language	English
source	Enthalten in Journal of luminescence 226 volume:226
sourceStr	Enthalten in Journal of luminescence 226 volume:226
format_phy_str_mv	Article
bklname	Physik: Allgemeines
institution	findex.gbv.de
topic_facet	Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking
dewey-raw	530
isfreeaccess_bool	false
container_title	Journal of luminescence
authorswithroles_txt_mv	Zhu, Yiwen @@aut@@ Hou, Jinqiang @@aut@@ Huang, Xuan-He @@aut@@ Zhong, Dong-Xiao @@aut@@ Long, Wei @@aut@@ Liu, Wenjie @@aut@@ Lu, Yu-Jing @@aut@@ Zhang, Kun @@aut@@ Wong, Wing-Leung @@aut@@
publishDateDaySort_date	2020-01-01T00:00:00Z
hierarchy_top_id	302468749
dewey-sort	3530
id	ELV004479726
language_de	englisch
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author	Zhu, Yiwen
spellingShingle	Zhu, Yiwen ddc 530 bkl 33.00 misc Fluorescent binding ligand misc Ligand-DNA interaction misc G-quadruplex DNA recognition misc Molecular docking Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
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topic_title	530 DE-600 33.00 bkl Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA Fluorescent binding ligand Ligand-DNA interaction G-quadruplex DNA recognition Molecular docking
topic	ddc 530 bkl 33.00 misc Fluorescent binding ligand misc Ligand-DNA interaction misc G-quadruplex DNA recognition misc Molecular docking
topic_unstemmed	ddc 530 bkl 33.00 misc Fluorescent binding ligand misc Ligand-DNA interaction misc G-quadruplex DNA recognition misc Molecular docking
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title	Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
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title_full	Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
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author_browse	Zhu, Yiwen Hou, Jinqiang Huang, Xuan-He Zhong, Dong-Xiao Long, Wei Liu, Wenjie Lu, Yu-Jing Zhang, Kun Wong, Wing-Leung
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title_sort	structural modification of nonspecific thiazole orange for ligand-dna interaction study: understanding the ligand recognition selectivity towards g4-dna over duplex-dna
title_auth	Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
abstract	The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined.
abstractGer	The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined.
abstract_unstemmed	The study of ligand interactions with nucleic acid structures such as G-quadruplexes versus double-stranded DNA is important because these interactions are fundamental for many intracellular processes. In the investigation of ligand-DNA binding process, achieving high fluorescent signal discrimination with strong binding affinity is challenging. To develop binding ligands with excellent recognition ability towards G4-DNA over duplex-DNA, the design of appropriate molecular scaffolds that are able to match with the G4-DNA binding pocket (G-quartet) is crucial. In the present study, the new fluorescent DNA binding ligands were designed and synthesized through the integration of a small and conjugated substituent group at the 2-position of the 1-methylquinolinium moiety of the nonspecific thiazole orange scaffold. The ligands were investigated in fluorescence binding assays and showed different interaction properties and significant fluorescent recognition selectivity towards G4-DNA over duplex-DNA in vitro. Molecular docking study of the ligands in complex with telo21 G4-DNA and ds26 duplex DNA also revealed different binding modes. In addition, the cytotoxicity of the fluorescent DNA binding ligands was evaluated in MTT assays against two selected cancer cell lines (human prostate cancer cell (PC3) and human hepatoma cell (hepG2)). The IC50 was found in the range of 6.3–12.5 μM, indicating a relatively high cytotoxicity of the ligands towards the cancer cells examined.
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title_short	Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA
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author2	Hou, Jinqiang Huang, Xuan-He Zhong, Dong-Xiao Long, Wei Liu, Wenjie Lu, Yu-Jing Zhang, Kun Wong, Wing-Leung
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up_date	2024-07-06T23:07:51.900Z
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Structural modification of nonspecific thiazole orange for ligand-DNA interaction study: Understanding the ligand recognition selectivity towards G4-DNA over duplex-DNA

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