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Article: A Bifunctional Platinum(II) Complex Capable of Intercalation and Hydrogen-Bonding Interactions with DNA: Binding Studies and Cytotoxicity

TitleA Bifunctional Platinum(II) Complex Capable of Intercalation and Hydrogen-Bonding Interactions with DNA: Binding Studies and Cytotoxicity
Authors
KeywordsAntitumor agents
Bioinorganic chemistry
Luminescence
N ligands
Platinum
Issue Date2003
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2003, v. 9 n. 24, p. 6133-6144 How to Cite?
AbstractThe interactions of [Pt(CNN)(4-dpt)] PF6, (1; 4-dpt = 2,4-di-amino-6-(4-pyridyl)-1,3,5-triazine, HCNN = 6-phenyl-2,2′ -bipyridine) with double-stranded DNA, poly(dA-dT)2, and poly(dG-dC)2 were examined by spectroscopic, electrophoretic, and hydrodynamic methods. The spectroscopic data were analyzed with McGhee, van't Hoff, and Gibbs-Helmholtz equations. In a comparative study, [Pt(CNN)(py)]PF6 (2; py = pyridine) was prepared and the nature of its binding towards DNA was investigated [preliminary results: ChemBioChem 2003, 4, 62-68]. For reactions with calf thymus DNA at 20°C, the intrinsic binding constants for 1 and 2 are (4.6 ± 0.2) × 105 and (2.3 ± 0.3) × 104 mol-1 dm3, respectively. Results of DNA-binding reactions revealed that 1 and 2 preferentially bind to the AT sequence of duplex DNA. Intercalation is the preferred binding mode for 2, whereas both intercalation and minor-groove binding are observed for 1. Complex 1 is cytotoxic against a number of carcinoma cell lines, including KB-3-1, CNE-3, and HepG2, and remains potent against multidrug- or cisplatin-resistant KB-V-1 and CNE1 cell lines, for which the resistance ratios are 1.6 and 1.5, respectively. Importantly, 1 is almost an order of magnitude less toxic to the normal cell line CCD-19Lu (IC 50 = 176 ± 1.7 μm) and it selectively induced apoptosis leading to cancer cell death with less than 5% detectable necrosis.
Persistent Identifierhttp://hdl.handle.net/10722/69439
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorMa, DLen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:13:40Z-
dc.date.available2010-09-06T06:13:40Z-
dc.date.issued2003en_HK
dc.identifier.citationChemistry - A European Journal, 2003, v. 9 n. 24, p. 6133-6144en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69439-
dc.description.abstractThe interactions of [Pt(CNN)(4-dpt)] PF6, (1; 4-dpt = 2,4-di-amino-6-(4-pyridyl)-1,3,5-triazine, HCNN = 6-phenyl-2,2′ -bipyridine) with double-stranded DNA, poly(dA-dT)2, and poly(dG-dC)2 were examined by spectroscopic, electrophoretic, and hydrodynamic methods. The spectroscopic data were analyzed with McGhee, van't Hoff, and Gibbs-Helmholtz equations. In a comparative study, [Pt(CNN)(py)]PF6 (2; py = pyridine) was prepared and the nature of its binding towards DNA was investigated [preliminary results: ChemBioChem 2003, 4, 62-68]. For reactions with calf thymus DNA at 20°C, the intrinsic binding constants for 1 and 2 are (4.6 ± 0.2) × 105 and (2.3 ± 0.3) × 104 mol-1 dm3, respectively. Results of DNA-binding reactions revealed that 1 and 2 preferentially bind to the AT sequence of duplex DNA. Intercalation is the preferred binding mode for 2, whereas both intercalation and minor-groove binding are observed for 1. Complex 1 is cytotoxic against a number of carcinoma cell lines, including KB-3-1, CNE-3, and HepG2, and remains potent against multidrug- or cisplatin-resistant KB-V-1 and CNE1 cell lines, for which the resistance ratios are 1.6 and 1.5, respectively. Importantly, 1 is almost an order of magnitude less toxic to the normal cell line CCD-19Lu (IC 50 = 176 ± 1.7 μm) and it selectively induced apoptosis leading to cancer cell death with less than 5% detectable necrosis.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectAntitumor agentsen_HK
dc.subjectBioinorganic chemistryen_HK
dc.subjectLuminescenceen_HK
dc.subjectN ligandsen_HK
dc.subjectPlatinumen_HK
dc.titleA Bifunctional Platinum(II) Complex Capable of Intercalation and Hydrogen-Bonding Interactions with DNA: Binding Studies and Cytotoxicityen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=9&spage=6133&epage=6144&date=2003&atitle=A+bifunctional+platinum(II)+complex+capable+of+intercalation+and+hydrogen-bonding+interactions+with+DNA:+binding+studies+and+cytotoxicityen_HK
dc.identifier.emailMa, DL:edmondma@hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityMa, DL=rp00760en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.200304964en_HK
dc.identifier.pmid14679525-
dc.identifier.scopuseid_2-s2.0-0347362661en_HK
dc.identifier.hkuros94146en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0347362661&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume9en_HK
dc.identifier.issue24en_HK
dc.identifier.spage6133en_HK
dc.identifier.epage6144en_HK
dc.identifier.isiWOS:000187425200018-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridMa, DL=7402075538en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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