File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines

TitlePlatinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines
Authors
KeywordsAntitumor agents
Bioinorganic chemistry
DNA recognition
Luminescence
Platinum
Issue Date1999
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, 1999, v. 5 n. 11, p. 3350-3356 How to Cite?
AbstractThe synthesis and spectroscopic characterization of a new class of DNA-intercalating platinum(II) complexes, [Pt(dppz) (tN∧C)] CF3SO3 (dppz = dipyrido[3,2-a:2′,3′-c]phenazine, tN∧CH = 4-tert-butyl-2-phenylpyridine) and [Pt(dppz)(L)2](CF3SO3)2 (L = 1-methylimidazole (Meim-1) or 4-aminopyridine (NH2py-4)) are described. All the complexes are photoluminescent in degassed acetonitrile at room temperature. [Pt(dppz)(tN∧C)]CF3SO3 shows a vibronic structured emission (λmax = 477 nm) which is assigned to the intraligand transition (IL) of the C-deprotonated 4-tert-butyl-2-phenylpyridine ligand. Both [Pt(dppz)(Meim-1)2]-(CF3SO3)2 and [Pt(dppz)(NH2py-4)2]-(CF3SO3) 2 display a lower energy emission band with λmax at 558 nm, which is originated from a 3MLCT state [5d(Pt) →π* (dppz)]. The binding reactions of platinum(II) complexes with double-stranded DNA (dsDNA) were studied by spectroscopic methods and the intrinsic binding constants (K) are 1.1 × 104 - 1.3 × 104 dm3mol-1. The results of gel electrophoresis and UV melting experiments revealed that they interact strongly with DNA. In aerated aqueous Tris buffer solution, [Pt(dppz)(tN∧C)]CF3SO3 is nonemissive. Upon intercalation of [Pt(dppz)-(tN∧C)]CF3SO3 into calf thymus DNA (ctDNA), a low energy emission with λmax = 650 nm is developed and this is ascribed to exciplex formation between the excited state of [Pt(dppz)(tN∧C)]+ with the DNA base pairs. The cytotoxicity of [Pt(dppz)(tN∧C)]CF3SO3 was compared to that of cisplatin using human carcinoma KB-3-1 and its multidrug-resistant subclone KB-V1 cell lines, which is 10 and 40 times more potent than cisplatin in the killing of KB-3-1 and KB-V1 cells, respectively.
Persistent Identifierhttp://hdl.handle.net/10722/68891
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
References

 

DC FieldValueLanguage
dc.contributor.authorChe, CMen_HK
dc.contributor.authorYang, Men_HK
dc.contributor.authorWong, KHen_HK
dc.contributor.authorChan, HLen_HK
dc.contributor.authorLam, Wen_HK
dc.date.accessioned2010-09-06T06:08:40Z-
dc.date.available2010-09-06T06:08:40Z-
dc.date.issued1999en_HK
dc.identifier.citationChemistry - A European Journal, 1999, v. 5 n. 11, p. 3350-3356en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68891-
dc.description.abstractThe synthesis and spectroscopic characterization of a new class of DNA-intercalating platinum(II) complexes, [Pt(dppz) (tN∧C)] CF3SO3 (dppz = dipyrido[3,2-a:2′,3′-c]phenazine, tN∧CH = 4-tert-butyl-2-phenylpyridine) and [Pt(dppz)(L)2](CF3SO3)2 (L = 1-methylimidazole (Meim-1) or 4-aminopyridine (NH2py-4)) are described. All the complexes are photoluminescent in degassed acetonitrile at room temperature. [Pt(dppz)(tN∧C)]CF3SO3 shows a vibronic structured emission (λmax = 477 nm) which is assigned to the intraligand transition (IL) of the C-deprotonated 4-tert-butyl-2-phenylpyridine ligand. Both [Pt(dppz)(Meim-1)2]-(CF3SO3)2 and [Pt(dppz)(NH2py-4)2]-(CF3SO3) 2 display a lower energy emission band with λmax at 558 nm, which is originated from a 3MLCT state [5d(Pt) →π* (dppz)]. The binding reactions of platinum(II) complexes with double-stranded DNA (dsDNA) were studied by spectroscopic methods and the intrinsic binding constants (K) are 1.1 × 104 - 1.3 × 104 dm3mol-1. The results of gel electrophoresis and UV melting experiments revealed that they interact strongly with DNA. In aerated aqueous Tris buffer solution, [Pt(dppz)(tN∧C)]CF3SO3 is nonemissive. Upon intercalation of [Pt(dppz)-(tN∧C)]CF3SO3 into calf thymus DNA (ctDNA), a low energy emission with λmax = 650 nm is developed and this is ascribed to exciplex formation between the excited state of [Pt(dppz)(tN∧C)]+ with the DNA base pairs. The cytotoxicity of [Pt(dppz)(tN∧C)]CF3SO3 was compared to that of cisplatin using human carcinoma KB-3-1 and its multidrug-resistant subclone KB-V1 cell lines, which is 10 and 40 times more potent than cisplatin in the killing of KB-3-1 and KB-V1 cells, respectively.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.subjectDNA recognitionen_HK
dc.subjectLuminescenceen_HK
dc.subjectPlatinumen_HK
dc.titlePlatinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell linesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=5&issue=11&spage=3350&epage=3356&date=1999&atitle=Platinum(II)+complexes+of+dipyridophenazine+as+metallointercalators+for+DNA+and+potent+cytotoxic+agents+against+carcinoma+cell+linesen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/(SICI)1521-3765(19991105)5:11<3350::AID-CHEM3350>3.0.CO;2-J-
dc.identifier.scopuseid_2-s2.0-0032756912en_HK
dc.identifier.hkuros53161en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0032756912&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume5en_HK
dc.identifier.issue11en_HK
dc.identifier.spage3350en_HK
dc.identifier.epage3356en_HK
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridYang, M=35204210300en_HK
dc.identifier.scopusauthoridWong, KH=7404758953en_HK
dc.identifier.scopusauthoridChan, HL=7403402315en_HK
dc.identifier.scopusauthoridLam, W=7203021943en_HK

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats