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- Publisher Website: 10.1002/(SICI)1521-3765(19991105)5:11<3350::AID-CHEM3350>3.0.CO;2-J
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Article: Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines
Title | Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines |
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Authors | |
Keywords | Antitumor agents Bioinorganic chemistry DNA recognition Luminescence Platinum |
Issue Date | 1999 |
Publisher | Wiley - 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? |
Abstract | The 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 Identifier | http://hdl.handle.net/10722/68891 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Che, CM | en_HK |
dc.contributor.author | Yang, M | en_HK |
dc.contributor.author | Wong, KH | en_HK |
dc.contributor.author | Chan, HL | en_HK |
dc.contributor.author | Lam, W | en_HK |
dc.date.accessioned | 2010-09-06T06:08:40Z | - |
dc.date.available | 2010-09-06T06:08:40Z | - |
dc.date.issued | 1999 | en_HK |
dc.identifier.citation | Chemistry - A European Journal, 1999, v. 5 n. 11, p. 3350-3356 | en_HK |
dc.identifier.issn | 0947-6539 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/68891 | - |
dc.description.abstract | The 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.language | eng | en_HK |
dc.publisher | Wiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry | en_HK |
dc.relation.ispartof | Chemistry - A European Journal | en_HK |
dc.subject | Antitumor agents | en_HK |
dc.subject | Bioinorganic chemistry | en_HK |
dc.subject | DNA recognition | en_HK |
dc.subject | Luminescence | en_HK |
dc.subject | Platinum | en_HK |
dc.title | Platinum(II) complexes of dipyridophenazine as metallointercalators for DNA and potent cytotoxic agents against carcinoma cell lines | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://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+lines | en_HK |
dc.identifier.email | Che, CM:cmche@hku.hk | en_HK |
dc.identifier.authority | Che, CM=rp00670 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/(SICI)1521-3765(19991105)5:11<3350::AID-CHEM3350>3.0.CO;2-J | - |
dc.identifier.scopus | eid_2-s2.0-0032756912 | en_HK |
dc.identifier.hkuros | 53161 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0032756912&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 5 | en_HK |
dc.identifier.issue | 11 | en_HK |
dc.identifier.spage | 3350 | en_HK |
dc.identifier.epage | 3356 | en_HK |
dc.identifier.isi | WOS:000083640300028 | - |
dc.publisher.place | Germany | en_HK |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_HK |
dc.identifier.scopusauthorid | Yang, M=35204210300 | en_HK |
dc.identifier.scopusauthorid | Wong, KH=7404758953 | en_HK |
dc.identifier.scopusauthorid | Chan, HL=7403402315 | en_HK |
dc.identifier.scopusauthorid | Lam, W=7203021943 | en_HK |
dc.identifier.issnl | 0947-6539 | - |