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dc.contributor.authorGuo, Si-Xuan
dc.contributor.authorMason, Dayna N
dc.contributor.authorTurland, Susan A
dc.contributor.authorLawrenz, Eric T
dc.contributor.authorKelly, Lance C
dc.contributor.authorFallon, Gary D
dc.contributor.authorGatehouse, Bryan M
dc.contributor.authorBond, Alan M
dc.contributor.authorDeacon, Glen B
dc.contributor.authorBattle, Andrew R
dc.contributor.authorHambley, Trevor W
dc.contributor.authorRainone, Silvina
dc.contributor.authorWebster, Lorraine K
dc.contributor.authorCullinane, Carleen
dc.date.accessioned2017-05-03T16:04:27Z
dc.date.available2017-05-03T16:04:27Z
dc.date.issued2012
dc.date.modified2013-06-26T03:40:25Z
dc.identifier.issn0162-0134
dc.identifier.doi10.1016/j.jinorgbio.2012.07.016
dc.identifier.urihttp://hdl.handle.net/10072/51961
dc.description.abstractThe putative platinum(IV) anticancer drugs, [Pt{((R)NCH2)2}(py)2XY] (X,Y = Cl, R = p-HC6F4 (1a), C6F5 (1b); X,Y = OH, R = p-HC6F4 (2); X = Cl, Y = OH, R = p-HC6F4 (3), py = pyridine) have been prepared by oxidation of the PtII anticancer drugs [Pt{((R)NCH2)2}(py)2] (R = p-HC6F4 (4a) or C6F5 (4b)) with PhICl2 (1a,b), H2O2 (2) and PhICl2/Bu4NOH (3). NMR spectroscopy and the X-ray crystal structures of 1b, 2 and 3 show that they have octahedral stereochemistry with the X,Y ligands in the trans-position. The net two electron electrochemical reduction of 1a, 2 and 3 has been studied by voltammetric, spectroelectrochemical and bulk electrolysis techniques in acetonitrile. NMR and other data reveal that reduction of 1a gives pure 4a via the elimination of both axial chloride ligands. In the case of 2, one end of the diamide ligand is protonated and the resulting -NH(p-HC6F4) group dissociated giving a [Pt{N(p-HC6F4)CH2CH2NH(p-HC6F4)}] arrangement, one pyridine ligand is lost and a hydroxide ion retained in the coordination sphere. Intriguingly, in the case of reduction of 3, a 50% mixture of the reduction products of pure 1a and 2 is formed. The relative ease of reduction is 1 > 3 > 2. Testing of 1a, 2 and 3 against L1210 and L1210(DDP) (DDP = cis-diamine-dichloroplatinum(II)) mouse leukaemia cells shows all to be cytotoxic with IC50 values of 1.0-3.5 μM. 2 and 3 are active in vivo against AHDJ/PC6 tumor line when delivered in peanut oil despite being hard to reduce electrochemically, and notably are more active than 4a delivered in this medium whilst comparable with 4a delivered in saline/Tween.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.publisherElsevier
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom226
dc.relation.ispartofpageto239
dc.relation.ispartofjournalJournal of Inorganic Biochemistry
dc.relation.ispartofvolume115
dc.rights.retentionY
dc.subject.fieldofresearchInorganic chemistry
dc.subject.fieldofresearchBioinorganic chemistry
dc.subject.fieldofresearchTheoretical and computational chemistry
dc.subject.fieldofresearchOther chemical sciences
dc.subject.fieldofresearchcode3402
dc.subject.fieldofresearchcode340201
dc.subject.fieldofresearchcode3407
dc.subject.fieldofresearchcode3499
dc.titleSystematic differences in electrochemical reduction of the structurally characterized anti-cancer platinum(IV) complexes [Pt{((p-HC6F4)NCH2)2}-(pyridine)2Cl2], [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)2], and [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)Cl]
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2012
gro.hasfulltextNo Full Text
gro.griffith.authorBattle, Andrew


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