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Redox-active cytotoxic diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes: Reduction behaviour and theoretical interpretation

2012-12Journal article Restricted access
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dc.contributor.authorShang, Xianmei M.
dc.contributor.authorAlegria, Elisabete
dc.contributor.authorGuedes Da Silva, M. Fátima C.
dc.contributor.authorKuznetsov, Maxim L.
dc.contributor.authorLi, Qingshan S.
dc.contributor.authorPombeiro, Armando
dc.date.accessioned2015-09-08T15:28:46Z
dc.date.available2015-09-08T15:28:46Z
dc.date.issued2012-12
dc.description.abstractTwo series of new diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes (cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl), formulated as the mononuclear [R2Sn(HL)(2)] (1:2) (a, R=Bu-n and Ph) and the polymeric [R2SnL](n) (1:1) (b, R=Bu-n) compounds, were prepared and fully characterized. Single crystal X-ray diffraction for [(Bu2Sn)-Bu-n{C5H9C(O)NHO}(2)] (3a) discloses the cis geometry and strong intermolecular NH center dot center dot center dot O interactions. The in vitro cytotoxic activities of the complexes were evaluated against HL-60, Bel-7402, BGC-823 and KB human tumour cell lines, the greater activity concerning [(Bu2Sn)-Bu-n(HL)(2)] [HL=C3H5C(O)NHO (1a), C6H11C(O)NHO (4a)] towards BGC-823. The complexes undergo, by cyclic voltammetry and controlled-potential electrolysis, one irreversible overall two-electron cathodic process at a reduction potential that does not appear to correlate with the antitumour activity. The electrochemical behaviour of [R2Sn(C5H9C(O)NHO)(2)] [R=Bu-n (3a), Ph (7a)] was also investigated using density functional theory (DFT) methods, showing that the ultimate complex structure and the mechanism of its formation are R dependent: for the aromatic (R = Ph) complex, the initial reduction step is centred on the phenyl ligands and at the metal, being followed by a second reduction with Sn-O and Sn-C ruptures, whereas for the alkyl (R=Bu-n) complex the first reduction step is centred on one of the hydroxamate ligands and is followed by a second reduction with Sn-O bond cleavages and preservation of the alkyl ligands. In both cases, the final complexes are highly coordinative unsaturated Sn-II species with the cis geometry, features that can be of biological significance.por
dc.identifier.citationSHANG, X. M.; [et al] – Redox-active cytotoxic diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes: Reduction behaviour and theoretical interpretation. Journal of Inorganic Biochemistry. ISSN: 0162-0134. Vol. 117 (2012), pp. 147-156por
dc.identifier.doi10.1016/j.jinorgbio.2012.08.019
dc.identifier.issn0162-0134
dc.identifier.urihttp://hdl.handle.net/10400.21/5121
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevier Science Incpor
dc.relationFoundation for Science and Technology (FCT), Portugal - PEst-OE/QUI/UI0100/2011
dc.relationMinistry of Science and Technology of China - 2009ZX09103-104
dc.relationFCT - SFRH/BPD/44773/2008
dc.relationFCT - PEst-OE/QUI/UI0100/2011
dc.relationNew Drug Development Programme from the Ministry of Science and Technology of China - No. 2009ZX09103-104
dc.relationFCT - SFRH/BPD/44773/2008
dc.subjectOrganotin(IV) complexespor
dc.subjectCycloaliphatic Hydroxamatepor
dc.subjectRedox Potentialpor
dc.subjectCytotoxic Activitypor
dc.subjectElectron-Transfer Induced Bond Cleavagepor
dc.subjectMechanism of Reductionpor
dc.subjectSN-119 NMR-spectra
dc.subjectAntitumor-activity
dc.subjectOrganotin(IV)(N+) complexes
dc.subjectCoordination-compounds
dc.subjectRuthenium complexes
dc.subjectCrystal-structures
dc.subjectAnticancer drugs
dc.subjectAcid
dc.subjectIminoacylation
dc.subjectOrganonitriles
dc.titleRedox-active cytotoxic diorganotin(IV) cycloalkylhydroxamate complexes with different ring sizes: Reduction behaviour and theoretical interpretationpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.conferencePlaceNew York
oaire.citation.endPage156por
oaire.citation.startPage147por
oaire.citation.titleJournal of Inorganic Biochemistrypor
oaire.citation.volume117por
person.familyNameAlegria
person.familyNameGuedes da Silva
person.familyNameKuznetsov
person.familyNamePombeiro
person.givenNameElisabete
person.givenNameM. Fátima C.
person.givenNameMaxim L.
person.givenNameArmando
person.identifier863202
person.identifier789079
person.identifier.ciencia-id8C1F-851A-9F1C
person.identifier.ciencia-id7619-8E8E-979A
person.identifier.ciencia-id7018-EEFE-E023
person.identifier.ciencia-id8311-38FA-CEFB
person.identifier.orcid0000-0003-4060-1057
person.identifier.orcid0000-0003-4836-2409
person.identifier.orcid0000-0001-5729-6189
person.identifier.orcid0000-0001-8323-888X
person.identifier.ridE-9945-2012
person.identifier.ridH-8274-2012
person.identifier.ridH-7934-2012
person.identifier.ridI-5945-2012
person.identifier.scopus-author-id8315848300
person.identifier.scopus-author-id6701761571
person.identifier.scopus-author-id7102379353
person.identifier.scopus-author-id7006067269
rcaap.rightsclosedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication6d781c38-c45e-4159-b795-8c8675606160
relation.isAuthorOfPublication18e14ad3-9937-46d0-83b2-36fab224c1c0
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relation.isAuthorOfPublication.latestForDiscovery6d18ff2e-5c33-4010-b1e7-964c72349813

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