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Novel 3-hydroxy-4-pyridinonato oxidovanadium(IV) complexes to investigate structure/activity relationships

2009Journal article Open access
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dc.contributor.authorRangel, Maria
dc.contributor.authorJoão Amorim, M.
dc.contributor.authorNunes, Ana
dc.contributor.authorLeite, Andreia
dc.contributor.authorPereira, Eulalia
dc.contributor.authorDe Castro, Baltazar
dc.contributor.authorSilva, Carla Sousa e
dc.contributor.authorYoshikawa, Yutaka
dc.contributor.authorSakurai, Hiromu
dc.date.accessioned2019-09-27T07:46:56Z
dc.date.available2019-09-27T07:46:56Z
dc.date.issued2009
dc.description.abstractA previous evaluation of the insulin-like activity of three 3-hydroxy-4-pyridinonato oxidovanadium(IV) complexes raised questions about structure/activity relationships, namely the influence of the hydrophilic/lipophilic balance of the complex and the capacity of the ligand to stabilize the +4 oxidation state of vanadium ion, on achieving an positive effect. To address these questions, we synthesized six new oxidovanadium(IV) complexes with variable hydrophilic/lipophilic balance, obtained by introducing different substituents on the nitrogen atom, and used two 3-hydroxy-4-pyrones as starting reagents to provide methyl and ethyl groups in the ortho position of the ring. For the new and previously reported complexes, we studied the oxidation–reduction properties and insulin-like activity in terms of inhibitory effect on Free fatty acid (FFA) release in isolated rat adipocytes. The results obtained show that only one of the complexes, Bis(3-hydroxy-1(H)-2-methyl-4-pyridonato)oxidovanadium(IV), VO(mpp)2, exhibits a significantly greater capacity to inhibit FFA release than VOSO4 and consequently is worthy to be considered for further studies. The establishment of structure activity relationships was not attainable but this study brings new information about the influence of some properties of the compounds on the achievement of an insulin-like effect. The results reveal that: (i) the oxidation–reduction cycles of the complexes are identical; (ii) the presence of more lipophilic substituents on the nitrogen atom does not enhance insulin-like properties; (iii) a high solubility in water proved to be not sufficient for a positive activity in inhibiting FFA release; (iv) a small molecular size may be an important property for reaching the right targets.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.jinorgbio.2008.12.019pt_PT
dc.identifier.eissn1873-3344
dc.identifier.issn0162-0134
dc.identifier.urihttp://hdl.handle.net/10284/8055
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/pii/S0162013409000142pt_PT
dc.subject3-Hydroxy-4-pyridinonespt_PT
dc.subjectOxovanadium(IV) complexespt_PT
dc.subjectInsulin enhancing compoundspt_PT
dc.subjectInhibition of FFA releasept_PT
dc.titleNovel 3-hydroxy-4-pyridinonato oxidovanadium(IV) complexes to investigate structure/activity relationshipspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage502pt_PT
oaire.citation.issue4pt_PT
oaire.citation.startPage496pt_PT
oaire.citation.titleJournal of Inorganic Biochemistrypt_PT
oaire.citation.volume103pt_PT
person.familyNameRangel
person.familyNameLeite
person.familyNamePereira
person.familyNamede Castro
person.familyNameSilva
person.givenNameMaria
person.givenNameAndreia
person.givenNameEulalia
person.givenNameBaltazar
person.givenNameCarla
person.identifierR-000-ARW
person.identifierR-000-4QG
person.identifier.ciencia-id2E18-5B36-29C0
person.identifier.ciencia-id8916-50A6-41A9
person.identifier.ciencia-idC21F-6B71-2272
person.identifier.ciencia-id4D13-899F-862C
person.identifier.ciencia-id2E1D-05DF-E0DB
person.identifier.orcid0000-0002-0998-1437
person.identifier.orcid0000-0002-1967-8853
person.identifier.orcid0000-0003-2086-5696
person.identifier.orcid0000-0001-9097-0171
person.identifier.orcid0000-0001-6467-4766
person.identifier.ridB-3732-2012
person.identifier.ridC-6282-2013
person.identifier.ridD-8306-2013
person.identifier.ridD-8159-2013
person.identifier.scopus-author-id55963098900
person.identifier.scopus-author-id8602521800
person.identifier.scopus-author-id7202834210
person.identifier.scopus-author-id7005254412
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
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