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Aminodi(hetero)arylamines in the thieno[3,2-b]pyridine series: synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using non-tumor cells

2012Journal article Open access
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dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorPeixoto, Daniela
dc.contributor.authorAbreu, Rui M.V.
dc.contributor.authorVale-Silva, Luís A.
dc.contributor.authorPinto, Eugénia
dc.contributor.authorLima, Raquel T.
dc.contributor.authorAlvelos, M. Inês
dc.contributor.authorVasconcelos, M. Helena
dc.contributor.authorQueiroz, Maria João R.P.
dc.date.accessioned2012-08-21T09:55:24Z
dc.date.available2012-08-21T09:55:24Z
dc.date.issued2012
dc.description.abstractThree aminodi(hetero)arylamines were prepared via a palladium-catalyzed C-N Buchwald-Hartwig coupling of methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate with different bromonitrobenzenes, followed by reduction of the nitro groups of the coupling products to the corresponding amino compounds. The aminodi(hetero)arylamines thus obtained were evaluated for their growth inhibitory effect on four human tumor cell lines MCF-7 (breast adenocarcinoma), A375-C5 (melanoma), NCI-H460 (non-small cell lung cancer) and HepG2 (hepatocellular carcinoma). The toxicity to non-tumor cells was also evaluated using a porcine liver primary cell culture (PLP1), established by us. The aminodi(hetero)arylamine with the NH2 group in the ortho position and an OMe group in the para position to the NH of the di(hetero)arylamine, is the most promising compound giving the lowest GI50 values (1.30–1.63 μM) in all the tested human tumor cell lines, presenting no toxicity to PLP1 at those concentrations. The effect of this compound on the cell cycle and induction of apoptosis was analyzed in the NCI-H460 cell line. It was observed that it altered the cell cycle profile causing a decrease in the percentage of cells in the G0/G1 phase and an increase of the apoptosis levels.por
dc.identifier.citationCalhelha, Ricardo C.; Ferreira, Isabel C.F.R.; Peixoto, Daniela; Abreu, Rui M.V.; Vale-Silva, Luís A.; Pinto, Eugénia; Lima, Raquel T.; Alvelos, M. Inês; Vasconcelos, M. Helena; Queiroz, Maria-João R.P. (2012) – Aminodi(hetero)arylamines in the thieno[3,2-b]pyridine series: synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using non-tumor cells. Molecules. ISSN 1420-3049. 17:4, p. 3834-3843por
dc.identifier.doi10.3390/molecules17043834
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10198/7370
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherMDPIpor
dc.relationPEst-C/QUI/UI686/2011
dc.relationStrategic Project - UI 690 - 2011-2012
dc.relationNEW ANTITUMOR AND/OR ANTI-ANGIOGENIC HETEROCYCLIC COMPOUNDS: SYNTHESIS, MOLECULAR MODELLING AND INHIBITION ENZYMATIC ASSAYS USING TYROSINE KINASE MEMBRANE GROWTH FACTOR RECEPTORS
dc.relationSMALL MOLECULES AS APOPTOSIS INDUCERS IN CANCER CELLS: INVESTIGATION OF THE MECHANISM OF ACTION
dc.subjectThieno[3,2-b]pyridinespor
dc.subjectAminodi(hetero)arylaminespor
dc.subjectBuchwald-Hartwig C-N couplingpor
dc.subjectAntitumoral activitypor
dc.subjectToxicitypor
dc.subjectCell cyclepor
dc.titleAminodi(hetero)arylamines in the thieno[3,2-b]pyridine series: synthesis, effects in human tumor cells growth, cell cycle analysis, apoptosis and evaluation of toxicity using non-tumor cellspor
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleStrategic Project - UI 690 - 2011-2012
oaire.awardTitleNEW ANTITUMOR AND/OR ANTI-ANGIOGENIC HETEROCYCLIC COMPOUNDS: SYNTHESIS, MOLECULAR MODELLING AND INHIBITION ENZYMATIC ASSAYS USING TYROSINE KINASE MEMBRANE GROWTH FACTOR RECEPTORS
oaire.awardTitleSMALL MOLECULES AS APOPTOSIS INDUCERS IN CANCER CELLS: INVESTIGATION OF THE MECHANISM OF ACTION
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876-PPCDTI/PTDC%2FQUI-QUI%2F111060%2F2009/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/PEst-OE%2FAGR%2FUI0690%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/FARH/SFRH%2FBPD%2F68344%2F2010/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F68787%2F2010/PT
oaire.citation.endPage3843por
oaire.citation.startPage3834por
oaire.citation.titleMoleculespor
oaire.citation.volume17por
oaire.fundingStream5876-PPCDTI
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamFARH
person.familyNameCalhelha
person.familyNameFerreira
person.familyNameAbreu
person.givenNameRicardo C.
person.givenNameIsabel C.F.R.
person.givenNameRui M.V.
person.identifier144781
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-id9418-CF95-9919
person.identifier.ciencia-id0F19-0DE2-12A2
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0003-4910-4882
person.identifier.orcid0000-0002-7745-8015
person.identifier.ridJ-2172-2014
person.identifier.ridE-8500-2013
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id36868826600
person.identifier.scopus-author-id7003290613
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspor
rcaap.typearticlepor
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