Repository logo
 
Publication

New di(hetero)arylethers and di(hetero)arylamines in the thieno[3,2-b]pyridine series: Synthesis, growth inhibitory activity on human tumor cell lines and non-tumor cells, effects on cell cycle and on programmed cell death

2013Journal article Open access
Simple item page
dc.contributor.authorQueiroz, Maria João R.P.
dc.contributor.authorPeixoto, Daniela
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorSoares, Pedro
dc.contributor.authorSantos, Tiago
dc.contributor.authorLima, Raquel T.
dc.contributor.authorCampos, Joana F.
dc.contributor.authorAbreu, Rui M.V.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorVasconcelos, M. Helena
dc.date.accessioned2014-01-27T14:53:56Z
dc.date.available2014-01-27T14:53:56Z
dc.date.issued2013
dc.description.abstractNew fluorinated and methoxylated di(hetero)arylethers and di(hetero)arylamines were prepared functionalizing the 7-position of the thieno[3,2-b]pyridine, using copper (C–O) or palladium (C–N) catalyzed couplings, respectively, of the 7-bromothieno[3,2-b]pyridine, also prepared, with ortho, meta and para fluoro or methoxy phenols and anilines. The compounds obtained were evaluated for their growth inhibitory activity on the human tumor cell lines MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), HCT15 (colon carcinoma), HepG2 (hepatocellular carcinoma) and HeLa (cervical carcinoma). The most active compounds, a di(hetero)arylether with a methoxy group in the meta position relative to the ether function and two di(hetero)arylamines with a methoxy group either in the ortho or in the meta position relative to the NH, were further tested at their GI50 concentrations on NCI-H460 cells causing pronounced alterations in the cell cycle profile and a strong and significant increase in the programmed death of these cells. The fluorinated and the other methoxylated compounds did not show important activity, presenting high GI50 values in all the cell lines tested. Furthermore, the hepatotoxicity of the compounds was assessed using porcine liver primary cells (PLP2), established by some of us. Results showed that one of the most active compounds was not toxic to the non-tumor cells at their GI50 concentrations showing to be the most promising as antitumoral.por
dc.description.sponsorshipFoundation for the Science and Technology (FCT–Portugal) for financial support through the NMR Portuguese network (Bruker 400 Avance III-Univ Minho); to FCT and FEDER-COMPETE/QREN/EU for financial support through the research unities PEst-C/QUI/UI686/2011 and PEst-OE/AGR/UI0690/2011, the research project PTDC/QUI-QUI/111060/2009 and the post-Doctoral grants attributed to R.C.C. (SFRH/BPD/68344/2010) and R.T.L. (SRH/BPD/68787/2010). IPATIMUP is an Associate Laboratory of the Portuguese Ministry of Science, Technology and Higher Education and is partially supported by FCT.por
dc.identifier.citationQueiroz, Maria João R.P.; Peixoto, Daniela; Calhelha, Ricardo C.; Soares, Pedro; Santos, Tiago; Lima, Raquel T.; Campos, Joana F.; Abreu, Rui M.V.; Ferreira, Isabel C.F.R.; Vasconcelos, M. Helena (2013). New di(hetero)arylethers and di(hetero)arylamines in the thieno[3,2-b]pyridine series: Synthesis, growth inhibitory activity on human tumor cell lines and non-tumor cells, effects on cell cycle and on programmed cell death. European Journal of Medicinal Chemistry. ISSN 0223-5234. 69, p. 855–862por
dc.identifier.issn0223-5234
dc.identifier.urihttp://hdl.handle.net/10198/9177
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
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.subjectDi(hetero)aryletherspor
dc.subjectDi(hetero)arylaminespor
dc.subjectThieno[3,2-b]pyridinespor
dc.subjectMetal-catalyzed couplingspor
dc.subjectTumor and nontumor cells growth inhibitionpor
dc.subjectCell cycle analysis and cell deathpor
dc.titleNew di(hetero)arylethers and di(hetero)arylamines in the thieno[3,2-b]pyridine series: Synthesis, growth inhibitory activity on human tumor cell lines and non-tumor cells, effects on cell cycle and on programmed cell deathpor
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.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.citation.endPage862por
oaire.citation.startPage855por
oaire.citation.titleEuropean Journal of Medicinal Chemistrypor
oaire.citation.volume69por
oaire.fundingStream5876-PPCDTI
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamFARH
person.familyNameCalhelha
person.familyNameAbreu
person.familyNameFerreira
person.givenNameRicardo C.
person.givenNameRui M.V.
person.givenNameIsabel C.F.R.
person.identifier144781
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-id0F19-0DE2-12A2
person.identifier.ciencia-id9418-CF95-9919
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0002-7745-8015
person.identifier.orcid0000-0003-4910-4882
person.identifier.ridJ-2172-2014
person.identifier.ridE-8500-2013
person.identifier.scopus-author-id6507978333
person.identifier.scopus-author-id7003290613
person.identifier.scopus-author-id36868826600
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
rcaap.rightsopenAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication2d5d1a41-7561-4a01-871c-b4c97da35053
relation.isAuthorOfPublicationcadb03a4-5e60-4745-b35f-fc3a97c071bc
relation.isAuthorOfPublicationbd0d1537-2e03-41fb-b27a-140af9c35db8
relation.isAuthorOfPublication.latestForDiscoverybd0d1537-2e03-41fb-b27a-140af9c35db8
relation.isProjectOfPublication9b495104-c0da-42f7-a1cf-3dd890babd69
relation.isProjectOfPublicationc59f09d4-9931-4f2e-babb-ef8bed998be7
relation.isProjectOfPublicationb598cc70-fee0-491e-a33b-641bd0a20490
relation.isProjectOfPublication.latestForDiscoveryc59f09d4-9931-4f2e-babb-ef8bed998be7

Files

Original bundle
Now showing 1 - 2 of 2
No Thumbnail Available
Name:
EJMC-MJRPQ-rev [espectros corrigidos].pdf
Size:
711.89 KB
Format:
Adobe Portable Document Format
Download
No Thumbnail Available
Name:
1-s2.0-S0223523413005965-main.pdf
Size:
1.04 MB
Format:
Adobe Portable Document Format
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.73 KB
Format:
Item-specific license agreed upon to submission
Description:
Download

Collections

CIMO - Artigos em Revistas Indexados à WoS/Scopus