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Synthesis, photochemical and in vitro cytotoxic evaluation of new iodinated aminosquaraines as potential sensitizers for photodynamic therapy

2019Journal article Open access
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dc.contributor.authorMandim, Filipa
dc.contributor.authorGraça, Vânia C.
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorMachado, Isabel Ferreira
dc.contributor.authorFerreira, Luis F.V.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.contributor.authorSantos, Paulo F.
dc.date.accessioned2018-02-19T10:00:00Z
dc.date.accessioned2020-01-03T17:07:24Z
dc.date.available2018-01-19T10:00:00Z
dc.date.available2020-01-03T17:07:24Z
dc.date.issued2019
dc.description.abstractIn this work, several benzothiazole-based aminosquaraine dyes, displaying strong absorption within the so-called phototherapeutic window (650–800 nm), were synthesized. The ability, of all the new dyes, to generate singlet oxygen was assessed by determining the correspondent phosphorescence emission and through the comparison with a standard. The quantum yields of singlet oxygen generation were determined and exhibited to be strongly dependent on the nature of the amino substituents introduced in the squaric ring. The photodynamic activity of the synthesized dyes was tested against four human tumor cell lines: breast (MCF-7), lung (NCI-H460), cervical (HeLa) and hepatocellular (HepG2) carcinomas; and a non-tumor porcine liver primary cell culture (PLP2). All the compounds synthesized were found to be able to inhibit tumor cells growth upon irradiation more than in the dark, in most of the cases, very significantly. Considering the photodynamic activity exhibited and the low toxicity displayed for the non-tumor cells, some of the synthetized dyes can be regarded as potential candidates as photosensitizers for PDT.
dc.description.sponsorshipThe authors are grateful to the Foundation for Science and Technology (FCT, Portugal) and FEDER for CIMO (UID/AGR/00690/2013) and CQ-VR (UID/QUI/00616/2013) financial support, as also for R. Calhelha contract.
dc.description.versioninfo:eu-repo/semantics/publishedVersionen_EN
dc.identifier.citationMandim, Filipa; Graça, Vânia C.; Calhelha, Ricardo C.; Machado, Isabel L.F.; Ferreira, Luis F.V.; Ferreira, Isabel C.F.R.; Santos, Paulo F. (2019). Synthesis, photochemical and in vitro cytotoxic evaluation of new iodinated aminosquaraines as potential sensitizers for photodynamic therapy. Molecules. ISSN 1420-3049. 24, p. 1-14en_EN
dc.identifier.doi10.3390/molecules24050863en_EN
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10198/20100
dc.language.isoeng
dc.peerreviewedyesen_EN
dc.subjectPhotodynamic therapyen_EN
dc.subjectSinglet oxygenen_EN
dc.subjectSquaraineen_EN
dc.titleSynthesis, photochemical and in vitro cytotoxic evaluation of new iodinated aminosquaraines as potential sensitizers for photodynamic therapyen_EN
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FAGR%2F00690%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00616%2F2013/PT
oaire.fundingStream5876
oaire.fundingStream5876
person.familyNameMandim
person.familyNameCalhelha
person.familyNameFerreira
person.givenNameFilipa
person.givenNameRicardo C.
person.givenNameIsabel C.F.R.
person.identifier144781
person.identifier.ciencia-idF318-9049-EB99
person.identifier.ciencia-idF313-E3CE-554E
person.identifier.ciencia-id9418-CF95-9919
person.identifier.orcid0000-0002-6494-2326
person.identifier.orcid0000-0002-6801-4578
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-id36868826600
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
rcaap.rightsopenAccessen_EN
rcaap.typearticleen_EN
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