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New fluorescent probes based on gallium(III) corrole complexes for the recognition of hydrogen sulfide: a journey from solution to intracellular site

2023Journal article Restricted access
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dc.contributor.authorSantos, Carla I.M.
dc.contributor.authorSantiago, Ana M.
dc.contributor.authorAraújo, Ana R.L.
dc.contributor.authorPinto, Sandra
dc.contributor.authorAgostinho, Rafaela
dc.contributor.authorSimão, Sónia
dc.contributor.authorAzevedo, Tomás Pais de
dc.contributor.authorAntunes, Catarina
dc.contributor.authorFaustino, M. Amparo F.
dc.contributor.authorAraujo, Ines
dc.contributor.authorNeves, M. Graça P.M.S.
dc.contributor.authorMartinho, José M.G.
dc.contributor.authorMaçôas, Ermelinda M.S.
dc.date.accessioned2023-06-21T14:44:38Z
dc.date.available2023-06-21T14:44:38Z
dc.date.issued2023
dc.description.abstractIn this work, three fluorescent probes for detection of hydrogen sulfide (H2S) where prepared based on gallium (III) corrole complexes bearing nitro groups at beta-pyrrolic positions. Two of the compounds selected, the 3-nitro5,10,15- tris(pentafluorophenyl)corrolatogallium(III)(pyridine) (CGa-NO2) and the 3,17-dinitro-5,10,15-tris (pentafluorophenyl)corrolatogallium(III)(pyridine) (CGa-2NO2) present one and two nitro groups directly linked to the beta-pyrrolic position. The third compound, the (E)-3-(2-nitroprop-1-en-1-yl)-5,10,15-tris(pentafluorophenyl)corrolatogallium(III)(pyridine) (CGa-EtNO2), has a carbon-carbon double bond spacer between the corrole unit and the nitro group. All these derivatives were obtained from 5,10,15-tris(pentafluorophenyl)corrolatogallium(III)(pyridine) (CGa). The precursor CGa and the derivative CGa-EtNO2 behaved as turn-OFF probes, while compound CGa-NO2 responded as a turn-ON probe in the presence of H2S in the pH range of 5-9. Mechanistic studies show that the interaction of H2S with the probes involves its coordination with gallium(III) and in some cases the reduction of the nitro group to a new aminated corrole. While the formation of the coordination complex with H2S is almost immediate, the kinetics of the reduction is slow. Interestingly, for CGaNO2 the two processes can be explored in a ratiometric sensing of H2S in a non-aqueous solution showing a good linearity over an extended concentration range (5-200 mu M). The response of the corroles to H2S in intracellular medium was studied in 2D cultured cells (HeLa).pt_PT
dc.description.sponsorshipLISBOA-01-0145-FEDER-029319; LA/P/0056/2020pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.dyepig.2023.111304pt_PT
dc.identifier.issn0143-7208
dc.identifier.urihttp://hdl.handle.net/10400.1/19734
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationCarbon Nanodots: who is the brightest of them all?
dc.relationIdentification of S-sulfhydration targets in Down Syndrome: the role of gasotransmitter hydrogen sulfide (H2S) signaling in neurodevelopment
dc.subjectCorrolespt_PT
dc.subjectGallium complexespt_PT
dc.subjectHydrogen sulfidept_PT
dc.subjectProbespt_PT
dc.subjectChemosensorspt_PT
dc.titleNew fluorescent probes based on gallium(III) corrole complexes for the recognition of hydrogen sulfide: a journey from solution to intracellular sitept_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCarbon Nanodots: who is the brightest of them all?
oaire.awardTitleIdentification of S-sulfhydration targets in Down Syndrome: the role of gasotransmitter hydrogen sulfide (H2S) signaling in neurodevelopment
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FQUI-QFI%2F29319%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FNAN-MAT%2F29317%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/EXPL%2FMED-NEU%2F1240%2F2021/PT
oaire.citation.startPage111304pt_PT
oaire.citation.titleDyes and Pigmentspt_PT
oaire.citation.volume216pt_PT
oaire.fundingStream9471 - RIDTI
oaire.fundingStream3599-PPCDT
oaire.fundingStream3599-PPCDT
person.familyNameRibeiro Agostinho
person.familyNameGlória Simão
person.familyNamePais de Azevedo
person.familyNameGarrido Antunes
person.familyNamePombinho de Araújo
person.givenNameRafaela
person.givenNameSónia Daniel
person.givenNameTomás
person.givenNameCatarina
person.givenNameInês Maria
person.identifierhttps://scholar.google.com/citations?hl=pt-PT&user=VLL3QD4AAAAJ&view_op=list_works&sortby=pubdate
person.identifierF-4703-2012
person.identifier.ciencia-id231B-D283-9C07
person.identifier.ciencia-idC612-D462-A564
person.identifier.ciencia-id1C18-6533-49F5
person.identifier.ciencia-id6D1B-3388-F4CF
person.identifier.ciencia-idD11F-D4CA-2947
person.identifier.orcid0000-0002-0238-6395
person.identifier.orcid0000-0002-3239-2198
person.identifier.orcid0000-0002-2438-0111
person.identifier.scopus-author-id983648
person.identifier.scopus-author-id55308096300
person.identifier.scopus-author-id56271084100
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.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
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