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A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

hal.structure.identifierA. N. Nesmeyanov Institute of Organoelement Compounds [INEOS]
hal.structure.identifierMendeleev University of Chemical Technology of Russia
dc.contributor.authorPANCHENKO, Pavel A.
hal.structure.identifierInstitute of Fine Chemical Technology [Moscow] [IFCT]
dc.contributor.authorGRIN, Mikhail A.
hal.structure.identifierA. N. Nesmeyanov Institute of Organoelement Compounds [INEOS]
hal.structure.identifierMendeleev University of Chemical Technology of Russia
dc.contributor.authorFEDOROVA, Olga A.
hal.structure.identifierA. N. Nesmeyanov Institute of Organoelement Compounds [INEOS]
dc.contributor.authorZAKHARKO, Marina A.
hal.structure.identifierInstitute of Fine Chemical Technology [Moscow] [IFCT]
dc.contributor.authorPRITMOV, Dmitriy A.
hal.structure.identifierInstitute of Fine Chemical Technology [Moscow] [IFCT]
dc.contributor.authorMIRONOV, Andrey F.
hal.structure.identifierA. N. Nesmeyanov Institute of Organoelement Compounds [INEOS]
dc.contributor.authorARKHIPOVA, Antonina N.
hal.structure.identifierA. N. Nesmeyanov Institute of Organoelement Compounds [INEOS]
dc.contributor.authorFEDOROV, Yuri V.
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorJONUSAUSKAS, Gediminas
hal.structure.identifierP. Hertsen Moscow Oncology Research Institute
dc.contributor.authorYAKUBOVSKAYA, Raisa I.
hal.structure.identifierP. Hertsen Moscow Oncology Research Institute
dc.contributor.authorMOROZOVA, Natalia B.
hal.structure.identifierLomonosov Moscow State University [MSU]
hal.structure.identifierShemyakin-Ovchinnikov Institute of Bioorganic Chemistry [IBCh RAS]
dc.contributor.authorIGNATOVA, Anastasia A.
hal.structure.identifierLomonosov Moscow State University [MSU]
hal.structure.identifierShemyakin-Ovchinnikov Institute of Bioorganic Chemistry [IBCh RAS]
dc.contributor.authorFEOFANOV, Alexey V
dc.date.created2017-07-02
dc.date.issued2017-11-28
dc.identifier.issn1463-9076
dc.description.abstractEnPropargyl-15 2 ,17 3-dimethoxy-13 1-amide of bacteriochlorin e (BChl) and a 4-(4-N,N-dimethylaminostyryl)-N-alkyl-1,8-naphthalimide bearing azide group in the N-alkyl fragment were conjugated by the copper(I)-catalyzed 1,3-dipolar cycloaddition to produce a novel dyad compound BChl–NI for anticancer photodynamic therapy (PDT) combining the modalities of a photosensitizer (PS) and a fluorescence imaging agent. A precise photo-physical investigation of the conjugate in solution using steady-state and time-resolved optical spectroscopy revealed that the presence of the naphthalimide (NI) fragment does not decrease the photosensitizing ability of the bacteriochlorin (BChl) core as compared with BChl; however, the fluorescence of naphthalimide is completely quenched due to resonance energy transfer (RET) to BChl. It has been shown that the BChl–NI conjugate penetrates into human lung adenocarcinoma A549 cells, and accumulates in the cytoplasm where it has a mixed granular-diffuse distribution. Both NI and BChl fluorescence in vitro provides registration of bright images showing perfectly intracellular distribution of BChl–NI. The ability of NI to emit light upon excitation in imaging experiments has been found to be due to hampering of RET as a result of photodestruction of the energy acceptor BChl unit. Phototoxicity studies have shown that the BChl–NI conjugate is not toxic for A549 cells at tested concentrations (o8 mM) without light-induced activation. At the same time, the concentration-dependent killing of cells is observed upon the excitation of the bacteriochlorin moiety with red light that occurs due to reactive oxygen species formation. The presented data demonstrate that the BChl–NI conjugate is a promissing dual function agent for cancer diagnostics and therapy.
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.rights.urihttp://creativecommons.org/licenses/by-sa/
dc.title.enA novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging
dc.typeArticle de revue
dc.identifier.doi10.1039/C7CP04449F
dc.subject.halChimie/Chimie thérapeutique
dc.subject.halChimie/Chimie organique
bordeaux.journalPhysical Chemistry Chemical Physics
bordeaux.page30195-30206
bordeaux.volume19
bordeaux.issue44
bordeaux.peerReviewedoui
hal.identifierhal-01662193
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01662193v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Physical%20Chemistry%20Chemical%20Physics&rft.date=2017-11-28&rft.volume=19&rft.issue=44&rft.spage=30195-30206&rft.epage=30195-30206&rft.eissn=1463-9076&rft.issn=1463-9076&rft.au=PANCHENKO,%20Pavel%20A.&GRIN,%20Mikhail%20A.&FEDOROVA,%20Olga%20A.&ZAKHARKO,%20Marina%20A.&PRITMOV,%20Dmitriy%20A.&rft.genre=article


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