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Electrostatic Modification for Promotion of Flavin-Mediated Oxidation of a Probe for Flavin Detection

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dc.contributor.authorLee, Dong-Nam-
dc.contributor.authorBae, Sohyeon-
dc.contributor.authorHan, Kyungja-
dc.contributor.authorShin, Ik-Soo-
dc.contributor.authorKim, Seong Keun-
dc.contributor.authorHong, Jong-In-
dc.date.available2018-05-08T14:27:09Z-
dc.date.created2018-04-17-
dc.date.issued2017-11-13-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://scholarworks.bwise.kr/ssu/handle/2018.sw.ssu/6196-
dc.description.abstractElectrostatic effects on the redox photochemistry of synthetic probes (1, 2, and 1-Zn) are examined by adjusting the thermodynamic driving force of their oxidation reactions. The redox photochemistry was simply controlled by introducing a zinc binding site (2,2'-dipicolylamine (DPA)) on the coumarin moiety of probe 2. Zinc complexation produced a positively charged environment on the coumarin (1-Zn), which lowered the electron density of a nearby 9H-xanthene ring, attenuating the auto-oxidation of 1-Zn by 45% compared with that of probe 1 at 298K. The positive net charge of 1-Zn also provided an attractive Coulombic force toward the phosphate of flavin mononucleotide and flavin adenine dinucleotide, which lowered the reduction potential of the electron acceptor (isoalloxazine) and improved intermolecular electron transfer from the 9H-xanthene ring to isoalloxazine. The flavin-mediated oxidation rate of 1-Zn was increased to 1.5 times that of probe 2. Probe 1-Zn showed highly selective sensing behaviour toward flavins, producing an intense brightness (epsilon phi(F) = 2.80x10(3)m(-1)cm(-1)) in the long-wavelength regions (lambda(max) = 588nm) upon flavin-mediated oxidation. Furthermore, probes 1-Zn and 2 were successfully applied to eosinophil imaging and the differential diagnosis of eosinophilia; this demonstrates their use as diagnostic tools.-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.relation.isPartOfCHEMISTRY-A EUROPEAN JOURNAL-
dc.subjectDESULFOVIBRIO-VULGARIS HILDENBOROUGH-
dc.subjectDIAZA-COPE REARRANGEMENT-
dc.subjectEOSINOPHIL AUTOFLUORESCENCE-
dc.subjectSTACKING INTERACTIONS-
dc.subjectREDUCTION POTENTIALS-
dc.subjectADENINE-DINUCLEOTIDE-
dc.subjectMODEL SYSTEMS-
dc.subjectCYTOCHROME-C-
dc.subjectPROTEIN-
dc.subjectFLAVODOXIN-
dc.titleElectrostatic Modification for Promotion of Flavin-Mediated Oxidation of a Probe for Flavin Detection-
dc.typeArticle-
dc.identifier.doi10.1002/chem.201703466-
dc.type.rimsART-
dc.identifier.bibliographicCitationCHEMISTRY-A EUROPEAN JOURNAL, v.23, no.63, pp.16078 - 16084-
dc.description.journalClass1-
dc.identifier.wosid000414990400033-
dc.identifier.scopusid2-s2.0-85031670202-
dc.citation.endPage16084-
dc.citation.number63-
dc.citation.startPage16078-
dc.citation.titleCHEMISTRY-A EUROPEAN JOURNAL-
dc.citation.volume23-
dc.contributor.affiliatedAuthorShin, Ik-Soo-
dc.type.docTypeArticle-
dc.subject.keywordAuthorelectrostatic modification-
dc.subject.keywordAuthoreosinophilia-
dc.subject.keywordAuthorflavin detection-
dc.subject.keywordAuthorphoto-oxidation-
dc.subject.keywordAuthorredox photochemistry-
dc.subject.keywordPlusDESULFOVIBRIO-VULGARIS HILDENBOROUGH-
dc.subject.keywordPlusDIAZA-COPE REARRANGEMENT-
dc.subject.keywordPlusEOSINOPHIL AUTOFLUORESCENCE-
dc.subject.keywordPlusSTACKING INTERACTIONS-
dc.subject.keywordPlusREDUCTION POTENTIALS-
dc.subject.keywordPlusADENINE-DINUCLEOTIDE-
dc.subject.keywordPlusMODEL SYSTEMS-
dc.subject.keywordPlusCYTOCHROME-C-
dc.subject.keywordPlusPROTEIN-
dc.subject.keywordPlusFLAVODOXIN-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
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