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dc.contributor.authorGonzalez-Vera, Juan A.
dc.contributor.authorLukovic, Elvedin
dc.contributor.authorImperiali, Barbara
dc.date.accessioned2012-03-08T17:24:17Z
dc.date.available2012-03-08T17:24:17Z
dc.date.issued2009-09
dc.date.submitted2009-06
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/1721.1/69597
dc.description.abstractProtein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel, red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used in kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 nm) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).en_US
dc.description.sponsorshipNational Institutes of Health (U.S.) (NIH Cell Migration Consortium (GM064346))en_US
dc.description.sponsorshipA.M. Escudero Foundationen_US
dc.description.sponsorshipMassachusetts Institute of Technology (Department of Chemistry Instrumentation Facility (NIH-1S10RR013886-01))en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/jo901369ken_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourceProf. Imperiali via Erja Kajosaloen_US
dc.titleSynthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensorsen_US
dc.typeArticleen_US
dc.identifier.citationGonzález-Vera, Juan A., Elvedin Luković, and Barbara Imperiali. “Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors.” The Journal of Organic Chemistry 74.19 (2009): 7309–7314.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Biologyen_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.approverImperiali, Barbara
dc.contributor.mitauthorImperiali, Barbara
dc.contributor.mitauthorGonzalez-Vera, Juan A.
dc.contributor.mitauthorLukovic, Elvedin
dc.relation.journalJournal of Organic Chemistryen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsGonzalez-Vera, Juan A.; Lukovic, Elvedin; Imperiali, Barbaraen
dc.identifier.orcidhttps://orcid.org/0000-0002-5749-7869
mit.licensePUBLISHER_POLICYen_US


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