The synthesis and fluorescent properties of analogues of the zinc (II) specific fluorophore zinquin ester

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dc.contributor.authorKimber, M.
dc.contributor.authorMahadevan, I.
dc.contributor.authorLincoln, S.
dc.contributor.authorWard, A.
dc.contributor.authorTiekink, E.
dc.date.issued2000
dc.descriptionCopyright © 2000 American Chemical Society
dc.description.abstractThe synthesis and fluorescent properties in the absence and presence of zinc(II) of a range of 2-substituted derivatives of N-(6-methoxy-2-methyl-8-quinolyl)-4-methylbenzenesulfonamide are described. These analogues formed complexes with zinc(II) as indicated by a bathochromic shift in their UV/vis spectra. Analogues with isobutenyl and isobutyl side chains at the 2-position formed fluorescent complexes whose fluorescence was stronger than that of the 2-methyl-containing parent. These derivatives were converted, via conversion to the phenol with boron tribromide and reaction with ethyl bromoacetate, to systems with ester-containing side chains analogous to zinquin ester, a specific cellular fluorophore for zinc(II). All of these ester derivatives formed complexes with zinc(II) resulting in a bathochomic shift in their UV/vis spectra. Compounds with isobutyl, isobutenyl, and styryl side chains exhibited increased fluorescence compared to that of zinquin ester in the presence of zinc(II). The compound with the 2-isobutyl side chain was more selective in its fluorescence for zinc(II) over cadmium(II) compared to zinquin ester.
dc.description.statementofresponsibilityMarc C. Kimber, Indumathy B. Mahadevan, Stephen F. Lincoln, A. David Ward and Edward R. T. Tiekink
dc.identifier.citationJournal of Organic Chemistry, 2000; 65(24):8204-8209
dc.identifier.doi10.1021/jo000678x
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/2440/4553
dc.language.isoen
dc.provenanceWeb Release Date: November 2, 2000
dc.publisherAmer Chemical Soc
dc.source.urihttps://doi.org/10.1021/jo000678x
dc.subjectTosyl Compounds
dc.subjectQuinolones
dc.subjectFluorescent Dyes
dc.subjectLigands
dc.titleThe synthesis and fluorescent properties of analogues of the zinc (II) specific fluorophore zinquin ester
dc.typeJournal article
pubs.publication-statusPublished

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