title: Bifunctional diaminoterephthalate scaffolds as fluorescence turn-on probes for thiols.
abstract: The fluorescent diaminoterephthalate scaffold was equipped by amidation with three types of reactive functions: thiols for metal-surface binding, alkynes for click reactions, and maleimides for ligation with proteins. Starting from a succinyl succinate derivative with two orthogonally cleavable ester functions, three monoamides (38-57% yield over three steps) and two bisamides (19 and 25% yield over five steps) were prepared. Although alkyne and thiol derivatized compounds showed reasonable luminescence behavior (Φ≈1-4%), the fluorescence was quenched by the maleimide moiety. It was turned on (10- to 20-fold increase of fluorescence quantum yield) by conjugate addition of thiols.
authors.affiliation: Institut für Chemie, Carl von Ossietzky Universität Oldenburg, 26111 Oldenburg (Germany), Fax: (+49) 441-798-3873 http://www.christoffers.chemie.uni-oldenburg.de/17321.html.
authors.forename: Lena
authors.initials: L
authors.lastname: Freimuth
authors.affiliation: Institut für Chemie, Carl von Ossietzky Universität Oldenburg, 26111 Oldenburg (Germany), Fax: (+49) 441-798-3873 http://www.christoffers.chemie.uni-oldenburg.de/17321.html. jens.christoffers@uni-oldenburg.de.
authors.forename: Jens
authors.initials: J
authors.lastname: Christoffers
mesh_terms: D000480:Alkynes / Q000737:chemistry; D057930:Click Chemistry; D003959:Diamines / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry; D010795:Phthalic Acids / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000032:analysis*
chemical_list: D000480:Alkynes; D003959:Diamines; D005456:Fluorescent Dyes; D008301:Maleimides; D010795:Phthalic Acids; D013438:Sulfhydryl Compounds; C043592:maleimide; C011363:terephthalic acid
keywords: alkynes; fluorescence; scaffolds; terephthalates; thiols