title: Bifunctional Diaminoterephthalate Fluorescent Dye as Probe for Cross-Linking Proteins.
abstract: Diaminoterephthalates are fluorescent dyes and define scaffolds, which can be orthogonally functionalized at their two carboxylate residues with functional residues bearing task specific reactive groups. The synthesis of monofunctionalized dyes with thiol groups for surface binding, an azide for click chemistry, and a biotinoylated congener for streptavidin binding is reported. Two bifunctionalized dyes were prepared: One with an azide for click chemistry and a biotin for streptavidin binding, the other with a maleimide for reaction with thiol and a cyclooctyne moiety for ligation with copper-free click chemistry. In general, the compounds are red to orange, fluorescent materials with an absorption at about 450 nm and an emission at 560 nm with quantum yields between 2-41 %. Of particular interest is the maleimide-functionalized compound, which shows low fluorescence quantum yield (2 %) by itself. After addition of a thiol, the fluorescence is "turned on"; quantum yield 41 %.
authors.affiliation: Institut für Chemie, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
authors.forename: Melanie
authors.initials: M
authors.lastname: Wallisch
authors.affiliation: Biochemistry Group, Department of Neuroscience, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Sulmann
authors.affiliation: Biochemistry Group, Department of Neuroscience, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
authors.forename: Karl-Wilhelm
authors.identifier: http://orcid.org/0000-0003-1501-0044
authors.initials: KW
authors.lastname: Koch
authors.affiliation: Institut für Chemie, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
authors.forename: Jens
authors.initials: J
authors.lastname: Christoffers
mesh_terms: D000818:Animals; D001386:Azides / Q000737:chemistry; D001710:Biotin / Q000737:chemistry* / Q000378:metabolism; D002417:Cattle; D057930:Click Chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D019281:Dimerization; D005456:Fluorescent Dyes / Q000737:chemistry*; D051606:G-Protein-Coupled Receptor Kinase 1 / Q000737:chemistry; D006801:Humans; D008301:Maleimides / Q000737:chemistry; D010795:Phthalic Acids / Q000737:chemistry*; D011485:Protein Binding; D051603:Recoverin / Q000737:chemistry; D019809:Streptavidin / Q000737:chemistry / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D001386:Azides; D003432:Cross-Linking Reagents; D005456:Fluorescent Dyes; D008301:Maleimides; D010795:Phthalic Acids; D013438:Sulfhydryl Compounds; D051603:Recoverin; C043592:maleimide; C011363:terephthalic acid; D001710:Biotin; D019809:Streptavidin; D051606:G-Protein-Coupled Receptor Kinase 1; C496764:GRK1 protein, human
keywords: azides; click chemistry; diaminoterephthalates; fluorescence; maleimides; thiols