title: A disulfide intercalator toolbox for the site-directed modification of polypeptides.
abstract: A disulfide intercalator toolbox was developed for site-specific attachment of a broad variety of functional groups to proteins or peptides under mild, physiological conditions. The peptide hormone somatostatin (SST) served as model compound for intercalation into the available disulfide functionalization schemes starting from the intercalator or the reactive SST precursor before or after bioconjugation. A tetrazole-SST derivative was obtained that undergoes photoinduced cycloaddition in mammalian cells, which was monitored by live-cell imaging.
authors.affiliation: Institute of Organic Chemistry III, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany), Fax: (+49) 731-5022883.
authors.forename: Tao
authors.initials: T
authors.lastname: Wang
authors.forename: Yuzhou
authors.initials: Y
authors.lastname: Wu
authors.forename: Seah Ling
authors.initials: SL
authors.lastname: Kuan
authors.forename: Oliver
authors.initials: O
authors.lastname: Dumele
authors.forename: Markus
authors.initials: M
authors.lastname: Lamla
authors.forename: David Y W
authors.initials: DY
authors.lastname: Ng
authors.forename: Matthias
authors.initials: M
authors.lastname: Arzt
authors.forename: Jessica
authors.initials: J
authors.lastname: Thomas
authors.forename: Jan O
authors.initials: JO
authors.lastname: Mueller
authors.forename: Christopher
authors.initials: C
authors.lastname: Barner-Kowollik
authors.forename: Tanja
authors.initials: T
authors.lastname: Weil
mesh_terms: D045744:Cell Line, Tumor; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D050091:Dendrimers / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D004317:Doxorubicin / Q000737:chemistry; D006801:Humans; D007364:Intercalating Agents / Q000737:chemistry*; D018613:Microscopy, Confocal; D013004:Somatostatin / Q000737:chemistry* / Q000378:metabolism; D013777:Tetrazoles / Q000737:chemistry; D014466:Ultraviolet Rays
chemical_list: D050091:Dendrimers; D004220:Disulfides; D007364:Intercalating Agents; C104700:PAMAM Starburst; D013777:Tetrazoles; C045574:1H-tetrazole; D013004:Somatostatin; D004317:Doxorubicin
keywords: disulfides; imaging agents; intercalation; peptides; somatostatin