title: S-[2-(4-azidosalicylamido)ethylthio]-2-thiopyridine: radioiodinatable, cleavable, photoactivatible cross-linking agent.
abstract: S-[2-(4-Azidosalicylamido)ethylthio]-2-thiopyridine (AET) contains a 2-thiopyridyl moiety, which permits cysteine-specific incorporation into protein through a cleavable disulfide bond, and a 4-azidosalicylamido moiety, which permits radioiodination and photoactivatible cross-linking. In contrast to the related compound S-[2-[N-[4-(4-azidosalicylamido)butyl]carbomoyl]ethylthio]-2 -thiopyridine [APDP; Zecherle, G., Oleinikov, A., and Traut, R. (1992) Biochemistry 31, 9526], AET contains a relatively short linker arm between the 2-thiopyridyl moiety and the 4-azidosalicylamido moiety. In a previous paper, it was shown that AET could be used in site-specific protein-protein photocross-linking to identify nearest-neighbor protein domains within a multiprotein complex [Chen, Y., Ebright, Y., and Ebright, R. (1994) Science 265, 90]. In this paper, the synthesis, radioiodination, and incorporation into protein of AET are described.
authors.affiliation: Department of Chemistry, Rutgers University, New Brunswick, New Jersey 08855, USA.
authors.forename: Y W
authors.initials: YW
authors.lastname: Ebright
authors.forename: Y
authors.initials: Y
authors.lastname: Chen
authors.forename: Y
authors.initials: Y
authors.lastname: Kim
authors.forename: R H
authors.initials: RH
authors.lastname: Ebright
mesh_terms: D001345:Autoradiography; D002855:Chromatography, Thin Layer; D003432:Cross-Linking Reagents / Q000032:analysis / Q000737:chemistry*; D002373:Cyclic AMP Receptor Protein / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry; D004926:Escherichia coli; D007457:Iodine Radioisotopes; D008623:Mercaptoethanol / Q000737:chemistry; D010777:Photochemistry; D010782:Photolysis; D011725:Pyridines / Q000032:analysis / Q000737:chemistry*; D012459:Salicylates / Q000032:analysis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013997:Time Factors
chemical_list: D003432:Cross-Linking Reagents; D002373:Cyclic AMP Receptor Protein; D004220:Disulfides; D007457:Iodine Radioisotopes; D011725:Pyridines; C101325:S-(2-(4-azidisalicylamido)ethylthio)-2-thiopyridine; D012459:Salicylates; D008623:Mercaptoethanol; D003545:Cysteine