title: O2-(N-hydroxy(methoxy)-2-ethanesulfonamido) protected diazen-1-ium-1,2-diolates: nitric oxide release via a base-induced β-elimination cleavage.
abstract: O(2)-(Ethanesulfohydroxamic acid) and O(2)-(N-methoxy-2-ethanesulfonylamido) diazen-1-ium-1,2-diolates (4-7), a novel type of O(2)-(protected) diazeniumdiolate, were synthesized using a key thioacetate oxidation reaction. Nitric oxide release studies showed that O(2)-(N-methoxy-2-ethanesulfonylamido) diazeniumdiolates 5 and 7 released NO in a nonphysiological alkaline buffer, in the presence of bases such as the basic natural amino acids Arg and His, or the non-nucleophilic organic base DBU in PBS at pH 7.4, via a β-elimination cleavage reaction.
authors.affiliation: Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, Canada.
authors.forename: Zhangjian
authors.initials: Z
authors.lastname: Huang
authors.forename: Edward E
authors.initials: EE
authors.lastname: Knaus
mesh_terms: D001120:Arginine / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002021:Buffers; D006639:Histidine / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009569:Nitric Oxide / Q000032:analysis; D020030:Nitric Oxide Donors / Q000737:chemistry*; D010084:Oxidation-Reduction; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D002021:Buffers; D006877:Hydroxamic Acids; D020030:Nitric Oxide Donors; D013449:Sulfonamides; C452539:diazeniumdiolate; D009569:Nitric Oxide; D006639:Histidine; D001120:Arginine