507264-57-5Relevant academic research and scientific papers
Nucleophilic reactivity of thiolate, hydroxide, and phenolate ions toward a model O2-arylated diazeniumdiolate prodrug in aqueous and cationic surfactant media
Ning, Matthew S.,Price, Stacy E.,Ta, Jackie,Davies, Keith M.
supporting information; experimental part, p. 220 - 226 (2010/09/07)
The kinetics of aromatic nucleophilic substitution of the nitric oxide-generating diazeniumdiolate ion, DEA/NO, by thiols (L-glutathione, L-cysteine, DL-homocysteine, 1-propanethiol, 2-mercaptoethanol, and sodium thioglycolate) from the prodrug, DNP-DEA/NO, has been examined in aqueous solution and in solutions of cationic DOTAP vesicles. Second-order rate constants in buffered aqueous solutions (kRS-=3.48-30.9M-1 s-1; 30°C) gave a linear Bronsted plot (βnuc=0.414±0.068) consistent with the rate-limiting SNAr nucleophilic attack by thiolate ions. Cationic DOTAP vesicles catalyze the thiolysis reactions with rate enhancements between 11 and 486-fold in Tris-HCl buffered solutions at pH 7.4. The maximum rate increase was obtained with thioglycolate ion. Thiolysis data are compared to data for nucleophilic displacement by phenolate (kPhO-=0.114M-1 s-1) and hydroxide (kOH-=1.82×10-2M-1 s -1, 37°C) ions. The base hydrolysis reaction is accelerated by CTAB micelles and DODAC vesicles, with the vesicles being ca 3-fold more effective as catalysts. Analysis of the data using pseudo-phase ion-exchange (PIE) formalism implies that the rate enhancement of the thiolysis and base hydrolysis reactions is primarily due to reactant concentration in the surfactant pseudo-phase. Copyright
Controlled photochemical release of nitric oxide from O2-naphthylmethyl- and O2-naphthylallyl-substituted diazeniumdiolates
Bushan, K. Mani,Xu, Hua,Ruane, Patrick H.,D'Sa, Raechelle A.,Pavlos, Christopher M.,Smith, Joseph A.,Celius, Tevye C.,Toscano, John P.
, p. 12640 - 12641 (2007/10/03)
The photochemistry of O2-naphthylmethyl- and O2-naphthylallyl-substituted diazeniumdiolates has been investigated. Electron-donating methoxy group substitution is shown to have a significant effect on the observed photochemistry, with the appropriate substitution pattern resulting in efficient diazeniumdiolate photorelease. Observed nitric oxide release rates from these photoprecursors are consistent with those expected for normal thermal dissociation of the diazeniumdiolate in aqueous solutions and show the same pH dependence. Copyright
