TY - JOUR
T1 - Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols
AU - García-Beltrán, Olimpo
AU - Santos, José G.
AU - Fuentealba, Sandra
AU - De La Torre, Pedro
AU - Pavez, Paulina
AU - Mena, Natalia
AU - Nuñez, Marco T.
AU - Aliaga, Margarita E.
N1 - Publisher Copyright:
© 2015 Elsevier Ltd.
PY - 2015/5/6
Y1 - 2015/5/6
N2 - We kinetically studied the reaction between endogenous thiols such as -γ-glutamylcysteine (γ-Glu-Cys), cysteine (Cys), glutathione (GSH), homocysteine (Hcy), cysteinylglycine (Cys-Gly), and dihydrolipoic acid (DHLA)- with (E)-2-(benzo[d]thiazol-2-yl)-3-(4-morpholinophenyl)acrylonitrile (JGB). Studies conducted by NMR and ESI-MS/MS have demonstrated that this reaction occurs via thiol-addition toward the double bond present in JGB. Considering the product analysis and the pH-dependence of the second order rate constant (kN), we proposed a mechanism that involves the rapid protonation of JGB giving place to an intermediate following by the thiolate attack yielding a final product. Moreover, this probe could successfully sense thiols in the human neuroblastoma SH-SY5Y cells.
AB - We kinetically studied the reaction between endogenous thiols such as -γ-glutamylcysteine (γ-Glu-Cys), cysteine (Cys), glutathione (GSH), homocysteine (Hcy), cysteinylglycine (Cys-Gly), and dihydrolipoic acid (DHLA)- with (E)-2-(benzo[d]thiazol-2-yl)-3-(4-morpholinophenyl)acrylonitrile (JGB). Studies conducted by NMR and ESI-MS/MS have demonstrated that this reaction occurs via thiol-addition toward the double bond present in JGB. Considering the product analysis and the pH-dependence of the second order rate constant (kN), we proposed a mechanism that involves the rapid protonation of JGB giving place to an intermediate following by the thiolate attack yielding a final product. Moreover, this probe could successfully sense thiols in the human neuroblastoma SH-SY5Y cells.
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U2 - 10.1016/j.tetlet.2015.03.083
DO - 10.1016/j.tetlet.2015.03.083
M3 - Article
AN - SCOPUS:84937758071
SN - 0040-4039
VL - 56
SP - 2437
EP - 2440
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 19
ER -