Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols

Olimpo García-Beltrán; José G. Santos; Sandra Fuentealba; Pedro De La Torre; Paulina Pavez; Natalia Mena; Marco T. Nuñez; Margarita E. Aliaga

doi:10.1016/j.tetlet.2015.03.083

Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols

Olimpo García-Beltrán, José G. Santos, Sandra Fuentealba, Pedro De La Torre, Paulina Pavez, Natalia Mena, Marco T. Nuñez, Margarita E. Aliaga

Olimpo

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Abstract

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 (k_N), 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.

Original language	English
Pages (from-to)	2437-2440
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2015.03.083
Publication status	Published - May 6 2015

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Publisher Copyright:
© 2015 Elsevier Ltd.

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols",

abstract = "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.",

author = "Olimpo Garc{\'i}a-Beltr{\'a}n and Santos, {Jos{\'e} G.} and Sandra Fuentealba and {De La Torre}, Pedro and Paulina Pavez and Natalia Mena and Nu{\~n}ez, {Marco T.} and Aliaga, {Margarita E.}",

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year = "2015",

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doi = "10.1016/j.tetlet.2015.03.083",

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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.

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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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols

Abstract

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