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

Universidad de ibagué

Resultado de la investigación: Contribución a una revista › Artículo

5 Citas (Scopus)

Resumen

Idioma original	Inglés estadounidense
Páginas (desde-hasta)	2437-2440
Número de páginas	2192
Publicación	Tetrahedron Letters
DOI	https://doi.org/10.1016/j.tetlet.2015.03.083
Estado	Publicada - 6 may 2015

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10.1016/j.tetlet.2015.03.083

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García-Beltrán, O., Santos, J. G., Fuentealba, S., De La Torre, P., Pavez, P., Mena, N., Nuñez, M. T., & Aliaga, M. E. (2015). Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols. Tetrahedron Letters, 2437-2440. https://doi.org/10.1016/j.tetlet.2015.03.083

@article{646ab560d9594d3b8756f9afa85de0a2,

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

abstract = "{\textcopyright} 2015 Elsevier Ltd. 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.}",

year = "2015",

month = may,

day = "6",

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

language = "American English",

pages = "2437--2440",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

}

Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols. / García-Beltrán, Olimpo; Santos, José G.; Fuentealba, Sandra; De La Torre, Pedro; Pavez, Paulina; Mena, Natalia; Nuñez, Marco T.; Aliaga, Margarita E.

En: Tetrahedron Letters, 06.05.2015, p. 2437-2440.

Resultado de la investigación: Contribución a una revista › Artículo

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.

PY - 2015/5/6

Y1 - 2015/5/6

N2 - © 2015 Elsevier Ltd. 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 - © 2015 Elsevier Ltd. 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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