The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

Olimpo García-Beltrán; Natalia Mena; Edwin G. Pérez; Bruce K. Cassels; Marco T. Nuñez; Francisca Werlinger; Daniel Zavala; Margarita E. Aliaga; Paulina Pavez

doi:10.1016/j.tetlet.2011.09.137

The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

Olimpo García-Beltrán, Natalia Mena, Edwin G. Pérez, Bruce K. Cassels, Marco T. Nuñez, Francisca Werlinger, Daniel Zavala, Margarita E. Aliaga, Paulina Pavez

Olimpo

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Abstract

Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.

Original language	English
Pages (from-to)	6606-6609
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	49
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.137
Publication status	Published - Dec 7 2011

Bibliographical note

Funding Information:
This work was supported by FONDECYT (Grants #11090115 and 1100640 ), and the Millennium Scientific Initiative (Grant P05-001-F ).

Funding

This work was supported by FONDECYT (Grants #11090115 and 1100640 ), and the Millennium Scientific Initiative (Grant P05-001-F ).

Funders	Funder number
Fondo Nacional de Desarrollo Científico, Tecnológico y de Innovación Tecnológica	11090115, P05-001-F, 1100640

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.09.137

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title = "The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study",

abstract = "Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.",

author = "Olimpo Garc{\'i}a-Beltr{\'a}n and Natalia Mena and P{\'e}rez, {Edwin G.} and Cassels, {Bruce K.} and Nu{\~n}ez, {Marco T.} and Francisca Werlinger and Daniel Zavala and Aliaga, {Margarita E.} and Paulina Pavez",

note = "Funding Information: This work was supported by FONDECYT (Grants #11090115 and 1100640 ), and the Millennium Scientific Initiative (Grant P05-001-F ). ",

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T1 - The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

AU - García-Beltrán, Olimpo

AU - Mena, Natalia

AU - Pérez, Edwin G.

AU - Cassels, Bruce K.

AU - Nuñez, Marco T.

AU - Werlinger, Francisca

AU - Zavala, Daniel

AU - Aliaga, Margarita E.

AU - Pavez, Paulina

N1 - Funding Information: This work was supported by FONDECYT (Grants #11090115 and 1100640 ), and the Millennium Scientific Initiative (Grant P05-001-F ).

PY - 2011/12/7

Y1 - 2011/12/7

N2 - Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.

AB - Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.

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The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

Abstract

Bibliographical note

Funding

ASJC Scopus Subject Areas

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