Nucleophilic reactivity of biothiols toward coumarin-based derivatives containing a chalcone moiety

Olimpo García-Beltrán; Christopher González; Edwin G. Pérezc; Bruce K. Cassels; José G. Santos; Daniela Millán; Natalia Mena; Paulina Pavez; Margarita E. Aliaga

doi:10.1002/poc.2975

Nucleophilic reactivity of biothiols toward coumarin-based derivatives containing a chalcone moiety

Olimpo García-Beltrán, Christopher González, Edwin G. Pérezc, Bruce K. Cassels, José G. Santos, Daniela Millán, Natalia Mena, Paulina Pavez, Margarita E. Aliaga

Olimpo

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Abstract

TheMichael addition reactions of the biothiols cysteine (Cys), glutathione (GSH), homocysteine (Hcy) and cysteinylglycine (Cys-Gly) with (E)-3-(3-(2-methoxyphenyl)acryloyl)-7-methoxy-2H-chromen-2-one and (E)-3-(3-(3-methoxyphenyl) acryloyl)-7-methoxy-2H-chromen-2-one (ChC2 and ChC3, respectively) in aqueous solution (25 °C, ionic strength 0.2M KCl) were followed fluorimetrically and evaluated kinetically. With a large excess of biothiol, pseudo-first-order rate coefficients (k_obsd) were found. Plots of k_obsd versus [biothiolate] are linear, with a pH-independent slope (k_N). With the kinetic results obtained, the following conclusions can be drawn: (i) the reactivity increases in the sequence Cys-Gly<Hcy GSH<Cys; (ii) similar reactivity toward biothiols was found for ChC2 and ChC3, and both probes are more reactive than (E)-3-cinnamoyl-7- methoxy-2H-chromen-2-one (ChC1); (iii) ChC2 and ChC3 display a highly selective fluorescence enhancement with biothiols, allowing these probes to be used for fluorimetric biothiol determination in SH-SY5Y cells.

Original language	English
Pages (from-to)	946-952
Number of pages	7
Journal	Journal of Physical Organic Chemistry
Volume	25
Issue number	11
DOIs	https://doi.org/10.1002/poc.2975
Publication status	Published - Nov 2012

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry

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@article{3db234c9f3824b7c973508ed366961ef,

title = "Nucleophilic reactivity of biothiols toward coumarin-based derivatives containing a chalcone moiety",

abstract = "TheMichael addition reactions of the biothiols cysteine (Cys), glutathione (GSH), homocysteine (Hcy) and cysteinylglycine (Cys-Gly) with (E)-3-(3-(2-methoxyphenyl)acryloyl)-7-methoxy-2H-chromen-2-one and (E)-3-(3-(3-methoxyphenyl) acryloyl)-7-methoxy-2H-chromen-2-one (ChC2 and ChC3, respectively) in aqueous solution (25 °C, ionic strength 0.2M KCl) were followed fluorimetrically and evaluated kinetically. With a large excess of biothiol, pseudo-first-order rate coefficients (kobsd) were found. Plots of kobsd versus [biothiolate] are linear, with a pH-independent slope (kN). With the kinetic results obtained, the following conclusions can be drawn: (i) the reactivity increases in the sequence Cys-Gly",

author = "Olimpo Garc{\'i}a-Beltr{\'a}n and Christopher Gonz{\'a}lez and P{\'e}rezc, {Edwin G.} and Cassels, {Bruce K.} and Santos, {Jos{\'e} G.} and Daniela Mill{\'a}n and Natalia Mena and Paulina Pavez and Aliaga, {Margarita E.}",

year = "2012",

month = nov,

doi = "10.1002/poc.2975",

language = "English",

volume = "25",

pages = "946--952",

journal = "Journal of Physical Organic Chemistry",

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T1 - Nucleophilic reactivity of biothiols toward coumarin-based derivatives containing a chalcone moiety

AU - García-Beltrán, Olimpo

AU - González, Christopher

AU - Pérezc, Edwin G.

AU - Cassels, Bruce K.

AU - Santos, José G.

AU - Millán, Daniela

AU - Mena, Natalia

AU - Pavez, Paulina

AU - Aliaga, Margarita E.

PY - 2012/11

Y1 - 2012/11

N2 - TheMichael addition reactions of the biothiols cysteine (Cys), glutathione (GSH), homocysteine (Hcy) and cysteinylglycine (Cys-Gly) with (E)-3-(3-(2-methoxyphenyl)acryloyl)-7-methoxy-2H-chromen-2-one and (E)-3-(3-(3-methoxyphenyl) acryloyl)-7-methoxy-2H-chromen-2-one (ChC2 and ChC3, respectively) in aqueous solution (25 °C, ionic strength 0.2M KCl) were followed fluorimetrically and evaluated kinetically. With a large excess of biothiol, pseudo-first-order rate coefficients (kobsd) were found. Plots of kobsd versus [biothiolate] are linear, with a pH-independent slope (kN). With the kinetic results obtained, the following conclusions can be drawn: (i) the reactivity increases in the sequence Cys-Gly

AB - TheMichael addition reactions of the biothiols cysteine (Cys), glutathione (GSH), homocysteine (Hcy) and cysteinylglycine (Cys-Gly) with (E)-3-(3-(2-methoxyphenyl)acryloyl)-7-methoxy-2H-chromen-2-one and (E)-3-(3-(3-methoxyphenyl) acryloyl)-7-methoxy-2H-chromen-2-one (ChC2 and ChC3, respectively) in aqueous solution (25 °C, ionic strength 0.2M KCl) were followed fluorimetrically and evaluated kinetically. With a large excess of biothiol, pseudo-first-order rate coefficients (kobsd) were found. Plots of kobsd versus [biothiolate] are linear, with a pH-independent slope (kN). With the kinetic results obtained, the following conclusions can be drawn: (i) the reactivity increases in the sequence Cys-Gly

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SN - 0894-3230

VL - 25

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JO - Journal of Physical Organic Chemistry

JF - Journal of Physical Organic Chemistry

IS - 11

ER -

Nucleophilic reactivity of biothiols toward coumarin-based derivatives containing a chalcone moiety

Abstract

ASJC Scopus Subject Areas

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