%0 Journal Article %1 RN66 %A Garcia-Beltran, O. %A Gonzalez, C. %A Perez, E.G. %A Cassels, B.K. %A Santos, J.G. %A Millan, D. %A Mena, N. %A Pavez, P. %A Aliaga, M.E. %D 2012 %I 2012 John Wiley & Sons, Ltd. %J Journal of Physical Organic Chemistry %K addition, biothiols, coumarin-based cysteine derivatives, dqcauchile fluorescence fluorescent glutathione, homocysteine, michael probe, probes, %N 11 %P 946-952 %R 10.1002/poc.2975 %T Nucleophilic Reactivity of Biothiols toward Coumarin-Based Derivatives Containing a Chalcone Moiety %U /brokenurl#<Go to ISI>://WOS:000310486900011 %V 25 %X The Michael 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 degrees C, ionic strength 0.2 M 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.

@article{RN66, abstract = {The Michael 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 degrees C, ionic strength 0.2 M 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.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Garcia-Beltran, O. and Gonzalez, C. and Perez, E.G. and Cassels, B.K. and Santos, J.G. and Millan, D. and Mena, N. and Pavez, P. and Aliaga, M.E.}, biburl = {https://www.bibsonomy.org/bibtex/259bbeeb4599db4124ca8fd22296b3d19/dqcauchile}, doi = {10.1002/poc.2975}, interhash = {ff878002720ea551769932fe809475b8}, intrahash = {59bbeeb4599db4124ca8fd22296b3d19}, issn = {0894-3230}, journal = {Journal of Physical Organic Chemistry}, keywords = {addition, biothiols, coumarin-based cysteine derivatives, dqcauchile fluorescence fluorescent glutathione, homocysteine, michael probe, probes,}, number = 11, pages = {946-952}, publisher = {2012 John Wiley & Sons, Ltd.}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Nucleophilic Reactivity of Biothiols toward Coumarin-Based Derivatives Containing a Chalcone Moiety}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000310486900011}, volume = 25, year = 2012 }