A mechanism for the oxidation of glutathione to glutathione disulfide with organotellurium(IV) and organoselenium(IV) compounds. A stepwise process with implications for photodynamic therapy and other oxidative chemotherapy
dc.contributor.author | Detty, Michael | en_US |
dc.contributor.author | Friedman, Alan | en_US |
dc.contributor.author | Oseroff, Alan | en_US |
dc.date.accessioned | 2006-08-18T15:31:43Z | en_US |
dc.date.available | 2006-08-18T15:31:43Z | en_US |
dc.date.issued | 1994-12-30 | en_US |
dc.identifier.citation | The Journal of Organic Chemistry 59N26 (1994) 8245-8250 | en_US |
dc.identifier.issn | 1520-6904 | en_US |
dc.identifier.uri | http://hdl.handle.net/1850/2304 | en_US |
dc.description.abstract | The reactions of telluroxides or their hydrates 3-5 with glutathione to give telluropyrylium dyes 1, 2 or diphenyl telluride, respectively, and glutathione disulfide have at least two discrete steps. A fast reaction, which is first-order in both substrate and glutathione, is observed with second-order rate constants of 2.30 x 10(7) L mol(-1) s(-1) at 285.4 K for 3, 1.66 x 10(7) L mol(-1) s(-1) at 293.2 K for 4, and 5.2 x 10(6) L mol(-1) s(-1) at 285.5 K for 5. This reaction is followed by a slower reaction, which is first-order in both substrate and glutathione, with second-order rate constants of 2.65 x 10(5) L mol(-1) s(-1) at 293.5 K for 3, 3.34 x 10(5) L mol(-1) s(-1) at 293.2 K for 4, and 7.64 x 10(3) L mol(-1) s(-1) at 285.5 K for 5. The slow reaction is accompanied by the generation of the corresponding tellurium-(II) compound. Diphenyl selenoxide hydrate (6) displays similar behavior, although the rate constants associated with the fast (2.26 x 10(2) L mol(-1) s(-1)) and slow (6.62 x 10(1) L mol(-1) s(-1)) reactions are many orders-of-magnitude less than observed for the tellurium analogues. | en_US |
dc.format.extent | 31371 bytes | en_US |
dc.format.mimetype | application/pdf | en_US |
dc.language.iso | en_US | en_US |
dc.publisher | The American Chemical Society: The Journal of Organic Chemistry | en_US |
dc.subject | Chemotherapy | en_US |
dc.subject | Gluthathione | en_US |
dc.subject | Oxidation | en_US |
dc.title | A mechanism for the oxidation of glutathione to glutathione disulfide with organotellurium(IV) and organoselenium(IV) compounds. A stepwise process with implications for photodynamic therapy and other oxidative chemotherapy | en_US |
dc.type | Abstract | en_US |
dc.identifier.url | http://dx.doi.org/10.1021/jo00105a049 |
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