First determination of the standard potential for the dissociative reduction of the antimalarial agent artemisinin

Journal of Physical Chemistry B

Volumn 102, Issue 21, 1998, Pages 4061-4063

  Donkers, Robert L ^a   Workentin, Mark S ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040077182     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp981457m     Document Type: Article

References (32)

1. Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Microbiol. Rev. 1996, 60, 301-315.
2. Haynes, R. K.; Vonwiller, S. C. Acc. Chem. Res. 1997, 30, 73-79.
3. Robert, A.; Meunier, B. J. Am. Chem. Soc. 1997, 119, 5968-5969.
4. Posner, G. H.; Park, S. B.; Gonzalez, L.; Wang, D.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A.; Bachi, M. D. J. Am. Chem. Soc. 1996, 118, 3537-3538.
5. Cummings, J. N.; Wang, D.; Park, S. B.; Shapiro, T. A.; Posner, G. H. J. Med. Chem. 1998, 41, 952-964 and references therein.
6. Zhang, F.; Gosser, D. K., Jr.; Meshnick, S. R. Biochem. Pharmacol. 1992, 43, 1805-1809.
7. Jiang, L. H.; Chen, K. X.; Tang, Y.; Chen, J. Z.; Li, Y.; Wang, M. Q.; Ji, R. Y.; Huang, Q. K. Indian J. Chem. 1997, 36B, 154-160.
8. Chen, Y.; He, C.-X.; Zhu, S.-M.; Chen, H.-Y. J. Electrochem Soc 1997, 144, 1891-1894.
9. Workentin, M. S.; Donkers, R. L. J. Am. Chem. Soc. 1998, 120 2664-2665.
10. Workentin, M. S.; Maran, F.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 2120-2121.
11. Antonello, S.; Musumeci, M.; Wayner, D. D. M.; Maran, F. J. Am. Chem. Soc. 1997, 119, 9541-9549.
12. Donkers, R. L.; Maran, F.; Wayner, D. D. M.; Workentin, M. S. Manuscript in preparation.
13. Fc+/Fc is 0.475 vs SCE in DMF). Artemisinin was obtained from Aldrich and used as received.
14. Savéant, J.-M. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press Inc.: Greenwich, CT, 1994; Vol. 4, pp 53-116 and references cited therein.
15. Savéant, J.-M. Acc. Chem. Res. 1993, 26, 455-461.
16. (a) Bulk electrolyses were carried out under constant potential conditions in a divided cell at both Hg and carbon cathodes, both in the presence and absence of a non-nucleophilic acid.
17. • or another easily reduced species formed by reaction of the initially formed distonic radical anion.
18. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, Fundamentals and Applications; Wiley: New York, 1980.
19. This observation and its ramifications will be reported separately.
20. Imbeaux, J. C.; Savéant, J.-M. J. Electroanal. Chem. 1973, 44, 169-187.
21. The first reduction involves cleavage of the O-O bond. Whether the second reduction involves reduction of the alkoxy radical or another radical intermediate, generated after initial cleavage, is not yet known. However, for the analysis of the data it is not important.
22. 1/2C*, where n equals the number of electrons, C* is the bulk concentration of the substrate, and using an electrode of known area (A). This value agrees with a value recently reported: Chen, Y.; Zhu, S. M.; Chen, H. Y.; Li, Y. Acta Chim. Sin. 1997, 55, 921-925.
23. (a) Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 10595-10602.
24. (b) Savéant, J.-M. J. Am. Chem. Soc. 1987, 109, 6788-6795.
25. (c) Marcus, R. A.; Sutin, N. Biochem. Biophys. Acta 1985, 811, 265.
26. We thank Professor Maran for supplying us with a copy of his data analysis program.
27. app/(1 - ∂φ†/ ∂E), where φ† is the difference between the potential of the bulk solution and the potential at the average distance at which ART is located when ET occurs.
28. Antonello, S.; Maran, F. J. Am. Chem. Soc. 1997, 119, 12595-12600.
29. -1. Full details of these calculations will be reported at a later date (Guthrie, J. P.; Workentin, M. S., work in progress).
30. (a) Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
31. (b) NIST Standard Reference Database 25. NIST Structures and Properties Database and Estimation Program. 1991; U.S. Department of Commerce: Gaithersburg, MD 20899, 1991.
32. (c) Ibrahim, M. R.; Schleyer, P. v. R. J. Comput. Chem. 1985, 6, 157-167.