Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs : relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity

Wang, X. and Creek, D. J. and Schiaffo, C. E. and Dong, Y. and Chollet, J. and Scheurer, C. and Wittlin, S. and Charman, S. A. and Dussault, P. H. and Wood, J. K. and Vennerstrom, J. L.. (2009) Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs : relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity. Bioorganic & medicinal chemistry letters : a Tetrahedron publication for the rapid dissemination of preliminary communications on all aspects of bioorganic chemistry, medicinal chemistry, bioinorganic chemistry and related disciplines, Vol. 19, H. 16. pp. 4542-4545.

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Official URL: http://edoc.unibas.ch/dok/A5843331

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Abstract

These data suggest that iron(II) reactivity for a set of homologous spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane peroxide heterocycles is a necessary, but insufficient, property of animalarial peroxides. Heme alkylation efficiency appears to give a more accurate prediction of antimalarial activity than FeSO(4)-mediated reaction rates, suggesting that antimalarial activity is not merely dependent on peroxide bond cleavage, but also on the ability of reactive intermediates to alkylate heme or other proximal targets

Faculties and Departments:	09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:	Wittlin, Sergio
Item Type:	Article, refereed
Article Subtype:	Research Article
Publisher:	Pergamon
ISSN:	0960-894X
Note:	Publication type according to Uni Basel Research Database: Journal article
Related URLs:	Document
Identification Number:	pmid: 19616946
Last Modified:	14 Sep 2012 07:18
Deposited On:	14 Sep 2012 06:46

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