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Molecules 2009, 14(6), 2062-2076;

Quantitative Structure ‒ Antiprotozoal Activity Relationships of Sesquiterpene Lactones

Westfälische Wilhelms-Universität Münster, Institut für Pharmazeutische Biologie und Phytochemie, Hittorfstraße 56, D-48149 Münster, Germany
University of Khartoum, Department of Pharmacognosy, Faculty of Pharmacy, P.O. box 1996, Khartoum, Sudan
Swiss Tropical Institute (STI), Socinstrasse 57, CH-4002 Basel, Switzerland
Author to whom correspondence should be addressed.
Received: 12 May 2009 / Revised: 4 June 2009 / Accepted: 5 June 2009 / Published: 8 June 2009
(This article belongs to the Special Issue Neglected Diseases: Medicinal Chemistry and Natural Product Chemistry)
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Prompted by results of our previous studies where we found high activity of some sesquiterpene lactones (STLs) against Trypanosoma brucei rhodesiense (which causes East African sleeping sickness), we have now conducted a structure-(in-vitro)-activity study on a set of 40 STLs against T. brucei rhodesiense, T. cruzi, Leishmania donovani and Plasmodium falciparum. Furthermore, cytotoxic activity against L6 rat skeletal myoblast cells was assessed. Some of the compounds possess high activity, especially against T. brucei (e.g. helenalin and some of its esters with IC50-values of 0.05-0.1 µM, which is about 10 times lower than their cytotoxic activity). It was found that all investigated antiprotozoal activities are significantly correlated with cytotoxicity and the major determinants for activity are a,b-unsaturated structural elements, also known to be essential for other biological activities of STLs. It was observed, however, that certain compounds are considerably more toxic against protozoa than against mammalian cells while others are more cytotoxic than active against the protozoa. A comparative QSAR analysis was therefore undertaken, in order to discern the antiparasitic activity of STLs against T. brucei and cytotoxicity. Both activities were found to depend to a large extent on the same structural elements and molecular properties. The observed variance in the biological data can be explained in terms of subtle variations in the relative influences of various molecular descriptors. View Full-Text
Keywords: Trypanosoma; Leishmania; Plasmodium; antiprotozoal activity; sesquiterpene lactone; QSAR Trypanosoma; Leishmania; Plasmodium; antiprotozoal activity; sesquiterpene lactone; QSAR

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Schmidt, T.J.; Nour, A.M.M.; Khalid, S.A.; Kaiser, M.; Brun, R. Quantitative Structure ‒ Antiprotozoal Activity Relationships of Sesquiterpene Lactones. Molecules 2009, 14, 2062-2076.

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