DL-2-Oxo-3-(2-mercaptoethyl)-5-phenylimidazolidine. A sulfhydryl metabolite of levamisole that interacts with microtubules

Chemico-biological Interactions
M De BrabanderH Van Belle

Abstract

DL-2-Oxo-3-(2-mercaptoethyl)-5-phenylimidazolidine (OMPI) a sulfhydryl metabolite of levamisole, unlike the parent compound, is shown to interfere with the morphological and functional integrity of microtubules in cultured cells at high concentrations (1.6-10(-4) M). Lower concentrations do not affect the cell morphology, viability or growth rate in any appreciable way. Both levamisole and OMPI, at low concentrations (10(-5)-10(-6) m), markedly enhance the antimicrotubular effect of mercaptoethanol. High concentrations of OMPI (+/- 10(-4) M) inhibit the self-assembly of microtubules in a cell free system. Low concentrations (+/- 10(-6) M) markedly enhance the polymerization rate of tubulin. Levamisole has no effect on tubulin polymerization. The effects of OMPI on microtubules in cells and in the polymerization system can be reversed by reduced glutathione, cysteine and dithiothreitol. The data indicate that OMPI interacts in a biphasic manner with microtubule formation probably through interaction with critical SH-groups on the tubulin molecule. It seems of interest to further investigate the hypothesis that the immunomodulating properties of levamisole are at least partially due to the formation of its metabolite (OMPI) which...Continue Reading

References

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Citations

Jan 1, 1979·International Journal of Immunopharmacology·M De BrabanderG Geuens
Jan 1, 1988·International Journal of Immunopharmacology·V Ruszala-MallonB S Wang
Jan 1, 1991·International Journal of Immunopharmacology·J Van Wauwe, P A Janssen
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Jun 1, 1991·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Y Z ShuT D Wilkins
Jan 1, 1986·Biopharmaceutics & Drug Disposition·E KouassiM Vézina

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