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

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 could enhance microtubule integrity and function in leukocytes.

journal_name

Chem Biol Interact

authors

De Brabander M,Aerts F,Geuens G,van Ginckel R,van de Veire R,van Belle H

doi

10.1016/0009-2797(78)90041-8

subject

Has Abstract

pub_date

1978-10-01 00:00:00

pages

45-63

issue

1

eissn

0009-2797

issn

1872-7786

pii

0009-2797(78)90041-8

journal_volume

23

pub_type

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