Antimitotic Action of Maleimide and Related Substances

Friedmann, E.; Marrian, D. H.; Simon‐Reuss, I.

doi:10.1111/j.1476-5381.1949.tb00521.x

Cited by 62 publications

(42 citation statements)

References 5 publications

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“…Most of them are localised in the cell interior, so that one may suppose that all maleimides used in our studies eventually crossed the mammalian cell membrane, not targeting β(1,3)-glucan synthase, as this enzyme is absent in mammalian cells. Most probably, the observed inhibition of growth of HeLa cells is a consequence of the previously reported anti-mitotic activity of maleimidic compounds 29 . Mammalian toxicity of maleimides disqualifies these compounds as drug candidates for chemotherapy of disseminated fungal infections, but their use for the treatment of superficial mycoses seems possible, as was previously shown for some other maleimide derivatives in an animal model of trichophytosis 30 .…”

Section: Discussionmentioning

confidence: 90%

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Salewska

Boros-Majewska

Łącka

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Discussionmentioning

confidence: 90%

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Salewska

Boros-Majewska

Łącka

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…(19,20). N-ethylmaleimide (NEM) 2 is an alkylating agent that forms stable addition products with sulfhydryl compounds (21)(22)(23). Both inhibitors react rather specifically with sulfhydryl groups in contradistinction to iodoacetate and the oxidizing agents (24).…”

Section: Methodsmentioning

confidence: 99%

Effects of Sulfhydryl Inhibition on Red Blood Cells. I. Mechanism of Hemolysis*

Jacob

Jandl²

1962

J. Clin. Invest.

300

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“…It was shown that N-ethylmaleimide (NEM) reacts rapidly and specifically with sulfhydryl groups to exert antimitotic action (6), and that this chemical nature of the substance is utilized for the titration of such groups in proteins (12). Thereafter, many studies on the bactericidal and fungicidal actions of NEM and its derivatives were reported (7,10).…”

mentioning

confidence: 99%

Antifungal Activities of N‐Substituted Maleimide Derivatives

Takatori

Hasegawa

Nakano

et al. 1985

Microbiology and Immunology

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It was shown that N-ethylmaleimide (NEM) reacts rapidly and specifically with sulfhydryl groups to exert antimitotic action (6), and that this chemical nature of the substance is utilized for the titration of such groups in proteins (12). Thereafter, many studies on the bactericidal and fungicidal actions of NEM and its derivatives were reported (7,10).In the present study, we synthesized N-substituted maleimides including Nalkyl, N-aralkyl, and N-1,3,4-thiadiazoly1 derivatives by the method of Kanaoka et al (9) and examined the antifungal activity of these compounds. The crystallized compounds to be tested were purified by recrystallization from the solvent and other liquid chemicals by silica gel chromatography using a mixture of ethyl acetate and chloroform as the eluent. The purity was verified by thin-layer chromatography, elementary analysis, melting point (mp) and mass spectrometry. The data for these chemicals are listed in Table 1.All the test chemicals were dissolved in dimethyl sulfoxide (DMSO) and were subjected to the following assay. By the plate dilution method, all the chemicals were tested for their inhibitory activities against Candida albicans (a clinical isolate), Aspergillus niger (IFO 6341), Penicillium citrinum (IFO 6352), and Trichophyton mentagrophytes (a clinical isolate) in Sabouraud dextrose agar (Difco) at pH 5.6 and 7.0 in the absence and presence of 10% beef serum. DMSO alone had no antifungal activity on the fungal cells under the experimental conditions used in this study. We used amphotericin B (Sankyo Co., Ltd., Tokyo, Japan) as a reference compound, which is clinically useful for the treatment of fungal diseases. Table 2 shows the antifungal activity of the N-substituted maleimide derivatives. N-alkyl maleimide derivatives were inactive against the tested microorganisms under the present conditions. On the other hand, N-thiadiazolyl derivatives of maleimide (TDZ, 5-Me-TDZ, and 5-Et-TDZ) exhibited antifungal activity against T. mentagrophytes at relatively low concentrations compared with N-alkyl maleimide derivatives, but they were less active than amphotericin B.Studies on interaction of N-alkylmaleimides with the sulfhydryl groups of several enzymes have been reported (1,2,5,8). They concluded that the Nalkylmaleimides interact with a hydrophobic region in the enzyme based on the facts that the inactivation of sulfhydryl groups is greatly affected by the chain length of the N-alkyl substituents of the maleimide derivatives, and that hydrophobicity 1237

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Antimitotic Action of Maleimide and Related Substances

Cited by 62 publications

References 5 publications

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Effects of Sulfhydryl Inhibition on Red Blood Cells. I. Mechanism of Hemolysis*

Antifungal Activities of N‐Substituted Maleimide Derivatives

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