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Mechanism of Action of Methanesulfonates

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Antineoplastic and Immunosuppressive Agents

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Abstract

The methane sulfonate esters of dihydric and polyhydric alcohols are biological alkylating agents since their alkyl-oxygen bonds undergo fission and react within the intracellular milieu. The structure of the alkyl group of these esters may vary around the carbon atom adjacent to the oxygen atom where fission is likely to occur. This means that the alkyl group will tend to favor entry into the confines of a sterically favorable nucleophilic site, unlike the ethylene immonium series whose chemically variable grouping will always be separated from the nucleophilic site by a three atom chain and hence exert less of an influence on it. The local structural characteristics of the nucleophile itself would thus assist in conferring a degree of selectivity on the action of the alkane sulfonates.

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  1. Brian W. Fox
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Editors and Affiliations

  1. Department of Pharmacology, Yale University School of Medicine, 06510, New Haven, Connecticut, USA

    Alan C. Sartorelli (Professor) (Professor)

  2. Laboratory of Chemical Pharmacology, National Cancer Institute, National Institutes of Health, 20014, Bethesda, Maryland, USA

    David G. Johns M.D.

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© 1975 Springer-Verlag Berlin • Heidelberg

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Fox, B.W. (1975). Mechanism of Action of Methanesulfonates. In: Sartorelli, A.C., Johns, D.G. (eds) Antineoplastic and Immunosuppressive Agents. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 38 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65806-8_4

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  • DOI: https://doi.org/10.1007/978-3-642-65806-8_4

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