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H2N-. , 1940) that isoelectric proteins are esterified by diazomethane which can react only with unionized carboxyl groups. The observation of Banks et al. (1946) that the amount of mustard gas that can combine with serum proteins is doubled if the amino groups have been reacted with isocyanate can also be interpreted according to this hypothesis, since after blocking the amino group the corresponding carboxyl groups will no longer be restrained as zwitterions and can then react with mustard gas a t pH 7.

No experiments have been carried out from which any valid deduction can be drawn concerning the reaction of carboxyl groups with nitrogen mustards; however, the available evidence shows that nitrogen mustards differ significantly from sulfur mustard in that they react with e-amino groups of protein. , 70%of the terminal amino and €-amino groups had reacted). At lower pH values the extent of this reaction was considerably less. These results were confirmed by Alexander and Fox (1953a) for three epoxides with wool and for a bisepoxide with serum albumin (see Table IV).

THE REACTIONS OF CARCINOGENS WITH MACROMOLECULES -C=rj- d-A 41 I-C=N-- -d+ CH,I bH* Such a structure would not be stable and may hydrolyze in such a way as to bring about peptide bond fission. An indirect indication that a cytotoxic alkylating agent degrades proteins came from the discovery that serum protein after incubation with mustard gas increased capillary permeability. Cullumbine and Rydon (1946), suggested that a polypeptide had been liberated since earlier workers had found a factor capable of inducing capillary permeahility in enzymatically digested proteins and had established that the active pria- FIG.

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Advances in Cancer Research [Vol II] by J. Greenstein, et al.,


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