By J. Greenstein, et al.,
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Additional info for Advances in Cancer Research [Vol II]
One suggestion is that they polymerize and that the side chains then bring about crosslinking with multipoint attachment of two protein or nucleoprotein chains of chromosomal origin. Another suggestion is that one arm of the monomeric form reacts with a cell compound followed by self condensation via the second reactive group. The polymerization hypothesis finds a measure of support from the fact that ethylene imines can polymerize under mild conditions according to this reaction: R I R I R The corresponding reaction with epoxides has also been recorded though only in alkaline media.
This objection was appreciated by Fraenkel-Conrat some years later when he and Olcott (1946) showed that the dye uptake method could not be used for following esterification of proteins by alcohols. The shift in the isoelectric point of egg albumin from pH 5 to 8 on treatment with propylene oxide noted by Fraenkel-Conrat (1944) could result from the blocking of approximately 10 % of the carboxyl groups and could also have been brought about by the quaternization of the imidazole group of histidine, which was shown to occur with mustard gas (Davies and Ross, 1947) ; it does not therefore provide confirmatory evidence for extensive reaction with the carboxyl groups.
In the mesyloxy series those compounds which cannot inhibit tumor growth and which cannot form cyclic compounds (see p. 10) are amongst the best crosslinking agents examined. It is interesting that the aliphatic mustards fail to crosslink wool although they will crosslink soluble protein. The experiments with wool fibers do not, of course, constitute proof against the crosslinking hypothesis, although in the author’s opinion they detract from the support which had been deduced from the fact that the cytotoxic alkylating agents were all capable of crosslinking macromolecules in one system or another.