By Jesse P. Greenstein and Alexander Haddow
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Extra info for Advances in Cancer Research, Vol. 2
Peters and Wakelin (1947) also found chlorine in mustard-treated kerateine, but observed that the amount decreased when the protein was washed for long periods with water. They attribute this to the slow hydrolysis of the chloroalkyl group introduced. , Stora et al. washed their proteins for eight days). Kinetic studies with mustard gas and related compounds (cf. , 1946) established quite definitely that the rate of hydrolysis is fast. (CH2)2Cl, convincing explanation would seem to be that the “combined” chlorine is present as a ‘ I gegen-ion ” necessary for maintaining electrical neutrality of the protein after esterification of carboxyl groups.
However, even such a polymerization is most unlikely, and no evidence for it could be found. Unless the mesyloxy compounds act by a different mechanism from that of the other alkylating agents, which is improbable in view of the general chemical similarities, the polymerization hypothesis will be difficult t o sustain. 24 PETER ALEXANDER 5. Reaction with Nucleic Acids A. Site of Reaction. Reference has already been made to the readiness with which nucleic acids react with mustard gas and HN2. From general considerations of the reactivity of these compounds reaction a t pH 7 is possible in nucleic acids with the primary and secondary phosphate groups which are fully dissociated and the amino groups of adenine, cytidine, and guanine; the last group, in view of its low basicity, is not very electrophilic and is thus unlikely t o have high competition factors.
Thus after a direct hit of a macromolecule (M) the following series of reactions may occur in a living system (Burton, 1952). , not within the target) the HOz radical produced may diffuse to the target site and react there. Considerations such as these may resolve the controversy (cf. Gray, 1952) whether the action of radiations on living cells is direct or via f ree radicals. In very dilute solutions it is improbable that an ionization of the macromolecule will occur and the ionization products of water have to be considered as the active intermediaries.
Advances in Cancer Research, Vol. 2 by Jesse P. Greenstein and Alexander Haddow