By Jesse P. Greenstein and Alexander Haddow
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Reaction between nitrogen mustards and protein carboxyl groups cannot readily be detected from changes in acid combination since the titration of ‘the mustard amine to its salt and the back titration of the carboxyl ion with acid occur in the same pH range. There is no reason to believe that the nitrogen mustard esters derived from proteins are exceptionally THE REACTIONS O F CARCINOGENS WITH MACROMOLECULES 39 labile since Davis and Ross (1950) found that the acetates of both aliphatic and aromatic mustards were more stable to acid hydrolyses and only slightly less stable to alkaline hydrolysis than ethyl acetate.
Kahler, 1948; Butler and James, 1951). From the foregoing it is obvious that the only valid conclusion which can be drawn from the physical changes produced by the mustards, such as decrease in viscosity and rate of sedimentation and increase in rate of diffusion, is that the extent of interaction between DNA molecules in solution is reduced. Depolymerization of the macromolecule as for example with x-rays, is only one way by which this can be brought about, but this seems an unlikely mechanism for the mustards since they do not form free radicals (see p.
Greenstein and Jenrette (1941) (see also Conway and Butler, 1952) showed that urea decreased the viscosity of DNA, and from this it can be 30 PETER ALEXANDER deduced that the intermolecular links are formed by hydrogen bonds, the formation of which can be prevented by blocking the amino and hydroxyl groups. This mechanism was favored by Butler, Conway, and James (1951) but seems difficult to sustain in view of the fact that mustards react with no more than 10% of the available amino groups (see p.