Biological potency of organic selenium compounds V. diselenides of alcohols and amines, and some selenium–containing ketones

Abstract

The diselenides of straight-chain aliphatic alcohols with 2 to 4 carbon atoms, and the acetic acid ester of the C 5 homolog were similar in potency to the corresponding carboxylic acids in protecting against dietary liver necrosis in the rat. As in carboxylic acids, substitution of a methyl group at the carbon atom adjacent to the selenium atom diminished activity, but a methyl group in the β position had no such effect. Two methyl groups in the β position, producing a quaternary carbon atom, abolished biological activity, as seen in other series of compounds. Diselenides of aliphatic and heterocyclic amines showed low biological activity. 3-Aminopropyl diselenide was half as active and dimethyl and diethyl amino derivatives with C 2 and C 3 carbon chains only approximately 1/10th as active as selenite. N-piperidyl and N-morpholinyl derivatives with C 2 and C 3 carbon chains also showed low activity. Monoseleno-ketones, on the other hand, with ketone oxygen in the β or γ position to the selenium atom showed good activity, indicating an enhancing effect of the ketone oxygen on the biological availability of the selenium atom. The dimethylacetal of benzylseleno-acetaldehyde afforded 50% protection at a level of 1.1 μg% selenium (0.011 ppm selenium) in the diet, i.e., it was twice as active as selenite selenium or the corresponding benzylselenocarboxylic acid.