Biological potency of organic selenium compounds: VI. Aliphatic seleninic acids and carboxyseleninic acids

✍ Scribed by Klaus Schwarz; Arne Fredga

• Publisher: Elsevier Science
• Year: 1975
• Weight: 493 KB
• Volume: 4
• Category: Article
• ISSN: 0006-3061
• DOI: 10.1016/s0006-3061(00)80106-4

✦ Synopsis

Straight-chain aliphatic seleninic acids, CH3-(CH2)n-SeOOH, with chain lengths from C4 to C17, a few dibasic acids of moderate chain length having seleninic acid groups on both ends of the molecule, HOOSe-(CH2)n-SeOOH, and a series of carbosyseleninic acids, HOOC-R-SeOOH, comprising chain lengths from C3 to C13 and several branched chains with 5 to 7 carbon atoms were tested for potency in the prevention of dietary liver necrosis in the rat. Alkylseleninic acids showed uniformly low activities, ranging from 18% to 56% of that of selenite selenium which served as a standard. There were no discernible trends or regularities with increasing chain lengths, in c-ntrast to other series of alkylselenium compounds. It is therefore unlikely that alkylseleninic acids are normal oxidation products of dialkyl mono- or diselenides in the organism. Compounds with seleninic acid groups at both ends of the chain were practically inactive. Carboxyseleninic acids carrying a carboxyl group distal to the seleninic acid group, on the other hand, were highly effective. A maximum of potency occurred at chain lengths C3 and C4, followed by a sharp decline between C4 and C6. A second maximum of activity occurred at C8. There was no alternating effect. This structure/activity pattern is analogous to that of the diselenodicarboxylic acids. However, the lower carboxyseleninic acids were, per atom of selenium, twice as active as the corresponding diseleno-dicarboxylic acids, of which the higher members were less potent. It is inferred that carboxyseleninic acids may be metabolically related to diseleno-dicarboxylic acids and that C3 and C4 carboxyseleninic acids may play a physiological role.