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

Abstract

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.

• Authors: K Schwarz, A Fredga
• Journal: Bioinorganic chemistry (Bioinorg Chem) Vol. 4 Issue 3 Pg. 235-43 (Apr 1975) ISSN: 0006-3061 [Print] United States
• PMID: 1125338 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Organometallic Compounds
• Selenium

Topics

• Animals
• Liver (drug effects)
• Necrosis (chemically induced)
• Organometallic Compounds (pharmacology)
• Rats
• Selenium (pharmacology)
• Structure-Activity Relationship