Out-to-in translocation of butanetriol-containing phospholipid analogs in human erythrocyte membrane

Abstract

Fluorescent butanetriol-containing phospholipids analogs were synthesized by replacing the glycerol moiety in 1-hexadecanoyl-2-[6-N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl) aminohexanoyl]-sn-glycero-3-phosphocholine, -phosphoethanolamine, -phosphoserine and 1-hexadecanoyl-2-[12-N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)aminododecanoyl]-sn-glycero-3-phosphocholine, -phosphoethanolamine, -phosphoserine by the 1,3,4-butanetriol residue, and their out-to-in translocation in the human erythrocyte membrane studied by ‘back exchanging’ the outer surface incorporated phospholipids using bovine serum albumin. The results of these studies indicate that the replacement of the glycerol moiety by the 1,3,4-butanetriol residue in aminophospholipids does not effect their out-to-in translocation in the human erythrocyte membrane. Furthermore, since earlier study by Arora and Gupta (Biochim. Biophys. Acta 1324 (1997) 47-60) has shown that the conformation lf the 1,3,4-butanetriol phospholipids possess the backbone conformation similar to that of glycerophospholipids, it is suggested that besides the normal phospholipids polar head-group, a normal phospholipids interface conformation may also be required for the aminophospholipid-tanslocase interactions.