426833-33-2Relevant academic research and scientific papers
Facilitated phosphatidylserine flip-flop across vesicle and cell membranes using urea-derived synthetic translocases
Sasaki, Yoshihiro,Shukla, Rameshwer,Smith, Bradley D.
, p. 214 - 219 (2004)
Tris(2-aminoethyl)amine derivatives with appended urea and sulfonamide groups are shown to facilitate the translocation of fluorescent phospholipid probes and endogenous phosphatidylserine across vesicle and erythrocyte cell membranes. The synthetic translocases appear to operate by binding to the phospholipid head groups and forming lipophilic supramolecular complexes which diffuse through the non-polar interior of the bilayer membrane.
Structure/activity study of tris(2-aminoethyl)amine-derived translocases for phosphatidylcholine
Boon, J. Middleton,Lambert, Timothy N.,Smith, Bradley D.,Beatty, Alicia M.,Ugrinova, Vesela,Brown, Seth N.
, p. 2168 - 2174 (2002)
Sulfonamide and amide derivatives of tris(aminoethyl)amine (TREN) are known to facilitate phospholipid translocation across vesicle and erythrocyte membranes; that is, they act as synthetic translocases. In this report, a number of new TREN-based translocases are evaluated for their abilities to bind phosphatidylcholine and translocate a fluorescent phosphatidylcholine probe. Association constants were determined from 1H NMR titration experiments, and translocation half-lives were determined via 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)/dithionite quenching assays. A rough correlation exists between translocase/phosphatidylcholine association constants and translocation half-lives. The tris-sulfonamide translocases are superior to the tris-amide versions because they associate more strongly with the phospholipid headgroup. The stronger association is due to the increased acidity of the sulfonamide NHs as well as a molecular geometry (as shown by X-ray crystallography) that is able to form tridentate complexes with one of the phosphate oxygens. Two fluorescent translocase analogues were synthesized and used to characterize membrane partitioning properties. The results indicate that the facilitated translocation of phospholipids by TREN-derived translocases is due to the formation of hydrogen-bonded complexes with the phospholipid headgroups. In the case of zwitterionic phosphatidylcholine, it is the neutral form of the translocases that rapidly associates with the phosphate portion of the phosphocholine headgroup. Complexation masks the headgroup polarity and promotes diffusion of the phospholipid-translocase complex across the lipophilic interior of the membrane.
Facilitated phospholipid translocation in vesicles and nucleated cells using synthetic small molecule scramblases
DiVittorio, Kristy M.,Hofmann, Frank T.,Johnson, James R.,Abu-Esba, Lica,Smith, Bradley D.
experimental part, p. 141 - 148 (2011/02/26)
A series of 16 synthetic scramblase candidates were prepared from a tris(aminoethyl)amine (TREN) scaffold and evaluated for ability to facilitate translocation of fluorescent phospholipid probes across vesicle membranes and endogenous phosphatidylserine a
