PMID: 11925224Apr 2, 2002Paper

Structure/activity study of tris(2-aminoethyl)amine-derived translocases for phosphatidylcholine

The Journal of Organic Chemistry
J Middleton BoonSeth N Brown

Abstract

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 (1)H 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 ...Continue Reading

References

Dec 24, 1991·Biochemistry·J C McIntyre, R G Sleight
Feb 24, 2001·Analytical Chemistry·Q QianH H Girault
Oct 15, 2001·Angewandte Chemie·Simone ValentePaolo Scrimin

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Citations

Dec 10, 2002·Current Opinion in Chemical Biology·J Middleton Boon, Bradley D Smith
Mar 3, 2012·Chemical & Pharmaceutical Bulletin·Nobuko MibuKunihiro Sumoto
Nov 10, 2006·Advanced Drug Delivery Reviews·Tian-Xiang Xiang, Bradley D Anderson
Jul 14, 2006·Bioorganic & Medicinal Chemistry·Suwanna VangveravongRobert H Mach
Jun 14, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Greta BergamaschiValeria Amendola
Mar 5, 2016·Physiological Reviews·Edouard M Bevers, Patrick L Williamson
Jan 4, 2013·Angewandte Chemie·Nathalie Busschaert, Philip A Gale
Apr 20, 2010·Inorganic Chemistry·Davide LionettiSeth N Brown
May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale
Sep 16, 2021·Organic & Biomolecular Chemistry·Luis Martínez-CrespoHennie Valkenier

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