title: Facilitated phosphatidylserine flip-flop across vesicle and cell membranes using urea-derived synthetic translocases.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sasaki
authors.forename: Rameshwer
authors.initials: R
authors.lastname: Shukla
authors.forename: Bradley D
authors.initials: BD
authors.lastname: Smith
mesh_terms: D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D001692:Biological Transport; D002352:Carrier Proteins / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004910:Erythrocyte Membrane / Q000378:metabolism*; D004912:Erythrocytes / Q000166:cytology / Q000378:metabolism; D005033:Ethylmaleimide / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000737:chemistry / Q000378:metabolism; D006207:Half-Life; D006801:Humans; D008081:Liposomes / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008565:Membrane Proteins / Q000037:antagonists & inhibitors; D010718:Phosphatidylserines / Q000737:chemistry / Q000378:metabolism*; D049294:Phospholipid Transfer Proteins; D017186:Titrimetry; D014166:Transferases / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D014508:Urea / Q000031:analogs & derivatives*
chemical_list: D002352:Carrier Proteins; D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D008081:Liposomes; D008565:Membrane Proteins; D010718:Phosphatidylserines; D049294:Phospholipid Transfer Proteins; C063384:1-oleoyl-2-((N-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino)caproyl)phosphatidylserine; D014508:Urea; D014166:Transferases; D009327:4-Chloro-7-nitrobenzofurazan; D005033:Ethylmaleimide