Abstract
Cholate esters with phenylurea groups at the 7alpha- and 12alpha-positions are highly effective promoters of phosphatidylcholine translocation across vesicle and cell membranes. The urea groups are essential for strong binding of the highly polar phosphate portion of the phosphocholine headgroup and apparently cannot be replaced by simple amide, alcohol, or amine moieties. NMR and UV studies show that these synthetic translocases have very weak affinity for phosphatidylethanolamine and phosphatidylserine.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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4-Chloro-7-nitrobenzofurazan / analogs & derivatives*
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4-Chloro-7-nitrobenzofurazan / chemistry
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4-Chloro-7-nitrobenzofurazan / metabolism
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Cell Membrane / metabolism
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Cholates / chemistry*
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Cholates / metabolism
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Dithionite / chemistry
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Fluorescent Dyes / chemistry
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Phosphatidylcholines / chemistry
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Phosphatidylcholines / metabolism
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Phosphatidylethanolamines / chemistry
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Phosphatidylethanolamines / metabolism
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Phosphatidylserines / chemistry
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Phosphatidylserines / metabolism
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Phospholipids / chemistry
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Phospholipids / metabolism*
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Transferases / chemistry*
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Transferases / metabolism
Substances
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1-acyl-2-(12-((7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)dodecanoyl)phosphatidylcholine
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Cholates
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Fluorescent Dyes
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N-(7-nitro-2,1,3-benzoxadiazol-4-yl)phosphatidylserine
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Phosphatidylcholines
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Phosphatidylethanolamines
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Phosphatidylserines
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Phospholipids
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Dithionite
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N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)phosphatidylethanolamine
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Transferases
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4-Chloro-7-nitrobenzofurazan
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1-palmitoyl-2-oleoylphosphatidylcholine