Chiral discrimination in the transport of ketoprofen and ibuprofen esters through an aqueous phase mediated by various serum albumins.
Serum albumins that act as carriers discriminated between enantiomers of alkyl esters of ketoprofen and ibuprofen in transport in the O/W/O (oil/water/oil) system using a U-shaped cell. The transport rate and the preferred enantiomer of the esters were substantially affected by pH, temperature, and species of albumin. Among five serum albumins studied, bovine serum albumin (BSA) showed the largest rate constant and rat serum albumin (RSA) manifested the highest enantioselectivity. Regarding enantiomer selectivity in transport overall, it is anticipated that the ester uptake step plays an important role for BSA, whereas the ester release is the key step for RSA.
Nakagawa
H
H
Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan.
Shimizu
K
K
Yamada
K
K
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification; D002417:Cattle; D006863:Hydrogen-Ion Concentration; D007052:Ibuprofen / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D066298:In Vitro Techniques; D007660:Ketoprofen / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D051381:Rats; D012709:Serum Albumin; D012710:Serum Albumin, Bovine; D012995:Solubility; D013237:Stereoisomerism; D013696:Temperature; D014867:Water
D000894:Anti-Inflammatory Agents, Non-Steroidal; D012709:Serum Albumin; D014867:Water; D012710:Serum Albumin, Bovine; D007660:Ketoprofen; D007052:Ibuprofen