{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,5,20]],"date-time":"2025-05-20T22:25:58Z","timestamp":1747779958882},"reference-count":14,"publisher":"Wiley","issue":"8-9","license":[{"start":{"date-parts":[[2006,9,23]],"date-time":"2006-09-23T00:00:00Z","timestamp":1158969600000},"content-version":"vor","delay-in-days":3918,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[1996,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Albumin binding<\/jats:bold> for the enantiomers of four closely related <jats:italic>N<\/jats:italic>\u2010methyl\u20105\u2010phenyl\u20105\u2010alkyl\u2010barbiturates <jats:bold>1\u20134<\/jats:bold> was investigated for three different mammalian species by means of equilibrium dialysis. Lipid solubility (<jats:italic>n<\/jats:italic>\u2010heptane\/phosphate buffer distribution coefficient) increased stepwise by a factor of 56 from <jats:bold>1<\/jats:bold> to <jats:bold>4.<\/jats:bold><\/jats:p><jats:p><jats:bold>Bovine serum albumin:<\/jats:bold> The (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010enantiomers of <jats:bold>1\u20134<\/jats:bold> were bound in a higher percentage than the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers; lengthening of the aliphatic side\u2010chain increased the binding extent in both enantiomeric groups.<\/jats:p><jats:p><jats:bold>Human serum albumin:<\/jats:bold> Binding of (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>1<\/jats:bold> and (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>4<\/jats:bold> was higher than that of the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers; with (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>2<\/jats:bold> and (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>3<\/jats:bold> it was much lower than that of the corresponding (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers. Lengthening of the aliphatic side chain increased the binding extent of the (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010 as well as of the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers, but with two exceptions: 1. The (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>1<\/jats:bold> binding exceeded that of the (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>2<\/jats:bold> by a factor of nearly two 2. The binding extent of (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010<jats:bold>4<\/jats:bold> was not further increased in comparison to (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010<jats:bold>3.<\/jats:bold><\/jats:p><jats:p><jats:bold>Rat serum albumin:<\/jats:bold> (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>1<\/jats:bold> and (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>2<\/jats:bold> were bound in a lower percentage than the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers, both <jats:bold>3<\/jats:bold>\u2010enantiomers showing an equal binding extent; (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010<jats:bold>4<\/jats:bold> was bound to a slightly greater extent than the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010<jats:bold>4.<\/jats:bold> In the group of the (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010enantiomers, the binding extent increased from <jats:bold>1<\/jats:bold> to <jats:bold>4<\/jats:bold>, whereas in that of the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010enantiomers only between <jats:bold>1<\/jats:bold> and <jats:bold>4.<\/jats:bold> Structural differences between the serum albumins of three mammalian species possibly cause the enantioselective binding pattern found for the enantiomers of <jats:bold>1\u20134<\/jats:bold>, and are responsible for the finding that the binding extent in some cases did not correlate with the lipid solubility of the compounds.<\/jats:p>","DOI":"10.1002\/ardp.19963290805","type":"journal-article","created":{"date-parts":[[2006,10,17]],"date-time":"2006-10-17T03:37:18Z","timestamp":1161056238000},"page":"399-402","source":"Crossref","is-referenced-by-count":1,"title":["Stereoselective Binding of the Enantiomers of Four Closely Related <i>N<\/i>\u2010Methyl\u2010Barbiturates to Human, Bovine, and Rat Serum Albumin"],"prefix":"10.1002","volume":"329","author":[{"given":"Horst Paul","family":"B\u00fcch","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Regina","family":"Krug","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joachim","family":"Knabe","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2006,9,23]]},"reference":[{"key":"e_1_2_1_2_2","first-page":"709","volume":"175","author":"B\u00fcch H. 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