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Synthesis of a New Lipophilic Bilirubin. Conformation, Transhepatic Transport and Glucuronidation by Justin O. Brower; David A. Lightner; Antony F. McDonagh is a Chemistry article available to read on EtoBox.

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AbstractÐAnalogs of symmetrical bilirubin isomers with vinyl groups replaced by n-butyls (1 and 2) were synthesized and found to be much more soluble in nonpolar solvents than either bilirubin itself or its analogs with ethyls in place of vinyls (3 and 4). The increased lipophilicity of 1 and 2 allowed, for the ®rst time, vapor pressure osmometric molecular wt. determinations of a bilirubin acid, showing in CHCl 3 solvent: MW obs 632^10 for 1, and 637^10 for 2 (both formula weight 644)Ðdata that clearly indicate monomers and no dimers. The induced circular dichroism (ICD) spectra of 1 and 2, with negative exciton chirality Cotton effects, are quite like those of 3 and 4 in chloroform containing quinine, but the ICDs in aqueous buffer containing human serum albumin differ considerably. Rubins 1, 3 and 4 exhibit dissimilar but positive exciton chirality Cotton effects, while 2 shows a negative exciton chirality Cotton effect. The metabolism of the n-butyl rubins in the rat is highly dependent on the speci®c endo or exo location of the n-butyl groups. Rubin 2, with two endo n-butyl groups was metabolized rather like the corresponding mesobilirubin (4) or natural bilirubin itself, bein

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Author

Justin O. Brower; David A. Lightner; Antony F. McDonagh

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)