caa a22 4500 467920524 CHVBK 20180406152916.0 cr unu---uuuuu 170328e20061101xx s 000 0 eng 10.1007/s00706-006-0543-8 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0543-8 Synthesis and Hepatic Metabolism of Xanthobilirubinic Acid Regioisomers [Elektronische Daten] [Stefan E. Boiadjiev, Brian A. Conley, Justin O. Brower, Antony F. McDonagh, David A. Lightner] Summary.: A set of four regioisomeric dipyrrinone propionic acids has been synthesized and their hepatic metabolism examined in rats: xanthobilirubinic acid and pseudo-xanthobilirubinic acid each with a propionic acid on a pyrrole ring; exo-ψ-xanthobilirubinic acid and endo-ψ-xanthobilirubinic acid, each with a propionic acid transposed to a lactam ring. After intravenous injection all four isomers were excreted to some degree in unchanged form in bile in normal rats. Xanthobilirubinic acid, the structurally closest dipyrrinone to bilirubin, and exo-ψ-xanthobilirubinic acid were excreted almost entirely in unchanged form. However, a small fraction of xanthobilirubinic acid acyl glucuronide was also detected. More extensive acyl glucuronidation was observed for pseudo-xanthobilirubinic acid, and endo-ψ-xanthobilirubinic acid underwent slow metabolism to unidentified more polar products that did not seem to be glucuronides. Springer-Verlag, 2006 Keywords. Pyrrole nationallicence Dipyrrinone nationallicence NMR nationallicence Boiadjiev Stefan E. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut Conley Brian A. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut Brower Justin O. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut McDonagh Antony F. Division of Gastroenterology and the Liver Center, University of California, San Francisco, California, USA aut Lightner David A. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1463-1476 0026-9247 137:11<1463 2006 137 706 https://doi.org/10.1007/s00706-006-0543-8 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0543-8 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Boiadjiev Stefan E. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut NATIONALLICENCE 700 1- Conley Brian A. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut NATIONALLICENCE 700 1- Brower Justin O. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut NATIONALLICENCE 700 1- McDonagh Antony F. Division of Gastroenterology and the Liver Center, University of California, San Francisco, California, USA aut NATIONALLICENCE 700 1- Lightner David A. Department of Chemistry, University of Nevada, Reno, Nevada, USA aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1463-1476 0026-9247 137:11<1463 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer