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The Journal of Lipid Research, Vol. 39, 1641-1646, August 1998
Copyright © 1998 by Lipid Research, Inc.

Original Article

Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid

Ashok K. Battaa, G. Stephen Tinta, Guorong Xua, Sarah Shefera, and Gerald Salena
a Department of Medicine and Liver Center, University of Medicine and Dentistry-New Jersey Medical School, Newark, NJ 07103, and Department of Veterans Affairs Medical Center, East Orange, NJ 07018

Correspondence to: Ashok K. Batta.

5-Aminosalicylic acid conjugate of ursodeoxycholic acid was synthesized in above 90% yield by adding a basic solution of 5-aminosalicylic acid into the mixed anhydride formed with ursodeoxycholic acid and ethyl chloroformate. The 5-aminosalicylic acid conjugate of ursodeoxycholic acid was poorly secreted into the bile and was deconjugated with cholylglycine hydrolase and Clostridium perfringens, that deconjugate naturally occurring glycine and taurine conjugates of bile acids. However, ursodeoxycholic acid 5-aminosalicylic acid conjugate was not absorbed from the duodenum but was concentrated in the colon where it was partially hydrolyzed by the intestinal bacteria to ursodeoxycholic acid and 5-aminosalicylic acid. We believe that this unique conjugation of ursodeoxycholic acid with 5-aminosalicylic acid may facilitate the transport of both 5-aminosalicylic acid and ursodeoxycholic acid to the colon and may be useful for the treatment of colonic inflammatory bowel diseases, ulcerative colitis and Crohn's disease.—Batta, A. K., G. S. Tint, G. Xu, S. Shefer, and G. Salen. Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid. J. Lipid. Res. 1998. 39: 1641–1646.

Supplementary key words: Ursodeoxycholic acid, ursodeoxycholic acid-5-aminosalicylic acid conjugate, intestinal bacteria, colon, inflammatory bowel disease, ulcerative colitis


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