Synthesis and intestinal metabolism of ursodeoxycholic acid conjugate with an antiinflammatory agent, 5-aminosalicylic acid.
作者： Ashok K. Batta , Sarah Shefer , Guorong Xu , Gerald Salen , G. Stephen Tint
DOI: 10.1016/S0022-2275(20)32193-3
关键词:
摘要: Aminosalicylic acid conjugate of ursodeoxycholic was synthesized in above 90% yield by adding a basic solution 5-aminosalicylic into the mixed anhydride formed with and ethyl chloroformate. The poorly secreted bile deconjugated cholylglycine hydrolase Clostridium perfringens, that deconjugate naturally occurring glycine taurine conju- gates acids. However, 5-amino- salicylic not absorbed from duode- num but concentrated colon wher e it partially hydrolyzed intestinal bacteria to ursodeoxy- cholic acid. We believe this unique conjugation 5-ami- nosalicylic may facilitate transpor t both 5- aminosalicylic be useful for treatment colonic inflamma- tory bowel diseases, ulcerative colitis Crohn's dis- ease.— Batta, A. K., G. S. Tint, Xu, Shefer, Salen. Synthesis metabolism an antiinflammatory agent, J. Lipid. Res. 1998. 39: 1641-1646.
sci-hub.st 参考文章(29)
Douglas M. Heuman, A.Scott Mills, Janice McCall, Philip B. Hylemon, W.Michael Pandak, Z.Reno Vlahcevic, Conjugates of ursodeoxycholate protect against cholestasis and hepatocellular necrosis caused by more hydrophobic bile salts Gastroenterology. ,vol. 100, pp. 203- 211 ,(1991) , 10.1016/0016-5085(91)90602-H
Hubert Allgayer, Sulfasalazine and 5-ASA compounds. Gastroenterology Clinics of North America. ,vol. 21, pp. 643- 658 ,(1992) , 10.1016/S0889-8553(21)00053-4
Sune Bergström, Henry Danielsson, Taro Kazuno, Bile acids and steroids. LXXXII. On the mechanism of deoxycholic acid formation in the rabbit. Journal of Biological Chemistry. ,vol. 234, pp. 2022- 2025 ,(1959) , 10.1016/S0021-9258(18)69464-5
Stephen Barnes, David N. Kirk, Nuclear Magnetic Resonance Spectroscopy of Bile Acids The Bile Acids: Chemistry, Physiology, and Metabolism. pp. 65- 136 ,(1988) , 10.1007/978-1-4613-0901-7_3
W Kramer, G Wess, G Schubert, M Bickel, F Girbig, U Gutjahr, S Kowalewski, K.H. Baringhaus, A Enhsen, H Glombik, Liver-specific drug targeting by coupling to bile acids. Journal of Biological Chemistry. ,vol. 267, pp. 18598- 18604 ,(1992) , 10.1016/S0021-9258(19)37003-6
P.P. Nair, Maureen Gordon, John Reback, The Enzymatic Cleavage of the Carbon-Nitrogen Bond in 3α,7α,12α-Trihydroxy-5β-cholan-24-oylglycine Journal of Biological Chemistry. ,vol. 242, pp. 7- 11 ,(1967) , 10.1016/S0021-9258(18)96311-8
A K Batta, G Salen, S Shefer, Substrate specificity of cholylglycine hydrolase for the hydrolysis of bile acid conjugates. Journal of Biological Chemistry. ,vol. 259, pp. 15035- 15039 ,(1984) , 10.1016/S0021-9258(17)42510-5
Rolf Olsson, Åke Danielsson, Gunnar Järnerot, Eva Lindström, Lars Lööf, Peter Rolny, Bengt-Olof Rydén, Curt Tysk, Sven Wallerstedt, Prevalence of primary sclerosing cholangitis in patients with ulcerative colitis Gastroenterology. ,vol. 100, pp. 1319- 1323 ,(1991) , 10.1016/0016-5085(91)70019-T
Douglas M. Heuman, Rohini Bajaj, Ursodeoxycholate conjugates protect against disruption of cholesterol-rich membranes by bile salts Gastroenterology. ,vol. 106, pp. 1333- 1341 ,(1994) , 10.1016/0016-5085(94)90027-2
A. Stiehl, P. Czygan, B. Kommerell, H.J. Weis, K.H. Holtermüller, Ursodeoxycholic acid versus chenodeoxycholic acid Gastroenterology. ,vol. 75, pp. 1016- 1020 ,(1978) , 10.1016/0016-5085(78)90068-9