Acetylated deoxycholic (DCA) and cholic (CA) acids are potent ligands of pregnane X (PXR) receptor

Toxicology Letters

Volumn 265, Issue , 2017, Pages 86-96

  Carazo, Alejandro ^a   Hyrsova, Lucie ^a   Dusek, Jan ^a   Chodounska, Hana ^b   Horvatova, Alzbeta ^a   Berka, Karel ^c   Bazgier, Vaclav ^c   Gan Schreier, Hongying ^d   Chamulitrat, Waleé ^d   Kudova, Eva ^b   Pavek, Petr ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c PALACKÝ UNIVERSITY   (Czech Republic)

^d Gastroenterology and Infectious Diseases   (Germany)

Author keywords

Bile acids; FXR; Metabolism; Nuclear receptors; PXR

Indexed keywords

CHOLIC ACID; CHOLIC ACID 3,7,12 TRIACETATE; CHOLIC ACID DERIVATIVE; CYTOCHROME P450 2B6; CYTOCHROME P450 3A4; DEOXYCHOLIC ACID; DEOXYCHOLIC ACID 3,12 DIACETATE; DEOXYCHOLIC ACID DERIVATIVE; FARNESOID X RECEPTOR; MESSENGER RNA; MULTIDRUG RESISTANCE PROTEIN 1; PREGNANE X RECEPTOR; RECOMBINANT RECEPTOR; UNCLASSIFIED DRUG; CALCITRIOL RECEPTOR; CELL RECEPTOR; CYTOCHROME P450 3A; FARNESOID X-ACTIVATED RECEPTOR; LIGAND; MULTIDRUG RESISTANCE PROTEIN; PROTEIN BINDING; STEROID RECEPTOR;

ACETYLATION; ARTICLE; CELL DIFFERENTIATION; CONTROLLED STUDY; DETOXIFICATION; FLUORESCENCE RESONANCE ENERGY TRANSFER; HEP-G2 CELL LINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RECEPTOR UPREGULATION; REPORTER GENE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; TANDEM MASS SPECTROMETRY; ANIMAL; CELL CULTURE TECHNIQUE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; GENETIC TRANSFECTION; GENETICS; LIVER CELL; METABOLISM; OXIDATION REDUCTION REACTION; PLASMID; TWO HYBRID SYSTEM;

ACETYLATION; ANIMALS; CELL CULTURE TECHNIQUES; CHOLIC ACID; CYTOCHROME P-450 CYP2B6; CYTOCHROME P-450 CYP3A; DEOXYCHOLIC ACID; DOSE-RESPONSE RELATIONSHIP, DRUG; GENES, REPORTER; HEP G2 CELLS; HEPATOCYTES; HUMANS; LIGANDS; MICE; MOLECULAR DOCKING SIMULATION; OXIDATION-REDUCTION; P-GLYCOPROTEIN; PLASMIDS; PROTEIN BINDING; RECEPTORS, CALCITRIOL; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, STEROID; TRANSFECTION; TWO-HYBRID SYSTEM TECHNIQUES;

EID: 84999836874     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2016.11.013     Document Type: Article

References (32)

1. Adachi, R., Honma, Y., Masuno, H., Kawana, K., Shimomura, I., Yamada, S., Makishima, M., Selective activation of vitamin D receptor by lithocholic acid acetate, a bile acid derivative. J. Lipid Res. 46 (2005), 46–57.
2. Ali, A.H., Carey, E.J., Lindor, K.D., Recent advances in the development of farnesoid X receptor agonists. Ann. Transl. Med., 3, 2015, 5.
3. Banerjee, M., Robbins, D., Chen, T., Targeting xenobiotic receptors PXR and CAR in human diseases. Drug Discov. Today 20 (2015), 618–628.
4. Chen, J., Zhao, K.N., Chen, C., The role of CYP3A4 in the biotransformation of bile acids and therapeutic implication for cholestasis. Ann. Transl. Med., 2, 2014, 7.
5. Cheng, J., Shah, Y.M., Gonzalez, F.J., Pregnane X receptor as a target for treatment of inflammatory bowel disorders. Trends Pharmacol. Sci. 33 (2012), 323–330.
6. Delfosse, V., Dendele, B., Huet, T., Grimaldi, M., Boulahtouf, A., Gerbal-Chaloin, S., Beucher, B., Roecklin, D., Muller, C., Rahmani, R., Cavailles, V., Daujat-Chavanieu, M., Vivat, V., Pascussi, J.M., Balaguer, P., Bourguet, W., Synergistic activation of human pregnane X receptor by binary cocktails of pharmaceutical and environmental compounds. Nat. Commun., 6, 2015, 8089.
7. Deo, A.K., Bandiera, S.M., 3-ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid. Drug Metab. Dispos. 37 (2009), 1938–1947.
8. Dusso, A.S., Brown, A.J., Slatopolsky, E., Vitamin D. Am. J. Physiol. Renal Physiol. 289 (2005), F8–28.
9. Gripon, P., Rumin, S., Urban, S., Le Seyec, J., Glaise, D., Cannie, I., Guyomard, C., Lucas, J., Trepo, C., Guguen-Guillouzo, C., Infection of a human hepatoma cell line by hepatitis B virus. Proc. Natl. Acad. Sci. U. S. A. 99 (2002), 15655–15660.
10. Hirsova, P., Karlasova, G., Dolezelova, E., Cermanova, J., Zagorova, M., Kadova, Z., Hroch, M., Sispera, L., Tomsik, P., Lenicek, M., Vitek, L., Pavek, P., Kucera, O., Cervinkova, Z., Micuda, S., Cholestatic effect of epigallocatechin gallate in rats is mediated via decreased expression of Mrp2. Toxicology 303 (2013), 9–15.
11. Hyrsova, L., Smutny, T., Carazo, A., Moravcik, S., Mandikova, J., Trejtnar, F., Gerbal-Chaloin, S., Pavek, P., The pregnane X receptor down-regulates organic cation transporter 1 (SLC22A1) in human hepatocytes by competing for (squelching) SRC-1 coactivator. Br. J. Pharmacol. 173 (2016), 1703–1715.
12. Ishizawa, M., Matsunawa, M., Adachi, R., Uno, S., Ikeda, K., Masuno, H., Shimizu, M., Iwasaki, K., Yamada, S., Makishima, M., Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. J. Lipid Res. 49 (2008), 763–772.
13. Jiao, L., Gan-Schreier, H., Tuma-Kellner, S., Stremmel, W., Chamulitrat, W., Sensitization to autoimmune hepatitis in group VIA calcium-independent phospholipase A2-null mice led to duodenal villous atrophy with apoptosis, goblet cell hyperplasia and leaked bile acids. Biochim. Biophys. Acta 1852 (2015), 1646–1657.
14. Krasowski, M.D., Yasuda, K., Hagey, L.R., Schuetz, E.G., Evolution of the pregnane x receptor: adaptation to cross-species differences in biliary bile salts. Mol. Endocrinol. 19 (2005), 1720–1739.
15. Krausova, L., Stejskalova, L., Wang, H., Vrzal, R., Dvorak, Z., Mani, S., Pavek, P., Metformin suppresses pregnane X receptor (PXR)-regulated transactivation of CYP3A4 gene. Biochem. Pharmacol. 82 (2011), 1771–1780.
16. Makishima, M., Okamoto, A.Y., Repa, J.J., Tu, H., Learned, R.M., Luk, A., Hull, M.V., Lustig, K.D., Mangelsdorf, D.J., Shan, B., Identification of a nuclear receptor for bile acids. Science 284 (1999), 1362–1365.
17. Makishima, M., Lu, T.T., Xie, W., Whitfield, G.K., Domoto, H., Evans, R.M., Haussler, M.R., Mangelsdorf, D.J., Vitamin D receptor as an intestinal bile acid sensor. Science 296 (2002), 1313–1316.
18. Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J. Comput. Chem. 30 (2009), 2785–2791.
19. Ngan, C.H., Beglov, D., Rudnitskaya, A.N., Kozakov, D., Waxman, D.J., Vajda, S., The structural basis of pregnane X receptor binding promiscuity. Biochemistry 48 (2009), 11572–11581.
20. Parks, D.J., Blanchard, S.G., Bledsoe, R.K., Chandra, G., Consler, T.G., Kliewer, S.A., Stimmel, J.B., Willson, T.M., Zavacki, A.M., Moore, D.D., Lehmann, J.M., Bile acids: natural ligands for an orphan nuclear receptor. Science 284 (1999), 1365–1368.
21. Ridlon, J.M., Bajaj, J.S., The human gut sterolbiome: bile acid-microbiome endocrine aspects and therapeutics. Acta Pharm. Sin. B 5 (2015), 99–105.
22. Ridlon, J.M., Kang, D.J., Hylemon, P.B., Bile salt biotransformations by human intestinal bacteria. J. Lipid Res. 47 (2006), 241–259.
23. Ridlon, J.M., Kang, D.J., Hylemon, P.B., Bajaj, J.S., Bile acids and the gut microbiome. Curr. Opin. Gastroenterol. 30 (2014), 332–338.
24. Rulcova, A., Prokopova, I., Krausova, L., Bitman, M., Vrzal, R., Dvorak, Z., Blahos, J., Pavek, P., Stereoselective interactions of warfarin enantiomers with the pregnane X nuclear receptor in gene regulation of major drug-metabolizing cytochrome P450 enzymes. J. Thromb. Haemost. 8 (2010), 2708–2717.
25. Smutny, T., Bitman, M., Urban, M., Dubecka, M., Vrzal, R., Dvorak, Z., Pavek, P., U0126, a mitogen-activated protein kinase kinase 1 and 2 (MEK1 and 2) inhibitor, selectively up-regulates main isoforms of CYP3A subfamily via a pregnane X receptor (PXR) in HepG2 cells. Arch. Toxicol. 88 (2014), 2243–2259.
26. Staudinger, J., Liu, Y., Madan, A., Habeebu, S., Klaassen, C.D., Coordinate regulation of xenobiotic and bile acid homeostasis by pregnane X receptor. Drug Metab. Dispos. 29 (2001), 1467–1472.
27. Staudinger, J.L., Goodwin, B., Jones, S.A., Hawkins-Brown, D., MacKenzie, K.I., LaTour, A., Liu, Y., Klaassen, C.D., Brown, K.K., Reinhard, J., Willson, T.M., Koller, B.H., Kliewer, S.A., The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity. Proc. Natl. Acad. Sci. U. S. A. 98 (2001), 3369–3374.
28. Trott, O., Olson, A.J., AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31 (2010), 455–461.
29. Venkatesh, M., Mukherjee, S., Wang, H., Li, H., Sun, K., Benechet, A.P., Qiu, Z., Maher, L., Redinbo, M.R., Phillips, R.S., Fleet, J.C., Kortagere, S., Mukherjee, P., Fasano, A., Le Ven, J., Nicholson, J.K., Dumas, M.E., Khanna, K.M., Mani, S., Symbiotic bacterial metabolites regulate gastrointestinal barrier function via the xenobiotic sensor PXR and toll-like receptor 4. Immunity 41 (2014), 296–310.
30. Wallace, K., Cowie, D.E., Konstantinou, D.K., Hill, S.J., Tjelle, T.E., Axon, A., Koruth, M., White, S.A., Carlsen, H., Mann, D.A., Wright, M.C., The PXR is a drug target for chronic inflammatory liver disease. J. Steroid Biochem. Mol. Biol. 120 (2010), 137–148.
31. Wang, H., Chen, J., Hollister, K., Sowers, L.C., Forman, B.M., Endogenous bile acids are ligands for the nuclear receptor FXR/BAR. Mol. Cell 3 (1999), 543–553.
32. Xie, W., Radominska-Pandya, A., Shi, Y., Simon, C.M., Nelson, M.C., Ong, E.S., Waxman, D.J., Evans, R.M., An essential role for nuclear receptors SXR/PXR in detoxification of cholestatic bile acids. Proc. Natl. Acad. Sci. U. S. A 98 (2001), 3375–3380.