Immunoprecipitation and MALDI-MS identification of lithocholic acid-tagged proteins in liver of bile duct-ligated rats

Journal of Lipid Research

Volumn 49, Issue 11, 2008, Pages 2463-2473

  Ikegawa, Shigeo ^a   Yamamoto, Tetsushi ^a,c   Ito, Hiromi ^a   Ishiwata, Shunji ^a   Sakai, Toshihiro ^a   Mitamura, Kuniko ^a   Maeda, Masako ^b  

^a KINKI UNIVERSITY   (Japan)

^b SHOWA UNIVERSITY   (Japan)

^c NIPPON MEDICAL SCHOOL   (Japan)

Author keywords

Antibody; Cytosol fractions; Matrix assisted laser desorption ionization time of flight mass spectrometry; Rab proteins; Rat liver; Two dimensional electrophoresis

Indexed keywords

AMINOCAPROIC ACID; LITHOCHOLIC ACID; LIVER PROTEIN; LYSINE; LYSOZYME; M RAS PROTEIN; OVALBUMIN; RAB PROTEIN; RAB12 PROTEIN; RAB16 PROTEIN; STEROID; SUCCINIC ACID; UNCLASSIFIED DRUG; PROTEIN;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIBODY AFFINITY; ANTIBODY RESPONSE; ANTIGEN RECOGNITION; ARTICLE; BILE DUCT; CARBOXY TERMINAL SEQUENCE; CHEMICAL LABELING; COMPUTER PROGRAM; CONTROLLED STUDY; COVALENT BOND; IMMUNOPRECIPITATION; MALE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MEMBRANE BINDING; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN ISOLATION; PROTEIN STRUCTURE; RABBIT; RAT; SEQUENCE TAGGED SITE; TRANSPORT VESICLE; TWO DIMENSIONAL ELECTROPHORESIS; AMINO ACID SEQUENCE; ANIMAL; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; FEMALE; IMMUNOLOGY; ISOLATION AND PURIFICATION; LIGATION; LIVER; MASS SPECTROMETRY; METABOLISM; MOLECULAR GENETICS; WISTAR RAT;

AMINO ACID SEQUENCE; ANIMALS; BILE DUCTS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; FEMALE; IMMUNOPRECIPITATION; LIGATION; LITHOCHOLIC ACID; LIVER; MALE; MOLECULAR SEQUENCE DATA; PROTEINS; RABBITS; RATS; RATS, WISTAR; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 58149473796     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M800350-JLR200     Document Type: Article

References (36)

1. Nair, P. P., A. I. Mendeloff, M. Vocci, J. Bankoski, M. Gorelik, G. Herman, and R. Plapinger. 1977. Lithocholic acid in human liver: identification of ε-lithocholyl lysine in tissue protein. Lipids. 12: 922-929.
2. Nair, P. P., R. Solomon, J. Bankoski, and R. Plapinger. 1978. Bile acids in tissue: binding of lithocholic acid to protein. Lipids. 13: 966-978.
3. Turjman, N., and P. P. Nair. 1981. Nature of tissue-bound lithocholic acid and its implications in the role of bile acids in carcinogenesis. Cancer Res. 41: 3761-3763.
4. Turjman, N., A. I. Mendeloff, C. Jacob, C. Guidry, and P. P. Nair. 1981. Isolation of tissue-bound lithocholic acid from livers of rats treated with methylazoxymethanol. J. Steroid Biochem. 14: 1237-1240.
5. Gelb, A. M., C. K. McSherry, J. R. Sadowsky, and E. H. Mosbach. 1982. Tissue bile acids in patients with colon cancer and colonic polyps. Am. J. Gastroenterol. 77: 314-317.
6. Turjman, N., and P. P. Nair. 1988. Tissue-bound bile acids. In The Bile Acids: Chemistry, Physiology and Metabolism. Vol. 4. Methods and Applications. K. D. R. Setchell, D. Kritchevsky, and P. P. Nair, editors. Plenum Press, New York. 373-378.
7. Nair, P. P., G. Kessie, R. Patnaik, and C. Guidry. 1994. Isolation and HPLC of N-ε-lithocholyl lysine as its fluorescamine and dimethylaminoazobenzene isothiocyanate derivatives. Steroids. 59: 212-216.
8. Summerton, J., N. Goeting, G. A. Trotter, and I. Taylor. 1985. Effect of deoxycholic acid on the tumour incidence, distribution, and receptor status of colorectal cancer in the rat model. Digestion. 31: 77-81.
9. Fickert, P., A. Fuchsbichler, H-U. Marschall, M. Wagner, G. Zollner, R. Krause, K. Zatloukal, H. Jaeschke, H. Denk, and M. Trauner. 2006. Lithocholic acid feeding induces segmental bile duct obstruction and destructive cholangitis in mice. Am. J. Pathol. 168: 410-422.
10. Tanida, N., K. Sawada, A. Kawaura, M. Oda, T. Shimoyama, and T. Narisawa. 1989. Effects of oral administration of sulfolithocholic acid disodium salt and lithocholic acid sodium salt on N-methyl-N-nitrosourea-induced colonic tumorigenesis in conventional rats. Cancer Res. 49: 1178-1181.
11. Tsujii, M., S. Kawano, and R. N. DuBois. 1997. Cyclooxygenase-2 expression in human colon cancer cells increases metastatic potential. Proc. Natl. Acad. Sci. USA. 94: 3336-3340.
12. Zhang, F., K. Subbaramaiah, N. Altorki, and A. J. Dannenberg. 1998. Dihydroxy bile acids activate the transcription of cyclooxygenase-2. J. Biol. Chem. 273: 2424-2428.
13. Mizushina, Y., T. Ohkubo, F. Sugawara, and K. Sakaguchi. 2000. Structure of lithocholic acid binding to the N-terminal 8-kDa domain of DNA polymerase β. Biochemistry. 39: 12606-12613.
14. Halvorsen, B., A. C. Staff, S. Ligaarden, K. Prydz, and S. O. Kolset. 2000. Lithocholic acid and sulphated lithocholic acid differ in the ability to promote matrix metalloproteinase secretion in the human colon cancer cell line CaCo-2. Biochem. J. 349: 189-193.
15. Debryune, P. R., E. A. Bruyneel, X. Li, A. Zimber, C. Gespach, and M. M. Mareel. 2001. The role of bile acids in carcinogenesis. Mutat. Res. 480-481: 359-369.
16. Glinghammar, B., H. Inoue, and J. J. Rafter. 2002. Deoxycholic acid causes DNA damage in colonic cells with subsequent induction of caspases, COX-2 promoter activity and the transcription factors NFkB and AP-1. Carcinogenesis. 23: 839-845.
17. Bernstein, H., C. Bernstein, C. M. Payne, K. Dvorakova, and H. Garewal. 2005. Bile acids as carcinogens in human gastrointestinal cancers. Mutat. Res. 589: 47-65.
18. Ikegawa, S., N. Murao, M. Nagata, S. Ohba, and J. Goto. 1999. Covalent binding of bile acid acyl glucuronide with protein. Anal. Sci. 15: 213-215.
19. Kakiyama, G., H. Tamegai, T. Iida, K. Mitamura, S. Ikegawa, T. Goto, N. Mano, J. Goto, P. Holz, L. R. Hagey, and A. F. Hofmann. 2007. Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15α-hydroxylithocholic acid. J. Lipid Res. 48: 2682-2692.
20. Panfil, I., P. A. Lehman, P. Zimniak, B. Ernst, T. Franz, R. Lester, and A. Radminska. 1992. Biosynthesis and chemical synthesis of carboxyllinked glucuronide of lithocholic acid. Biochim. Biophys. Acta. 1126: 221-228.
21. Goto, J., N. Murao, C. Nakada, T.Motoyama, J. Oohashi, T. Yanagihara, T. Niwa, and S. Ikegawa. 1998. Separation and characterization of carboxyl-linked glucuronides of bile acids in incubation mixture of rat liver microsomes. Steroids. 63: 186-192.
22. Ikegawa, S., H. Okuyama, J. Oohashi, N. Murao, and J. Goto. 1999. Separation and detection of bile acid 24-glucuronides in human urine by liquid chromatography combined with electrospray ionization mass spectrometry. Anal. Sci. 15: 625-631.
23. Mano, N., K. Nishimura, T. Narui, S. Ikegawa, and J. Goto. 2002. Characterization of rat liver bile acid acyl glucuronyltransferase. Steroids. 67: 257-262.
24. Ikegawa, S., H. Ishikawa, H. Oiwa, M. Nagata, J. Goto, T. Kozaki, M. Gotowda, and N. Asakawa. 1999. Characterization of cholyl-adenylate in rat liver microsomes by liquid chromatography/electrospray ionization-mass spectrometry. Anal. Biochem. 266: 125-132.
25. Goto, J., M. Nagata, N. Mano, N. Kobayashi, S. Ikegawa, and R. Kiyonami. 2001. Bile acid acyl adenylate: a possible intermediate to produce a protein-bound bile acid. Rapid Commun. Mass Spectrom. 15: 104-109.
26. Mano, N., K. Kasuga, N. Kobayashi, and J. Goto. 2004. A nonenzymatic modification of the amino-terminal domain of histone H3 by bile acid acyl adenylate. J. Biol. Chem. 279: 55034-55041.
27. Goto, J., G. Shao, H. Miura, and T. Nambara. 1989. Separation of C-25 epimers of 5β-cholestanoic acids by high performance liquid chromatography with precolumn fluorescence labeling. Anal. Sci. 5: 19-22.
28. Nair, P. P., G. Kessie, and N. Turjman. 1985. Synthesis of N-ε-lithocholyl-L-lysine, a component of tissue-bound lithocholic acid, via lithocholyl-N-hydroxysuccinimide. J. Steroid Biochem. 23: 573-576.
29. Miyairi, S., H. Shioya, M. Ebihara, H. Hosoda, and T. Nambara. 1984. Preparation of new haptens for use in immunoassay of glycineconjugated bile acids. Chem. Pharm. Bull. (Tokyo). 32: 1891-1897.
30. Wang, L., M. Chorev, J. Feingers, A. Levitzki, and M. Inbar. 1986. Stereospecific monoclonal antibodies to propranolol. FEBS Lett. 199: 173-178.
31. Ikegawa, S., N. M. R. Isriyanthi, M. Nagata, K. Yahata, H. Ito, N. Mano, and J. Goto. 2001. The enantioselective immunoaffinity extraction of an optically active ibuprofen-modified peptide fragment. Anal. Biochem. 296: 63-72.
32. Ito, H., S. Ishiwata, T. Kosaka, R. Nakashima, H. Takeshita, S. Negoro, M. Maeda, and S. Ikegawa. 2004. Enantioselective immunorecognition of protein modification with optically active ibuprofen using polyclonal antibody. J. Chromatogr. B. 806: 11-17.
33. Hassani, O., P. Mansuelle, S. Cestèle, M. Bourdeaux, H. Rochat, and F. Sampieri. 1999. Role of lysine and tryptophan residues in the biological activity of toxin VII (Ts γ) from the scorpion Tityus serrulatus. Eur. J. Biochem. 260: 76-86.
34. Tuvim, M. J., R. Adachi, S. Hoffenberg, and B. F. Dickey. 2001. Traffic control: Rab GTPase and the regulation of interorganellar transport. News Physiol. Sci. 16: 56-61.
35. Pereira-Leal, J. B., M. Strom, R. F. Godfrey, and M. C. Seabra. 2003. Structural determinants of Rab and Rab Escort Protein interaction: Rab family motifs define a conserved binding surface. Biochem. Biophys. Res. Commun. 301: 92-97.
36. Oxford, G., and D. Theodorescu. 2003. Ras superfamily monomeric G proteins in carcinoma cell motility. Cancer Lett. 189: 117-128.