Xanthine dehydrogenase processes retinol to retinoic acid in human mammary epithelial cells

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 23, Issue 3, 2008, Pages 317-327

  Taibi, Gennaro ^a   Di Gaudio, Francesca ^a   Nicotra, Concetta M A ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

CRABP; CRBP; Mammary epithelial cells; Retinoic acid biosynthesis; Retinol oxidation; Xanthine dehydrogenase

Indexed keywords

CELLULAR RETINOL BINDING PROTEIN; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIPURINOL; RETINAL; RETINOIC ACID; RETINOL; XANTHINE DEHYDROGENASE; XANTHINE OXIDASE;

ARTICLE; BIOSYNTHESIS; BREAST EPITHELIUM; CATALYSIS; CELL DIFFERENTIATION; CELL FUNCTION; CELL LINE; CELL PROLIFERATION; CONTROLLED STUDY; CYTOPLASM; ENZYME ACTIVITY; EPITHELIUM CELL; HUMAN; HUMAN CELL; IMMUNOASSAY; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN ISOLATION;

EPITHELIAL CELLS; HUMANS; MAMMARY GLANDS, HUMAN; METABOLIC NETWORKS AND PATHWAYS; MILK PROTEINS; NAD; OXYPURINOL; RECEPTORS, RETINOIC ACID; RETINOL-BINDING PROTEINS, CELLULAR; TRETINOIN; VITAMIN A; XANTHINE DEHYDROGENASE;

EID: 46649107524     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701584539     Document Type: Article

References (60)

1. Gudas, LJ, Sporn, MB and Roberts, AB (1994) Cellular biology and biochemistry of the retinoids. The retinoids: Biology, chemistry, and medicine, pp. 443-520. Raven Press, Ltd.,, New York
2. Lotan, R. (1980) Effect of vitamin A and its analogs (retinoid) on normal and neoplastic cells. Biochim Biophys Acta, 605, pp. 33-91.
3. Orphanos, CE (1980) Oral retinoids-present status. Br J Dermatol, 103, pp. 473-481.
4. Chytil, F. (1984) Retinoic acid, biochemistry, pharmacology, toxicology and therapeutic use. Pharmacol Rev, 36, pp. 93S-100S.
5. Kraemer, KH, Di Giovanna, JJ, Moshell, AN, Tarone, RE and Peck, GL (1988) Prevention of skin cancer in xeroderma pigmentosum with the use of oral isotretinoin. N Engl J Med, 318, pp. 1633-1637.
6. Kim, CL, Leo, MA and Lieber, CS (1992) Retinol forms retinoic acid via retinal. Arch Biochem Biophys, 294, pp. 388-393.
7. Blaner, WS and Olson, JA (1994) Retinol and retinoic acid metabolism. The retinoids: Biology, chemistry, and medicine, pp. 229-255. Raven Press, Ltd., New York
8. Napoli, JL (1996) Retinoic acid biosynthesis and metabolism. FASEB J, 10, pp. 993-1001.
9. Napoli, JL (2001) 17β-Hydroxysteroid dehydrogenase type 9 and other short-chain dehydrogenases/reductases that catalyze retinoid, 17β- and 3α-hydroxysteroid metabolism. Mol Cell Endocrinol, 171, pp. 103-109.
10. Taibi, G. and Nicotra, CMA (2007) Xanthine oxidase catalyzes the oxidation of retinol. J Enz Inhib Med Chem, 22, pp. 471-476.
11. Chen, H., Howald, WN and Juchau, MR (2000) Biosynthesis of all trans-retinoic acid from all trans-retinol: Catalysis of all trans-retinol oxidation by human P-450 cytocromes. Drug Metab Dispos, 28, pp. 315-322.
12. Rexer, BN, Zheng, WL and Ong, DE (2001) Retinoic acid biosynthesis by normal human breast epithelium is via aldehyde dehydrogenase 6, absent in MCF7 cells. Cancer Res, 61, pp. 7065-7070.
13. Ong, DE, MacDonald, PN and Gubitosi, AM (1988) Esterification of retinol in rat liver: Possible participation by cellular retinol-binding protein and cellular retinol binding protein (II). J Biol Chem, 263, pp. 5789-5796.
14. Ottonello, S., Scita, G., Mantovani, G., Cavazzini, D. and Rossi, GL (1993) Retinol bound to cellular retinol-binding protein is a substrate for cytosplasmic retinoic acid synthesis. J Biol Chem, 268, pp. 27133-27142.
15. Jing, Y., Zhang, J., Bleiweiss, IJ, Waxman, S., Zelent, A. and Mira-Y-Lopez, R. (1996) Defective expression of cellular retinol binding protein type I and retinoic acid receptors α2, β2 and γ2 in human breast cancer cells. FASEB J, 10, pp. 1064-1070.
16. Kuppumbatti, YS, Bleiweiss, IJ, Mandeli, JP, Waxman, S. and Mira-Y-Lopez, R. (2000) Cellular retinol-binding protein expression and breast cancer. J Natl Cancer Inst, 92, pp. 475-480.
17. Hayden, LJ and Satre, MA (2002) Alterations in cellular retinol metabolism contribute to differential retinoid responsiveness in normal human mammary epithelial cells versus breast cancer cells. Breast Cancer Res Tr, 72, pp. 95-105.
18. Chytil, F. and Ong, DE (1976) Mediation of retinoic acid-induced growth and antitumor activity Nature, 260, pp. 49-51.
19. Ong, DE, Markert, C. and Chiu, JF (1978) Cellular binding proteins for vitamin A in colorectal adenocarcinoma of rat. Cancer Res, 38, pp. 4422-4426.
20. Taibi, G., Paganini, A., Gueli, MC, Ampola, F. and Nicotra, CMA (2001) Xanthine oxidase catalyzes the synthesis of retinoic acid. J Enz Inhib, 16, pp. 275-285.
21. Kurosaki, M., Zanotta, S., Li Calzi, M, Garattini, E. and Terao, M. (1996) Expression of xanthine oxidoreductase in mouse mammary epithelium during pregnancy and lactation: Regulation of gene expression by glucocorticoids and prolactin. Biochem J, 319, pp. 801-810.
22. McManaman, JL, Hanson, L., Neville, MC and Wright, MR (2000) Lactogenic hormones regulate xanthine oxidoreductase and β-casein levels in mammary epithelial cells by distinct mechanisms. Arch Biochem Biophys, 373, pp. 318-327.
23. Frolik, CA, Tavela, TE, Peck, GL and Sporn, MB (1978) High-Pressure Liquid Chromatographic determination of 13-cis-retinoic acid and all-trans-retinoic acid in human plasma. Anal Biochem, 86, pp. 743-750.
24. Kock, R., Delvoux, B. and Greiting, H. (1993) A comparative study of the concentrations of hypoxanthine, xanthine, uric acid and allantoin in the peripheral blood of normals and patients with acute myocardial infarction and other ischaemic diseases. Eur J Clin Chem Clin Biochem, 31, pp. 303-310.
25. Groenendijk, GWT, Jensen, PAA, Bonting, SL and Daemen, FJM (1980) Analysis of geometrically isomeric vitamin A compounds. Meth Enzymol, 67, pp. 203-220.
26. Segel, IH (1975) Enzyme kinetics, Wiley Interscience, New York
27. Snedecor, G. and Cochran, W. (1967) Statistical Methods.pp. 120-134. Iowa State University Press, Ames, IA
28. Erikson, U., Das, K., Busch, C., Nordlinder, H., Rask, L., Sundelin, J., Sailstrom, J. and Peterson, PA (1984) Cellular retinol-binding protein quantitation and distribution. J Biol Chem, 259, pp. 13464-13470.
29. Levin, MS, Li, E., Ong, DE and Gordon, JI (1987) Comparison of the tissue-specific expression and developmental regulation of two closely linked rodent genes encoding cytosolic retinol-binding proteins. J Biol Chem, 262, pp. 718-7124.
30. Schaefer, WH, Kakkad, B., Crow, JA, Blair, IA and Ong, DE (1989) Purification, primary structure characterization, and cellular distribution of two form of cellular retinol-binding protein, type II from adult rat small intestine. J Biol Chem, 264, pp. 4212-4221.
31. Thompson, JR, Bratt, JM and Banaszak, LJ (1995) Crystal structure of cellular retinoic acid binding protein I shows increased access to the binding cavity due to formation of an intermolecular β-sheet. J Mol Biol, 252, pp. 433-446.
32. Piantedosi, R., Ghyselinck, N., Blaner, WS and Vogel, S. (2005) Cellular retinol-binding protein type III is needed for retinoid incorporation into milk. J Biol Chem, 280, pp. 24286-24292.
33. Fiorella, PD, Giguere, V. and Napoli, JL (1993) Expression of Cellular Retinoic Acid-binding Protein (Type II) in Escherichia Coli. J Biol Chem, 268, pp. 21545-21552.
34. Folli, C., Calderone, V., Ottonello, S., Bolchi, A., Zanotti, G., Stoppini, M. and Berni, R. (2001) Identification, retinoid binding, and x-ray analysis of a human retinol-binding protein. Proc Nat Acad Sci USA, 98, pp. 3710-3715.
35. Castro, GD, Delgado de Layno, AMA, Costantini, MH and Castro, JA (2001) Cytosolic xanthine oxidoreductase mediated bioactivation of ethanol to acetaldehyde and free radicals in rat breast tissue. Its potential role in alcohol-promoted mammary cancer. Toxicology, 160, pp. 11-18.
36. Mehta, RG and Moon, RC (1981) Hormonal regulation of retinoic acid binding proteins in the mammary gland. Biochem J, 200, pp. 591-595.
37. Roman, SD, Clarke, CL, Hall, RE, Alexander, IE and Sutherland, RL (1992) Expression and regulation of retinoic acid receptors in human breast cancer cells. Cancer Res, 52, pp. 2236-2242.
38. Budhu, A., Gillilan, R. and Noy, N. (2001) Localizzation of the RAR interaction domain of cellular retinoic acid binding protein-II. J Mol Biol, 305, pp. 939-949.
39. Stirpe, F. and Della Corte, E. (1969) The regulation of rat liver xanthine oxidase. Conversion in vitro of the enzyme activity from dehydrogenase (type D) to oxidase (type O). J Biol Chem, 244, pp. 3855-3863.
40. Waud, WR and Rajagopalan, KV (1976) The mechanism of conversion of rat liver xanthine dehydrogenase from an NAD-dependent form (type D) to an O2-dependent type (type O). Arch Biochem Biophys, 172, pp. 354-364.
41. McManaman, JL and Bain, DL (2002) Structural and conformational analysis of the oxidase to dehydrogenase conversion of xanthine oxidoreductase. J Biol Chem, 277, pp. 21261-21268.
42. Massey, V., Schopfer, LM, Nishino, T. and Nishino, T. (1989) Differences in protein structure of xanthine dehydrogenase and xanthine oxidase revealed by reconstitution with flavine active site probes. J Biol Chem, 264, pp. 10567-10573.
43. Saito, T., Nishino, T. and Massey, V. (1989) Differences in environment of FAD between NAD-dependent and O2-dependent types of rat liver xanthine dehydrogenase shown by active site probe study. J Biol Chem, 264, pp. 15930-15935.
44. Hille, R. and Nishino, T. (1995) Flavoprotein structure and mechanism. 4. Xanthine oxidase and xanthine dehydrogenase. FASEB J, 9, pp. 995-1003.
45. Saito, T. and Nishino, T. (1989) Differences in redox and kinetic properties between NAD-dependent and O2-dependent types of rat liver xanthine dehydrogenase. J Biol Chem, 264, pp. 10015-10022.
46. Hunt, J. and Massey, V. (1992) Purification and properties of milk xanthine dehydrogenase. J Biol Chem, 267, pp. 21479-21485.
47. Kooij, A., Schiller, HJ Schijns, M. et al. (1994) Conversion of xanthine dehydrogenase into xanthine oxidase in rat liver and plasma at the onset of reperfusion after ischemia. Hepatology, 19, pp. 1488-1495.
48. Bray, RC (1975) The enzymes, pp. 299-419. Academic Press, New York
49. Ikegami, T. and Nishino, T. (1986) The presence of desulfo xanthine dehydrogenase in purified and crude enzyme preparations from rat liver. Arch Biochem Biophys, 247, pp. 254-260.
50. Abadeh, S., Killacky, J., Benboubetra, M. and Harrison, R. (1992) Purification and partial characterization of xanthine oxidase from human milk. Biochim Biophys Acta, 1117, pp. 25-32.
51. Massey, V., Brumby, PE, Komai, H. and Palmer, G. (1969) Studies on milk xanthine oxidase. Some spectral and kinetic properties. J Biol Chem, 244, pp. 1682-1691. .
52. Okamoto, K., Matsumoto, K., Hille, R., Eger, BT, Pai, EF and Nishino, T. (2004) The crystal structure of Xanthine oxidoreductase during catalysis: Implications for reaction mechanism and enzyme inhibition. Proc Natl Acad Sci USA, 101, pp. 7931-7936.
53. Shao, ZM, Dawson, ML, Li, XS, Rishi, AK, Sheikh, MS, Han, QX, Ordonez, JV, Shroot, B. and Fontana, JA (1995) p53 independent G0/G1 arrest and apoptosis induced by a novel retinoid in human breast cancer cells. Oncogene, 11, pp. 493-504.
54. Seewaldt, VL, Kim, JH, Caldwell, LE, Johnson, BS, Swisshelm, K. and Collins, SJ (1997) All-trans-retinoic acid mediates G1 arrest but no apoptosis of normal human mammary epithelial cells. Cell Growth Differ, 8, pp. 631-641.
55. Farhana, L., Dawson, M., Rishi, AK, Zang, Y., Van Buren, E., Trivedi, C., Reichert, U., Fang, G., Kirschner, MW and Fontana, JA (2002) Cyclin B and E2F-1 expression in prostate carcinoma cells treated with the novel retinoid CD437 are regulated by the ubiquitin-mediated pathway. Cancer Res, 62, pp. 3842-3849.
56. Rishi, AK, Zhang, L., Boyanapalli, M., Wali, A., Mohammad, RM, Yu, Y., Fontana, JA, Hatfield, JS, Dawson, MI, Majumdar, APN and Reichert, U. (2003) Identification and characterization of a cell cycle and apoptosis regulatory protein-1 as a novel mediator of apoptosis signaling by retinoid CD437. J Biol Chem, 278, pp. 33422-33435.
57. Futterman, S. (1962) Enzymatic oxidation of vitamin A aldehyde to vitamin A acid. J Biol Chem, 237, pp. 677-680.
58. Olson, JA (1967) The metabolism of vitamin A. Pharmacol Rev, 19, pp. 559-596.
59. Franzoni, L., Lucke, C., Perez, C., Cavazzini, D., Rademacher, M., Ludwig, C., Spisni, A., Rossi, GL and Ruterjans, H. (2002) Structure and backbone dynamics of apo- and holo-cellular binding protein in solution. J Biol Chem, 277, pp. 21983-21997.
60. Lu, J., Cistola, DP and Li, E. (2003) Two homologous rat cellular retinol-binding proteins differ in local conformational flexibility. J Mol Biol, 330, pp. 799-812.