The biological role of D-glucaric acid and its derivatives: Potential use in medicine;Biologiczna rola kwasu D-glukarowego i jego pochodnych; potencjalne zastosowanie w medycynie

Postepy Higieny i Medycyny Doswiadczalnej

Volumn 62, Issue , 2008, Pages 451-462

  Zółtaszek, Robert ^a   Hanausek, Margaret ^a   Kiliańska, Zofia M ^b   Walaszek, Zbigniew ^a  

^a Mays Cancer Center at UT Health San Antonio   (United States)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

Apoptosis; Cancers; D glucaric acid; D glucaro 1,4 lactone; Inflammation; Oxidative stress; glucuronidase

Indexed keywords

BETA GLUCURONIDASE; DRUG DERIVATIVE; SACCHARIC ACID; SACCHAROLACTONE;

ANIMAL; APOPTOSIS; HUMAN; METABOLISM; NEOPLASM; OXIDATIVE STRESS; REVIEW; RISK FACTOR;

ANIMALS; APOPTOSIS; GLUCARIC ACID; GLUCURONIDASE; HUMANS; NEOPLASMS; OXIDATIVE STRESS; RISK FACTORS;

EID: 58149374098     PISSN: 00325449     EISSN: 17322693     Source Type: Journal    
DOI: None     Document Type: Article

References (93)

1. Abou-Issa H.M., Duruibe V.A., Minton J.P., Larroya S., Dwivedi C., Webb T.E.: Putative metabolites derived from dietary combinations of calcium glucarate and N-(4-hydroxyphenyl)retinamide act synergistically to inhibit the induction of rat mammary tumors by 7,12-dimethylbenz[a]anthracene. Proc. Natl. Acad. Sci. USA, 1988; 85: 4181-4184
2. Abou-Issa H., Koolemans-Beynen A., Minton J.P., Webb T.E.: Synergistic interaction between 13-cis-retinoic acid and glucarate: activity against rat mammary tumor induction and MCF-7 cells. Biochem. Biophys. Res. Commun., 1989; 163: 1364-1369
3. Abou-Issa H., Webb T.E., Minton J.P., Moeschberger M.: Chemotherapeutic evaluation of glucarate and N-(4-hydroxyphenyl) retinamide alone and in combination in the rat mammary tumor model. J. Natl. Cancer Inst., 1989; 81: 1820-1823
4. Beland F.A., Kadlubar F.F.: Factors involved in the induction of urinary bladder cancer by aromatic amines. Banbury Rep., 1986; 23: 315-326
5. Boyland E., Wallace D.M., Williams D.C.: Enzyme activity in relation to cancer: inhibition of urinary β-glucuronidase of patients with cancer of the bladder by oral administration of 1:4-saccharolactone and related compounds. Br. J. Cancer, 1957; 11: 578-589
6. Burchell B., Coughtrie M.W.: UDP-glucuronosyltransferases. Pharmacol. Ther., 1989; 43: 261-289
7. Carr A.J.: Effect of some glycosidase inhibitors on experimental tumours in the mouse. Nature, 1963; 198: 1104-1105
8. Carr A.J.: Effect of feeding potassium acid saccharate in the diet of rats for successive generations. Proc. Soc. Exp. Biol. Med., 1947; 65: 189-191
9. Cattaneo M.: Hyperhomocysteinemia, atherosclerosis and thrombosis. Thromb. Haemost., 1999; 81: 165-176
10. Clark A.G., Fischer L.J., Millburn P., Smith R.L., Williams R.T.: The role of gut flora in the enterohepatic circulation of stilboestrol in the rat. Biochem. J., 1969; 112: 17P-18P
11. Colombi A., Maroni M., Antonini C., Fait A., Zocchetti C, Foa V.: Influence of sex, age, and smoking habits on the urinary excretion of D-glucaric acid. Clin. Chim. Acta, 1983; 128: 349-358
12. Darley-Usmar V., Halliwell B.: Blood radicals: reactive nitrogen species, reactive oxygen species, transition metal ions, and the vascular system. Pharm. Res., 1996; 13: 649-662
13. Ding S.Z, Minohara Y., Fan X.J., Wang J., Reyes V.E., Patel J., Dirden-Kramer B., Boldogh I., Ernst P.B., Crowe S.E.: Helicobacter pylori infection induces oxidative stress and programmed cell death in human gastric epithelial cells. Infect. Immun., 2007; 75: 4030-4039
14. Doctor V.M., Shepherd B., McCullough W.: Anticoagulant action of glucuronolactone in rat. Thromb. Res., 1972; 1: 311-316
15. Dohrmann R.E.: β-Glucuronidase. Springer Verlag, Berlin-Heidelberg-New York, 1969
16. Dutton G.J.: Glucuronidation of drugs and other compounds. CRC Press, Boca Raton, FL, 1980
17. Dwivedi C., Downie A.A., Webb T.E.: Modulation of chemically initiated and promoted skin tumorigenesis in CD-1 mice by dietary glucarate. J. Environ. Pathol. Toxicol. Oncol., 1989; 9: 253-259
18. Dwivedi C., Oredipe O.A., Barth R.F., Downie A.A., Webb T.E.: Effects of the experimental chemopreventative agent, glucarate, on intestinal carcinogenesis in rats. Carcinogenesis, 1989; 10: 1539-1541
19. Egan B.J., Holmes K., O'Connor H.J., O'Morain C.A.: Helicobacter pylori gastritis, the unifying concept for gastric diseases. Helicobacter, 2007; 12 (Suppl.2): 39-44
20. Fearon E.R., Vogelstein B.: A genetic model for colorectal tumorigenesis. Cell, 1990; 61: 759-767
21. Furuno K., Matsushita H., Nagashima R., Nakano H., Suzuki S.: Effect of D-glucaric acid derivatives on stability of rat liver lysosomes and erythrocytes. Jpn. J. Pharmacol., 1974; 24: 843-852
22. Giri S.N., Hollinger M.A.: Effect of cadmium on lung lysosomal enzymes in vitro. Arch. Toxicol., 1995; 69: 341-345
23. Hanausek M., Walaszek Z., Slaga T.J.: Detoxifying cancer causing agents to prevent cancer. Integr. Cancer Ther., 2003; 2: 139-144
24. Hanausek M., Walaszek Z., Wang S., Sherman U., Mirowski M., Adams A.K.: Potential use of a 65 kDa tumor-associated protein (p65) in diagnosis of prostate cancer. Genitourinary Oncology Conference: The Clinical Implication of Prostate Cancer Biology, Houston. 1993; Abstract 5: 19
25. Harigaya S.: Studies on glucosaccharolactones. II. Glucosaccharol: 4,3:6-dilactone and its inhibitory effect on β-glucuronidase. J. Biochem., 1964; 56: 392-399
26. Heerdt A.S., Young C.W., Borgen P.I.: Calcium glucarate as a chemopreventive agent in breast cancer. Isr. J. Med. Sci., 1995; 31: 101-105
27. Ho K.J., Hsu S.C., Chen J.S., Ho L.H.: Human biliary β-glucuronidase: correlation of its activity with deconjugation of bilirubin in the bile. Eur. J. Clin. Invest., 1986; 16: 361-367
28. Ho Y.D., Ho K.J.: Biliary D-glucaric acid: its quantitation and preventive role in gallstone formation. Scand. J. Gastroenterol., 1990; 25: 631-640
29. Horton D., Walaszek Z.: Conformations of the D-glucarolactones and D-glucaric acid in solution. Carbohydr. Res., 1982; 105: 95-109
30. Iida R., Nagata S., Kakimoto M., Akaike H., Watanabe H., Shioya A.: 2,5-Di-O-acetyl-D-glucosaccharo-(l-4),(6-3)-dilactone, a new potent β-glucuronidase inhibitor. Jpn. J. Pharmacol., 1965; 15: 88-90
31. Ischii Y., Kihara A., Noguchi H., Shimada T., Ohara H., Wada T.: Studies on abnormalities of glucuronidation in carcinoma hosts. Tumor Res., 1968; 3: 75-90
32. Isomatsu Y., Kaburagi Y., Jinbo S., Nashimo T., Miki M., Yamanaka M.: Clinical study on prophylaxis of diacetyl-glucaro-(1-4) (6-3) dilactone for recurrence of bladder cancer. Gan To Kagaku Ryoho, 1983; 10: 1958-1962
33. Karunairatnam M.C., Levvy G.A.: The inhibition of β-glucuronidase by saccharic acid and the role of the enzyme in glucuronide synthesis. Biochem. J., 1949; 44: 599-604
34. King C.M., Weber W.W.: Formation, metabolic activation by N-Oacyltransfer, and hydrolysis of N-acyl-N-arylamine derivatives. Natl. Cancer Inst. Monogr., 1981; 58: 117-122
35. Klaunig J.E., Kamendulis L.M.: The role of oxidative stress in carcinogenesis. Annu. Rev. Pharmacol. Toxicol., 2004; 44: 239-267
36. Levvy G.A.: The preparation and properties of β-glucuronidase. IV. Inhibition by sugar acids and their lactones. Biochem. J., 1952; 52: 464-472
37. Levvy G.A., Conchie J.: β-glucuronidase and the hydrolysis of glucuronides. W: Glucuronic Acid: Free and Combined, red.: G.J. Dutton. Academic Press, New York, 1966; 301-364
38. Macfadyen A., Ho K.J.: D-glucaro-l,4-lactone: its excretion in the bile and urine and effect on the biliary secretion of β-glucuronidase after oral administration in rats. Hepatology, 1989; 9: 552-556
39. Makola D., Peura D.A., Crowe S.E.: Helicobacter pylori infection and related gastrointestinal diseases. J. Clin. Gastroenterol., 2007; 41: 548-558
40. Marselos M., Dutton G., Hänninen O.: Evidence that D-glucaro-l,4-lactone shortens the pharmacological action of drugs being disposed via the bile as glucuronides. Biochem. Pharmacol., 1975; 24: 1855-1858
41. Marsh C.A.: Metabolism of D-glucuronolactone in mammalian systems. Inhibitory properties of the products of D-glucuronolactone-dehydrogenase action. Biochem. J., 1966; 99: 22-27
42. Marshall T., Shult P., Busse W.W.: Release of lysosomal enzyme β-glucuronidase from isolated human eosinophils. J. Allergy Clin. Immunol., 1988; 82: 550-555
43. Matsui M., Okada M., Ishidate M.: Studies on the glucaric acid pathway in the metabolism of D-glucuronic acid in mammals. II. Excretion of D-glucaric acid in urine after administration of several monosaccharides and their derivatives to mammals. Chem. Pharm. Bull., 1969; 17: 1064-1071
44. Mehta R.G., Rao K.V., Kelloff G., Moon R.C.: Evaluation of potential chemopreventive agents for their activity against carcinogen-induced development of mammary lesions in vitro. Proc. Am. Assoc. Cancer Res., 1989; 30: 170
45. Minton J.P., Walaszek Z., Schooley W., Hanausek-Walaszek M., Webb T.E.: β-Glucuronidase levels in patients with fibrocystic breast disease. Breast Cancer Res. Treat., 1986; 8: 217-222
46. Miyakawa M., Yoshida O., Harada T., Kato T.: The effect of urinary β-glucuronidase inhibition on the induction of bladder tumors with 2-acetylaminofluorene in rats. Invest Urol., 1973; 10: 256-261
47. Morita N., Walaszek Z., Kinjo T., Nishimaki T., Hanausek M., Slaga T.J., Mori H., Yoshimi N.: Effect of synthetic and natural in vivo inhibitors of β-glucuronidase on azoxymethane-induced colon carcinogenesis in rats. Mol. Med. Rep., 2008; (w druku)
48. Morton K.C., Wang C.Y.: Effect of phenothiazine, allopurinol, and glucaron on nitrofuran binding in rats. Drug. Metab. Dispos., 1984; 12: 672-673
49. Nowak P., Olas B., Bald E., Gowacki R., Wachowicz B.: Peroxynitriteinduced changes of thiol groups in human blood platelets. Platelets, 2003; 14: 375-379
50. Okazaki M., Ito H., Takano M., Hino M.: Effect of a β-glucuronidase inhibitor (2,5-di-O-acetyl-D-glucurodilactone and sodium D-glucurolactonate) on rheumatoid arthritis. Iryo, 1969; 23: 1484-1495
51. Olas B., Saluk-Juszczak J., Nowak P., Gowacki R., Bald E., Wachowicz B.: Protective effects of D-glucaro-1,4-lactone against oxidative/nitrative modifications of plasma proteins. Nutrition, 2007; 23: 164-171
52. Olas B., Saluk-Juszczak J., Wachowicz B.: D-glucaro-1,4-lactone and resveratrol as antioxidants in blood platelets. Cell Biol. Toxicol., 2008; 24: 189-199
53. Oredipe O.A., Barth R.F., Dwivedi C., Webb T.E.: Chemopreventative activity of dietary glucarate on azoxymethane-induced altered hepatic foci in rats. Res. Commun. Chem. Pathol. Pharmacol., 1989; 65: 345-359
54. Oredipe O.A., Barth R.F., Hanausek-Walaszek M., Sautins I., Walaszek Z., Webb T.E.: Effects of calcium glucarate on the promotion of diethylnitrosamine-initiated altered hepatic foci in rats. Cancer Lett., 1987; 38: 95-99
55. Paumgartner G., Sthiel A., Gerok W.: Enterohepatic circulation of bile acids and sterol metabolism. Kluwer Academic Publishers 1985
56. Pegram R.A., Allaben W.T., Chou M.W.: Effect of caloric restriction on aflatoxin B1-DNA adduct formation and associated factors in Fischer 344 rats: preliminary findings. Mech. Ageing Dev., 1989; 48: 167-177
57. Reddy B.S., Weisburger J.H., Wynder E.L.: Fecal bacterial β-glucuronidase: control by diet. Science, 1974; 183: 416-417
58. Robinson K., Argent R.H., Atherton J.C.: The inflammatory and immune response to Helicobacter pylori infection. Best Pract. Res. Clin. Gastroenterol., 2007; 21: 237-259
59. Sacquet E., Van Heijenoort Y., Riottot M., Leprince C.: Action of microbial flora of the digestive tract on the metabolism of bile acids in the rat. Biochim. Biophys. Acta, 1975; 380: 52-65
60. Saluk-Juszczak J., Olas B., Nowak P., Staroñ A., Wachowicz B.: Protective effects of D-glucaro-1,4-lactone against oxidative modifications in blood platelets. Nutr. Metab. Cardiovasc. Dis., 2008; 18: 422-428
61. Sandstad O., Osnes T., Skar V.: D-glucaric acid in common duct bile and relation to choledocholithiasis. Scand. J. Gastroenterol., 2002; 37: 488-492
62. Selhub J.: Homocysteine metabolism. Annu. Rev. Nutr., 1999; 19: 217-246
63. Sepulveda A.R., Graham D.Y.: Role of Helicobacter pylori in gastric carcinogenesis. Gastroenterol Clin. North. Am., 2002; 31: 517-535
64. Shimoi K., Saka N., Nozawa R., Sato M., Amano I., Nakayama T., Kinae N.: Deglucuro-nidation of a flavonoid, luteolin monoglucuronide, during inflammation. Drug Metab. Dispos., 2001; 29: 1521-1524
65. Steele V.E., Kelloff G.J., Wilkinson B.P., Arnold J.T.: Inhibition of transformation in cultured rat tracheal epithelial cells by potential chemopreventive agents. Cancer Res., 1990; 50: 2068-2074
66. Takada H., Hirooka T., Hiramatsu Y., Yamamoto M.: Effect of β-glucuronidase inhibitor on azoxymethane-induced colonic carcinogenesis in rats. Cancer Res., 1982; 42: 331-334
67. Wada T., Ohara H., Ischii Y., Noto A., Kihara A., Noguchi H.: Studies on the correlation between glucuronic acid metabolism and β-glucuronidase activity in cancer hosts. Tumor Res., 1966; 1: 123-142
68. Walaszek Z.: Chemopreventive properties of D-glucaric acid derivatives. Cancer Bull., 1993; 45: 453-457
69. Walaszek Z.: Potential use of D-glucaric acid derivatives in cancer prevention. Cancer Lett., 1990; 54: 1-8
70. Walaszek Z., Flores E., Adams A.K.: Effect of dietary glucarate on estrogen receptors and growth of 7,12-dimethylbenz[a]anthraceneinduced rat mammary carcinomas. Breast Cancer Res. Treat., 1988; 12: 128
71. Walaszek Z., Hanausek M.: Molecular markers of apoptosis as prognostic indicators in cancer. Cell Mol. Biol. Lett., 2000; 5: 278-279
72. Walaszek Z., Hanausek M., Adams A.K.: Similar metabolism but different absorption and excretion of calcium D-glucarate and potassium hydrogen D-glucarate in female rats: relevance to cancer. Proc. Am. Assoc. Cancer Res., 1998; 39: 118
73. Walaszek Z., Hanausek M., Narog M.L., Zoltaszek R., Slaga T.J.: Modulation of biomarkers of inflammation and inhibition of mouse skin tumorigenesis by a natural β-glucuronidase inhibitor and its precursor. Proc. Am. Assoc. Cancer Res., 2005; 46: 1016
74. Walaszek Z., Hanausek M, Sherman U., Adams A.K.: Antiproliferative effect of dietary glucarate on the Sprague-Dawley rat mammary gland. Cancer Lett., 1990; 49: 51-57
75. Walaszek Z., Hanausek M., Sherman U., Del Rio M., Adams A.K.: Effects of (+) glucaric acid derivatives and tamoxifen on human breast cancer cells (MCF-7). Breast Cancer Res. Treat, 1989; 14: 175
76. Walaszek Z., Hanausek M., Slaga T.J.: Mechanisms of chemoprevention. Chest, 2004; 125 (Suppl.5): 128S-133S
77. Walaszek Z., Hanausek M., Szemraj J., Adams A.K.: D-glucaric acid as a prospective tumor marker. Meth. Mol. Med., 1998; 14: 487-495
78. Walaszek Z., Hanausek M, Szemraj J., Zoltaszek R., Slaga T.J.: In vitro growth inhibition of Helicobacter pylori by D-glucaric acid derivatives. Proc. Am. Assoc. Cancer Res., 2006; 47; 1129
79. Walaszek Z., Hanausek M., Zoltaszek R., Slaga T.J.: Inhibitory effect of post-initiation dietary D-glucarate on benzo[a]pyrene-induced inflammation during lung tumorigenesis in A/J mice. Proc. Am. Assoc. Cancer Res., 2004; 45: 724
80. Walaszek Z., Hanausek-Walaszek M., Minton J.P., Webb T.E.: Dietary glucarate as anti-promoter of 7,12-dimethylbenz[a]anthracene-induced mammary tumorigenesis. Carcinogenesis, 1986; 7: 1463-1466
81. Walaszek Z., Hanausek-Walaszek M., Webb T.E.: Dietary glucaratemediated reduction of sensitivity of murine strains to chemical carcinogenesis. Cancer Lett., 1986; 33: 25-32
82. Walaszek Z., Hanausek-Walaszek M., Webb T.E.: Inhibition of 7,12-dimethylbenzanthracene-induced rat mammary tumorigenesis by 2,5-di-O-acetyl-D-glucaro-l,4:6,3-dilactone, an in vivo β-glucuronidase inhibitor. Carcinogenesis, 1984; 5: 767-772
83. Walaszek Z., Hanausek-Walaszek M., Webb T.E.: Repression by sustained-release β-glucuronidase inhibitors of chemical carcinogen-mediated induction of a marker oncofetal protein in rodents. J. Toxicol. Environ. Health, 1988; 23: 15-27
84. Walaszek Z., Hanausek-Walaszek M., Webb T.E.: A de-glucuronidation inhibitor reduces the induction by benzo[a]pyrene of a 60-kilodalton oncofetal protein and DNA binding in vivo. W: Polynuclear Aromatic Hydrocarbons: Chemistry, Characterization and Carcinogenesis, Ninth International Symposium, red.: M. Cooke, A.J. Dennis. Battele Press, Columbus, Ohio 1986; 947-959
85. Walaszek Z., Hanausek-Walaszek M., Webb T.E.: Inhibition of N-methyl-N-nitrosourea-induced mammary tumorigenesis in the rat by a bglucuronidase inhibitor. IRCS Medical Science, 1986; 14: 677-678
86. Walaszek Z., Szemraj J., Hanausek M., Adams A.K., Sherman U.: Dglucaric acid content of various fruits and vegetables and cholesterollowering effects of dietary D-glucarate in the rat. Nutr. Res., 1996; 16: 673-681
87. Walaszek Z., Szemraj J., Narog M., Adams A.K., Kilgore J., Sherman U., Hanausek M.: Metabolism, uptake, and excretion of a D-glucaric acid salt and its potential use in cancer prevention. Cancer Detect. Prev., 1997; 21: 178-190
88. Wang C.Y., Hayashida S.: Enhancement by phenothiazine and 2,5-di-O-acetyl-D-glucosaccharo-(l,4)(6,3)-dilactone of bladder carcinogenicity of N-4-(5-nitro-2-furyl)-2-thiazolyl-formamide in rats. Cancer Lett., 1984; 24: 37-43
89. Yokoyama M., Matsuoka S., Wakui A.: Activation of tegafur and urinary excretion of glucaric acid in tumor bearing hosts. W: Recent Adv. Chemother., Proc. Int. Congr. Chemother., 14th, red.: J. Ishigami. Univ. Tokyo Press, Tokyo 1985, 113-115
90. Yonese Y. Takayasu H., Okada M., Ishidate M.: Attempted prophylaxis of bladder cancer with D-glucaro-l,4;6,3-dilactone, a potent oral β-glucuronidase inhibitor. Abst. Pap. Int. Congress, 9th, Tokyo, 1966; S1285: 700
91. Yoshimi N., Walaszek Z., Mori H., Hanausek M., Szemraj J., Slaga T.J.: Inhibition of azoxymethane-induced rat colon carcinogenesis by potassium hydrogen D-glucarate. Int. J. Oncol., 2000; 16: 43-48
92. Zoltaszek R., Grzelak M., Hanausek M., Kilianska Z., Slaga T.J., Walaszek Z.: Effects of dietary D-glucarate on biomarkers of inflammation during early post-initiation stages of benzo[a]pyrene (B[a]P)-induced lung tumorigenesis in A/J mice. Proc. Am. Assoc. Cancer Res., 2008; 49: 532
93. Zoltaszek R., Hanausek M., Slaga T.J., Walaszek Z.: Proapoptotic effects of D-glucarate on chemically induced lung tumorigenesis in A/J mice. Proc. Am. Assoc. Cancer Res., 2007; 48: 795