Cancer morbidity in rheumatoid arthritis: Role of estrogen metabolites

BioMed Research International

Volumn 2013, Issue , 2013, Pages

  Khan, Wahid Ali ^a   Khan, Mohd Wajid Ali ^b  

^a KING KHALID UNIVERSITY   (Saudi Arabia)

^b CARDIFF UNIVERSITY SCHOOL OF MEDICINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYESTRADIOL; 4 HYDROXYESTRADIOL; AUTOANTIBODY; BENZALKONIUM CHLORIDE; CATECHOL ESTROGEN; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 3A4; ESTRADIOL; ESTRIOL; ESTROGEN DERIVATIVE; ESTRONE; FREE RADICAL; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REACTIVE OXYGEN METABOLITE; ESTROGEN; QUINONE DERIVATIVE;

AEROBIC METABOLISM; ANTIANGIOGENIC ACTIVITY; AUTOIMMUNITY; BASAL CELL CARCINOMA; BREAST CANCER; CANCER RISK; COVALENT BOND; DNA ADDUCT; DNA DAMAGE; DNA MODIFICATION; ENDOMETRIUM CARCINOMA; ESTROGEN METABOLISM; GENOMIC INSTABILITY; HUMAN; HUMORAL IMMUNITY; HYDROXYLATION; IMMUNOGENICITY; IMMUNOGLOBULIN PRODUCTION; LIPID PEROXIDATION; LIVER MICROSOME; METABOLIC ACTIVATION; MORBIDITY; NEOPLASM; NONHODGKIN LYMPHOMA; NONHUMAN; OXIDATION; OXIDATION REDUCTION REACTION; REVIEW; RHEUMATOID ARTHRITIS; SKIN CARCINOMA; TUMOR IMMUNITY; IMMUNOLOGY; METABOLISM; MORTALITY; PATHOLOGY;

ARTHRITIS, RHEUMATOID; ESTROGENS; ESTROGENS, CATECHOL; FREE RADICALS; HUMANS; NEOPLASMS; OXIDATION-REDUCTION; QUINONES;

EID: 84885608884     PISSN: 23146133     EISSN: 23146141     Source Type: Journal    
DOI: 10.1155/2013/748178     Document Type: Review

References (71)

1. Worthington J., Investigating the genetic basis of susceptibility to rheumatoid arthritis. Journal of Autoimmunity 2005 25 16 20 2-s2.0-28444463663 10.1016/j.jaut.2005.09.011 (Pubitemid 41728038)
2. Kinlen L., Vainio H., Magee P., McGregor D., McMicheal A., Immuno suppression and cancer. Mechanism of Carcinogenesis in Risk Identification 1992 Lyon, France International Agency for Research on Cancer 237 253
3. Symmons D. P. M., Lymphoma and rheumatoid arthritis-again. Rheumatology 2007 46 1 1 2 2-s2.0-33845583291 10.1093/rheumatology/kel303 (Pubitemid 44932775)
4. Prior P., Symmons D. P. M., Hawkins C. F., Cancer morbidity in rheumatoid arthritis. Annals of the Rheumatic Diseases 1984 43 2 128 131 2-s2.0-0021260359 (Pubitemid 14125170)
5. Swerdlov S. H., Campo E., Harris N. L., WHO Classification of Tumors of Haematopoietic and Lymphoid Tissue 2008 Lyon, France International Agency for Research on Cancer
6. Kristinsson S. Y., Goldin L. R., Björkholm M., Koshiol J., Turesson I., Landgren O., Genetic and immune-related factors in the pathogenesis of lymphoproliferative and plasma cell malignancies. Haematologica 2009 94 11 1581 1589 2-s2.0-70449337660 10.3324/haematol.2009.008979
7. Bongartz T., Sutton A. J., Sweeting M. J., Buchan I., Matteson E. L., Montori V., Anti-TNF antibody therapy in rheumatoid arthritis and the risk of serious infections and malignancies: systematic review and meta-analysis of rare harmful effects in randomized controlled trials. Journal of the American Medical Association 2006 295 19 2275 2285 2-s2.0-33646696885 10.1001/jama.295.19.2275 (Pubitemid 43736578)
8. Wolfe F., Michaud K., Lymphoma in rheumatoid arthritis: the effect of methotrexate and anti-tumor necrosis factor therapy in 18,572 patients. Arthritis and Rheumatism 2004 50 6 1740 1751 2-s2.0-2642554059 10.1002/art.20311 (Pubitemid 38725085)
9. Chakravarty E. F., Michaud K., Wolfe F., Skin cancer, rheumatoid arthritis, and tumor necrosis factor inhibitors. Journal of Rheumatology 2005 32 11 2130 2135 2-s2.0-27744499707 (Pubitemid 41587856)
10. Weidler C., Härle P., Schedel J., Schmidt M., Schölmerich J., Straub R. H., Patients with rheumatoid arthritis and systemic lupus erythematosus have increased renal excretion of mitogenic estrogens in relation to endogenous antiestrogens. Journal of Rheumatology 2004 31 3 489 494 2-s2.0-1542724803 (Pubitemid 38337606)
11. Khan W. A., Alam K., Moinuddin M., Catechol-estrogen modified DNA: a better antigen for cancer autoantibody. Archives of Biochemistry and Biophysics 2007 465 1 293 300 2-s2.0-34548033304 10.1016/j.abb.2007.06.006 (Pubitemid 47284002)
12. Khan W. A., Alam K., Moinuddin, Preferential recognition of catechol-estrogen modified DNA by circulating autoantibodies in cancer patients. Biocimie 2013 95 1 329 335
13. Straub R. H., The complex role of estrogens in inflammation. Endocrine Reviews 2007 28 5 521 574 2-s2.0-34547792318 10.1210/er.2007-0001 (Pubitemid 47236336)
14. Newbold R. R., Liehr J. G., Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens. Cancer Research 2000 60 2 235 237 2-s2.0-0034650264 (Pubitemid 30070740)
15. Liehr J. G., Is estradiol a genotoxic mutagenic carcinogen? Endocrine Reviews 2000 21 1 40 54 2-s2.0-0034463957 10.1210/er.21.1.40 (Pubitemid 32260395)
16. Suchar L. A., Chang R. L., Rosen R. T., Lech J., Conney A. H., High-performance liquid chromatography separation of hydroxylated estradiol metabolites: formation of estradiol metabolites by liver microsomes from male and female rats. Journal of Pharmacology and Experimental Therapeutics 1995 272 1 197 206 2-s2.0-0028859196
17. Hoffman A. R., Paul S. M., Axelrod J., The enzymatic formation of catecholestrogens from 2-methoxyestrogens by rat liver microsomes. Endocrinology 1980 107 4 1192 1197 2-s2.0-0018929939 (Pubitemid 10019115)
18. Strauss J. F., Barbieri R. L., Yen and Jaffe's Reproductive Endocrinology: Physiology, Pathophysiology and Clinical Management 2009 6th Elsevier Health Science
19. Yue W., Santen R. J., Wang J.-P., Li Y., Verderame M. F., Bocchinfuso W. P., Korach K. S., Devanesan P., Todorovic R., Rogan E. G., Cavalieri E. L., Genotoxic metabolites of estradiol in breast: potential mechanism of estradiol induced carcinogenesis. Journal of Steroid Biochemistry and Molecular Biology 2003 86 3-5 477 486 2-s2.0-10744224293 10.1016/S0960-0760(03)00377-7 (Pubitemid 37412587)
20. Dawling S., Roodi N., Mernaugh R. L., Wang X., Parl F. F., Catechol-O-methyltransferase (COMT)-mediated metabolism of catechol estrogens: comparison of wild-type and variant COMT isoforms. Cancer Research 2001 61 18 6716 6722 2-s2.0-0035884689 (Pubitemid 32896493)
21. Deng H. W., Shen H., Long J. R., Current topic in human genetics: studies in complex diseases. Genes in Oestrogen Metabolism Pathways and Breast Cancer 2007 World Scientific Publishing 759
22. Lee A. J., Conney A. H., Zhu B. T., Human cytochrome P450 3A7 has a distinct high catalytic activity for the 16 α -hydroxylation of estrone but not 17 β -estradiol. Cancer Research 2003 63 19 6532 6536 2-s2.0-0141987947 (Pubitemid 37255207)
23. Gupta M., McDougal A., Safe S., Estrogenic and antiestrogenic activities of 16 α-and 2-hydroxy metabolites of 17 β -estradiol in MCF-7 and T47D human breast cancer cells. Journal of Steroid Biochemistry and Molecular Biology 1998 67 5-6 413 419 2-s2.0-0032448464 10.1016/S0960-0760(98)00135-6 (Pubitemid 29049414)
24. Bolton J. L., Pisha E., Zhang F., Qiu S., Role of quinoids in estrogen carcinogenesis. Chemical Research in Toxicology 1998 11 10 1113 1127 2-s2.0-0031741669 10.1021/tx9801007 (Pubitemid 28500791)
25. Bradlow H. L., Sepkovic D. W., Telang N. T., Osborne M. P., Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent. Annals of the New York Academy of Sciences 1999 889 204 213 2-s2.0-0033427186 (Pubitemid 30040438)
26. Huang Z., Guengerich F. P., Kaminsky L. S., 16 α -Hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis 1998 19 5 867 872 2-s2.0-0031595251 10.1093/carcin/19.5.867 (Pubitemid 28376780)
27. Cavalieri E., Frenkel K., Liehr J. G., Rogan E., Roy D., Estrogens as endogenous genotoxic agents-DNA adducts and mutations. Journal of the National Cancer Institute. Monographs 2000 27 75 93 2-s2.0-0033655310
28. Embrechts J., Lemière F., Van Dongen W., Esmans E. L., Buytaert P., Van Marck E., Kockx M., Makar A., Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. Journal of the American Society for Mass Spectrometry 2003 14 5 482 491 2-s2.0-0037487092 10.1016/S1044-0305(03)00130-2 (Pubitemid 36871629)
29. Markushin Y., Zhong W., Cavalieri E. L., Rogan E. G., Small G. J., Yeung E. S., Jankowiak R., Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract. Chemical Research in Toxicology 2003 16 9 1107 1117 2-s2.0-0141848390 10.1021/tx0340854 (Pubitemid 37163216)
30. Stack D. E., Byun J., Gross M. L., Rogan E. G., Cavalieri E. L., Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides. Chemical Research in Toxicology 1996 9 5 851 859 2-s2.0-0029680465
31. Li K.-M., Todorovic R., Devanesan P., Higginbotham S., Köfeler H., Ramanathan R., Gross M. L., Rogan E. G., Cavalieri E. L., Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo. Carcinogenesis 2004 25 2 289 297 2-s2.0-1242353081 10.1093/carcin/bgg191 (Pubitemid 38239812)
32. Li K. M., Davanson P., Rogan E. G., Cavalieri E. L., Formation of the depurinating 4-hydroxyestradiol (4-OHE2)-1-N7 Gua and 4-OHE2-1-N3 Ade adducts by reaction of E2-3, 4-quinone with DNA. Proceeding for American Association of Cancer Research 1998 636
33. Terashima I., Suzuki N., Shibutani S., Mutagenic properties of estrogen quinone-derived DNA adducts in Simian kidney cells. Biochemistry 2001 40 1 166 172 2-s2.0-0035830448 10.1021/bi002273c (Pubitemid 32052688)
34. Chakravarti D., Mailander P. C., Li K.-M., Higginbotham S., Zhang H. L., Gross M. L., Meza J. L., Cavalieri E. L., Rogan E. G., Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and forms mutations in the H-ras gene. Oncogene 2001 20 55 7945 7953 2-s2.0-0035969644 10.1038/sj/onc/1204969 (Pubitemid 34001555)
35. Liehr J. G., Hormone-associated cancer: Mechanistic similarities between human breast cancer and estrogen-induced kidney carcinogenesis in hamsters. Environmental Health Perspectives 1997 105 3 565 569 2-s2.0-0030986245 (Pubitemid 27246417)
36. Wang M.-Y., Liehr J. G., Lipid hydroperoxide-induced endogenous DNA adducts in hamsters: Possible mechanism of lipid hydroperoxide-mediated carcinogenesis. Archives of Biochemistry and Biophysics 1995 316 1 38 46 2-s2.0-0028837477 10.1006/abbi.1995.1007
37. Khan W. A., Moinuddin M., Binding characteristics of SLE anti-DNA autoantibodies to catecholestrogen-modified DNA. Scandinavian Journal of Immunology 2006 64 6 677 683 2-s2.0-33750726981 10.1111/j.1365-3083.2006.01855.x (Pubitemid 44704317)
38. Khan W. A., Habib S., Khan W. A., Alam K., Moinuddin M., Enhanced binding of circulating SLE autoantibodies to catecholestrogen-copper-modified DNA. Molecular and Cellular Biochemistry 2008 315 1-2 143 150 2-s2.0-46749145282 10.1007/s11010-008-9798-1
39. Khan W. A., Uddin M., Khan M. W. A., Chabbra H. S., Catecholoestrogens: possible role in systemic lupus erythematosus. Rheumatology 2009 48 11 1345 1351 2-s2.0-73349129358
40. Khan W. A., Moinuddin M., Assiri A. S., Immunochemical studies on catechol-estrogen modified plasmid: possible role in rheumatoid arthritis. Journal of Clinical Immunology 2011 31 1 22 29 2-s2.0-79953901963 10.1007/s10875-010-9455-9
41. Roy D., Liehr J. G., Estrogen, DNA damage and mutations. Mutation Research 1999 424 1-2 107 115 2-s2.0-0033535424 10.1016/S0027-5107(99)00012-3 (Pubitemid 29101612)
42. Metzler M., Pfeiffer E., Schuler M., Rosenberg B., Li J. J., Nandi S., Li S. A., Gustafasson J., Sekely L., Effect of estrogen on microtubule assembly: significance for aneuploidy. Hormonal Carcinogenesis II 1996 New York, NY, USA Spinger 193 199
43. Cutolo M., Villaggio B., Craviotto C., Pizzorni C., Seriolo B., Sulli A., Sex hormones and rheumatoid arthritis. Autoimmunity Reviews 2002 1 5 284 289 2-s2.0-0041467355 10.1016/S1568-9972(02)00064-2 (Pubitemid 38352571)
44. Nalbandian G., Kovats S., Estrogen, immunity & autoimmune disease. Current Medicinal Chemistry 2005 5 1 85 91 2-s2.0-13844267012 10.2174/1568013053005418 (Pubitemid 40246737)
45. Castagnetta L. A., Carruba G., Granata O. M., Stefano R., Miele M., Schmidt M., Cutolo M., Straub R. H., Increased estrogen formation and estrogen to androgen ratio in the synovial fluid of patients with rheumatoid asrthritis. Journal of Rheumatology 2003 30 12 2597 2605 2-s2.0-0345472069 (Pubitemid 37549336)
46. Yager J. D., Davidson N. E., Estrogen carcinogenesis in breast cancer. The New England Journal of Medicine 2006 354 3 228 282 2-s2.0-30944469849 10.1056/NEJMra050776 (Pubitemid 43113032)
47. Dubey R. K., Tyurina Y. Y., Tyurin V. A., Gillespie D. G., Branch R. A., Jackson E. K., Kagan V. E., Estrogen and tamoxifen metabolites protect smooth muscle cell membrane phospholipids against peroxidation and inhibit cell growth. Circulation Research 1999 84 2 229 239 2-s2.0-0033524745 (Pubitemid 29070119)
48. Dubey R. K., Jackson E. K., Invited review: cardiovascular protective effects of 17 β -estradiol metabolites. Journal of Applied Physiology 2001 91 4 1868 1883 2-s2.0-0034807672 (Pubitemid 32900383)
49. Folomeev M., Dougados M., Beaune J., Kouyoumdjian J. C., Nahoul K., Amor B., Alekberova Z., Plasma sex hormones and aromatase activity in tissues of patients with systemic lupus erythematosus. Lupus 1992 1 3 191 195 2-s2.0-0026864781
50. Kramer P. R., Kramer S. F., Guan G., 17 β -estradiol regulates cytokine release through modulation of CD16 expression in monocytes and monocyte-derived macrophages. Arthritis and Rheumatism 2004 50 6 1967 1975 2-s2.0-2642566162 10.1002/art.20309 (Pubitemid 38725109)
51. Fotsis T., Zhang Y., Pepper M. S., Adlercreutz H., Montesano R., Nawrotht P. P., Schweigerer L., The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growth. Nature 1994 368 6468 237 239 2-s2.0-0028220858 10.1038/368237a0 (Pubitemid 24108838)
52. Cooke M. S., Mistry N., Wood C., Herbert K. E., Lunec J., Immunogenicity of DNA damaged by reactive oxygen species-implications for anti-DNA antibodies in lupus. Free Radical Biology and Medicine 1996 22 1-2 151 159 2-s2.0-0029912029 10.1016/S0891-5849(96)00283-3 (Pubitemid 26399320)
53. Frenkel K., Karkoszka J., Glassman T., Dubin N., Toniolo P., Taioli E., Mooney L. A., Kato I., Serum autoantibodies recognizing 5-hydroxymethyl-2'- deoxyuridine, an oxidized DNA base, as biomarkers of cancer risk in women. Cancer Epidemiology Biomarkers and Prevention 1998 7 1 49 57 2-s2.0-0031884174 (Pubitemid 28087142)
54. Jansson G., Oestrogen-induced enhancement of myeloperoxidase activity in human polymorphonuclear leukocytes-a possible cause of oxidative stress in inflammatory cells. Free Radical Research Communications 1991 14 3 195 208 2-s2.0-0025907448
55. Chakravarty E. F., Genovese M. C., Associations between rheumatoid arthritis and malignancy. Rheumatic Disease Clinics of North America 2004 30 2 271 284 2-s2.0-2542476069 10.1016/j.rdc.2004.01.007 (Pubitemid 38692561)
56. Wolfe F., Michaud K., Lymphoma in rheumatoid arthritis: the effect of methotrexate and anti-tumor necrosis factor therapy in 18,572 patients. Arthritis and Rheumatism 2004 50 6 1740 1751 2-s2.0-2642554059 10.1002/art.20311 (Pubitemid 38725085)
57. Mellemkjær L., Linet M. S., Gridley G., Frisch M., Møller H., Olsen J. H., Rheumatoid arthritis and cancer risk. European Journal of Cancer A 1996 32 10 1753 1757 2-s2.0-0006050423 10.1016/0959-8049(96)00210-9 (Pubitemid 26306889)
58. Bongartz T., Sutton A. J., Sweeting M. J., Buchan I., Matteson E. L., Montori V., Anti-TNF antibody therapy in rheumatoid arthritis and the risk of serious infections and malignancies: systematic review and meta-analysis of rare harmful effects in randomized controlled trials. Journal of the American Medical Association 2006 295 19 2275 2285 2-s2.0-33646696885 10.1001/jama.295.19.2275 (Pubitemid 43736578)
59. Cutolo M., Estrogen metabolites: increasing evidence for their role in rheumatoid arthritis and systemic lupus erythematosus. Journal of Rheumatology 2004 31 3 419 421 2-s2.0-1542410406 (Pubitemid 38337597)
60. Vandewalle B., Lefebvre J., Opposite effects of estrogen and catecholestrogen on hormone-sensitive breast cancer cell growth and differentiation. Molecular and Cellular Endocrinology 1989 61 2 239 246 2-s2.0-0024552204 (Pubitemid 19038903)
61. Fishman J., Schneider J., Hershcopf R. J., Bradlow H. L., Increased estrogen-16 α -hydroxylase activity in women with breast and endometrial cancer. Journal of Steroid Biochemistry 1984 20 4, part 2 1077 1081 2-s2.0-0021270323 10.1016/0022-4731(84)90021-9 (Pubitemid 14101045)
62. Telang N. T., Suto A., Wong G. Y., Osborne M. P., Bradlow H. L., Induction by estrogen metabolite 16 α -hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. Journal of the National Cancer Institute 1992 84 8 634 638 2-s2.0-0026582407
63. Schneider J., Huh M. M., Bradlow H. L., Fishman J., Antiestrogen action of 2-hydroxyesterone on MCF-7 human breast cancer cells. Journal of Biological Chemistry 1984 259 8 4840 4845 2-s2.0-0021352552 (Pubitemid 14144204)
64. Bradlow H. L., Telang N. T., Sepkovic D. W., Osborne M. P., 2-Hydroxyesterone: the "good" estrogen. Journal of Endocrinology 1996 150 S259 S265 2-s2.0-0029856102
65. Lahita R. G., Bradlow H. L., Kunkel H. G., Fishman J., Alterations of estrogen metabolism in systemic lupus erythematosus. Arthritis and Rheumatism 1979 22 11 1195 1198 2-s2.0-0018639820 (Pubitemid 10163784)
66. Sowers M. R., McConnell D., Jannausch M., Buyuktur A. G., Hochberg M., Jamadar D. A., Estradiol and its metabolites and their association with knee osteoarthritis. Arthritis and Rheumatism 2006 54 8 2481 2487 2-s2.0-33746940311 10.1002/art.22005 (Pubitemid 44205008)
67. Li J. J., Li S. A., Estrogen carcinogenesis in Syrian hamster tissues: role of metabolism. Federation Proceedings 1987 46 5 1858 1863 2-s2.0-0023181602 (Pubitemid 17075932)
68. Cavalieri E., Kohli E., Zahid M., Rogan E., Greater reactivity of estradiol-3, 4-quinone vs estradiol-2, 3-quinone with DNA in the formation of depurinating DNA adducts. Proceeding for American Association of Cancer Research 2003 44 180
69. Rogan E. G., Badawi A. F., Devanesan P. D., Meza J. L., Edney J. A., West W. W., Higginbotham S. M., Cavalieri E. L., Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: potential biomarkers of susceptibility to cancer. Carcinogenesis 2003 24 4 697 702 2-s2.0-0038393297 10.1093/carcin/bgg004 (Pubitemid 36592404)
70. Cutolo M., Sulli A., Straub R. H., Estrogen metabolism and autoimmunity. Autoimmunity Reviews 2012 11 6-7 A460 A464 2-s2.0-84858438060 10.1016/j.autrev.2011.11.014
71. Cutolo M., Hormone therapy in rheumatic diseases. Current Opinion in Rheumatology 2010 22 3 257 263 2-s2.0-77950282191 10.1097/BOR.0b013e328336ec24