Mass spectrometry evidence for formation of estrogen-homocysteine conjugates: Estrogens can regulate homocysteine levels

Free Radical Biology and Medicine

Volumn 65, Issue , 2013, Pages 1447-1454

  Gaikwad, Nilesh W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Catechol estrogens; Conjugates; Estrogen; Free radicals; Homocysteine; Mass spectrometry; Myeloperoxidase; Quinone

Indexed keywords

DNA; ESTROGEN; HOMOCYSTEINE; METAL ION; MYELOPEROXIDASE; OXIDOREDUCTASE; OXYGEN; QUINONE DERIVATIVE;

ARTICLE; CARDIOVASCULAR DISEASE; ELECTROPHILICITY; ENDOTHELIUM CELL; MASS SPECTROMETRY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; URINE LEVEL;

HUMAN ECHOVIRUS 1;

CARDIOVASCULAR DISEASE; CATECHOL ESTROGENS; CONJUGATES; CVD; E; ESTROGEN; FREE RADICALS; HCYS; HOMOCYSTEINE; MASS SPECTROMETRY; MPO; MYELOPEROXIDASE; QUINONE;

ALKYLATION; CARDIOTONIC AGENTS; CARDIOVASCULAR DISEASES; DNA; ESTRADIOL CONGENERS; ESTROGENS; ESTROGENS, CATECHOL; GLUTATHIONE; HOMOCYSTEINE; MASS SPECTROMETRY; OXIDATION-REDUCTION; PEROXIDASE; QUINONES;

EID: 84890428357     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2013.07.041     Document Type: Article

References (56)

1. C.T. Esmon, and W.G. Owen Identification of an endothelial cell cofactor for thrombin-catalyzed activation of protein C Proc. Natl. Acad. Sci. USA 78 1981 2249 2252
2. K. Janani, J. Sowmiya, and M. Nandhitha Homocysteine - a potent modulator. Biotechnol Mol. Biol. 7 2012 1 4
3. K.S. McCully Vascular pathology of homocysteinemia: implications for the pathogenesis of arteriosclerosis Am. J. Pathol. 56 1969 111 128
4. D.E.L Wilcken, and B. Wilcken The pathogenesis of coronary artery disease: a possible role for methionine metabolism J. Clin. Invest. 57 1976 1079 1082
5. V. Veeranna, S.K. Zalawadiya, A. Niraj, J. Pradhan, B. Ference, R.C. Burack, S. Jacob, and L. Afonso Homocysteine and reclassification of cardiovascular disease risk J. Am. Coll. Cardiol. 58 2011 1025 1033
6. M.L. Bots, L.J. Launer, J. Lindemans, A. Hofman, and D.E. Grobbee Homocysteine, atherosclerosis and prevalent cardiovascular disease in the elderly: the Rotterdam Study J. Intern. Med. 242 1997 339 347
7. T.P. Vacek, J.C. Vacek, N. Tyagi, and S.C. Tyagi Autophagy and heart failure: a possible role for homocysteine Cell Biochem. Biophys. 62 2012 1 11
8. D. Tayal, B. Goswami, B.C. Koner, and V. Mallika Role of homocysteine and lipoprotein (A) in atherosclerosis: an update Biomed. Res. 22 2011 391 405
9. W. Herrmann, and R. Obeid Homocysteine: a biomarker in neurodegenerative diseases Clin. Chem. Lab. Med. 49 2011 435 441
10. B.N. Manolescu, E. Oprea, I.C. Farcasanu, M. Berteanu, and C. Cercasov Homocysteine and vitamin therapy in stroke prevention and treatment: a review Acta Biochem. Pol. 57 2010 467 477
11. B-J. Kim, J-M. Koh, S.H. Ahn, S.H. Lee, E.H. Kim, S.J. Bae, H-K. Kim, J.W. Choe, K-H. Lim, and K.H. Pyun High serum total homocysteine levels accelerate hip bone loss in healthy premenopausal women and men Bone 52 2013 56 62
12. P. Gu, L.F. DeFina, D. Leonard, S. John, M.F. Weiner, and E.S. Brown Relationship between serum homocysteine levels and depressive symptoms: the Cooper Center Longitudinal Study J. Clin. Psychiatry 73 2012 691 695
13. M. Laskowska, K. Laskowska, and J. Oleszczuk Differences in the association between maternal serum homocysteine and ADMA levels in women with pregnancies complicated by preeclampsia and/or intrauterine growth restriction Hypertens. Pregnancy 32 2013 83 93
14. M. Cankurtaran, Y. Yesil, M.E. Kuyumcu, Z.A. Ozturk, B.B. Yavuz, M. Halil, Z. Ulger, E.S. Cankurtaran, and S. Ariogul Altered levels of homocysteine and serum natural antioxidants links oxidative damage to Alzheimer's disease J. Alzheimers Dis 33 2013 1051 1058
15. C. Isobe, T. Murata, C. Sato, and Y. Terayama Increase of total homocysteine concentration in cerebrospinal fluid in patients with Alzheimer's disease and Parkinson's disease Life Sci. 77 2005 1836 1843
16. L. Kevere, S. Purvina, D. Bauze, M. Zeibarts, R. Andrezina, A. Rizevs, S. Jelisejevs, L. Piekuse, M. Kreile, and I. Purvins Elevated serum levels of homocysteine as an early prognostic factor of psychiatric disorders in children and adolescents Schizophr. Res. Treat. 373261 2012 7
17. C-C. Wu, C-M. Zheng, Y-F. Lin, L. Lo, M-T. Liao, and K-C. Lu Role of homocysteine in end-stage renal disease Clin. Biochem. 45 2012 1286 1294
18. L. Parnetti, T. Bottiglieri, and D. Lowenthal Role of homocysteine in age-related vascular and non-vascular diseases Aging 9 1997 241 257
19. M. Klerk, P. Verhoef, and R. Clarke MTHFR 677C T polymorphism and risk of coronary heart disease: a meta-analysis JAMA 288 2002 2023 2031
20. R. Clarke, R. Collins, S. Lewington, A. Donald, G. Alfthan, J. Tuomilehto, E. Arnesen, K. Bonaa, J. Blacher, and G.H.J. Boers Homocysteine and risk of ischemic heart disease and stroke: a meta-analysis JAMA 288 2002 2015 2022
21. W. Herrmann, and J-P. Knapp Hyperhomocysteinemia: a new risk factor for degenerative diseases Clin. Lab. 48 2002 471 481
22. R. Obeid, and W. Herrmann Mechanisms of homocysteine neurotoxicity in neurodegenerative diseases with special reference to dementia FEBS Lett. 580 2006 2994 3005
23. S. Kalmijn, L.J. Launer, J. Lindemans, M.L. Bots, A. Hojman, and M.M. Breteler Total homocysteine and cognitive decline in a community-based sample of elderly subjects: the Rotterdam Study Am. J. Epidemiol. 150 1999 283 289
24. J. Selhub Homocysteine metabolism Annu. Rev. Nutr. 19 1999 217 246
25. J.M. Armitage, L. Bowman, and R.J. Clarke Effects of homocysteine lowering with folic acid plus vitamin B12 vs placebo on mortality and major morbidity in myocardial infarction survivors: a randomized trial JAMA 303 2010 2486 2494
26. K.H. Bonaa, I. Njolstad, and P.M. Ueland Homocysteine lowering and cardiovascular events after acute myocardial infarction N. Engl. J. Med. 354 2006 1578 1588
27. E. Lonn, S. Yusuf, and M.J. Arnold Homocysteine lowering with folic acid and B vitamins in vascular disease N. Engl. J. Med. 354 2006 1567 1577
28. E.R. Miller, S. Juraschek, R. Pastor-Barriuso, L.A. Bazzano, L.J. Appel, and E. Guallar Meta-analysis of folic acid supplementation trials on risk of cardiovascular disease and risk interaction with baseline homocysteine levels Am. J. Cardiol. 106 2010 517 527
29. G. Starkebaum, and J.M. Harlan Endothelial cell injury due to copper catalysed hydrogen peroxide generation from homocysteine J. Clin. Invest. 77 1993 1370 1376
30. N.P.B. Dudman, S.E. Temple, X.W. Guo, W.Y. Fu, and M.A. Perry Homocysteine enhances neutrophil endothelial interactions in vivo Circ. Res. 84 1999 409 416
31. D. Liao, H. Tan, R. Hui, Z. Li, X. Jiang, J. Gaubatz, F. Yang, and W. Durante Hyperhomocysteinemia decreases circulating high-density lipoprotein by inhibiting apolipoprotein A-I protein synthesis and enhancing HDL cholesterol clearance Circ. Res 99 2006 598 603
32. A.M. Emsley, J.V. Jeremy, G.N. Gomes, G.D. Angelini, and F. Plane Investigation of the inhibitory effects of homocysteine and copper on nitric oxide mediated relaxation of rat isolated aorta Br. J. Pharmacol. 126 1999 1034 1040
33. M.M. Steed, and S.C. Tyagi Mechanisms of cardiovascular remodeling in hyperhomocysteinemia Antioxid. Redox Signalling 15 2011 1926 1943
34. R.K. Dubey, S.P. Tofovic, and E.K. Jackson Cardiovascular pharmacology of estradiol metabolites J. Pharmacol. Exp. Ther. 308 2004 403 409
35. S.P. Tofovic Estrogens and development of pulmonary hypertension: interaction of estradiol metabolism and pulmonary vascular disease J. Cardiovasc. Pharmacol. 56 2010 696 708
36. X. Guo, M. Razandi, A. Pedram, G. Kassab, and E.R. Levin Estrogen induces vascular wall dilation: mediation through kinase signaling to nitric oxide and estrogen receptors α and β J. Biol. Chem. 280 2005 19704 19710
37. E.A. Booth, and B.R. Lucchesi Estrogen-mediated protection in myocardial ischemia-reperfusion injury Cardiovasc. Toxicol. 8 2008 101 113
38. D.N. Masood, E.C. Roach, K.G. Beauregard, and R.A. Khalil Impact of sex hormone metabolism on the vascular effects of menopausal hormone therapy in cardiovascular disease Curr. Drug Metab. 11 2010 693 714
39. R.K. Dubey, and E.K. Jackson Cardiovascular protective effects of 17β-estradiol metabolites J. Appl. Physiol. 91 2001 1868 1883
40. N.W. Gaikwad, L. Yang, P. Muti, J. Meza, S. Pruthi, J. Ingle, E. Rogan, and E. Cavalieri The molecular etiology of breast cancer and biomarkers of risk Int. J. Cancer 122 2008 1949 1957
41. R.K. Dubey, D.G. Gillespie, L.C. Zacharia, F. Barchiesi, B. Imthurn, and E.K. Jackson CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs Hypertension 41 2003 807 813
42. R.K. Dubey, S.P. Tofovic, and E.K. Jackson Cardiovascular pharmacology of estradiol metabolites J. Pharmacol. Exp. Ther. 308 2004 403 409
43. F. Barchiesi, E.K. Jackson, D.G. Gillespie, L.C. Zacharia, J. Fingerle, and R.K. Dubey Methoxyestradiols mediate estradiol-induced antimitogenesis in human aortic SMCs Hypertension 39 2002 874 879
44. J. Liehr Is estradiol a genotoxic mutagenic carcinogen? Endocr. Rev. 21 2000 40 54
45. Gaikwad, N.W. Metabolomic profiling unravels DNA adducts in human breast that are formed from peroxidase mediated activation of estrogens to quinone methides, PLoS One, 8, 2013, e65826.
46. E. Cavalieri Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention Biochim. Biophys. Acta Rev. Cancer 1766 2006 63 78
47. N.W. Gaikwad, L. Yang, S. Pruthi, J. Ingle, E. Rogan, and E. Cavalieri Urine biomarkers of risk in the molecular etiology of breast cancer Breast Cancer Basic Clin, Res. 3 2009 1 8
48. N.W. Gaikwad Ultra performance liquid chromatography-tandem mass spectrometry method for profiling of steroid metabolome in human tissue Anal. Chem. 85 2013 4951 4960
49. J.M. Scott, and D.G. Weir Folic acid, homocysteine and one-carbon metabolism: a review of the essential biochemistry J. Cardiovasc. Risk 5 1998 223 227
50. A.L. Miller, and G.S. Kelly Homocysteine metabolism: nutritional modulation and impact on health and disease Altern. Med. Rev. 2 1997 234 254
51. F.D. Urnov Methylation and the genome: the power of a small amendment J. Nutr. 132 2002 2450 2456
52. O. Nygard, J.E. Nordvehaug, H. Refsum, P.M. Ueland, M. Farstad, and S.E. Vollset Plasma homocysteine levels and mortality in patients with coronary artery disease N. Engl. J. Med. 337 1997 230 236
53. S. Kaul, A.A. Zadeh, K. Prediman, and P.K. Shah Homocysteine hypothesis for atherothrombotic cardiovascular disease: not validated Am. Coll. Cardiol. 48 2006 914 923
54. X. Wang, X. Qin, H. Demirtas, J. Li, G. Mao, Y. Huo, N. Sun, L. Liu, and X. Xu Efficacy of folic acid supplementation in stroke prevention: a meta-analysis Lancet 369 2007 1876 1882
55. K.S. McCully Homocysteine, vitamins, and vascular disease prevention Am. J. Clin. Nutr. 86 2007 1563S 1568S
56. H. McNulty, K. Pentieva, L. Hoey, and M. Ward Homocysteine, B-vitamins and CVD Proc. Nutr. Soc. 67 2008 232 237