Estrogen and tamoxifen metabolites protect smooth muscle cell membrane phospholipids against peroxidation and inhibit cell growth

Circulation Research

Volumn 84, Issue 2, 1999, Pages 229-239

  Dubey, Raghvendra K ^a,d   Tyurina, Yulia Y ^a   Tyurin, Vladimir A ^a   Gillespie, Delbert G ^a   Branch, Robert A ^a   Jackson, Edwin K ^a,b   Kagan, Valerian E ^a,c  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^d UNIVERSITY OF PITTSBURGH MEDICAL CENTER   (United States)

Author keywords

Antioxidant; Cardiovascular disease; Estrogen; Free radical; Metabolism

Indexed keywords

2,2' AZOBIS(2,4 DIMETHYLVALERONITRILE); 2,2,5,7,8 PENTAMETHYL 6 HYDROCHROMANE; ALPHA TOCOPHEROL; DROLOXIFENE; ESTROGEN; ESTRONE; PARINARIC ACID; PHOSPHOLIPID; TAMOXIFEN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CELL GROWTH; CELL MEMBRANE; CELL MIGRATION; CELL PROLIFERATION; DNA SYNTHESIS; GROWTH INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; NONHUMAN; PHOSPHOLIPID METABOLISM; PRIORITY JOURNAL; RAT; SMOOTH MUSCLE FIBER;

EID: 0033524745     PISSN: 00097330     EISSN: None     Source Type: Journal    
DOI: 10.1161/01.RES.84.2.229     Document Type: Article

References (48)

1. Lerner DJ, Kannel WB. Patterns of coronary heart disease morbidity and mortality in the sexes: a 26-year follow-up of the Framingham population. Am Heart J. 1986;111:383-390.
2. Wenger NK, Speroff L, Packard B. Cardiovascular health and disease in women. N Engl J Med. 1993;329:247-256.
3. Stampfer MJ, Colditz GA. Estrogen replacement therapy and coronary heart disease: a quantitative assessment of the epidemiologic evidence. Prev Med. 1991;20:47-63.
4. Notelovitz M. Estrogen replacement therapy: indications, contraindications, and agent selection. Am J Obstet Gynecol. 1989;161:1832-1841.
5. American Heart Association. Heart and Stroke Facts. Dallas, TX: American Heart Association; 1992.
6. Niki E, Nakano M. Estrogens as antioxidants. Methods Enzymol. 1990; 186:330-336.
7. MacDonald CC, Stewart HJ. Fatal myocardial infarction in the Scottish adjuvant tamoxifen trial. BMJ. 1991;303:435-437.
8. Wiseman H, Paganga G, Rice-Evans C, Halliwell B. Protective actions of tamoxifen and 4-OH-tamoxifen against oxidative damage to human low-density lipoproteins: a mechanism accounting for the cardioprotective action of tamoxifen. Biochem J. 1993;292:635-638.
9. Shwaery GT, Vita JA, Keaney JF. Antioxidant protection of LDL by physiological concentrations of 17β-estradiol: requirement for estradiol modification. Circulation. 1997;95:1378-1385.
10. Rifici VA, Khachadurian AK. The inhibition of low-density lipoprotein oxidation by 17β-estradiol. Metabolism. 1992;41:1110-1114.
11. Maziere C, Auclair M, Ronveaux MF, Salmon S, Santus R, Maziere J-C. Estrogens inhibit copper and cell-mediated modification of low density lipoprotein. Atherosclerosis. 1991;89:175-182.
12. Keaney JF, Shwaery GT, Xu A, Nicolosi RJ, Loscalzo J, Foxall TL, Vita JA. 17β-Estradiol preserves endothelial vasodilator function and limits low-density lipoprotein oxidation in hypercholesterolemic swine. Circulation. 1994;89:2251-2259.
13. Tang M, Abplanalp W, Ayres S, Subbiah MTR. Superior and distinct antioxidant effects of selected estrogen metabolites on lipid peroxidation. Metabolism. 1996;45:411-414.
14. Oparil S, Levine RL, Chen YF. Sex hormones and the vasculature. In: Sowers JR, Walsh M, eds. Endocrinology of the Vasculature. Totwa, NJ: Humana Press, Inc; 1996:225-237.
15. Krasinski K, Spyridopoulos I, Asahara T, van der Zee R, Isner JM, Losordo DW. Estradiol accelerates functional endothelial recovery after arterial injury. Circulation. 1997;95:1768-1772.
16. Oparil S, Levine RL, Chen S-J, Durand J, Chen YF. Sexually dimorphic response of the balloon-injured rat carotid artery to hormone treatment. Circulation. 1997;95:1301-1307.
17. Foegh M, Asotra S, Howell M, Ramwell P. Estradiol inhibition of arterial neointimal hyperplasia after balloon injury. J Vasc Surg. 1994;14: 722-726.
18. Kehrer JP. Free radicals as mediators of tissue injury and disease. Crit Rev Toxicol. 1993;23:21-48.
19. Fabisiak JP, Kagan VE, Ritov VB, Johnson DE, Lazo JS. Bcl-2 inhibits selective oxidation and externalization of phosphatidylserine during paraquat-induced apoptosis. Am J Physiol. 1997;272:C675-C684.
20. Keaney JF Jr, Vita JA. Atherosclerosis, oxidative stress, and antioxidant protection in endothelium-derived relaxing factor action. Prog Cardiovasc Dis. 1995;38:129-154.
21. Alexander RW. Hypertension and the pathogenesis of atherosclerosis: oxidative stress and the mediation of arterial inflammatory response: a new perspective. Hypertension. 1995;25:155-161.
22. Ritov VB, Banni S, Yalowich JC, Day BW, Claycomp HG, Corongiu FP, Kagan VE. Non-random peroxidation of different classes of membrane phospholipids in live cells detected by metabolically integrated cis-parinaric acid. Biochim Biophys Acta. 1996;1283:127-140.
23. Krainev AG, Bigelow DJ. Comparison of 2,2′-azobis(2-amidinopropane) hydrochloride (AAPH) and 2,2′-azobis(2,4-dimethylvaleronitrile) (AMVN) as free radical initiators: a spin-trapping study. J Chem Soc Perkin Trans. 1996;2:747-754.
24. Dubey RK, Jackson EK Luscher TF. Nitric oxide inhibits angiotensin II-induced migration of rat aortic smooth muscle cell: role of cyclic-nucleotides and angiotensin I receptors. J Clin Invest. 1995;96: 141-149.
25. Dubey RK, Roy A, Overbeck HW. Culture of renal arteriolar smooth muscle cells: mitogenic responses to angiotensin II. Circ Res. 1992;71: 1143-1152.
26. Niki E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol. 1990;186:100-108.
27. Folch J, Lees M, Sloan-Stanley GH. A simple method for isolation and purification of total lipids from animal tissues. J Biol Chem. 1957;226: 497-509.
28. Geurts van Kessel WSM, Hax WMA, Demel RA, DeGier J. High performance liquid chromatographic separation and direct ultraviolet detection of phospholipids. Biochem Biophys Acta. 1977;486: 524-530.
29. Chalvardjian A, Rubnicki E. Determination of lipid phosphorous in the nanomolar range. Anal Biochem. 1996;36:225-226.
30. Arduini A, Tyurin V, Tyuruna Y, Arrigoni-Martelli E, Molajoni F, Dottori S, Federici G. Acyl-trafficking in membrane phospholipid fatty acid turnover: the transfer of fatty acid from acyl-L-carnitine pool to membrane phospholipids in intact human erythrocytes. Biochem Biophys Res Commun. 1992;187:353-358.
31. Ellman GL. Tissue sulfhydryl groups. Arch Biochem Biophys. 1959;82: 302-310.
32. Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987;47: 936-942.
33. Gelbke HP, Ball P, Knuppen R. 2-Hydroxyoestrogens: chemistry, biogenesis, metabolism and physiological significance. In: Briggs MH, Christie GA, eds. Advances in Steroid Biochemistry and Pharmacology. Vol 6. New York, NY: Academic Press; 1977:81-154.
34. Adlercreutz H, Gorbach SL, Goldin BR, Woods MN, Dwyer JT, Hämäläinen E. Estrogen metabolism and excretion in Oriental and Caucasian women. J Natl Cancer Inst. 1994;86:1076-1082.
35. Ke HZ, Simmons HA, Pirie CM, Crawford DT, Thompson DD. Droloxifene, a new estrogen antagonist/agonist, prevents bone loss in ovariectomized rats. Endocrinology. 1995;136:2435-2441.
36. van den Berg JJM, Kuypers FA, Lubin BH, Roelofsen B, Op den Kamp JAF. Direct and continuous measurement of hydroperoxide-induced oxidative stress on the membrane of intact erythrocytes. Free Radical Biol Med. 1991;11:255-261.
37. Nishigaki I, Sasaguri Y, Yagi K. Anti-proliferative effect of 2-methoxyestradiol on cultured smooth muscle cells from rabbit aorta. Atherosclerosis. 1995;113:167-170.
38. Dubey RK, Gillespie DG, Jackson EK, Keller PJ. 17β-Estradiol, its metabolites and progesterone inhibit cardiac fibroblast growth. Hypertension 1998;31(1 pt 2):522-528.
39. Isfrati MD, Karas RH, Aronovitz M, Kim S, Sullivan TR Jr, Lubahn DB, O'Donell TF Jr, Korach KS, Mendelsohn ME. Estrogen inhibits the vascular injury response in estrogen receptor α-deficient mice. Nat Med. 1997;3:545-548.
40. Tyurina YY, Tyurin VA, Yalowich JC, Quinn PJ, Claycamp HG, Schor NF, Pitt BR, Kagan VE. Phenoxyl radicals of etoposide (VP-16) can directly oxidize intracellular thiols: protective versus damaging effects of phenolic antioxidants. Toxicol Appl Pharmacol. 1995;131: 277-288.
41. Boscoboinik DO, Chatelain E, Bartoli GM, Stauble B, Azzi A. Inhibition of protein kinase C activity and vascular smooth muscle cell growth by D-alpha-tocopherol. Biochim Biophys Acta. 1994;122:418-426.
42. Meister A, Anderson ME. Glutathione. Annu Rev Biochem. 1983;52: 711-760.
43. Rao GN, Alexander RW, Runge MS. Linoleic acid and its metabolites, hydroperoxyocta-decadienoic acids, stimulate c-Fos, c-Jun and c-Myc mRNA expression, mitogen-activated protein kinase activation, and growth in rat aortic smooth muscle cells. J Clin Invest. 1995;96: 842-847.
44. Ruef J, Rao GN, Li F, Bode C, Patterson C, Bhatnagar A, Runge MS. Induction of rat aortic smooth muscle cell growth by lipid peroxidation product 4-hydroxy-2-nonenal. Circulation. 1998;97: 1071-1078.
45. Nakanishi H, Brewer KA, Exton JH. Activation of the zeta isozyme of protein kinase C by phosphatidylinositol 3,4,5-triphosphate. J Biol Chem. 1993;268:13-16.
46. Sen CK, Packer L. Antioxidant and redox regulation of gene transcription. FASEB J. 1996;10:709-720.
47. Lander HM. An essential role for free radicals and derived species in signal transduction. FASEB J. 1991;11:118-124.
48. Larner JM, Pahuja SL, Shackleton CH, McMurray WJ, Giordano G, Hochberg RB. The isolation and characterization of estradiol-fatty acid esters in human ovarian follicular fluid: identification of an endogenous long-lived and potent family of estrogens. J Biol Chem. 1993;268:13893-13899.