Protective effect of photodegradation product of nifedipine against tumor necrosis factor alpha-induced oxidative stress in human glomerular endothelial cells

Journal of Medical Investigation

Volumn 58, Issue 1-2, 2011, Pages 118-126

  Fukuhara, Yayoi ^a   Tsuchiya, Koichiro ^a   Horinouchi, Yuya ^a   Tajima, Soichiro ^a   Kihira, Yoshitaka ^a   Hamano, Shuichi ^b   Kawazoe, Kazuyoshi ^c   Ikeda, Yasumasa ^a   Ishizawa, Keisuke ^a   Tomita, Shuhei ^a   Tamaki, Toshiaki ^a  

^a Department of Pharmacology ^*  (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c TOKUSHIMA UNIVERSITY HOSPITAL   (Japan)

Author keywords

Antioxidant; Cumene hydroperoxide; Endothelial cells; Nifedipine; Nitrosonifedipine; Reactive oxygen species; Tumor necrosis factor

Indexed keywords

CUMENE HYDROPEROXIDE; INTERCELLULAR ADHESION MOLECULE 1; NIFEDIPINE; NIFEDIPINE DERIVATIVE; NITROSONIFEDIPINE; TROLOX C; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL DAMAGE; CELL MEMBRANE; CELL PROTECTION; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; ENDOTHELIUM CELL; GLOMERULUS; HUMAN; HUMAN CELL; OXIDATIVE STRESS; PHOTODEGRADATION; PROTEIN EXPRESSION;

EID: 79951919933     PISSN: 13431420     EISSN: None     Source Type: Journal    
DOI: 10.2152/jmi.58.118     Document Type: Article

References (57)

1. Fassi A, Sangalli F, Colombi F, Perico N, Remuzzi G, Remuzzi A: Beneficial effects of calcium channel blockade on acute glomerular hemo-dynamic changes induced by cyclosporine. Am J Kidney Dis 33: 267-275, 1999
2. Simon A, Gariepy J, Moyse D, Levenson J: Differential effects of nifedipine and co-amilozide on the progression of early carotid wall changes. Circulation 103: 2949-2954, 2001
3. Poole-Wilson PA, Lubsen J, Kirwan BA, van Dalen FJ, Wagener G, Danchin N, Just H, Fox KA, Pocock SJ, Clayton TC, Motro M, Parker JD, Bourassa MG, Dart AM, Hildebrandt P, Hjalmarson A, Kragten JA, Molhoek GP, Otterstad JE, Seabra-Gomes R, Soler-Soler J, Weber S: Effect of long-acting nifedipine on mortality and cardiovascular morbidity in patients with stable angina requiring treatment (ACTION trial): randomised controlled trial. Lancet 364: 849-857, 2004
4. Yui Y, Sumiyoshi T, Kodama K, Hirayama A, Nonogi H, Kanmatsuse K, Origasa H, Iimura O, Ishii M, Saruta T, Arakawa K, Hosoda S, Kawai C: Nifedipine retard was as effective as angiotensin converting enzyme inhibitors in preventing cardiac events in high-risk hypertensive patients with diabetes and coronary artery disease: the Japan Multicenter Investigation for Cardiovascular Diseases-B (JMIC-B) subgroup analysis. Hypertens Res 27: 449-456, 2004
5. Shinoda E, Yui Y, Kodama K, Hirayama A, Nonogi H, Haze K, Sumiyoshi T, Hosoda S, Kawai C: Quantitative coronary angiogram analysis: nifedipine retard versus angiotensin-converting enzyme inhibitors (JMIC - B side arm study). Hypertension 45: 1153-1158, 2005
6. Ding Y, Vaziri ND: Nifedipine and diltiazem but not verapamil up - regulate endothelial nitric -oxide synthase expression. J Pharmacol Exp Ther 292: 606-609, 2000
7. Taddei S, Virdis A, Ghiadoni L, Sudano I, Salvetti A: Antihypertensive drugs and reversing of en-dothelial dysfunction in hypertension. Curr Hy-pertens Rep 2: 64-70, 2000
8. Berkels R, Egink G, Marsen TA, Bartels H, Roesen R, Klaus W: Nifedipine increases en-dothelial nitric oxide bioavailability by antioxi-dative mechanisms. Hypertension 37: 240-245, 2001
9. Brovkovych VV, Kalinowski L, Muller-Peddinghaus R, Malinski T: Synergistic Anti-hypertensive Effects of Nifedipine on Endothe-lium: Concurrent Release of NO and Scavenging of Superoxide. Hypertension 37: 34-39, 2001
10. Verhaar MC, Honing ML, van Dam T, Zwart M, Koomans HA, Kastelein JJ, Rabelink TJ: Nifedipine improves endothelial function in hy-percholesterolemia, independently of an effect on blood pressure or plasma lipids. Cardiovasc Res 42: 752-760, 1999
11. Sugano M, Tsuchida K, Makino N: Nifedipine prevents apoptosis of endothelial cells induced by oxidized low-density lipoproteins. J Cardio-vasc Pharmacol 40: 146-152, 2002
12. Yamasaki K, Aoki M, Makino H, Hashiya N, Shimizu H, Ohishi M, Ogihara T, Morishita R: Effect of nifedipine on endothelial function in normotensive smokers: potential contribution of increase in circulating hepatocyte growth factor. J Hum Hypertens 18: 701-705, 2004
13. Himmel HM, Whorton AR, Strauss HC: Intracellular calcium, currents, and stimulus-response coupling in endothelial cells. Hypertension 21: 112-127, 1993
14. Hempel A, Lindschau C, Maasch C, Mahn M, Bychkov R, Noll T, Luft FC, Haller H: Calcium antagonists ameliorate ischemia-induced endo-thelial cell permeability by inhibiting protein kinase C. Circulation 99: 2523-2529, 1999
15. Matsumori A, Nunokawa Y, Sasayama S: Nifedipine inhibits activation of transcription factor NF - kappaB. Life Sci 67: 2655-2661, 2000
16. Sugawara H, Tobise K, Kikuchi K: Antioxidant effects of calcium antagonists on rat myocar-dial membrane lipid peroxidation. Hypertens Res 19: 223-228, 1996
17. Mak IT, Zhang J, Weglicki WB: Protective effects of dihydropyridine Ca-blockers against endothelial cell oxidative injury due to combined nitric oxide and superoxide. Pharmacol Res 45: 27-33, 2002
18. Yamagishi S, Nakamura K: Revival of nifedipine, a dihydropyridine-based calcium blocker. Med Hypotheses 68: 565-567, 2007
19. Majeed IA, Murray WJ, Newton DW, Othman S, Al-Turk WA: Spectrophotometric study of the photodecomposition kinetics of nifedipine. J Pharm Pharmacol 39: 1044-1046, 1987
20. Nunez-Vergara LJ, Bollo S, Fuentealba J, Sturm JC, Squella JA: Electrochemical and spectroelectrochemical behavior of the main photodegradation product of nifedipine: the ni-trosopyridine derivative. Pharm Res 19: 522-529, 2002
21. Stasko A, Brezova V, Biskupic S, Ondrias K, Misik V: Reactive radical intermediates formed from illuminated nifedipine. Free Radic Biol Med 17: 545-556, 1994
22. de Vries H, Beijersbergen van Henegouwen GM: Photoreactivity of nifedipine in vitro and in vivo. J Photochem Photobiol B43: 217-221, 1998
23. Bauer V, Rekalov VV, Juranek I, Gergel D, Bohov P: Effect of illuminated nifedipine, a potent antioxidant, on intestinal and vascular smooth muscles. Br J Pharmacol 115: 871-874, 1995
24. +3/ascorbate-stimulated lipid peroxidation in rat brain slices. Gen Pharmacol 31: 385-391, 1998
25. Ohkubo T, Noro H, Sugawara K: High-performance liquid chromatographic determination of nifedipine and a trace photodegradation product in hospital prescriptions. J Pharm Biomed Anal 10: 67-70, 1992
26. Fujii H, Berliner LJ: In vivo EPR evidence for free radical adducts of nifedipine. Magn Reson Med 42: 691-694, 1999
27. Sanguinetti MC, Kass RS: Photoalteration of calcium channel blockade in the cardiac Purk-inje fiber. Biophys J 45: 873-880, 1984
28. Gurney AM, Nerbonne JM, Lester HA: Pho-toinduced removal of nifedipine reveals mechanisms of calcium antagonist action on single heart cells. J Gen Physiol 86: 353-379, 1985
29. Hayase N, Inagaki S, Abiko Y: Effects of photodegradation products of nifedipine: the nitroso-derivative relaxes contractions of the rat aortic strip induced by norepinephrine and other agonists. J Pharmacol Exp Ther 275: 813-821, 1995
30. Yanez C, Lopez-Alarcon C, Camargo C, Valenzuela V, Squella JA, Nunez-Vergara LJ: Structural effects on the reactivity 1,4-dihydro-pyridines with alkylperoxyl radicals and ABTS radical cation. Bioorg Med Chem 12: 2459-2468, 2004
31. Horinouchi Y, Tsuchiya K, Taoka C, Tajima S, Kihira Y, Shisido K, Hamano S, Kawazoe K, Ikeda Y, Ishizawa K, Tomita S, Tamaki T: Antioxidant effects of photodegra-dation product of nifedipine. Chem Pharm Bull (in press).
32. Zoccali C: The endothelium as a target in renal diseases. J Nephrol 20: S39-S44, 2007
33. Futrakul N, Panichakul T, Sirisinha S, Futrakul P, Siriviriyakul P: Glomerular endothelial dysfunction in chronic kidney disease. Ren Fail 26: 259-264, 2004
34. Yilmaz MI, Saglam M, Carrero JJ, Qureshi AR, Caglar K, Eyileten T, Sonmez A, Cakir E, Yenicesu M, Lindholm B, Stenvinkel P, Axelsson J: Endothelial dysfunction in type-2 diabetics with early diabetic nephropathy is associated with low circulating adiponectin. Nephrol Dial Transplant 23: 959-965, 2008
35. Kaur G, Alam MS, Athar M: Cumene hydrop-eroxide debilitates macrophage physiology by inducing oxidative stress: possible protection by alpha-tocopherol. Chem Biol Interact 179: 94-102, 2009
36. Suranyi MG, Guasch A, Hall BM, Myers BD: Elevated levels of tumor necrosis factor-alpha in the nephrotic syndrome in humans. Am J Kidney Dis 21: 251-259, 1993
37. Kohan DE: Role of endothelin and tumour necrosis factor in the renal response to sepsis. Nephrol Dial Transplant 9 (Suppl 4): 73-77, 1994
38. Donnahoo KK, Shames BD, Harken AH, Meldrum DR: Review article: the role of tumor necrosis factor in renal ischemia-reperfusion injury. J Urol 162: 196-203, 1999
39. Zhang B, Ramesh G, Norbury CC, Reeves WB: Cisplatin-induced nephrotoxicity is mediated by tumor necrosis factor-alpha produced by renal parenchymal cells. Kidney Int 72: 37-44, 2007
40. Niewczas MA, Ficociello LH, Johnson AC, Walker W, Rosolowsky ET, Roshan B, Warram JH, Krolewski AS: Serum concentrations of markers of TNFalpha and Fas-mediated pathways and renal function in nonproteinuric patients with type 1 diabetes. Clin J Am Soc Nephrol 4: 62-70, 2009
41. Fujita Y, Izawa Y, Ali N, Kanematsu Y, Tsuchiya K, Hamano S, Tamaki T, Yoshizumi M: Pramipexole protects against H2O2-induced PC12 cell death. Naunyn Schmiedebergs Arch Pharmacol 372: 257-266, 2006
42. Kanigur-Sultuybek G, Ozdas SB, Curgunlu A, Tezcan V, Onaran I: Does metformin prevent short-term oxidant-induced dna damage? In vitro study on lymphocytes from aged subjects. J Basic Clin Physiol Pharmacol 18: 129-140, 2007
43. van der Kraaij AM, de Jonge HR, Esterbauer H, de Vente J, Steinbusch HW, Koster JF: Cu-mene hydroperoxide, an agent inducing lipid peroxidation, and 4-hydroxy-2,3-nonenal, a per-oxidation product, cause coronary vasodilata-tion in perfused rat hearts by a cyclic nucleo-tide independent mechanism. Cardiovasc Res 24: 144-150, 1990
44. Hayashi K, Homma K, Wakino S, Tokuyama H, Sugano N, Saruta T, Itoh H: T-type Ca channel blockade as a determinant of kidney protection. Keio J Med 59: 84-95, 2010
45. Yamagishi S, Nakamura K, Matsui T: Role of oxidative stress in the development of vascular injury and its therapeutic intervention by nifedipine. Curr Med Chem 15: 172-177, 2008
46. Kitakaze M, Asanuma H, Takashima S, Minamino T, Ueda Y, Sakata Y, Asakura M, Sanada S, Kuzuya T, Hori M: Nifedipine-induced coronary vasodilation in ischemic hearts is attributable to bradykinin- and NO-dependent mechanisms in dogs. Circulation 101: 311-317, 2000
47. Lichtlen PR, Hugenholtz PG, Rafflenbeul W, Hecker H, Jost S, Deckers JW: Retardation of angiographic progression of coronary artery disease by nifedipine. Results of the International Nifedipine Trial on Antiatherosclerotic Therapy (INTACT). INTACT Group Investigators. Lancet 335: 1109-1113, 1990
48. Fukuo K, Yang J, Yasuda O, Mogi M, Suhara T, Sato N, Suzuki T, Morimoto S, Ogihara T: Nifedipine indirectly upregulates superoxide dismutase expression in endothelial cells via vascular smooth muscle cell-dependent pathways. Circulation 106: 356-361, 2002
49. Misik V, Stasko A, Gergel D, Ondrias K: Spin-trapping and antioxidant properties of illuminated and nonilluminated nifedipine and ni-modipine in heart homogenate and model system. Mol Pharmacol 40: 435-439, 1991
50. Kuzuya M, Naito M, Funaki C, Hayashi T, Asai K, Kuzuya F: Probucol prevents oxidative injury to endothelial cells. J Lipid Res 32: 197-204, 1991
51. Polunovsky VA, Wendt CH, Ingbar DH, Peterson MS, Bitterman PB: Induction of endothelial cell apoptosis by TNF alpha: modulation by inhibitors of protein synthesis. Exp Cell Res 214: 584-594, 1994
52. Toborek M, Blanc EM, Kaiser S, Mattson MP, Hennig B: Linoleic acid potentiates TNF-mediated oxidative stress, disruption of calcium homeostasis, and apoptosis of cultured vascular endothelial cells. J Lipid Res 38: 2155-2167, 1997
53. Pfeffer K, Matsuyama T, Kundig TM, Wakeham A, Kishihara K, Shahinian A, Wiegmann K, Ohashi PS, Kronke M, Mak TW: Mice deficient for the 55 kd tumor necrosis factor receptor are resistant to endotoxic shock, yet succumb to L. monocytogenes infection. Cell 73: 457-467, 1993
54. Pober JS, Cotran RS: Cytokines and endothe-lial cell biology. Physiol Rev 70: 427-451, 1990
55. Yoshizumi M, Fujita Y, Izawa Y, Suzaki Y, Kyaw M, Ali N, Tsuchiya K, Kagami S, Yano S, Sone S, Tamaki T: Ebselen inhibits tumor necrosis factor-alpha-induced c-Jun N-terminal kinase activation and adhesion molecule expression in endothelial cells. Exp Cell Res 292: 1-10, 2004
56. Springer TA: Traffic signals for lymphocyte recirculation and leukocyte emigration: the multistep paradigm. Cell 76: 301-314, 1994
57. Modur V, Zimmerman GA, Prescott SM, McIntyre TM: Endothelial cell inflammatory responses to tumor necrosis factor alpha. Ceramide-dependent and -independent mitogen-activated protein kinase cascades. J Biol Chem 271: 13094-13102, 1996