Antihypertensive effect of mitochondria-targeted proxyl nitroxides

Redox Biology

Volumn 4, Issue , 2015, Pages 355-362

  Dikalova, Anna E ^a   Kirilyuk, Igor A ^b,c   Dikalov, Sergey I ^a  

^a VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

^b N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

Antioxidant; Endothelial cells; Hypertension; Mitochondria; Nitroxide; Superoxide

Indexed keywords

3 [2 (TRIPHENYPHOSPHONIO)ACETAMIDOMETHYL] 2,2,5,5 TETRAMETHYLPYRROLIDINE 1 OXYL; 3 [2 (TRIPHENYPHOSPHONIO)ACETAMIDO]; ANGIOTENSIN II; ANTIHYPERTENSIVE AGENT; HYDROGEN PEROXIDE; MITOTEMPO; NITRIC OXIDE; NITROXIDE; OXYGEN; UNCLASSIFIED DRUG; AMINE OXIDE; ANTIOXIDANT; ORGANOPHOSPHORUS COMPOUND; PIPERIDINE DERIVATIVE; PROXYL NITROXIDE; SUPEROXIDE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERTENSIVE ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BIOREDUCTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACCUMULATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; HYPERTENSION; IN VIVO STUDY; MALE; METABOLISM; MITOCHONDRIAL RESPIRATION; MOUSE; NONHUMAN; SYSTOLIC BLOOD PRESSURE; ANIMAL; ANTAGONISTS AND INHIBITORS; AORTA; BLOOD PRESSURE; C57BL MOUSE; CELL LINE; CHEMICALLY INDUCED; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; IMPLANTABLE INFUSION PUMP; MITOCHONDRION; MOLECULARLY TARGETED THERAPY; SYNTHESIS;

MUS;

ANGIOTENSIN II; ANIMALS; ANTIHYPERTENSIVE AGENTS; ANTIOXIDANTS; AORTA; BLOOD PRESSURE; CELL LINE; CYCLIC N-OXIDES; ENDOTHELIAL CELLS; HUMANS; HYDROGEN PEROXIDE; HYPERTENSION; INFUSION PUMPS, IMPLANTABLE; MALE; MICE; MICE, INBRED C57BL; MITOCHONDRIA; MOLECULAR TARGETED THERAPY; ORGANOPHOSPHORUS COMPOUNDS; PIPERIDINES; SUPEROXIDES;

EID: 84922390030     PISSN: 22132317     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.redox.2014.12.012     Document Type: Article

References (35)

1. Kearney P.M., Whelton M., Reynolds K., Muntner P., Whelton P.K., He J. Global burden of hypertension: analysis of worldwide data. Lancet 2005, 365(9455):217-223. http://www.ncbi.nlm.nih.gov/pubmed/15652604, 10.1016/S0140-6736(05)17741-1.
2. Sacco R.L., Benjamin E.J., Broderick J.P., Dyken M., Easton J.D., Feinberg W.M., Goldstein L.B., Gorelick P.B., Howard G., Kittner S.J., Manolio T.A., Whisnant J.P., Wolf P.A. American Heart Association prevention conference. IV. Prevention and rehabilitation of stroke. risk factors. Stroke 1997, 28(7):1507-1517. http://www.ncbi.nlm.nih.gov/pubmed/9227708, 10.1161/01.STR.28.7.1507.
3. Harrison D.G., Marvar P.J., Titze J.M. Vascular inflammatory cells in hypertension. Frontiers in Physiology 2012, 3:128. http://www.ncbi.nlm.nih.gov/pubmed/22586409, 10.3389/fphys.2012.00128.
4. Byrd J.B., Zeng C., Tavel H.M., Magid D.J., O'Connor P.J., Margolis K.L., Selby J.V., Ho P.M. Combination therapy as initial treatment for newly diagnosed hypertension. American Heart Journal 2011, 162(2):340-346. http://www.ncbi.nlm.nih.gov/pubmed/21835296, 10.1016/j.ahj.2011.05.010.
5. Harrison D.G., Gongora M.C., Guzik T.J., Widder J. Oxidative stress and hypertension. Journal of the American Society of Hypertension 2007, 1(1):30-44. http://www.ncbi.nlm.nih.gov/pubmed/20409831, 10.1016/j.jash.2006.11.006.
6. Dikalova A.E., Bikineyeva A.T., Budzyn K., Nazarewicz R.R., McCann L., Lewis W., Harrison D.G., Dikalov S.I. Therapeutic targeting of mitochondrial superoxide in hypertension. Circulation Research 2010, 107(1):106-116. http://www.ncbi.nlm.nih.gov/pubmed/20448215, 10.1161/CIRCRESAHA.109.214601.
7. Dikalov S.I., Nazarewicz R.R., Bikineyeva A., Hilenski L., Lassègue B., Griendling K.K., Harrison D.G., Dikalova A.E. Nox2-induced production of mitochondrial superoxide in angiotensin II-mediated endothelial oxidative stress and hypertension. Antioxidants & Redox Signaling 2014, 20(2):281-294. http://www.ncbi.nlm.nih.gov/pubmed/24053613, 10.1089/ars.2012.4918.
8. Griendling K.K., Harrison D.G. Out, damned dot: studies of the nadph oxidase in atherosclerosis. Journal of Clinical Investigation 2001, 108(10):1423-1424. http://www.ncbi.nlm.nih.gov/pubmed/11714732, 10.1172/JCI14453.
9. Rodriguez-Iturbe B., Sepassi L., Quiroz Y., Ni Z., Wallace D.C., Vaziri N.D. Association of mitochondrial SOD deficiency with salt-sensitive hypertension and accelerated renal senescence. Journal of Applied Physiology 2007, 102(1):255-260. http://www.ncbi.nlm.nih.gov/pubmed/17023572, 10.1152/japplphysiol.00513.2006.
10. Ohashi M., Runge M.S., Faraci F.M., Heistad D.D. Mnsod deficiency increases endothelial dysfunction in apoe-deficient mice. Arteriosclerosis, Thrombosis, and Vascular Biology 2006, 26(10):2331-2336. http://www.ncbi.nlm.nih.gov/pubmed/16873728, 10.1161/01.ATV.0000238347.77590.c9.
11. Murphy M.P., Smith R.A. Drug delivery to mitochondria: the key to mitochondrial medicine. Advanced Drug Delivery Reviews 2000, 41(2):235-250. http://www.ncbi.nlm.nih.gov/pubmed/10699318, 10.1016/S0169-409X(99)00069-1.
12. Murphy M.P., Smith R.A. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annual Review of Pharmacology and Toxicology 2007, 47:629-656. http://www.ncbi.nlm.nih.gov/pubmed/17014364, 10.1146/annurev.pharmtox.47.120505.105110.
13. O'Malley Y., Fink B.D., Ross N.C., Prisinzano T.E., Sivitz W.I. Reactive oxygen and targeted antioxidant administration in endothelial cell mitochondria. Journal of Biological Chemistry 2006, 281(52):39766-39775. http://www.ncbi.nlm.nih.gov/pubmed/17060316, 10.1074/jbc.M608268200.
14. Doughan A.K., Dikalov S.I. Mitochondrial redox cycling of mitoquinone leads to superoxide production and cellular apoptosis. Antioxidants & Redox Signaling 2007, 9(11):1825-1836. http://www.ncbi.nlm.nih.gov/pubmed/17854275, 10.1089/ars.2007.1693.
15. Krishna M.C., Russo A., Mitchell J.B., Goldstein S., Dafni H., Samuni A. Do nitroxide antioxidants act as scavengers of O2-. or as sod mimics?. Journal of Biological Chemistry 1996, 271(42):26026-26031. http://www.ncbi.nlm.nih.gov/pubmed/8824242, 10.1074/jbc.271.42.26026.
16. Soule B.P., Hyodo F., Matsumoto K., Simone N.L., Cook J.A., Krishna M.C., Mitchell J.B. The chemistry and biology of nitroxide compounds. Free Radical Biology and Medicine 2007, 42(11):1632-1650. http://www.ncbi.nlm.nih.gov/pubmed/17462532, 10.1016/j.freeradbiomed.2007.02.030.
17. Namiecinski M., Pulaski L., Kochman A., Skolimowski J., Bartosz G., Metodiewa D. Cytotoxicity, cytoprotection and neurotoxicity of novel deprenyl-related propargylamines, stable nitroxide free radicals, in vitro and in vivo. In Vivo 2004, 18(2):171-180. http://www.ncbi.nlm.nih.gov/pubmed/15113044.
18. Mildaziene V., Baniene R., Marcinkeviciute A., Nauciene Z., Kalvenas A., Zimkus A. Tetraphenylphosphonium inhibits oxidation of physiological substrates in heart mitochondria. Molecular and Cellular Biochemistry 1997, 174(1-2):67-70. http://www.ncbi.nlm.nih.gov/pubmed/9309667, 10.1023/A:1006812128286.
19. Dhanasekaran A., Kotamraju S., Karunakaran C., Kalivendi S.V., Thomas S., Joseph J., Kalyanaraman B. Mitochondria superoxide dismutase mimetic inhibits peroxide-induced oxidative damage and apoptosis: role of mitochondrial superoxide. Free Radical Biology and Medicine 2005, 39(5):567-583. http://www.ncbi.nlm.nih.gov/pubmed/16085176, 10.1016/j.freeradbiomed.2005.04.016.
20. Trnka J., Blaikie F.H., Smith R.A., Murphy M.P. A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria. Free Radical Biology and Medicine 2008, 44(7):1406-1419. http://www.ncbi.nlm.nih.gov/pubmed/18206669, 10.1016/j.freeradbiomed.2007.12.036.
21. Jagtap A.P., Krstic I., Kunjir N.C., Hänsel R., Prisner T.F., Sigurdsson S.T. Sterically shielded spin labels for in-cell epr spectroscopy: analysis of stability in reducing environment. Free Radical Research 2015, 49(1):78-85. http://www.ncbi.nlm.nih.gov/pubmed/25348344, 10.3109/10715762.2014.979409.
22. Rozantsev E.G. Free Nitroxyl Radicals 1970, 249. Plenum Press, New York.
23. Hankovszky H.O., Hideg K., Lex L. Nitroxyls; VIII. Synthesis of nitroxylphosphinimines; a convenient route to amine, isothiocyanate, aminocarbonylaziridine, and carbodiimide nitroxyls. Synthesis 1981, 147-149.
24. Kirilyuk I.A., Kaledin V.I., Popova N.A., Nikolin V.P., Vasil'eva E.D., Grigor'ev I.A., Lushnikova E.L., Nepomnyashchikh L.M. Nitroxyl antioxidant tppa-tempo increases the efficacy of antitumor therapy on the model of transplantable mouse tumor. Bulletin of Experimental Biology and Medicine 2010, 150(1):75-78. http://www.ncbi.nlm.nih.gov/pubmed/21161057, 10.1007/s10517-010-1073-2.
25. Dikalova A., Clempus R., Lassègue B., Cheng G., McCoy J., Dikalov S., San Martin A., Lyle A., Weber D.S., Weiss D., Taylor W.R., Schmidt H.H., Owens G.K., Lambeth J.D., Griendling K.K. Nox1 overexpression potentiates angiotensin II-induced hypertension and vascular smooth muscle hypertrophy in transgenic mice. Circulation 2005, 112(17):2668-2676. http://www.ncbi.nlm.nih.gov/pubmed/16230485, 10.1161/CIRCULATIONAHA.105.538934.
26. Krege J.H., Hodgin J.B., Hagaman J.R., Smithies O. A noninvasive computerized tail-cuff system for measuring blood pressure in mice. Hypertension 1995, 25(5):1111-1115. http://www.ncbi.nlm.nih.gov/pubmed/7737724, 10.1161/01.HYP.25.5.1111.
27. Widder J.D., Guzik T.J., Mueller C.F., Clempus R.E., Schmidt H.H., Dikalov S.I., Griendling K.K., Jones D.P., Harrison D.G. Role of the multidrug resistance protein-1 in hypertension and vascular dysfunction caused by angiotensin II. Arteriosclerosis, Thrombosis, and Vascular Biology 2007, 27(4):762-768. http://www.ncbi.nlm.nih.gov/pubmed/17272743, 10.1161/01.ATV.0000259298.11129.a2.
28. Trnka J., Blaikie F.H., Logan A., Smith R.A., Murphy M.P. Antioxidant properties of mito-TEMPOl and its hydroxylamine. Free Radical Research 2009, 43(1):4-12. http://www.ncbi.nlm.nih.gov/pubmed/19058062, 10.1080/10715760802582183.
29. Ilan Y., Shafferman A., Feinberg B.A., Lau Y.K. Partitioning of electrostatic and conformational contributions in the redox reactions of modified cytochromes c. Biochimica et Biophysica Acta 1979, 548(3):565-578. http://www.ncbi.nlm.nih.gov/pubmed/228716, 10.1016/0005-2728(79)90065-3.
30. Harrison D.G. Endothelial function and oxidant stress. Clinical Cardiology 1997, 20:II-11-II-17.
31. Harrison D.G., Cai H., Landmesser U., Griendling K.K. Interactions of angiotensin II with NAD(P)H oxidase, oxidant stress and cardiovascular disease. Journal of the Renin-Angiotensin-Aldosterone System 2003, 4(2):51-61. http://www.ncbi.nlm.nih.gov/pubmed/12806586, 10.3317/jraas.2003.014.
32. Zhao H., Joseph J., Fales H.M., Sokoloski E.A., Levine R.L., Vasquez-Vivar J., Kalyanaraman B. Detection and characterization of the product of hydroethidine and intracellular superoxide by hplc and limitations of fluorescence. Proceedings of the National Academy of Sciences of the United States of America 2005, 102(16):5727-5732. http://www.ncbi.nlm.nih.gov/pubmed/15824309, 10.1073/pnas.0501719102.
33. Dikalov S., Fink B. ESR techniques for the detection of nitric oxide in vivo and in tissues. Methods in Enzymology 2005, 396:597-610. http://www.ncbi.nlm.nih.gov/pubmed/16291267, 10.1016/S0076-6879(05)96052-7.
34. Wilcox C.S., Pearlman A. Chemistry and antihypertensive effects of tempol and other nitroxides. Pharmacological Reviews 2008, 60(4):418-469. http://www.ncbi.nlm.nih.gov/pubmed/19112152, 10.1124/pr.108.000240.
35. Dikalov S., Griendling K.K., Harrison D.G. Measurement of reactive oxygen species in cardiovascular studies. Hypertension 2007, 49(4):717-727. http://www.ncbi.nlm.nih.gov/pubmed/17296874, 10.1161/01.HYP.0000258594.87211.6b.