Nitrosyl-cobinamide, a new and direct nitric oxide-releasing drug effective in vivo

Experimental Biology and Medicine

Volumn 232, Issue 11, 2007, Pages 1432-1440

  Broderick, Kate E ^a   Alvarez, Luis ^a   Balasubramanian, Mahesh ^a   Belke, Darrell D ^a   Makino, Ayako ^a   Chan, Adriano ^a   Woods Jr , Virgil L ^a   Dillmann, Wolfgang H ^a   Sharma, Vijay S ^a   Pilz, Renate B ^a   Bigby, Timothy D ^b   Boss, Gerry R ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b VA SAN DIEGO HEALTHCARE SYSTEM   (United States)

Author keywords

Hypertension; Nitric oxide; Nitrosyl cobinamide

Indexed keywords

CYCLIC GMP; NITRIC OXIDE; NITROSYL COBINAMIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DROSOPHILA MELANOGASTER; DRUG RELEASE; DRUG STABILITY; IN VIVO CULTURE; MOUSE; NONHUMAN; PROTEIN PHOSPHORYLATION; SMOOTH MUSCLE FIBER;

ANGINA PECTORIS; ANIMALS; AORTA; BLOOD PRESSURE; COBAMIDES; CORONARY CIRCULATION; DROSOPHILA MELANOGASTER; DRUG EVALUATION, PRECLINICAL; HEART FAILURE; HYPERTENSION; MALPIGHIAN TUBULES; MICE; MUSCLE RELAXATION; MUSCLE, SMOOTH, VASCULAR; MYOCARDIUM; NITRIC OXIDE; NITRIC OXIDE DONORS; NITROSO COMPOUNDS; ORGAN CULTURE TECHNIQUES; RATS; VASODILATOR AGENTS;

ANGINA; DROSOPHILA MELANOGASTER; MUS; RATTUS;

EID: 36849058150     PISSN: 15353702     EISSN: 15353699     Source Type: Journal    
DOI: 10.3181/0703-RM-70     Document Type: Article

References (39)

1. Lloyd-Jones DM, Bloch KD. The vascular biology of nitric oxide and its role in atherogenesis. Annu Rev Med 47:365-375, 1996.
2. Haj RM, Cinco JE, Mazer CD. Treatment of pulmonary hypertension with selective pulmonary vasodilators. Curr Opin Anaesthesiol 19:88-95, 2006.
3. Sydow K, Daiber A, Oelze M, Chen Z, August M, Wendt M, Ullrich V, Mulsch A, Schulz E, Keaney JF Jr, Stamler JS, Munzel T. Central role of mitochondrial aldehyde dehydrogenase and reactive oxygen species in nitroglycerin tolerance and cross-tolerance. J Clin Invest 113:482-489, 2004.
4. Daiber A, Mulsch A, Hink U, Mollnau H, Warnholtz A, Oelze M, Munzel T. The oxidative stress concept of nitrate tolerance and the antioxidant properties of hydralazine. Am J Cardiol. 96:25i-36i, 2005.
5. Parker JD. Nitrate tolerance, oxidative stress, and mitochondrial function: another worrisome chapter on the effects of organic nitrates. J Clin Invest 113:352-354, 2004.
6. Leeuwenkamp OR, Van Bennekom WP, Van der Mark EJ, Bult A. Nitroprusside, antihypertensive drug and analytical reagent. Review of (photo)stability, pharmacology and analytical properties. Pharm Weekbl Sci 6:129-140, 1984.
7. Schulz V. Clinical pharmacokinetics of nitroprusside, cyanide, thiosulphate and thiocyanate. Clin Pharmacokinet 9:239-251, 1984.
8. Posner MA, Rodkey FL, Tobey RE. Nitroprusside-induced cyanide poisoning: antidotal effect of hydroxocobalamin. Anesthesiology 44:330-335, 1976.
9. Merrifield AJB. Toxicity of sodium nitroprusside. Br J Anaesth 46:324, 1974.
10. Thatcher GR. An introduction to NO-related therapeutic agents. Curr Top Med Chem 5:597-601, 2005.
11. Sharma VS, Pilz RB, Boss GB, Magde D. Reactions of nitric oxide with vitamin B12 and its precursor, cobinamide. Biochemistry 42:8900-8908, 2003.
12. Broderick KE, Singh V, Zhuang S, Kambo A, Chen JC, Sharma VS, Pilz RB, Boss GR. Nitric oxide scavenging by the cobalamin precursor cobinamide. J Biol Chem 280:8678-8685, 2005.
13. Idriss SD, Gudi T, Casteel DE, Kharitonov VG, Pilz RB, Boss GR. Nitric oxide regulation of gene transcription via soluble guanylate cyclase and type I cGMP-dependent protein kinase. J Biol Chem 274:9489-9493, 1999.
14. Butt E, Abel K, Krieger M, Palm D, Hoppe V, Hoppe J, Walter U. cAMP- and cGMP-dependent protein kinase phosphorylation sites of the focal adhesion vasodilator-stimulated phosphoprotein (VASP) in vitro and in intact human platelets. J Biol Chem 269:14509-14517, 1994.
15. Zhuang S, Nguyen GT, Chen Y, Gudi T, Eigenthaler M, Jarchau T, Walter U, Boss GR, Pilz RB. Vasodilator-stimulated phosphoprotein activation of serum response element-dependent transcription occurs downstream of RhoA and is inhibited by cGMP-dependent protein kinase phosphorylation. J Biol Chem 279:10379-10407, 2004.
16. Ibarra-Alvarado C, Galle J, Melichar VO, Mameghani A, Schmidt HH. Phosphorylation of blood vessel vasodilator-stimulated phosphoprotein at serine 239 as a functional biochemical marker of endothelial nitric oxide/cyclic GMP signaling. Mol Pharmacol 61:312-319, 2002.
17. Smolenski A, Bachmann C, Reinhard K, Hoenig-Liedl P, Jarchau T, Hoschuetzky H, Walter U. Analysis and regulation of vasodilator-stimulated phosphoprotein serine 239 phosphorylation in vitro and in intact cells using a phosphospecific monoclonal antibody. J Biol Chem 273:20029-20035, 1998.
18. Broderick KE, Feala J, McCulloch A, Paternostro G, Sharma VS, Pilz RB, Boss GR. The nitric oxide scavenger cobinamide profoundly improves survival in a Drosophila Melanogaster model of bacterial sepsis. FASEB J 20:1865-1873, 2006.
19. Parinandi NL, Kleinberg MA, Usatyuk PV, Cummings RJ, Pennathur A, Cardounel AJ, Zweier JL, Garcia JG, Natarajan V. Hyperoxia-induced NAD(P)H oxidase activation and regulation by MAP kinases in human lung endothelial cells. Am J Physiol Lung Cell Mol Physiol 284:L26-L38, 2003.
20. Li H, Witte K, August M, Brausch I, Godtel-Armbrust U, Habermeier A, Closs EI, Oelze M, Munzel T, Forstermann U. Reversal of endothelial nitric oxide synthase uncoupling and up-regulation of endothelial nitric oxide synthase expression lowers blood pressure in hypertensive rats. J Am Coll Cardiol 47:2536-2544, 2006.
21. Belke DD, Swanson E, Suarez J, Scott BT, Stenbit AE, Dillmann WH. Increased expression of SERCA in the hearts of transgenic mice results in increased oxidation of glucose. Am J Physiol Heart Circ Physiol 292:H1755-H1763, 2007.
22. Maia L, Duarte RO, Ponces-Freire A, Moura JJG, Mira L. NADH oxidase activity of rat and human liver xanthine oxidoreductase: potential role in superoxide production. J Biol Inorg Chem 12:777-787, 2007.
23. Belke DD, Swanson EA, Dillmann WH. Decreased sarcoplasmic reticulum activity and contractility in diabetic db/db mouse heart. Diabetes 53:3201-3208, 2004.
24. Kharitonov VG, Sundquist AR, Sharma VS. Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen. J Biol Chem 270:28158-28164, 1995.
25. Mollnau H, Wendt M, Szocs K, Lassegue B, Schulz E, Oelze M, Li H, Bodenschatz M, August M, Kleschyov AL, Tsilimingas N, Walter U, Forstermann U, Meinertz T, Griendling K, Munzel T. Effects of angiotensin II infusion on the expression and function of NAD(P)H oxidase and components of nitric oxide/cGMP signaling. Circ Res 90: E58-E65, 2002.
26. Broderick KE, MacPherson MR, Regulski M, Tully T, Dow JA, Davies SA. Interactions between epithelial nitric oxide signaling and phosphodiesterase activity in Drosophila. Am J Physiol Cell Physiol 285:C1207-C1218, 2003.
27. Munzel T, Feil R, Mulsch A, Lohmann SM, Hofmann F, Walter U. Physiology and pathophysiology of vascular signaling controlled by guanosine 3′,5′-cyclic monophosphate-dependent protein kinase [corrected]. Circulation 108:2172-2183, 2003.
28. Schwemmer M, Bassenge E. New approaches to overcome tolerance to nitrates. Cardiovasc Drugs Ther 17:159-173, 2003.
29. Mollnau H, Wenzel P, Oelze M, Treiber N, Pautz A, Schulz E, Schuhmacher S, Reifenberg K, Stalleicken D, Scharffetter-Kochanek K, Kleinert H, Munzel T, Daiber A. Mitochondrial oxidative stress and nitrate tolerance-comparison of nitroglycerin and pentaerithrityl tetranitrate in Mn-SOD+/- mice. BMC Cardiovasc Disord 6:44, 2006.
30. Bauer JA, Morrison BH, Grane RW, Jacobs BS, Dabney S, Gamero AM, Carnevale KA, Smith DJ, Drazba J, Seetharam B, Linder DJ. Effects of interferon beta on transcobalamin II-receptor expression and antitumor activity of nitrosylcobalamin. J Natl Cancer Inst 94:1010-1019, 2002.
31. Tang Z, Bauer JA, Morrison B, Lindner DJ. Nitrosylcobalamin promotes cell death via S nitrosylation of Apo2L/TRAIL receptor DR4. Mol Cell Biol 26:5588-5594, 2006.
32. Kondo H, Binder MJ, Kolhouse JF, Smythe WR, Podell ER, Allen RH. Presence and formation of cobalamin analogues in multivitamin-mineral pills. J Clin Invest 70:889-898, 1982.
33. Kolhouse JF, Kondo H, Allen NC, Podell E, Allen RH. Cobalamin analogues are present in human plasma and can mask cobalamin deficiency because current radioisotope dilution assays are not specific for true cobalamin. N Engl J Med 299:785-792, 1978.
34. el Kholty S, Gueant JL, Bressler L, Djalali M, Boissel P, Gerard P, Nicolas JP. Portal and biliary phases of enterohepatic circulation of corrinoids in humans. Gastroenterology 101:1399-1408, 1991.
35. Fedosov SN, Berglund L, Fedosova NU, Nexo E, Petersen TE. Comparative analysis of cobalamin binding kinetics and ligand protection for intrinsic factor, transcobalamin, and haptocorrin. J Biol Chem 277:9989-9996, 2002.
36. Kanazawa S, Terada H, Iseki T, Iwasa S, Okuda K, Kondo H, Okuda K. Binding of cobalamin analogs to intrinsic factor-cobalamin receptor and its prevention by R binder. Proc Soc Exp Biol Med 183:333-338, 1986.
37. Coates ME, Davies MK, Dawson R, Harrison GF, Holdsworth ES, Kon SK, Porter JW. The activity for chicks of some vitamin B12-like compounds. Biochem J 64:682-686, 1956.
38. Stabler SP, Brass EP, Marcell PD, Allen RH. Inhibition of cobalamin-dependent enzymes by cobalamin analogues in rats. J Clin Invest 87:1422-1430, 1991.
39. Clancy RM, Abramson SB. Nitric oxide: a novel mediator of inflammation. Proc Soc Exp Biol Med 210:93-101, 1995.