Cobinamides are novel coactivators of nitric oxide receptor that target soluble guanylyl cyclase catalytic domain

Journal of Pharmacology and Experimental Therapeutics

Volumn 340, Issue 3, 2012, Pages 723-732

  Sharina, Iraida ^a   Sobolevsky, Michael ^a   Doursout, Marie Francoise ^b   Gryko, Dorota ^c   Martin, Emil ^a  

^a UNIVERSITY OF TEXAS   (United States)

^b UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 5 CYCLOPROPYL 2 [1 (2 FLUOROBENZYL) 1H PYRAZOLO[3,4 B]PYRIDIN 3 YL]PYRIMIDINE; ADENYLATE CYCLASE; ATACIGUAT; CINACIGUAT; COBINAMIDE; CYANOCOBALAMIN; CYCLIC GMP; DICYANOCOBINAMIDE; FORSKOLIN; GUANOSINE TRIPHOSPHATE; GUANYLATE CYCLASE; HEME; NITRIC OXIDE; PHENYLEPHRINE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL TISSUE; AORTA CONSTRICTION; ARTICLE; CELL ISOLATION; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENTIATION; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME PURIFICATION; ENZYME REGULATION; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN TARGETING; RAT; REGULATORY MECHANISM; VASODILATATION;

ANIMALS; CATALYTIC DOMAIN; CELL LINE, TUMOR; COBAMIDES; GUANYLATE CYCLASE; HUMANS; MALE; NITRIC OXIDE; PYRAZOLES; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN B 12;

EID: 84857263747     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.111.186957     Document Type: Article

References (39)

1. Brenner M, Kim JG, Mahon SB, Lee J, Kreuter KA, Blackledge W, Mukai D, Patterson S, Mohammad O, Sharma VS, et al. (2010) Intramuscular cobinamide sulfite in a rabbit model of sublethal cyanide toxicity. Ann Emerg Med 55:352-363.
2. Broderick KE, Alvarez L, Balasubramanian M, Belke DD, Makino A, Chan A, Woods VL Jr, Dillmann WH, Sharma VS, Pilz RB, et al. (2007) Nitrosyl-cobinamide, a new and direct nitric oxide releasing drug effective in vivo. Exp Biol Med (Maywood) 232:1432-1440. (Pubitemid 350220541)
3. Broderick KE, Potluri P, Zhuang S, Scheffler IE, Sharma VS, Pilz RB, and Boss GR (2006) Cyanide detoxification by the cobalamin precursor cobinamide. Exp Biol Med (Maywood) 231:641-649.
4. Broderick KE, Singh V, Zhuang S, Kambo A, Chen JC, Sharma VS, Pilz RB, and Boss GR (2005) Nitric oxide scavenging by the cobalamin precursor cobinamide. J Biol Chem 280:8678-8685. (Pubitemid 40409555)
5. Denninger JW, Schelvis JP, Brandish PE, Zhao Y, Babcock GT, and Marletta MA (2000) Interaction of soluble guanylate cyclase with YC-1: kinetic and resonance Raman studies. Biochemistry 39:4191-4198. (Pubitemid 30210399)
6. Derbyshire ER, Fernhoff NB, Deng S, and Marletta MA (2009) Nucleotide regulation of soluble guanylate cyclase substrate specificity. Biochemistry 48:7519-7524.
7. Derbyshire ER and Marletta MA (2009) Biochemistry of soluble guanylate cyclase. Handb Exp Pharmacol 191:17-31.
8. 1 subunits. Eur J Biochem 240:380-386.
9. Friebe A, Russwurm M, Mergia E, and Koesling D (1999) A point-mutated guanylyl cyclase with features of the YC-1-stimulated enzyme: implications for the YC-1 binding site? Biochemistry 38:15253-15257. (Pubitemid 129520357)
10. Friebe A, Schultz G, and Koesling D (1996) Sensitizing soluble guanylyl cyclase to become a highly CO-sensitive enzyme. EMBO J 15:6863-6868. (Pubitemid 27023257)
11. Garthwaite J, Southam E, Boulton CL, Nielsen EB, Schmidt K, and Mayer B (1995) Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H- [1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one. Mol Pharmacol 48:184-188.
12. Hardlei TF and Nexo E (2009) A new principle for measurement of cobalamin and corrinoids, used for studies of cobalamin analogs on serum haptocorrin. Clin Chem 55:1002-1010.
13. Hoenicka M, Becker EM, Apeler H, Sirichoke T, Schröder H, Gerzer R, and Stasch JP (1999) Purified soluble guanylyl cyclase expressed in a baculovirus/Sf9 system: stimulation by YC-1, nitric oxide, and carbon monoxide. J Mol Med 77:14-23. (Pubitemid 29146177)
14. Koesling D and Friebe A (1999) Soluble guanylyl cyclase: structure and regulation. Rev Physiol Biochem Pharmacol 135:41-65.
15. Koglin M and Behrends S (2003) A functional domain of the alpha1 subunit of soluble guanylyl cyclase is necessary for activation of the enzyme by nitric oxide and YC-1 but is not involved in heme binding. J Biol Chem 278:12590-12597. (Pubitemid 36800249)
16. Kräutler B (2005) Vitamin B12: chemistry and biochemistry. Biochem Soc Trans 33:806-810.
17. Ma X, Sayed N, Baskaran P, Beuve A, and van den Akker F (2008) PAS-mediated dimerization of soluble guanylyl cyclase revealed by signal transduction histidine kinase domain crystal structure. J Biol Chem 283:1167-1178.
18. Martin E, Czarnecki K, Jayaraman V, Murad F, and Kincaid J (2005) Resonance Raman and infrared spectroscopic studies of high-output forms of human soluble guanylyl cyclase. J Am Chem Soc 127:4625-4631. (Pubitemid 40489618)
19. Martin E, Lee YC, and Murad F (2001) YC-1 activation of human soluble guanylyl cyclase has both heme-dependent and heme-independent components. Proc Natl Acad Sci USA 98:12938-12942. (Pubitemid 33051298)
20. Martin E, Sharina I, Kots A, and Murad F (2003) A constitutively activated mutant of human soluble guanylyl cyclase (sGC): implication for the mechanism of sGC activation. Proc Natl Acad Sci USA 100:9208-9213. (Pubitemid 37033908)
21. Martin F, Baskaran P, Ma X, Dunten PW, Schaefer M, Stasch JP, Beuve A, and van den Akker F (2010) Structure of cinaciguat (BAY 58-2667) bound to Nostoc H-NOX domain reveals insights into heme-mimetic activation of the soluble guanylyl cyclase. J Biol Chem 285:22651-22657.
22. Mujoo K, Sharin VG, Martin E, Choi BK, Sloan C, Nikonoff LE, Kots AY, and Murad F (2010) Role of soluble guanylyl cyclase-cyclic GMP signaling in tumor cell proliferation. Nitric Oxide 22:43-50.
23. Scatena R, Bottoni P, Pontoglio A, and Giardina B (2010) Pharmacological modulation of nitric oxide release: new pharmacological perspectives, potential benefits and risks. Curr Med Chem 17:61-73.
24. Schindler U, Strobel H, Schönafinger K, Linz W, Löhn M, Martorana PA, Rütten H, Schindler PW, Busch AE, Sohn M, et al. (2006) Biochemistry and pharmacology of novel anthranilic acid derivatives activating heme-oxidized soluble guanylyl cyclase. Mol Pharmacol 69:1260-1268.
25. Schmidt HH, Schmidt PM, and Stasch JP (2009) NO- and haem-independent soluble guanylate cyclase activators. Handb Exp Pharmacol 191:309-339.
26. Schmidt P, Schramm M, Schröder H, and Stasch JP (2003) Mechanisms of nitric oxide independent activation of soluble guanylyl cyclase. Eur J Pharmacol 468:167-174. (Pubitemid 36712896)
27. Schmidt PM, Schramm M, Schröder H, Wunder F, and Stasch JP (2004) Identification of residues crucially involved in the binding of the heme moiety of soluble guanylate cyclase. J Biol Chem 279:3025-3032. (Pubitemid 38114295)
28. Sousa EH, Garay PA, Tinianow JN, and Gerber NC (2006) Development of a spectrophotometric assay for cyclase activity. Anal Biochem 348:57-63. (Pubitemid 41796456)
29. Stasch JP, Becker EM, Alonso-Alija C, Apeler H, Dembowsky K, Feurer A, Gerzer R, Minuth T, Perzborn E, Pleiss U, et al. (2001) NO-independent regulatory site on soluble guanylate cyclase. Nature 410:212-215. (Pubitemid 32216593)
30. Stasch JP, Dembowsky K, Perzborn E, Stahl E, and Schramm M (2002) Cardiovascular actions of a novel NO-independent guanylyl cyclase stimulator, BAY 41-8543: in vivo studies. Br J Pharmacol 135:344-355. (Pubitemid 34151166)
31. Stasch JP and Hobbs AJ (2009) NO-independent, haem-dependent soluble guanylate cyclase stimulators. Handb Exp Pharmacol 191:277-308.
32. Stasch JP, Pacher P, and Evgenov OV (2011) Soluble guanylate cyclase as an emerging therapeutic target in cardiopulmonary disease. Circulation 123:2263-2273.
33. Stasch JP, Schmidt PM, Nedvetsky PI, Nedvetskaya TY, H S AK, Meurer S, Deile M, Taye A, Knorr A, Lapp H, et al. (2006) Targeting the heme-oxidized nitric oxide receptor for selective vasodilatation of diseased blood vessels. J Clin Invest 116:2552-2561. (Pubitemid 44330154)
34. 12 and redox homeostasis: cob(II)alamin reacts with superoxide at rates approaching superoxide dismutase (SOD). J Am Chem Soc 131:15078-15079.
35. Sunahara RK, Beuve A, Tesmer JJ, Sprang SR, Garbers DL, and Gilman AG (1998) Exchange of substrate and inhibitor specificities between adenylyl and guanylyl cyclases. J Biol Chem 273:16332-16338. (Pubitemid 28311412)
36. Wedel B, Harteneck C, Foerster J, Friebe A, Schultz G, and Koesling D (1995) Functional domains of soluble guanylyl cyclase. J Biol Chem 270:24871-24875.
37. Whisnant RE, Gilman AG, and Dessauer CW (1996) Interaction of the two cytosolic domains of mammalian adenylyl cyclase. Proc Natl Acad Sci USA 93:6621-6625. (Pubitemid 26230358)
38. Zhao Y, Schelvis JP, Babcock GT, and Marletta MA (1998) Identification of histidine 105 in the beta1 subunit of soluble guanylate cyclase as the heme proximal ligand. Biochemistry 37:4502-4509. (Pubitemid 28217168)
39. Zhou Z, Gross S, Roussos C, Meurer S, Müller-Esterl W, and Papapetropoulos A (2004) Structural and functional characterization of the dimerization region of soluble guanylyl cyclase. J Biol Chem 279:24935-24943. (Pubitemid 38756741)