Structure/activity relationships of (M)ANT- and TNP-nucleotides for inhibition of rat Soluble guanylyl cyclase α1β1

Molecular Pharmacology

Volumn 85, Issue 4, 2014, Pages 598-607

  Dove, Stefan ^a   Danker, Kerstin Yvonne ^b   Stasch, Johannes Peter ^b,c   Kaever, Volkhard ^b   Seifert, Roland ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b HANNOVER MEDICAL SCHOOL   (Germany)

^c Institute of Cardiovascular Research   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2' O ( N METHYLANTHRANILOYL) 3' DEOXY ADENOSINE TRIPHOSPHATE; 2',3' O ( 2,4,6 TRINITROPHENYL)GUANOSINE TRIPHOSPHATE; ADENYLATE CYCLASE; GUANYLATE CYCLASE; GUANYLATE CYCLASE INHIBITOR; GUANYLYL CYCLASE ALPHA1BETA1; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DRUG POTENCY; DRUG SELECTIVITY; ENZYME ACTIVE SITE; ENZYME INHIBITION; FLUORESCENCE SPECTROSCOPY; MOLECULAR DOCKING; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ADENYLATE CYCLASE; ANIMALS; GUANYLATE CYCLASE; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR DOCKING SIMULATION; NITRO COMPOUNDS; ORTHO-AMINOBENZOATES; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN SUBUNITS; PURINE NUCLEOTIDES; PYRIMIDINE NUCLEOTIDES; RATS; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84896885811     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.113.091017     Document Type: Article

References (47)

1. Allerston CK, Von Delft F, and Gileadi O (2013) Crystal structures of the catalytic domain of human soluble guanylate cyclase. PLoS ONE 8:e57644.
2. Bähre H, Danker KY, Stasch JP, Kaever V, and Seifert R (2014) Nucleotidyl cyclase activity of soluble guanylyl cyclase in intact cells. Biochem Biophys Res Commun 443:1195-1199.
3. Baskaran P, Heckler EJ, Van Den Akker F, and Beuve A (2011) Identification of residues in the heme domain of soluble guanylyl cyclase that are important for basal and stimulated catalytic activity. PLoS ONE 6:e26976.
4. Beste KY, Burhenne H, Kaever V, Stasch JP, and Seifert R (2012) Nucleotidyl cyclase activity of soluble guanylyl cyclase a1b1. Biochemistry 51:194-204.
5. Beste KY, Spangler CM, Burhenne H, Koch KW, Shen Y, Tang WJ, Kaever V, and Seifert R (2013) Nucleotidyl cyclase activity of particulate guanylyl cyclase A: comparison with particulate guanylyl cyclases E and F, soluble guanylyl cyclase and bacterial adenylyl cyclases CyaA and edema factor. PLoS ONE 8:e70223.
6. Braeunig JH, Schweda F, Han PL, and Seifert R (2013) Similarly potent inhibition of adenylyl cyclase by P-site inhibitors in hearts from wild type and AC5 knockout mice. PLoS ONE 8:e68009.
7. Brand CS, Hocker HJ, Gorfe AA, Cavasotto CN, and Dessauer CW (2013) Isoform selectivity of adenylyl cyclase inhibitors: characterization of known and novel compounds. J Pharmacol Exp Ther 347:265-275.
8. Busker M, Neidhardt I, and Behrends S (2014) Nitric oxide activation of guanylate cyclase pushes the a1 signaling helix and the b1 heme-binding domain closer to the substrate-binding site. J Biol Chem 289:476-484.
9. Clark M, Cramer RD, III, and Van Opdenbosch N (1989) Validation of the general purpose tripos 5.2 force field. J Comput Chem 10:982-1012.
10. Cornell WD, Cieplak P, Bayly CI, Gould IR, Merz KM, Ferguson DM, Spellmeyer DC, Fox T, Caldwell JW, and Kollman PA (1995) A second generation force field for the simulation of proteins and nucleic acids. J Am Chem Soc 117:5179-5197.
11. Daiber A, Münzel T, and Gori T (2010) Organic nitrates and nitrate tolerance-state of the art and future developments. Adv Pharmacol 60:177-227.
12. Derbyshire ER and Marletta MA (2012) Structure and regulation of soluble guanylate cyclase. Annu Rev Biochem 81:533-559.
13. Follmann M, Griebenow N, Hahn MG, Hartung I, Mais FJ, Mittendorf J, Schäfer M, Schirok H, Stasch JP, and Stoll F et al. (2013) The chemistry and pharmacology of soluble guanylate cyclase stimulators and activators. Angew Chem Int Ed Engl 52:9442-9462.
14. Friebe A and Koesling D (2009) The function of NO-sensitive guanylyl cyclase: what we can learn from genetic mouse models. Nitric Oxide 21:149-156.
15. Geduhn J, Dove S, Shen Y, Tang WJ, König B, and Seifert R (2011) Bis-halogenanthraniloyl-substituted nucleoside 59-triphosphates as potent and selective inhibitors of Bordetella pertussis adenylyl cyclase toxin. J Pharmacol Exp Ther 336:104-115.
16. Gheorghiade M, Marti CN, Sabbah HN, Roessig L, Greene SJ, Böhm M, Burnett JC, Campia U, Cleland JGF, and Collins SP et al.; Academic Research Team in Heart Failure (ART-HF) (2013) Soluble guanylate cyclase: a potential therapeutic target for heart failure. Heart Fail Rev 18:123-134.
17. Ghose AK, Viswanadhan VN, and Wendoloski JJ (1998) Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: An analysis of ALOGP and CLOGP methods. J Phys Chem A 102:3762-3772. (Pubitemid 128611348)
18. Gille A, Lushington GH, Mou TC, Doughty MB, Johnson RA, and Seifert R (2004) Differential inhibition of adenylyl cyclase isoforms and soluble guanylyl cyclase by purine and pyrimidine nucleotides. J Biol Chem 279:19955-19969. (Pubitemid 38623438)
19. Harteneck C, Wedel B, Koesling D, Malkewitz J, Böhme E, and Schultz G (1991) Molecular cloning and expression of a new a-subunit of soluble guanylyl cyclase. Interchangeability of the a-subunits of the enzyme. FEBS Lett 292:217-222.
20. Heiden W, Moeckel G, and Brickmann J (1993) A new approach to analysis and display of local lipophilicity/hydrophilicity mapped on molecular surfaces. J Comput Aided Mol Des 7:503-514.
21. 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 (Berl) 77:14-23. (Pubitemid 29146177)
22. Hübner M, Dixit A, Mou TC, Lushington GH, Pinto C, Gille A, Geduhn J, König B, Sprang SR, and Seifert R (2011) Structural basis for the high-affinity inhibition of mammalian membranous adenylyl cyclase by 29, 39-O-(N-methylanthraniloyl) - inosine 59-triphosphate. Mol Pharmacol 80:87-96.
23. Humbert P, Niroomand F, Fischer G, Mayer B, Koesling D, Hinsch KD, Gausepohl H, Frank R, Schultz G, and Böhme E (1990) Purification of soluble guanylyl cyclase from bovine lung by a new immunoaffinity chromatographic method. Eur J Biochem 190:273-278. (Pubitemid 20201512)
24. Koesling D, Harteneck C, Humbert P, Bosserhoff A, Frank R, Schultz G, and Böhme E (1990) The primary structure of the larger subunit of soluble guanylyl cyclase from bovine lung. Homology between the two subunits of the enzyme. FEBS Lett 266:128-132. (Pubitemid 20194190)
25. Kots AY, Bian K, and Murad F (2011) Nitric oxide and cyclic GMP signaling pathway as a focus for drug development. Curr Med Chem 18:3299-3305.
26. Kumar V, Martin F, Hahn MG, Schaefer M, Stamler JS, Stasch JP, and Van Den Akker F (2013) Insights into BAY 60-2770 activation and S- nitrosylationdependent desensitization of soluble guanylyl cyclase via crystal structures of homologous nostoc H-NOX domain complexes. Biochemistry 52:3601-3608.
27. Mou TC, Gille A, Fancy DA, Seifert R, and Sprang SR (2005) Structural basis for the inhibition of mammalian membrane adenylyl cyclase by 2' (3')-O-(N-methylanthraniloyl) - guanosine 5'-triphosphate. J Biol Chem 280:7253-7261. (Pubitemid 40341283)
28. Mou TC, Gille A, Suryanarayana S, Richter M, Seifert R, and Sprang SR (2006) Broad specificity of mammalian adenylyl cyclase for interaction with 29, 39-substituted purine- and pyrimidine nucleotide inhibitors. Mol Pharmacol 70:878-886. (Pubitemid 44268445)
29. Pinto C, Hübner M, Gille A, Richter M, Mou TC, Sprang SR, and Seifert R (2009) Differential interactions of the catalytic subunits of adenylyl cyclase with forskolin analogs. Biochem Pharmacol 78:62-69.
30. Pinto C, Lushington GH, Richter M, Gille A, Geduhn J, König B, Mou TC, Sprang SR, and Seifert R (2011) Structure-activity relationships for the interactions of 29- and 39-(O) - (N-methyl) anthraniloyl-substituted purine and pyrimidine nucleotides with mammalian adenylyl cyclases. Biochem Pharmacol 82:358-370.
31. Robinson JW and Potter LR (2012) Guanylyl cyclases A and B are asymmetric dimers that are allosterically activated by ATP binding to the catalytic domain. Sci Signal 5:ra65.
32. Schermuly RT, Janssen W, Weissmann N, Stasch JP, Grimminger F, and Ghofrani HA (2011) Riociguat for the treatment of pulmonary hypertension. Expert Opin Investig Drugs 20:567-576.
33. Seifert R (2014) Vidarabine is neither a potent nor a selective AC5 inhibitor. Biochem Pharmacol 87:543-546.
34. Seifert R and Beste KY (2012) Allosteric regulation of nucleotidyl cyclases: an emerging pharmacological target. Sci Signal 5:pe37.
35. Seifert R and Dove S (2012) Towards selective inhibitors of adenylyl cyclase toxin from Bordetella pertussis. Trends Microbiol 20:343-351.
36. Seifert R and Dove S (2013) Inhibitors of Bacillus anthracis edema factor. Pharmacol Ther 140:200-212.
37. Seifert R, Lushington GH, Mou TC, Gille A, and Sprang SR (2012) Inhibitors of membranous adenylyl cyclases. Trends Pharmacol Sci 33:64-78.
38. Stasch JP and Evgenov OV (2013) Soluble guanylate cyclase stimulators in pulmonary hypertension. Handbook Exp Pharmacol 218:279-313.
39. Stasch JP, Becker EM, Alonso-Alija C, Apeler H, Dembowsky K, Feurer A, Gerzer R, Minuth T, Perzborn E, and Pleiss U et al. (2001) NO-independent regulatory site on soluble guanylate cyclase. Nature 410:212-215. (Pubitemid 32216593)
40. 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)
41. Suryanarayana S, Göttle M, Hübner M, Gille A, Mou TC, Sprang SR, Richter M, and Seifert R (2009) Differential inhibition of various adenylyl cyclase isoforms and soluble guanylyl cyclase by 29, 39-O-(2, 4, 6-trinitrophenyl)-substituted nucleoside 59-triphosphates. J Pharmacol Exp Ther 330:687-695.
42. Strasser A, Wittmann HJ, Buschauer A, Schneider EH, and Seifert R (2013) Speciesdependent activities of G-protein-coupled receptor ligands: lessons from histamine receptor orthologs. Trends Pharmacol Sci 34:13-32.
43. Tesmer JJ, Sunahara RK, Gilman AG, and Sprang SR (1997) Crystal structure of the catalytic domains of adenylyl cyclase in a complex with Gsa. GTPgS. Science 278:1907-1916. (Pubitemid 28013225)
44. Tesmer JJ, Sunahara RK, Johnson RA, Gosselin G, Gilman AG, and Sprang SR (1999) Two-metal-Ion catalysis in adenylyl cyclase. Science 285:756-760.
45. Tesmer JJ, Dessauer CW, Sunahara RK, Murray LD, Johnson RA, Gilman AG, and Sprang SR (2000) Molecular basis for P-site inhibition of adenylyl cyclase. Biochemistry 39:14464-14471.
46. Underbakke ES, Iavarone AT, and Marletta MA (2013) Higher-order interactions bridge the nitric oxide receptor and catalytic domains of soluble guanylate cyclase. Proc Natl Acad Sci USA 110:6777-6782.
47. Vatner SF, Park M, Yan L, Lee GJ, Lai L, Iwatsubo K, Ishikawa Y, Pessin J, and Vatner DE (2013) Adenylyl cyclase type 5 in cardiac disease, metabolism, and aging. Am J Physiol Heart Circ Physiol 305:H1-H8.