Synthesis and evaluation of bifunctional sGC regulators: Optimization of a connecting linker

Journal of Medicinal Chemistry

Volumn 56, Issue 18, 2013, Pages 7260-7277

  Chromiński, Mikołaj ^a   Banach, Łukasz ^a   Karczewski, Maksymilian ^a   Ó Proinsias, Keith ^a   Sharina, Iraida ^b   Gryko, Dorota ^a   Martin, Emil ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [1 (2 FLUOROBENZYL) 1H PYRAZOLO[3,4 B]PYRIDIN 3 YL] 5 MORPHOLINO 4,6 PYRIMIDINEDIAMINE; 4 AMINO 5 CYCLOPROPYL 2 [1 (2 FLUOROBENZYL) 1H PYRAZOLO[3,4 B]PYRIDIN 3 YL]PYRIMIDINE; ATACIGUAT; CINACIGUAT; COBINAMIDE; CYCLIC GMP; GUANOSINE TRIPHOSPHATE; GUANYLATE CYCLASE; GUANYLATE CYCLASE ACTIVATOR; HEME; LIFICIGUAT; PROTOPORPHYRIN; TRIAZOLE;

AMIDATION; ARTICLE; ATOM; BINDING AFFINITY; CATALYSIS; CYCLOADDITION; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ESTERIFICATION; HUMAN; HYBRID; IN VITRO STUDY;

CHEMISTRY TECHNIQUES, SYNTHETIC; COPPER; ENZYME ACTIVATION; GUANYLATE CYCLASE; HUMANS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PROTEIN CONFORMATION; PROTOPORPHYRINS; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84884992774     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400715h     Document Type: Article

References (40)

1. Derbyshire, E. R.; Marletta, M. A. Structure and Regulation of Soluble Guanylate Cyclase Annu. Rev. Biochem. 2012, 81, 533-559
2. Russwurm, M.; Koesling, D. Isoforms of NO-sensitive guanylyl cyclase Mol. Cell. Biochem. 2002, 230, 159-164 (Pubitemid 34257252)
3. Ma, X.; Sayed, N.; Baskaran, P.; Beuve, A.; van den Akker, F. PAS-mediated Dimerization of Soluble Guanylyl Cyclase Revealed by Signal Transduction Histidine Kinase Domain Crystal Structure J. Biol. Chem. 2008, 283, 1167-1178
4. Fritz, B. G.; Roberts, S. A.; Ahmed, A.; Breci, L.; Li, W.; Weichsel, A.; Brailey, J. L.; Wysocki, V. H.; Tama, F.; Montfort, W. R. Molecular Model of a Soluble Guanylyl Cyclase Fragment Determined by Small-Angle X-ray Scattering and Chemical Cross-Linking Biochemistry 2013, 52, 1568-1582
5. Winger, J. A.; Marletta, M. A. Expression and Characterization of the Catalytic Domains of Soluble Guanylate Cyclase: Interaction with the Heme Domain Biochemistry 2005, 44, 4083-4090 (Pubitemid 40358061)
6. Murad, F. Nitric Oxide and Cyclic GMP in Cell Signaling and Drug Development N. Engl. J. Med. 2006, 355, 2003-2011 (Pubitemid 44708019)
7. Vita, J. A. Endothelial Function Circulation 2011, 124, 906-912
8. Munzel, T.; Daiber, A.; Gori, T. Nitrate Therapy: New Aspects Concerning Molecular Action and Tolerance Circulation 2011, 123, 2132-2144
9. Stasch, J. P.; Pacher, P.; Evgenov, O. V. Soluble Guanylate Cyclase as an Emerging Therapeutic Target in Cardiopulmonary Disease Circulation 2011, 123, 2263-2273
10. ó Proinsias, K.; Giedyk, M.; Sharina, I.; Martin, E.; Gryko, D. Synthesis of New Hydrophilic and Hydrophobic Cobinamides as NO-Independent sGC Activators ACS Med. Chem. Lett. 2012, 3, 476-479
11. Sharina, I.; Sobolevsky, M.; Doursout, M. F.; Gryko, D.; Martin, E. Cobinamides Are Novel Coactivators of Nitric Oxide Receptor That Target Soluble Guanylyl Cyclase Catalytic Domain J. Pharmacol. Exp. Ther. 2011, 340, 723-732
12. Chromiński, M.; ó Proinsias, K.; Martin, E.; Gryko, D. Protoporphyrin IX/Cobyrinate Derived Hybrids-Novel Activators of Soluble Guanylyl Cyclase Eur. J. Org. Chem. 2013, 8, 1530-1537
13. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem. 2002, 114, 2708-2711
14. Shao, C.; Cheng, G.; Su, D.; Xu, J.; Wang, X.; Hu, Y. Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition Adv. Synth. Catal. 2010, 352, 1587-1592
15. Tornøe, Ch. W.; Meldal, M. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
16. Bock, V. D.; Himestra, H.; van Maarseveen, J. H. Cu(I)-Catalyzed Alkyne-Azide "Click" Cycloadditions from a Mechanistic and Synthetic Perspective Eur. J. Org. Chem. 2006, 51-68
17. Moses, J. E.; Moorhouse, A. D. The Growing Application of Click Chemistry Chem. Soc. Rev. 2007, 36, 1249-1262
18. Jewett, J. C.; Bertozzi, C. R. Cu-Free Click Cycloaddition Reactions in Chemical Biology Chem. Soc. Rev. 2010, 39, 1272-1279
19. Dumoulin, F.; Ahsen, V. Click Chemistry: The Emerging Role of the Azide-Alkyne Huisgen Dipolar Addition in the Preparation of Substituted Tetrapyrrolic Derivatives J. Porphyrins Phthalocyanines 2011, 15, 486-504
20. 12 Derivatives with Peripheral Tris(oxyethylene) Chains Helv. Chim. Acta 1998, 81, 1105-1116 (Pubitemid 128497317)
21. 12 Chem. Rev. 2005, 105, 2075-2150
22. 12 Covalently Immobilized onto Platinum Electrode Chem. Commun. 2004, 50-51 (Pubitemid 38121956)
23. Sieber, P. Der 2-Trimethylsilyläthyl-Rest als selektiv abspaltbare Carboxy-Schutzgruppe Helv. Chim. Acta 1977, 60, 2711-2716
24. Back, T. G.; Wulff, A. Stereodivergent Synthesis of Virantmycin by an Enzyme-Mediated Diester Desymmetrization and a Highly Hindered Aryl Amination Angew. Chem Int. Ed. 2004, 43, 6493-6496 (Pubitemid 40029504)
25. 12 Derivatives: Unprecedented Formation of a 7-Membered Lactam Eur. J. Org. Chem. 2012, 154-159
26. Grossauer, A.; Heise, K.-P.; Götze, H.; Inhoffen, H. H. Derivate des Dicyano-cobrinsäure-hexamethylester-c-lactons Justus Liebigs Ann. Chem. 1977, 1480-1499
27. 12 Having a Benzo-18-crown-6 moiety at the C10 Position of the Corrin Ring Tetrahedron Lett. 2003, 44, 6421-6424 (Pubitemid 36936932)
28. ó Proinsias, K.; Giedyk, M.; Banach, Ł.; Rutkowska-Zbik, D.; Gryko, D. Selectively Modified Cobyrinic Acid Derivatives Asian J. Org. Chem. 2013, 2, 504-513
29. Morphy, R.; Rankovic, Z. Designed Multiple Ligands. An Emerging Drug Discovery Paradigm J. Med. Chem. 2005, 48, 6524-6543
30. Morphy, R.; Rankovic, Z. The Physiological Challenges of Designing Multiple Ligands J. Med. Chem. 2006, 49, 4961-4970 (Pubitemid 44201054)
31. Martin, E.; Sharina, I.; Kots, A.; Murad, F. A Constitutively Activated Mutant of Human Soluble Guanylyl Cyclase (sGC): Implication for the Mechanism of sGC Activation Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 9208-9213 (Pubitemid 37033908)
32. Foerster, J.; Harteneck, C.; Malkewitz, J.; Schultz, G.; Koesling, D. A Functional Heme-Binding Site of Soluble Guanylyl Cyclase Requires Intact N-Termini of α1 and β1 Subunits Eur. J. Biochem. 1996, 240, 380-386 (Pubitemid 26292745)
33. Ignarro, L. J.; Wood, K. S.; Wolin, M. S. Activation of Purified Soluble Guanylate Cyclase by Protoporphyrin IX Proc. Natl. Acad. Sci. U. S. A. 1982, 79, 2870-2873 (Pubitemid 12032334)
34. Ma, X.; Sayed, N.; Beuve, A.; van den Akker, F. NO and CO differentially Activate Soluble Guanylyl Cyclase via a Heme Pivot-Bend Mechanism EMBO J. 2007, 26, 578-588 (Pubitemid 46160957)
35. Baskaran, P.; Heckler, E. J.; van den Akker, F.; Beuve, A. Aspartate 102 in the Heme Domain of Soluble Guanylyl Cyclase Has a Key Role in NO Activation Biochemistry 2011, 50, 4291-4297
36. Martin, F.; Baskaran, P.; Ma, X.; Dunten, P. W.; Schaefer, M.; Stasch, J. P.; Beuve, A.; van den Akker, F. 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. 2010, 285, 22651-22657
37. Allerston, C. K.; von Delft, F.; Gileadi, O. Crystal Structures of the Catalytic Domain of Human Soluble Guanylate Cyclase PLoS One 2013, 8, e57644
38. 12 Derivatives as Activators of Soluble Guanylyl Cyclase J. Med. Chem. 2012, 55, 8943-8947
39. Martin, E.; Lee, Y. C.; Murad, F. YC-1 Activation of Human Soluble Guanylyl Cyclase Has Both Heme-Dependent and Heme-Independent Components Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 12938-12942 (Pubitemid 33051298)
40. Arnold, K.; Bordoli, L.; Kopp, J.; Schwede, T. The SWISS-MODEL Workspace: A Web-Based Environment for Protein Structure Homology Modelling Bioinformatics 2006, 22, 195-201