Structure-activity relationship of (N)-methanocarba phosphonate analogues of 5′-AMP as cardioprotective agents acting through a cardiac P2X receptor

Journal of Medicinal Chemistry

Volumn 53, Issue 6, 2010, Pages 2562-2576

  Santhosh Kumar, T ^a   Zhou, Si Yuan ^b   Joshi, Bhalchandra V ^a,c   Balasubramanian, Ramachandran ^a   Yang, Tiehong ^b   Liang, Bruce T ^b   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF CONNECTICUT HEALTH CENTER   (United States)

^c NEKTAR THERAPEUTICS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4' (6 AMINO 2 AMINOPURIN 9 YL) 2',3' (DIHYDROXY) 1' (PHOSPHONOETHENYL)BICYCLO[3.1.0]HEXANE; 4' (6 AMINO 2 CHLOROPURIN 9 YL) 2',3' (DIHYDROXY) 1' (PHOSPHONOETHENYL)BICYCLO[3.1.0]HEXANE; 4' (6 AMINO 2 CHLOROPURIN 9 YL) 2',3' (DIHYDROXY) 1' (PHOSPHONOMETHYLENE)BICYCLO[3.1.0]HEXANE; 4' (6 AMINO 2 CHLOROPURIN 9 YL) 2',3' DIHYDROXY 1' (METHYLPHOSPHONICACID)BICYCLO[3.1.0]HEXANE; 4' (6 AMINOPURIN 9 YL) 2',3' DIHYDROXY 1' (METHYLPHOSPHONICACID)BICYCLO[3.1.0]HEXANE; MRS 2775; MRS 2935; PHOSPHONIC ACID DERIVATIVE; PURINERGIC P2X RECEPTOR; PURINERGIC P2Y1 RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ECHOCARDIOGRAPHY; HEART CONTRACTION; HEART FAILURE; HEART PROTECTION; HUMAN; HUMAN CELL; MITSUNOBU REACTION; MOUSE; NONHUMAN; OSMOTIC PUMP; STRUCTURE ACTIVITY RELATION; WITTIG REACTION;

ADENOSINE MONOPHOSPHATE; ANIMALS; CALCIUM; CARDIOTONIC AGENTS; CELL LINE, TUMOR; ECHOCARDIOGRAPHY; FEMALE; HEART; HUMANS; INFUSION PUMPS; INTRACELLULAR SPACE; MALE; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MYOCARDIUM; PHOSPHONIC ACIDS; RECEPTORS, PURINERGIC P2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77949794068     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9018542     Document Type: Article

References (35)

1. North, R. A. Molecular physiology of P2X receptors. Physiol. Rev. 2002, 82, 1013-1067.
2. Ralevic, V.; Burnstock, G. Receptors for purines and pyrimidines. Pharmacol. Rev. 1998, 50, 413-492.
3. Vassort, G. Adenosine 5′-triphosphate: a P2-purinergic agonist in the myocardium. Physiol. Rev. 2001, 81, 767-806.
4. 4 receptors. FASEB J. 2006, 20, 277-284.
5. Scamps, F.; Vassort, G. Pharmacological profile of the ATP-mediated increase in L-type calcium current amplitude and activation of a nonspecific cation current in rat ventricular cells. Br. J. Pharmacol. 1994, 113, 982-986.
6. Parker, K. E.; Scarpa, A. An ATP-activated nonselective cation channel in guinea pig ventricular myocytes. Am. J. Physiol. 1995, 269, H789-H797.
7. 4 receptors in heart failure: rescuing the calsequestrin- overexpression model of cardiomyopathy. Am. J. Physiol. 2004, 287, H1096-H1103.
8. Shen, J. B.; Cronin, C.; Sonin, D.; Joshi, B. V.; Carolina, M.; Nieto, G.; Harrison, D.; Jacobson, K. A.; Liang, B. T. P2X purinergic receptor-mediated ionic current in cardiac myocytes of calsequestrin model of cardiomyopathy. Implications for the treatment of heart failure. Am. J. Physiol. Heart Circ. Physiol. 2007, 292, H1077-H1084.
9. 1 receptor agonists. J. Med. Chem. 2002, 45, 2090-2100.
10. 2+ signaling in transgenic mouse cardiac myocytes overexpressing calsequestrin. J. Clin. Invest. 1998, 101, 1385-1393.
11. Knollman, B. C.; Knollmann-Ritschel, B. E. C.; Weismann, N. J.; Jones, L. R.; Morad, M. Remodeling of ionic currents in hypertrophied and failing hearts of transgenic mice overexpressing calsequestrin. J. Physiol. 2000, 525, 483-498.
12. 4: an ATP-activated ionotropic receptor cloned from rat brain. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3684-3688.
13. Joshi, B. V.; Melman, A.; Mackman, R. L.; Jacobson, K. A. Synthesis of ethyl (1S,2R,3S,4S,5S)-2,3-O-(isopropylidene)-4-hydroxy-bicyclo[3.1.0]hexane- carboxylate from L-ribose: A versatile chiral synthon for preparation of adenosine and P2 receptor ligands. Nucleosides, Nucleotides Nucleic Acids 2008, 27, 279-291.
14. 2 receptor antagonists. Bioorg. Med. Chem. 2009, 17, 5071-5079.
15. Cosyn, L.; Van Calenbergh, S.; Joshi, B. V.; Ko, H.; Carter, R. L.; Harden, T. K.; Jacobson, K. A. Synthesis and P2Y receptor activity of nucleotide 5′-phosphonate derivatives. Bioorg. Med. Chem. Lett. 2009, 19, 3002-3005.
16. Xu, B.; Stephens, A.; Kirschenheuter, G.; Greslin, A. F.; Cheng, X.; Sennelo, J.; Cattaneo, M.; Zighetti, M. L.; Chen, A.; Kim, S. A.; Kim, H. S.; Bischofberger, N.; Cook, G.; Jacobson, K. A. Acyclic analogues of adenosine bisphosphates as P2Y receptor antagonists: Phosphate substitution leads to multiple pathways of inhibition of platelet aggregation. J. Med. Chem. 2002, 45, 5694-5709.
17. 1 receptors. J. Med. Chem. 2001, 44, 340-349.
18. 4 receptor transgenic mouse. FASEB J. 2001, 15, 2739-2741.
19. Curcio, A.; Noma, T.; Prasad, S. V. N.; Wolf, M. J.; Lemaire, A.; Perrino, C.; Mao, L.; Rockman, H. A. Competitive displacement of phosphoinoside 3-kinase from β;-adrenergic receptor kinase-1 improves postinfarction adverse myocardial remodeling. Am. J. Phsyiol. Heart Circ. Physiol. 2006, 291, H1754-H1760.
20. Tsoporis, J. N.; Marks, A.; Haddad, A.; Dawood, F.; Liu, P. P.; Parker, T. G. S100B expression modulates left ventricular remodeling after myocardial infarction in mice. Circulation 2005, 111, 598-606.
21. Moss, G. P. Extension and revision of the von Baeyer system for naming polycyclic compounds (including bicyclic compounds). Pure Appl. Chem. 1999, 71, 513-529.
22. Bichlmaier, I.; Kurkela, T.; Joshi, M.; Siiskonen, A.; Rv̈ffer, T.; Lang, H.; Suchanova, B.; Vahermo, M.; Finel, M.; Yli-Kauhaluoma, J. Isoform-Selective Inhibition of the Human UDP-Glucuronosyltransferase 2B7 by Isolongifolol Derivatives. J. Med. Chem. 2007, 50, 2655-2664.
23. Samadder, P.; Bittman, R.; Byun, H.-S.; Arthur, G. Synthesis and use of novel ether phospholipid enantiomers to probe the molecular basis of the antitumor effects of alkyllysophospholipids: Correlation of differential activation of c-Jun NH2-terminal protein kinase with antiproliferative effects in neuronal tumor cells. J. Med. Chem. 2004, 47, 2710-2713.
24. Salvatori, D.; Volpini, R.; Vincenzetti, S.; Vita, A.; Costanzi, S.; Lambertucci, C.; Cristalli, G.; Vittori, S. Adenine and deazaadenine nucleoside and deoxynucleoside analogues: Inhibition of viral replication of sheep MVV (In vitro model for HIV) and bovine BHV-1. Bioorg. Med. Chem. 2002, 10, 2973-2980.
25. Hoffmann, M. F. H.; Brückner, A. M.; Hupp, T.; Engels, B.; Diederichsen, U. Specific purine-purine base pairing in linear alanyl-peptide nucleic acids. Helv. Chim. Acta 2000, 83, 2580-2593.
26. 4 subunits. J. Neurochem. 2005, 92, 925-933.
27. 4-deficient mice. Nat. Med. 2006, 12, 133-137.
28. 12 receptors. Biochem. Pharmacol. 2006, 72, 1031-1041.
29. Peyrottesm, S.; Gallier, F.; Béjaud, J.; Périgaud, C. Use of microwave irradiation for sugar and nucleoside phosphonates synthesis. Tetrahedron Lett. 2006, 47, 7719-7721.
30. De Clercq, E. The acyclic nucleoside phosphonates from inception to clinical use: historical perspective. Antiviral Res. 2007, 75, 1-13.
31. 7 Heteromeric Receptors. Mol. Pharmacol. 2007, 72, 1402-1405.
32. 4 receptors studied with an ectodomain antibody. Cell Tissue Res. 2003, 313, 159-165.
33. Tsuda, M.; Tozaki-Saitoh, H.; Inoue, K. Pain and purinergic signaling. Brain Res. Rev. 2010, doi:10.1016/j.brainresrev.2009.11.003 [Epub ahead of print].
34. 6 receptor inhibits its assembly and exit from the endoplasmic reticulum. Mol. Pharmacol. 2006, 69, 1692-1700
35. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Mitsunobu and related reactions: Advances and applications. Chem. Rev., 2009, 109, 2551-2651.