Cardioprotective effects of novel tetrahydroisoquinoline analogs of nitrobenzylmercaptopurine riboside in an isolated perfused rat heart model of acute myocardial infarction

American Journal of Physiology - Heart and Circulatory Physiology

Volumn 292, Issue 6, 2007, Pages

  Zhu, Z ^a   Hofmann, P A ^b   Buolamwini, J K ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^b UNIVERSITY OF TENNESSEE COLLEGE OF MEDICINE   (United States)

Author keywords

Adenosine potentiation; Cardioprotection; End diastolic pressure; Infarct size reduction; Ischemia; Left ventricular developed pressure; Nucleoside transport inhibitors; Reperfusion

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE NITROBENZYLMERCAPTOPURINE RIBOSIDE; TETRAHYDROISOQUINOLINE NITROBENZYLMERCAPTOPURINE RIBOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACUTE HEART INFARCTION; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; FEMALE; HEART INFARCTION SIZE; HEART LEFT VENTRICLE PRESSURE; HEART PERFUSION; HEART PROTECTION; ISOLATED HEART; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CARDIOTONIC AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; EQUILIBRATIVE NUCLEOSIDE TRANSPORTER 1; FEMALE; HEART; MYOCARDIAL INFARCTION; MYOCARDIAL ISCHEMIA; MYOCARDIAL REPERFUSION INJURY; MYOCARDIUM; PERFUSION; RATS; RATS, WISTAR; TETRAHYDROISOQUINOLINES; THIOINOSINE; VENTRICULAR FUNCTION, LEFT; VENTRICULAR PRESSURE;

EID: 34447498745     PISSN: 03636135     EISSN: 15221539     Source Type: Journal    
DOI: 10.1152/ajpheart.01191.2005     Document Type: Article

References (61)

1. Abd-Elfattah AS, Ding M, Jessen ME, Wechsler AS. Nucleoside trapping during reperfusion prevents ventricular dysfunction "stunning" in absence of adenosine: possible separation between ischemic and reperfusion injury. J Thorac Cardiovasc Surg 108: 269-278, 1994.
2. Abd-Elfattah AS, Ding M, Wechsler AS. Protection of the stunned myocardium: selective nucleoside transport blocker (NBMPR) administered after 20 min of ischemia treatments and recovery of ventricular function. Circulation 88: 335-343, 1993.
3. Abd-Elfattah AS, Ding M, Wechsler AS. Intermittent warm aortic cross-clamping prevents cumulative ATP depletion, ventricular fibrillation and dysfunction "stunning": is it preconditioning? J Thorac Cardiovasc Surg 110: 328-339, 1995.
4. Abd-Elfattah AS, Hoehner J, Wechsler AS. Identification of nucleoside transport binding sites in the human myocardium. Mol Cell Biochem 180: 105-110, 1998.
5. Abd-Elfattah AS, Jessen ME, Hanan SA, Tuchy G, Wechsler AS. Is adenosine-5′-triphosphate derangement or free-radical-mediated injury the major cause of ventricular dysfunction during reperfusion? Role of adenine nucleoside transport in myocardial reperfusion injury. Circulation 82 Suppl IV: 341-350, 1990.
6. Abd-Elfattah AS, Jessen ME, Lekven J, Doherty NE 3rd, Brunsting LA, Wechsler AS. Myocardial reperfusion injury. Role of myocardial hypoxanthine and xanthine in free radical-mediated reperfusion injury. Circulation 78: III-224-III-235, 1988.
7. Abd-Elfattah AS, Jessen ME, Lekven J, Wechsler AS. Different cardioprotection with selective inhibitors of adenosine metabolism and transport: role of purine release in ischemic and reperfusion injury. Mol Cell Biochem 180: 179-191, 1998.
8. Abd-Elfattah AS, Maddox R, Jessen ME, Hanan SA, Wechsler AS. Selective nucleoside transport blocker NBMPR attenuates myocardial stunning in a rabbit model deficient of xanthine oxidase. In: Purines and Myocardial Protection, edited by AS Abd-Elfattah and AS Wechsler. Amsterdam: Kluwer Academic, 1995.
9. Abd-Elfattah AS, Wechsler AS. Separation between ischemic and reperfusion injury by site-specific entrapment of endogenous adenosine and inosine using NBMPR and EHNA. J Card Surg 9 Suppl: 387-396, 1994.
10. Abd-Elfattah AS, Wechsler AS. Nucleoside transport and myocardial injury and protection: possible separation between ischemic and reperfusion injury by selective nucleoside transport blocker NBMPR. In: Purines and Myocardial Protection, edited by AS Abd-Elfattah and AS Wechsler. Amsterdam: Kluwer Academic, 1995.
11. Baldwin SA, Beal PR, Yao SY, King AE, Cass CE, Young JD. The equilibrative nucleoside transporter family, SLC29. Pflügers Arch 447: 735-743, 2004.
12. Belardinelli L, Linden J, Berne RM. The cardiac effects of adenosine. Prog Cardiovasc Dis 32: 73-97, 1989.
13. Benedict WF, Baker L, Haroun L, Choi E, Ames BN. Mutagenicity of cancer chemotherapeutic agents in the Salmonella/microsome test. Cancer Res 37: 2209-2213, 1977.
14. Buolamwini JK. Nucleoside transport inhibitors: structure-activity relationships and potential therapeutic application. Curr Med Chem 4: 35-66, 1997.
15. Elion GB. Pharmacologic and physical agents. Immunosuppressive agents. Transplant Proc 9: 975-979, 1977.
16. Engler RL. Harnessing nature's own cardiac defense mechanism with acadesine, an adenosine regulating agent: importance of the endothelium. J Card Surg 9 Suppl: 482-492, 1994.
17. Erion MD. Adenosine receptors as pharmacological targets. Annu Rev Med Chem 28: 295-303, 1993.
18. FitzGerald GA. Dipyridamole. N Engl J Med 316: 1247-1256, 1987.
19. Ge ZD, Peart JN, Wan TC, Kreckler LM, Jacobson MA, Gross GJ, Auchampach JA. Cl-IB-MECA reduces ischemia/reperfusion injury in mice by activating the A3 adenosine receptor. J Pharmacol Exp Ther 319: 1200-1210, 2006.
20. Geiger JD, Parkinson FE, Kowaluk EA. Regulators of endogenous adenosine levels as therapeutic agents. In: Purinergic Approaches in Experimental Therapeutics, edited by KA Jacobson and MF Jarvis. New York: Wiley-Liss, 1997, p. 55-84.
21. Gray JH, Owen RP, Giacomini KM. The concentrative nucleoside transporter family, SLC28. Pflügers Arch 447: 728-734, 2004.
22. Gross ER, Gross GJ. Ligand triggers of classical preconditioning and postconditioning. Cardiovasc Res 70: 212-221, 2006.
23. Grover GJ, Sleph PG. The cardioprotective effects of R-75231 and lidoflazine are not caused by adenosine A1 receptor activation. J Pharmacol Exp Ther 268: 90-96, 1994.
24. Headrick JP, Hack B, Ashton KJ. Acute adenosinergic cardioprotection in ischemic-reperfused hearts. Am J Physiol Heart Circ Physiol 285: H1797-H1818, 2003.
25. Hirari K, Ashraf M. Modulation of adenosine effects in attenuation of ischemia and reperfusion injury in rat heart. J Mol Cell Cardiol 30: 1803-1815, 1998.
26. Jacobson KA, Costanzi S, Kim SK, Roh E, Joshi BV, Tchilibon S, Duong HT, Gao ZG. Action of nucleosides and nucleotides at 7 transmembrane- spanning receptors. Nucleosides Nucleotides Nucleic Acids 25: 1425-1436, 2006.
27. Kaiser HJ, Stumpfig D, Flammer J. Short-term effect of dipyridamole on blood flow velocities in the extraocular vessels. Int Ophthalmol 19: 355-358, 1996.
28. Karsai D, Zsuga J, Juhasz B, Der P, Szentmiklosi AJ, Tosaki A, Gesztelyi R. Effect of nucleoside transport blockade on the interstitial adenosine level characterized by a novel method in guinea pig atria. J Cardiovasc Pharmacol 47: 103-109, 2006.
29. Keeling IM, Obermayr RP, Schneider B, Spieckermann PG. Postischemic cardiac function recovery in the isolated rat heart: effects of adenosine deaminase and nucleoside transport inhibition. Langenbecks Arch Surg 385: 531-537, 2000.
30. King AE, Ackley MA, Cass CE, Young D, Baldwin SA. Nucleoside transporters: from scavengers to novel therapeutic targets. Trends Pharmacol Sci 27: 416-425, 2006.
31. Linden J. Molecular approach to adenosine receptors: receptor-mediated mechanisms of tissue protection. Annu Rev Pharmacol Toxicol 41: 775-787, 2001.
32. Liu GS, Thornton J, Van Winkle DM, Stanley AWH, Olsson RA, Downey JM. Protection against infarction afforded by preconditioning is mediated by A1 adenosine receptors in rabbit heart. Circulation 84: 350-356, 1991.
33. Masuda M, Chang-chun C, Mollhoff T, Van Belle H, Flameng W. Effects of nucleoside transport inhibition on long-term ex vivo preservation of canine hearts. J Thorac Cardiovasc Surg 104: 1610-1617, 1992.
34. Masuda M, Demeulemeester A, Chang-chun C, Hendrikx M, Van Belle H, Flameng W. Cardioprotective effects of nucleoside transport inhibition in rabbit hearts. Ann Thorac Surg 52: 1300-1305, 1991.
35. Mullane K, Bullough D. Harnessing an endogenous cardioprotective mechanism: cellular sources and sites of action of adenosine. J Mol Cell Cardiol 27: 1041-1054, 1995.
36. Musa H, Dobrzynski H, Berry Z, Abidi F, Cass CE, Young JD, Baldwin SA, Boyett MR. Immunocytochemical demonstration of the equilibrative nucleoside transporter rENT1 in rat sinoatrial node. J Histochem Cytochem 50: 305-309, 2002.
37. Nalysnyk L, Fahrbach K, Reynolds MW, Zhao SZ, Ross S. Adverse events in coronary artery bypass graft (CABG) trials: a systematic review and analysis. Heart 89: 767-772, 2003.
38. Nicolini F, Beghi C, Muscari C, Agostinelli AM, Budillon A, Spaggiari I, Gherli T. Myocardial protection in adult cardiac surgery: current options and future challenges. Eur J Cardiothorac Surg 24: 986-993, 2003.
39. Ohta A, Stkovski M. The role of G-protein-coupled adenosine receptors in downregulation of inflammation and protection from tissue damage. Nature 414: 916-920, 2001.
40. Paterson ARP, Jacobs ES, Harley ER, Fu NW, Robins MJ, Cass CE. Measurement and inhibition of membrane transport of adenosine. In: Regulatory Functions of Adenosine, edited by RM Berne, TW Rall, and R Rubio. The Hague: Nijhoff, 1983, p. 203-220.
41. Paul B, Chen MF, Paterson ARP. Inhibitors of nucleoside transport: structure-activity relationships. J Med Chem 18: 968-973, 1975.
42. Peart J, Willems L, Headrick JP. Receptor and non-receptor- dependent mechanisms of cardioprotection with adenosine. Am J Physiol Heart Circ Physiol 284: H519-H527, 2003.
43. Pelleg A, Belardinelli L. Cardiac electrophysiology and pharmacology of adenosine: basic and clinical aspects. Cardiovasc Res 27: 54-61, 1993.
44. Sheldrick A, Gray KM, Drew GM, Louttit JB. The effect of body temperature on myocardial protection conferred by ischaemic preconditioning or the selective adenosine A1 receptor agonist GR79236 in an anaesthetized rabbit model of myocardial ischaemia and reperfusion. Br J Pharmacol 128: 385-395, 1999.
45. Sugiyama S, Ozawa T. Biochemical basis for reperfusion arrhythmias. J Mol Cell Cardiol 19 Suppl 5: 67-75, 1987.
46. 1-selective adenosine analogues protects the heart against infarction. Circulation 85: 659-665, 1992.
47. Van Belle H. Nucleoside transport inhibition: a therapeutic approach to cardioprotection via adenosine? Cardiovasc Res 27: 68-76, 1993.
48. Van Belle H. Adenosine promoters: an overview of existing strategies. Curr Opin Invest Drugs 2: 1191-1199, 1993.
49. Van Belle H. Adenosine uptake blockers for cardioprotection. In: Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology, edited by L Belardinelli and A Pelleg. Boston: Kluwer, 1995, p. 373-378.
50. Van Belle H. In vivo effects of inhibitors of adenosine uptake. In: Adenosine and Adenine Nucleotides: Physiology and Pharmacology, edited by DM Paton. London: Taylor and Francis, 1998, p. 251-258.
51. Van Belle H, Goossen F, Wynants J. Biochemical and functional effects of nucleoside transport inhibition in the isolated cat heart. J Mol Cell Cardiol 21: 797-805, 1985.
52. Van Belle H, Janssen PAJ. Comparative pharmacology of nucleoside transport inhibitors. Nucleosides Nucleotides 10: 975-982, 1991.
53. Van Belle H, Wynants J, Ver Donck K. Comparison of the existing nucleoside transport inhibitors: in vitro and in vivo data. In: Purine and Pyrimidine Metabolism in Man, edited by RA Harkness, GB Elion, and N Zollner. New York: Plenum, 1991, vol. 7, p. 419-422.
54. Van Belle H, Xhonneux R, Flameng W, Wynants J. Oral pretreatment with mioflazine completely changes the pattern and remarkably prolongs the accumulation of nucleosides in ischemic and reperfused myocardium. Basic Res Cardiol 81: 407-416, 1986.
55. Ver Donck K. Purine metabolism in the heart. Strategies for protection against myocardial ischaemia. Pharm World Sci 16: 69-76, 1994.
56. Vinten-Johansen J, Thourani VH, Ronson RS, Jordan JE, Zhao ZQ, Nakamura M, Velez D, Guyton RA. Broad-spectrum cardioprotection with adenosine. Ann Thorac Surg 68: 1942-1948, 1999.
57. Yellon DM, Hausenloy DJ. Realizing the clinical potential of ischemic preconditioning and postconditioning. Nat Clin Pract Cardiovasc Med 2: 568-575, 2005.
58. Zaugg M, Schaub, MC, Foex P. Myocardial injury and its prevention in the perioperative setting. Br J Anaesth 93: 21-33, 2004.
59. Zhao ZQ, Vinten-Johansen J. Postconditioning: reduction of reperfusion-induced injury. Cardiovasc Res 70: 200-211, 2006.
60. Zhu Z, Furr J, Buolamwini JK. Synthesis and flow cytometric evaluation of novel 1,2,3,4-tetrahydroisoquinoline conformationally constrained analogues of nitrobenzylmercaptopurine riboside (NBMPR) designed for probing its conformation when bound to the es nucleoside transporter. J Med Chem 46: 831-837, 2003.
61. Zughaib ME, Abd-Elfattah AS, Jeroudi MO, Sun JZ, Sekili S, Tang XL, Bolli R. Augmentation of endogenous adenosine attenuates myocardial "stunning" independently of coronary flow or hemodynamic effects. Circulation 88: 2359-2369, 1993.