Novel isoquinolinone-derived inhibitors of poly(ADP-ribose) polymerase-1: Pharmacological characterization and neuroprotective effects in an in vitro model of cerebral ischemia

Journal of Pharmacology and Experimental Therapeutics

Volumn 305, Issue 3, 2003, Pages 943-949

  Chiarugi, Alberto ^a   Meli, Elena ^a   Calvani, Maura ^a   Picca, Roberta ^a   Baronti, Roberto ^a   Camaioni, Emidio ^b   Costantino, Gabriele ^b   Marinozzi, Maura ^b   Pellegrini Giampietro, Domenico E ^a   Pellicciari, Roberto ^b   Moroni, Flavio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DIPHOSPHATE RIBOSE; ADENOSINE TRIPHOSPHATE; GLUCOSE; ISOQUINOLINE DERIVATIVE; NEUROPROTECTIVE AGENT; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE INHIBITOR; OXYGEN; THIENO[2,3 C]ISOQUINOLIN 5 ONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BRAIN ISCHEMIA; CELL ENERGY; CONTROLLED STUDY; CONVALESCENCE; DRUG EFFECT; ENZYME ACTIVATION; ENZYME ACTIVITY; FLOW CYTOMETRY; IC 50; MOUSE; NERVE CELL LESION; NEUROPROTECTION; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; BRAIN ISCHEMIA; CELLS, CULTURED; DISEASE MODELS, ANIMAL; ISOQUINOLINES; MICE; NEUROPROTECTIVE AGENTS; PHENANTHRENES; PIPERIDINES; POLY(ADP-RIBOSE) POLYMERASES; THIOPHENES;

EID: 0038476526     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.048934     Document Type: Article

References (38)

1. Affar EB, Duriez PJ, Shah RG, Winstall E, Germain M, Boucher C, Bourassa S, Kirkland JB, and Poirier GG (1999) Immunological determination and size characterization of poly(ADP-ribose) synthesized in vitro and in vivo. Biochim Biophys Acta 1428:137-146.
2. Arundel-Suto CM, Scavone SV, Turner WR, Suto MJ, and Sebolt-Leopold JS (1991) Effect of PD 128763, a new potent inhibitor of poly(ADP-ribose) polymerase, on X-ray-induced cellular recovery processes in Chinese hamster V79 cells. Radiat Res 126:367-371.
3. Banasik M, Komura H, Shimoyama M, and Ueda K (1992) Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase. J Biol Chem 267: 1569-1575.
4. Bowes J and Thiemermann C (1998) Effects of inhibitors of the activity of poly(ADPribose) synthetase on the liver injury caused by ischaemia-reperfusion: a comparison with radical scavengers. Br J Pharmacol 124:1254-1260.
5. Canan Koch SS, Thoresen LH, Tikhe JG, Maegley KA, Almassy RJ, Li J, Yu XH, Zook SE, Kumpf RA, et al. (2002) Novel tricyclic poly(ADP-ribose) polymerase-1 inhibitors with potent anticancer chemopotentiating activity: design, synthesis and X-ray cocrystal structure. J Med Chem 45:4961-4974.
6. Chiarugi A (2002) Poly(ADP-ribose) polymerase: killer or conspirator? The 'suicide hypothesis' revisited. Trends Pharmacol Sci 23:122-129.
7. Cosi C, Suzuki H, Milani D, Facci L, Menegazzi M, Vantini G, Kanai Y, and Skaper SD (1994) Poly(ADP-ribose) polymerase: early involvement in glutamate-induced neurotoxicity in cultured cerebellar granule cells. J Neurosci Res 39:38-46.
8. Costantino G, Macchiarulo A, Camaioni E, and Pellicciari R (2001) Modeling of poly(ADP-ribose)polymerase (PARP) inhibitors. Docking of ligands and quantitative structure-activity relationship analysis. J Med Chem 44:3786-3794.
9. D'Amours D, Desnoyers S, D'Silva I, and Poirier GG (1999) Poly(ADP-ribosyl)ation reactions in the regulation of nuclear functions. Biochem J 342:249-268.
10. de Murcia G, Schreiber V, Molinete M, Saulier B, Poch O, Masson M, Niedergang C, and Ménissier-de Murcia J (1994) Structure and function of poly(ADP-ribose) polymerase. Mol Cell Biochem 138:15-24.
11. Eliasson MJL, Sampei K, Mandir AS, Hum PD, Traystman RJ, Bao J, Pieper A, Wang Z-Q, Dawson TM, Snyder SH, and Dawson VL (1997) Poly(ADP-ribose) polymerase gene disruption renders mice resistant to cerebral ischemia. Nat Med 3:1089-1095.
12. Endres M, Wang Z-Q, Namura S, Waeber C, and Moskowitz MA (1997) Ischemic brain injury is mediated by the activation of poly(ADP-ribose) polymerase. J Cereb Blood Flow Metab 17:1143-1151.
13. Gan L, Anton KE, Masterson BA, Vincent VA, Ye S, and Gonzalez-Zulueta M (2002) Specific interference with gene expression and gene function mediated by long dsRNA in neural cells. J Neurosci Meth 121:151-157.
14. Griffin RJ, Srinivasan S, Bowman K, Calvert AH, Curtin NJ, Newell DR, Pemberton LC, and Golding BT (1998) Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADPribose) polymerase (PARP). J Med Chem 41:5247-5256.
15. Ha HC and Snyder SH (1999) Poly(ADP-ribose) polymerase is a mediator of necrotic cell death by ATP depletion. Proc Natl Acad Sci USA 96:13978-13982.
16. Ha HC and Snyder SH (2000) Poly(ADP-ribose) polymerase-1 in the nervous system. Neurobiol Dis 7:225-239.
17. Herceg Z and Wang ZQ (2001) Functions of poly(ADP-ribose) polymerase (PARP) in DNA repair, genomic integrity and cell death. Mutat Res 477:97-110.
18. Liaudet L, Soriano FG, Szabo E, Virag L, Mabley JG, Salzman AL, and Szabó C (2000) Protection against hemorrhagic shock in mice genetically deficient in poly(ADP-ribose) polymerase. Proc Natl Acad Sci USA 97:10203-10208.
19. McDonald MC, Mota-Filipe H, Wright JA, Abdelrahman M, Threadgill MD, Thompson AS, and Thiemermann C (2000) Effects of 5-aminoisoquinolinone, a watersoluble, potent inhibitor of the activity of poly(ADP-ribose) polymerase on the organ injury and dysfunction caused by haemorrhagic shock. Br J Pharmacol 130:843-850.
20. Moroni F, Meli E, Peruginelli F, Chiarugi A, Cozzi A, Picca R, Romagnoli P, Pellicciari R, and Pellegrini-Giampietro DE (2001) Poly(ADP-ribose) polymerase inhibitors attenuate necrotic but not apoptotic neuronal death in experimental models of cerebral ischemia. Cell Death Differ 8:921-932.
21. Pellegrini-Giampietro DE, Cozzi A, Peruginelli F, Leonardi P, Meli E, Pellicciari R, and Moroni F (1999a) 1-Amino-1,5-dicarboxylic acid and (S)-(+)-2-(3′carboxybicyclo[1.1.1]pentyl)-glycine, two mGlu1 receptor-preferring antagonists, reduce neuronal death in in vitro and in vivo models of cerebral ischemia. Eur J Neurosci 11:3637-3647.
22. Pellegrini-Giampietro DE, Peruginelli F, Meli E, Cozzi A, Albani Torregrossa S, Pellicciari R, and Moroni F (1999b) Protection with metabotropic glutamate 1 receptor antagonists in models of ischemic neuronal death: time-course and mechanisms. Neuropharmacology 38:1607-1619.
23. Pellicciari R, Camaioni E, Costantino G, Marinozzi M, Macchiarulo A, Moroni F, and Natalini B (2003) Towards new neuroprotective agents: design and synthesis of 4H-thieno[2,3-c]-isoquinolinon-5-one as a potent PARP-1 inhibitor. Farmaco, in press.
24. Perkins E, Sun D, Nguyen A, Tulac S, Francesco M, Tavana H, Nguyen H, Tugendreich S, Barthmaier P, Couto J, et al. (2001) Novel inhibitors of poly(ADP-ribose) polymerase/PARP1 and PARP2 identified using a cell-based screen in yeast. Cancer Res 61:4175-4183.
25. Pieper AA, Brat DJ, Krug DK, Watkins CC, Gupta A, Blackshaw S, Verma A, Wang ZQ, and Snyder SH (1999) Poly(ADP-ribose) polymerase-deficient mice are protected from streptozotocin-induced diabetes. Proc Natl Acad Sci USA 96:3059-3064.
26. Popoff I, Jijon H, Monia B, Tavernini M, Ma M, McKay R, and Madsen K (2002) Antisense oligonucleotides to poly(ADP-ribose) polymerase-2 ameliorate colitis in interleukin-10-deficient mice. J Pharmacol Exp Ther 303:1145-1154.
27. RufA, de Murcia G, and Schulz GE (1998) Inhibitor and NAD+ binding to poly(ADPribose) polymerase as derived from crystal structures and homology modeling. Biochemistry 37:3893-3900.
28. Ruf A, Mennissier de Murcia J, de Murcia G, and Schulz GE (1996) Structure of the catalytic fragment of poly(ADP-ribose) polymerase from chicken. Proc Natl Acad Sci USA 93:7481-7485.
29. Shall S and de Murcia G (2000) Poly(ADP-ribose) polymerase-1: what have we learned from the deficient mouse model? Mutat Res 460:1-15.
30. Smith S (2001) The world according to PARP. Trends Biochem Sci 26:174-179.
31. Soriano FG, Virag L, and Szabo C (2001) Diabetic endothelial dysfunction: role of reactive oxygen and nitrogen species production and poly(ADP-ribose) polymerase activation. J Mol Med 79:437-448.
32. Suto MJ, Turner WR, Arundel-Suto CM, Werbel LM, and Sebolt-Leopold JS (1991) Dihydroisoquinolinones: the design and synthesis of a new series of potent inhibitors of poly(ADP-ribose) polymerase. Anticancer Drug Des 6:107-117.
33. Szabó C and Dawson VL (1998) Role of poly(ADP-ribose) synthetase in inflammation and ischaemia-reperfusion. Trends Pharmacol Sci 19:287-298.
34. Takahashi K and Greenberg JH (1999) The effect of reperfusion on neuroprotection using an inhibitor of poly(ADP-ribose) polymerase. NeuroReport 10:2017-2022.
35. Takahashi K, Greenberg JH, Jackson P, Maclin K, and Zhang J (1997) Neuroprotective effects of inhibiting poly(ADP-ribose) synthetase on focal cerebral ischemia in rats. J Cereb Blood Flow Metab 17:1137-1142.
36. Virag L and Szabo C (2001) Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death. FASEB J 15:99-107.
37. Yu S-W, Wang H, Poitras MF, Coombs C, Bowers WJ, Federoff HJ, Poirier GG, Dawson TM, and Dawson VL (2002) Mediation of poly(ADP-ribose) polymerase-1dependent cell death by apoptosis-inducing factor. Science (Wash DC) 297:259-263.
38. Zhang J, Dawson VL, Dawson TM, and Snyder SH (1994) Nitric oxide activation of poly(ADP-ribose) synthetase in neurotoxicity. Science (Wash DC) 263:687-689.