V-PROLI/NO, a nitric oxide donor prodrug, protects liver cells from arsenic-induced toxicity

Cancer Science

Volumn 100, Issue 3, 2009, Pages 382-388

  Qu, Wei ^a   Liu, Jie ^a   Dill, Anna L ^a   Saavedra, Joseph E ^b   Keefer, Larry K ^c   Waalkes, Michael P ^a  

^a National Cancer Institute   (United States)

^b SAIC FREDERICK INC   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ARSENITE SODIUM; CYTOCHROME P450 2E1; DNA; METALLOTHIONEIN; NITRIC OXIDE; O VINYL 1 [2 (CARBOXYLATO)PYRROLIDIN 1 YL]DIAZEN 1 IUM 1,2 DIOLATE; STRESS ACTIVATED PROTEIN KINASE; UNCLASSIFIED DRUG; NITRIC OXIDE DONOR; ORGANOARSENIC DERIVATIVE; PRODRUG;

APOPTOSIS; ARTICLE; CELL CULTURE; CELL PROTECTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA FRAGMENTATION; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER CELL; LIVER TOXICITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN INDUCTION; STRUCTURE ANALYSIS; DRUG EFFECT; GENE EXPRESSION; METABOLISM; WESTERN BLOTTING;

APOPTOSIS; ARSENICALS; BLOTTING, WESTERN; CYTOCHROME P-450 CYP2E1; DNA FRAGMENTATION; GENE EXPRESSION; HEPATOCYTES; HUMANS; JNK MITOGEN-ACTIVATED PROTEIN KINASES; NITRIC OXIDE; NITRIC OXIDE DONORS; PRODRUGS;

EID: 62849125347     PISSN: 13479032     EISSN: 13497006     Source Type: Journal    
DOI: 10.1111/j.1349-7006.2008.01050.x     Document Type: Article

References (39)

1. Chen GQ, Zhu J, Shi XG et al. In vitro studies on cellular and molecular mechanisms of arsenic trioxide (As2O3) in the treatment of acute promyelocytic leukemia: As2O3 induces NB4 cell apoptosis with downregulation of Bcl-2 expression and modulation of PML-RAR alpha/PML proteins. Blood 1996; 88: 1052-61.
2. Shen ZX, Chen GQ, Ni JH et al. Use of arsenic trioxide (As2O3) in the treatment of acute promyelocytic leukemia (APL). II. Clinical efficacy and pharmacokinetics in relapsed patients. Blood 1997; 89: 3354-60.
3. Wang ZY, Chen Z. Acute promyelocytic leukemia: From highly fatal to highly curable. Blood 2008; 111: 2505-15.
4. Hede K. Chinese folk treatment reveals power of arsenic to treat cancer, new studies under way. J Natl Cancer Inst 2007; 99: 667-8.
5. Mathews V, Desire S, George B et al. Hepatotoxicity profile of single agent arsenic trioxide in the treatment of newly diagnosed acute promyelocytic leukemia, its impact on clinical outcome and the effect of genetic polymorphisms on the incidence of hepatotoxicity. Leukemia 2006; 20: 881-3.
6. Liu J, Waalkes MP. Liver is a target of arsenic carcinogenesis. Toxicol Sci 2008; 105: 24-32.
7. Kozoni V, Rosenberg T, Rigas B. Development of novel agents based on nitric oxide for the control of colon cancer. Acta Pharmacologica Sinica 2007; 28: 1429-33.
8. Keefer LK. Progress toward clinical application of the nitric oxide-releasing diazeniumdiolates. Annu Rev Pharmacol Toxicol 2003; 43: 585-607.
9. Saavedra JE, Billiar TR, Williams DL, Kim YM, Watkins SC, Keefer LK. Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-alpha-induced apoptosis and toxicity in the liver. J Med Chem 1997; 40: 1947-54.
10. Liu J, Li C, Waalkes MP et al. The nitric oxide donor, V-PYRRO/NO, protects against acetaminophen-induced hepatotoxicity in mice. Hepatology 2003; 37: 324-33.
11. Qu W, Liu J, Fuquay R, Saavedra JE, Keefer LK, Waalkes MP. The nitric oxide prodrug, V-PYRRO/NO, mitigates arsenic-induced liver cell toxicity and apoptosis. Cancer Lett 2007; 256: 238-45.
12. Chakrapani H, Showalter BM, Kong L, Keefer LK, Saavedra JE. V-PROLI/NO, a prodrug of the nitric oxide donor, PROLI/NO. Org Lett 2007; 9: 3409-12.
13. Inami K, Nims RW, Srinivasan A et al. Metabolism of a liver-selective nitric oxide-releasing agent, V-PYRRO/NO, by human microsomal cytochromes P450. Nitric Oxide 2006; 14: 309-15.
14. Douer D, Tallman MS. Arsenic trioxide: New clinical experience with an old medication in hematologic malignancies. J Clin Oncol 2005; 23: 2396-410.
15. Klaassen CD, Liu J, Choudhuri S. Metallothionein: An intracellular protein to protect against cadmium toxicity. Ann Rev Pharmacol Toxicol 1999; 39: 267-94.
16. Liu J, Cheng ML, Yang Q et al. Blood metallothionein transcript as a biomarker for metal sensitivity: Low blood metallothionein transcripts in arsenicosis patients from Guizhou, China. Environ Health Perspect 2007; 115: 1101-6.
17. Jiang G, Gong Z, Li XF, Cullen WR, Le XC. Interaction of trivalent arsenicals with metallothionein. Chem Res Toxicol 2003; 16: 873-80.
18. Kreppel H, Bauman JW, Liu J, McKim JM Jr, Klaassen CD. Induction of metallothionein by arsenicals in mice. Fundam Appl Toxicol 1993; 20: 184-9.
19. Falnoga I, Stibilj E, Tusek-Znidaric M et al. Effect of arsenic trioxide on metallothionein and its conversion to different arsenic metabolites in hen liver. Biol Trace Elem Res 2001; 78: 241-54.
20. Katakai K, Liu J, Nakajima K, Keefer LK, Waalkes MP. Nitric oxide induces metallothionein (MT) gene expression apparently by displacing zinc bound to MT. Toxicol Lett 2001; 119: 103-8.
21. Qu W, Bortner CD, Sakurai T, Hobson MJ, Waalkes MP. Acquisition of apoptotic resistance in arsenic-induced malignant transformation: Role of the JNK signal transduction pathway. Carcinogenesis 2002; 23: 151-9.
22. Eaton DL, Toal BF. Evaluation of the Cd/hemoglobin affinity assay for the rapid determination of metallothionein in biological tissues. Toxicol Appl Pharmacol 1982; 66: 134-42.
23. Levy M, Wofford MM, Powell BL, McLean TW. Hyperleukocytosis from arsenic trioxide. Pediatr Blood Cancer 2008; 50: 1265-7.
24. Kozoni V, Rosenberg T, Rigas B. Development of novel agents based on nitric oxide for the control of colon cancer. Acta Pharmacol Sin 2007; 28: 1429-33.
25. Waterhouse DJ, Saavedra JE, Davies KM et al. Injectable formulation of disodium 1-[2-(carboxylato) pyrrolidin-1-yl]diazen-1-ium-1,2-diolate (PROLI/NO), an ultrafast nitric oxide donor prodrug. J Pharm Sci 2006; 95: 108-15.
26. Saavedra JE, Southan GJ, Davies KM et al. Localizing antithrombotic and vasodilatory activity with a novel, ultrafast nitric oxide donor. J Med Chem 1996; 39: 4361-5.
27. Adrie C, Hirani WM, Holzmann A, Keefer L, Zapol WM, Hurford WE. Selective pulmonary vasodilation by intravenous infusion of an ultrashort half-life nucleophile/nitric oxide adduct. Anesthesiology 1998; 88: 190-5.
28. Chen C, Hanson SR, Keefer LK et al. Boundary layer infusion of nitric oxide reduces early smooth muscle cell proliferation in the endarterectomized canine artery. J Surg Res 1997; 67: 26-32.
29. Qu W, Liu J, Fuquay R et al. The nitric oxide prodrug, V-PYRRO/NO, protects against cadmium toxicity and apoptosis at the cellular level. Nitric Oxide 2005; 12: 114-20.
30. Liu J, Qu W, Saavedra JE, Waalkes MP. The nitric oxide donor, O2-vinyl 1-(pyrrolidin-1-yl) diazen-1-ium-1,2-diolate (V-PYRRO/NO), protects against cadmium-induced hepatotoxicity in mice. J Pharmacol Exp Ther 2004; 310: 18-24.
31. Xia Z, Dickens M, Raingeaud J, Davis RJ, Greenberg ME. Opposing effects of ERK and JNK-p38 MAP kinases on apoptosis. Science 1995; 270: 1326-31.
32. Samet JM, Graves LM, Quay J et al. Activation of MAPKs in human bronchial epithelial cells exposed to metals. Am J Physiol 1998; 275: L551-8.
33. Huang C, Ma WY, Li J, Dong Z. Arsenic induces apoptosis through a c-Jun NH2-terminal kinase-dependent, p53-independent pathway. Cancer Res 1999; 59: 3053-8.
34. Park HS, Huh SH, Kim MS, Lee SH, Choi EJ. Nitric oxide negatively regulates c-Jun N-terminal kinase/stress-activated protein kinase by means of S-nitrosylation. Proc Natl Acad Sci USA 2000; 97: 14382-7.
35. Lo YY, Wong JM, Cruz TF. Reactive oxygen species mediate cytokine activation of c-Jun NH2-terminal kinases. J Biol Chem 1996; 271: 15703-7.
36. Wang D, Yu X, Brecher P. Nitric oxide and N-acetylcysteine inhibit the activation of mitogen-activated protein kinases by angiotensin II in rat cardiac fibroblasts. J Biol Chem 1998; 273: 33027-34.
37. Flora SJ, Tripathi N. Hepatic and renal metallothionein induction following single oral administration of gallium arsenide in rats. Biochem Mol Biol Int 1998; 45: 1121-7.
38. Ngu TT, Stillman MJ. Arsenic binding to human metallothionein. J Am Chem Soc 2006; 128: 12473-83.
39. Liu J, Liu Y, Goyer RA, Achanzar W, Waalkes MP. Metallothionein-I/II null mice are more sensitive than wild-type mice to the hepatotoxic and nephrotoxic effects of chronic oral or injected inorganic arsenicals. Toxicol Sci 2000; 55: 460-7.