Prodrug modification increases potassium tricyclo[5.2.1.0 2,6]-decan-8-yl dithiocarbonate (D609) chemical stability and cytotoxicity against U937 leukemia cells

Journal of Pharmacology and Experimental Therapeutics

Volumn 309, Issue 3, 2004, Pages 1051-1059

  Bai, Aiping ^a   Meier, G Patrick ^b   Wang, Yong ^a   Luberto, Chiara ^a   Hannun, Yusuf A ^a   Zhou, Daohong ^a  

^a MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^b WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; CERAMIDE; PRODRUG; TRICYCLO[4.3.0.1]DECAN 9 YL XANTHOGENATE; XANTHIC ACID DERIVATIVE;

APOPTOSIS; ARTICLE; CELL STRAIN U937; CONTROLLED STUDY; CYTOTOXICITY; DISULFIDE BOND; DRUG STABILITY; HUMAN; HUMAN CELL; LEUKEMIA CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TUMOR CELL DESTRUCTION;

ANTINEOPLASTIC AGENTS; BRIDGED COMPOUNDS; CELL SURVIVAL; CERAMIDES; DRUG DESIGN; DRUG STABILITY; ESTERASES; HUMANS; HYDROLYSIS; LEUKEMIA; PRODRUGS; THIONES; TUMOR CELLS, CULTURED; U937 CELLS;

EID: 2442698935     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.064600     Document Type: Article

References (27)

1. Amtmann E, Muller K, Knapp A, and Sauer G (1985) Reversion of bovine papillomavirus-induced transformation and immortalization by a xanthate compound. Exp Cell Res 161:541-550.
2. Amtmann E and Sauer G (1987) Selective killing of tumor cells by xanthates. Cancer Lett 35:237-244.
3. Amtmann E and Sauer G (1990) Tumor necrosis factor induces necrosis of human carcinoma xenografts in the presence of tricyclodecan-9-yl-xanthogenate and lauric acid. Int J Cancer 45:1113-1118.
4. Bettaieb A, Plo I, Mansat-De Mas V, Quillet-Mary A, Levade T, Laurent G, and Jaffrezou JP (1999) Daunorubicin- and mitoxantrone-triggered phosphatidylcholine hydrolysis: implication in drug-induced ceramide generation and apoptosis. Mol Pharmacol 55:118-125.
5. Bodor N, Sloan KB, Kaminski JJ, Shih C, and Pogany S (1983) A convenient synthesis of (acyloxy)alkyl α-ethers of phenols. J Org Chem 48:5280-5284.
6. Capizzi RL (1999) The preclinical basis for broad-spectrum selective cytoprotection of normal tissues from cytotoxic therapies by amifostine. Semin Oncol 26:3-21.
7. Culy CR and Spencer CM (2001) Amifostine: an update on its clinical status as a cytoprotectant in patients with cancer receiving chemotherapy or radiotherapy and its potential therapeutic application in myelodysplastic syndrome. Drugs 61:641-684.
8. Gilmer JF, Moriarty LM, Lally MN, and Clancy JM (2002) Isosorbide-based aspirin prodrugs. II. Hydrolysis kinetics of isosorbide diaspirinate. Eur J Pharm Sci 16:297-304.
9. Giron-Calle J, Srivatsa K, and Forman HJ (2002) Priming of alveolar macrophage respiratory burst by H(2)O(2) is prevented by phosphatidylcholine-specific phospholipase C inhibitor tricyclodecan-9-yl-xanthate (D609). J Pharmacol Exp Ther 301:87-94.
10. Hansen MB, Nielsen SE, and Berg K (1989) Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Methods 119:203-210.
11. Lauderback CM, Drake J, Zhou D, Hackett JM, Castegna A, Kanski J, Tsoras M, Varadarajan S, and Butterfield DA (2003) Derivatives of xanthic acid are novel antioxidants: application to synaptosomes. Free Radic Res 37:355-365.
12. Luberto C and Hannun YA (1998) Sphingomyelin synthase, a potential regulator of intracellular levels of ceramide and diacylglycerol during SV40 transformation. Does sphingomyelin synthase account for the putative phosphatidylcholine-specific phospholipase C? J Biol Chem 273:14550-14559.
13. Meng A, Luberto C, Meier P, Bai A, Yang X, Hannun YA, and Zhou D (2004) Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells. Exp Cell Res 292:385-392.
14. Nudelman A, Gnizi E, Katz Y, Azulai R, Cohen-Ohana M, Zhuk R, Sampson SR, Langzam L, Fibach E, Prus E, et al. (2001) Prodrugs of butyric acid. Novel derivatives possessing increased aqueous solubility and potential for treating cancer and blood diseases. Eur J Med Chem 36:63-74.
15. Perry RJ and Ridgway ND (2004) The role of de novo ceramide synthesis in the mechanism of action of the tricyclic xanthate D609. J Lipid Res 45:164-173.
16. Pettus BJ, Bielawska A, Kroesen BJ, Moeller PD, Szulc ZM, Hannun YA, and Busman M (2003a) Observation of different ceramide species from crude cellular extracts by normal-phase high-performance liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom 17:1203-1211.
17. Pettus BJ, Bielawski J, Porcelli AM, Reames DL, Johnson KR, Morrow J, Chalfant CE, Obeid LM, and Hannun YA (2003b) The sphingosine kinase 1/sphingosine-1-phosphate pathway mediates COX-2 induction and PGE2 production in response to TNF-α. FASEB J 17:1411-1421.
18. Poggi MM, Coleman CN, and Mitchell JB (2001) Sensitizers and protectors of radiation and chemotherapy. Curr Probl Cancer 25:334-411.
19. Porn-Ares MI, Chow SC, Slotte JP, and Orrenius S (1997) Induction of apoptosis and potentiation of TNF- and Fas-mediated apoptosis in U937 cells by the xanthogenate compound D609. Exp Cell Res 235:48-54.
20. Rao SR (1971) Xanthates and Related Compounds, Marcel Dekker, Inc., New York, NY.
21. Sauer G, Amtmann E, and Hofmann W (1990) Systemic treatment of a human epidermoid non-small cell lung carcinoma xenograft with a xanthate compound causes extensive intratumoral necrosis. Cancer Lett 53:97-102.
22. Schick HD, Amtmann E, Berdel WE, Danhauser-Riedl S, Reichert A, Steinhauser G, Rastetter J, and Sauer G (1989a) Antitumoral activity of a xanthate compound. I. Cytotoxicity studies with neoplastic cell lines in vitro. Cancer Lett 46:143-147.
23. Schick HD, Danhauser-Riedl S, Amtmann E, Busch R, Reichert A, Steinhauser G, Rastetter J, Sauer G, and Berdel WE (1989b) Antitumoral activity of a xanthate compound. II. Therapeutic studies in murine leukemia and tumor models in vivo. Cancer Lett 46:149-152.
24. Sinkula AA and Yalkowsky SH (1975) Rationale for design of biologically reversible drug derivatives: prodrugs. J Pharm Sci 64:181-210.
25. Smith FT and Clark CR (1998) Drug latentiation and prodrugs, in Textbook of Organic Medicine and Pharmaceutical Chemistry (Delgado JN and Remers WA eds) pp 123-138, Lippincott-Raven Publishers, Philadelphia, PA.
26. Spencer CM and Goa KL (1995) Amifostine. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic potential as a radioprotector and cytotoxic chemoprotector. Drugs 50:1001-1031.
27. Zhou D, Lauderback CM, Yu T, Brown SA, Butterfield DA, and Thompson JS (2001) D609 inhibits ionizing radiation-induced oxidative damage by acting as a potent antioxidant. J Pharmacol Exp Ther 298:103-109.