Anti-proliferative and anti-leukemic activity of DDE46 (compound WHI-07), a novel bromomethoxylated arylphosphate derivative of zidovudine, and related compounds: Studies using human acute lymphoblastic leukemia cells and the zebrafish model

Arzneimittel-Forschung/Drug Research

Volumn 55, Issue 2, 2005, Pages 114-122

  Benyumov, Alexey O ^a,c,d   Venkatachalam, Taracad K ^a,c,d   Grigoriants, Olga O ^a,c   Vassilev, Alexei O ^a,c,d   Tibbles, Heather E ^a,c,d   Downs, Suzanne ^a,c   Dumez, Darin ^a,b,c   Uckun, Fatih M ^a,b,c  

^a Department of Embryology ^*  (United States)

^b Drug Discovery Program   (United States)

^c PARKER HUGHES INSTITUTE   (United States)

^d Paradigm Pharmaceuticals   (United States)

Author keywords

CAS 213982 96 8; DDE46, antileukemic activity, apoptosis, Zebrafish model; Zidovudine, bromomethoxylated arylphosphate derivative

Indexed keywords

CASPASE 3; CASPASE 6; CASPASE 8; CASPASE 9; DDE 46; PHOSPHATE; UNCLASSIFIED DRUG; WHI 07; ZIDOVUDINE DERIVATIVE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL DIVISION; CELL FUSION; CELL PROLIFERATION; DRUG FORMULATION; EMBRYO (ANATOMY); ENZYME ANALYSIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA; NONHUMAN; ZEBRA FISH;

EID: 14744277358     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296832     Document Type: Article

References (41)

1. Levy, J. A., Pathogenesis of human immunodeficiency virus infection. Microbiol. Rev 57, 183 (1993).
2. Greene, W. C., The molecular biology of human immunodeficiency virus type 1 infection. N. Engl. J. Med. 324, 308 (1991)
3. De Clercq, E., HIV inhibitors targeted at the reverse transcriptase. AIDS Res. Hum. Retroviruses 8, 119 (1992)
4. Mitsuya, H., R. Yarchoan, and S. Broder, Molecular targets for AIDS therapy. Science 249, 1533. (1990)
5. Hajós, G., Riedl, Z., Molnár, J. et al., Nonnucleoside reverse transcriptase inhibitors. Drugs Future 25, 47 (2000)
6. Jonckheere, H., Anne, J., De Clercq, E., The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Med. Res. Rev. 20, 129 (2000)
7. Centers for Disease Control and Prevention, Atlanta, GA, USA, IV/AIDS Surveillance Report 1997, p. 1-37
8. Plosker, G. L., Figgitt, D. P., Oral fludarabine. Drugs 63, 2317 (2003)
9. Van Rompay, A. R., Johansson, M., Karlsson, A., Substrate specificity and phosphorylation of antiviral and anticancer nucleoside analogs by human deoxyribonucleoside kinases and ribonucleoside kinases. Pharmacol. Ther. 100, 119 (2003)
10. Galmarini, C. M., Jordheim, L., Dumontet, C., Pyrimidine nucleoside analogs in cancer treatment. Expert Rev. Anticancer Ther. 3, 717 (2003)
11. Garcia-Manteiga, J., Molina-Arcas, M., Casado, F. J. et al., Nucleoside transporter profiles in human pancreatic cancer cells: role of hCNT1 in 2′,2′-difluorodeoxycytidine- induced cytotoxicity. Clin. Cancer Res. 9, 5000 (2003)
12. Jordheim, L., Galmarini, C. M., Dumontet, C., Drug resistance to cytotoxic nucleoside analogs. Curr. Drug Targets 4, 443 (2003)
13. Gill, P. S., Harrington, W., Jr., Kaplan, M. H. et al., Treatment of adult T-cell leukemia-lymphoma with a combination of interferon alfa and zidovudine. N. Engl. J. Med. 332, 1744 (1995)
14. White, J. D., Wharfe, G., Stewart, D. M. et al., The combination of zidovudine and interferon alpha-2B in the treatment of adult T-cell leukemia/lymphoma. Leuk Lymphoma 40, 287 (2001)
15. Hermine, O., Allard, I., Levy, V. et al., A prospective phase II clinical trial with the use of zidovudine and interferon-alpha in the acute and lymphoma forms of adult T-cell leukemia/lymphoma. Hematol. J. 3, 276 (2002)
16. Modica-Napolitano, J. S., Nalbandian, R., Kidd, M. E. et al., The selective in vitro cytotoxicity of carcinoma cells by AZT is enhanced by concurrent treatment with delocalized lipophilic cations. Cancer Lett. 198, 59 (2003)
17. Lee, R. K., Cai, J. P., Deyev, V. et al., Azidothymidine and interferon-alpha induce apoptosis in herpesvirus-associated lymphomas. Cancer Res. 59, 5514 (1999)
18. Toomey, N. L., Deyev, V. V., Wood, C. et al., Induction of a TRAIL-mediated suicide program by interferon alpha in primary effusion lymphoma. Oncogene 20, 7029 (2001)
19. Ghosh, S. K., Wood, C., Boise, L. H. et al., Potentiation of TRAIL-induced apoptosis in primary effusion lymphoma through azidothymidine-mediated inhibition of NF-kappa B. Blood 101, 2321 (2003)
20. Collier, A. C., Helliwell, R. J., Keelan, J. A. et al., 3′-Azido-3′-deoxythymidine (AZT) induces apoptosis and alters metabolic enzyme activity in human placenta. Toxicol. Appl. Pharmacol. 192, 164 (2003)
21. Bazarbachi, A., Nasr, R., El-Sabban, M. E. et al., Evidence against a direct cytotoxic effect of alpha interferon and zidovudine in HTLV-I associated adult T cell leukemia/ lymphoma. Leukemia 14, 716 (2000)
22. Navara, C. S., Benyumov, A., Vassilev, A. et al, Vanadocenes as potent anti-proliferative agents disrupting mitotic spindle formation in cancer cells. Anticancer Drugs 12, 369 (2001)
23. Westerfield, M., The Zebrafish Book, 2nd ed., p. 4.1. University of Oregon Press, Eugene (1995)
24. Jan, S. T., Shih, M. J., Venkatachalam, T. K. et al., Synthesis of dual function (5R,6R)- and (5S,6S)-5-bromo-6-methoxy-5,6-dihydro-AZT-5′-(para- bromophenyl methoxyalaninyl phosphate) as novel spermicidal and anti-HIV agents. Antivir. Chem. Chemother. 10, 39 (1999)
25. Jan, S. T., Zhu, Z., Tai, H. L. et al., AZT-5′-(p-bromophenyl methoxyalaninyl phosphate) as a potent and non-toxic anti-human immunodeficiency virus agent. Antivir. Chem. Chemother. 10, 47 (1999)
26. Williams, R. C., Jr., Lee, J. C., Preparation of tubulin from brain. Methods Enzymol. B 85, 376 (1982)
27. Bradford, M. M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem 72, 248 (1976)
28. Kumar, R., Wang, L., Wiebe, L. I. et al., Synthesis, in vitro biological stability, and anti-HIV activity of 5-halo-6-alkoxy(or azido)-5,6-dihydro- 3′-azido-3′-deoxythymidine diastereomers as potential prodrugs to 3′-azido-3′-deoxythymidine (AZT). J. Med. Chem. 37, 4297 (1994)
29. McGuigan, C., Pathirana, R. N., Balzarini, J. et al., Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT. J. Med. Chem. 36, 1048 (1993)
30. McGuigan, C., Canard, D., Sheeka, H. M. et al., Phosphoramidate derivatives of d4T with improved anti-HIV efficacy retain full activity in thymidine kinase-deficient cells. Bioorg. Med. Chem. Lett. 6, 1183 (1996)
31. McGuigan, C., Cahard, D., Sheeka, H. M. et al., Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite. J. Med. Chem. 39, 1748 (1996)
32. Vig, R., Venkatachalam, T. K., Uckun, E M., D4T-5′-[p-bromophenyl methoxyalaninyl phosphate] as a potent and non-toxic anti-human immunodeficiency virus agent. Antivir. Chem. Chemother. 9, 445 (1998)
33. Detrich, H. W., 3rd, Westerfield, M., Zon, L. I., Overview of the Zebrafish system. Methods Cell Biol. 59, 3 (1999)
34. Ghosh, P., Ghosh, S., Navara, C. et al., X-ray structure, solution properties, and biological activity profile of vanadocene(IV) acetylacetonate complex. J. Inorg. Biochem. 84, 241 (2001)
35. Benyumov, A. O., Dubrovskaya, T. A., Barmintsev, V A. et al., Duration of the first mitotic cycles and staging of embryogenesis in Danio rerio. Rus. J. Dev. Biol. 26, 132 (1995)
36. Kimmel, C. B., Ballard, W. W., Kimmel, S. R. et al., Stages of embryonic development of the zebrafish. Dev. Dyn. 203, 253 (1995)
37. Bai, R., Cichacz, Z. A., Herald, C. L. et al., Spongistatin 1, a highly cytotoxic, sponge-derived, marine natural product that inhibits mitosis, microtubule assembly, and the binding of vinblastine to tubulin. Mol. Pharmacol. 44, 757 (1993)
38. Abal, M., Andreu, J. M., Barasoain, I., Taxanes: microtubule and centrosome targets, and cell cycle dependent mechanisms of action. Curr. Cancer Drug Targets 3, 193 (2003)
39. Earnshaw, W. C., Martins, L. M., Kaufmann, S. H., Mammalian caspases: structure, activation, substrates, and functions during apoptosis. Annu. Rev. Biochem. 68, 383 (1999)
40. Budihardjo, I., Oliver, H., Lutter, M. et al., Biochemical pathways of caspase activation during apoptosis. Annu. Rev. Cell Dev. Biol. 15, 269 (1999)
41. Avramis, V. I., Kwock, R., Solorzano, M. M. et al., Evidence of in vitro development of drug resistance to azidothymidine in T-lymphocytic leukemia cell lines (Jurkat E6-1/AZT-100) and in pediatric patients with HIV-1 infection. J. Acquir. Immune Defic. Syndr. 6, 1287 (1993)