Bis(dialkyl)dithiocarbamato cobalt(III) complexes of bidentate nitrogen mustards: Synthesis, reduction chemistry and biological evaluation as hypoxia-selective cytotoxins

Anti-Cancer Drug Design

Volumn 13, Issue 2, 1998, Pages 81-103

  Ware, David C ^a   Palmer, Helen R ^a   Pruijn, Frederik B ^a   Anderson, Robert F ^a   Brothers, Penelope J ^a   Denny, William A ^a   Wilson, William R ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Bioreductive drugs; Cobalt complexes; Hypoxia selective cytotoxins; Nitrogen mustards

Indexed keywords

ANTINEOPLASTIC AGENT; CHLORMETHINE DERIVATIVE; COBALT COMPLEX; DITHIOCARBAMIC ACID; WATER;

ANIMAL CELL; ARTICLE; CELL CULTURE; CELL KILLING; CONTROLLED STUDY; CULTURE MEDIUM; CYCLIC POTENTIOMETRY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; HUMAN; HUMAN CELL; HYPOXIA; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PULSE RADIOLYSIS; STEADY STATE; STOICHIOMETRY;

ANIMALIA; APOIDEA; BRASSICACEAE;

EID: 0031881875     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. ADAMS, G.E. & STRATFORD, I.J. (1994). Bioreductive drugs for cancer therapy: the search for tumor specificity. International Journal of Radiation Oncology, Biology and Physics, 29, 231.
2. ANDERSON, R.F., DENNY, W A., WARE, D.C. & WILSON, W.R. (1996). Pulse radiolysis studies on the hypoxia-selective toxicity of a cobalt-mustard complex. British Journal of Cancer, 74(Suppl. XXVII), S48.
3. BOND, A.M. & MARTIN, R.L. (1984). Electrochemistry and redox behaviour of transition metal dithiocarbamates. Coordination Chemistry Reviews, 54, 23.
4. BOND, A.M., MARTIN, R.L. & MASTERS, A.F (1975). Influence of oxygen and sulfur donor atoms on the electrochemistry of transition metal tris chelates. Inorganic Chemistry, 14, 1432.
5. BOND, A.M., MARTIN, R.L. & MASTERS, A.F. (1976). Influence of oxygen and sulfur donor atoms on the electrochemistry of bis-chelates of nickel(II). Journal of Electroanalytical Chemistry, 72, 187.
6. BOND, A.M., HENDRICKSON, A R., MARTIN, R.L., MOIR, J.E. & PAGE, D.R. (1983). Electrochemical reduction and oxidation of cobalt(III)-dithiocarbamates. Inorganic Chemistry, 22, 3440.
7. +, and related complexes in dichloromethane using electrochemical and cobalt-59 NMR techniques. Inorganic Chemistry, 24, 4402.
8. BROWN, J.M. & SIIM, B.C. (1996). Hypoxia specific cytotoxins in cancer therapy. Seminars in Radiation Oncology, 6, 22.
9. DENNY, W.A, WILSON, W.R. & HAY, M.P. (1996). Recent developments in the design of bioreductive drugs. British Journal of Cancer, 74(Suppl. XXVII), S32.
10. DEPLANDO, P. & TROGU, E.F. (1983). Ligand substitution at a hexacoordinate centre. Part III. Preparation and spectroscopic study of Co(III) diethyldithiocarbamato complexes containing ethylenediamines. Inorganica Chimica Acta, 68, 147-152.
11. EL A'MMA, A.G. & DRAGO, R.S. (1977). Unusual oxidation-state stabilisation of iron complexes by the pyrrole-N-carbodithioate ligand. Inorganic Chemistry, 16, 2975.
12. FACKLER, J.P. & HOLAH, D.C. (1966). Sulfur chelates II. Five coordinate transition metal complexes. Inorganic and Nuclear Chemistry Letters, 2, 251.
13. FINLAY, C.J., BACULEY, B.C. & WILSON, W.R. (1984). A semiautomated microculture method for investigating growth inhibitory effects of cytotoxic compounds on exponentially growing carcinoma cells. Analytical Biochemistry, 139, 272-277.
14. GAGNE, R R., KOVAL, C.A & LISENSKY, G.C. (1980). Ferrocene as an internal standard for electrochemical measurements. Inorganic Chemistry, 19, 2854.
15. GATENBY, R.A., KESSLER, H.B., ROSENBLUM, J.S., COIA, L.R , MOLDOFSKY, P.J. & HARTZ, W.H. (1988). Oxygen distribution in squamous cell carcinoma metastases and its relationship to outcome of radiation therapy. International Journal of Radiation Oncology, Biology and Physics, 14, 831.
16. +: X-ray structural analysis of pentakis(diethyldithiocarbamato)dicobalt(III) tetrafluoroborate. Journal of the Chemical Society, Dalton Transactions, 2182.
17. 4. Australian Journal of Chemistry, 29, 269.
18. HÖCKEL, M., SCHLENGER, K., MITZE, M., SCHEEFER, U. & VAUPEL, P (1996). Hypoxia and radiation response in human tumors. Seminars in Radiation Oncology, 6, 3.
19. HOLAH, D.G. & MURPHY, C.N. (1971). Reactions of sodium N,N-diethyldithiocarbamate and potassium ethyl xanthate with some 3d transition metal halides in the presence of 2,2′-bipyridyl and 1,10-phenanthroline. Canadian Journal of Chemistry, 49, 2726.
20. JANNAKOUDAKIS, A.D., TSIAMIS, C., JANNAKOUDAKIS, P.D. & THEODORIDOU E. (1985). Electrochemical behaviour of tris(β-diketonato)cobalt(III) chelates on mercury and carbon fibre electrodes. Journal of Electroanalytical Chemistry, 184, 123.
21. KENNEDY, K.A., TEICHER, B.A., ROCKWELL, S.A & SARTORELLI, A.C. (1980). The hypoxic tumour cell: a target for selective cancer chemotherapy. Biochemical Pharmacology, 29, 1.
22. 500-dimethyldithiocarbamatobis(ethylenediamine)cobalt(III) bis[μ-(R,R)tartrato]diantimonate(III) pentahydrate. Bulletin of the Chemical Society of Japan, 62, 23.
23. MOHINDRU, A., FISHER, J.M. & RABINOVITZ, M. (1983). Bathocuproine sulfonate: a tissue culture-compatible indicator of copper-mediated toxicity. Nature, 303, 64.
24. NOBEL, C.S.I., KIMLAND, M., LIND, B., ORRENIUS, S. & SLATER, A.F.G. (1995). Dithiocarbamates induce apoptosis in thymocytes by raising the intracellular level of redox-active copper. Journal of Biological Chemistry, 270, 26202.
25. PALMER, B.D., WILSON, W.R., CLIFFE, S & DENNY, W.A. (1992). Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroanline mustards with selective cytotoxicity for hypoxic mammalian cells. Journal of Medicinal Chemistry, 35, 3214.
26. PALMER, B.D., VAN ZIJL, P, DENNY, W.A. & WILSON, W.R. (1995). Reductive chemistry of the novel hypoxia-selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (SN 23862). Journal of Medicinal Chemistry, 38, 1229.
27. PLUMB, J.A., GERRITSEN, M., MILROY, R., THOMSON, P. & WORKMAN, P. (1994). Relative importance of DT diaphorase and hypoxia in the bioactivation of EO9 by human lung tumor cell lines. International Journal of Radiation Oncology, Biology and Physics, 29, 295.
28. ROSTON, D.A (1984). Precolumn chelation with 4(2-pyridylazo)resorcinol for simultaneous determination of metal ions by liquid chromatography. Analytical Chemistry, 56, 241.
29. SIIM, B.G., ATWELL, G.J. & WILSON, W.R. (1994). Oxygen dependence of the cytotoxicity and metabolic activation of 4-alkylamino-5-nitroquinoline bioreductive drugs. British Journal of Cancer, 70, 596.
30. SIMIC, M. & LILIE, J. (1974), Kinetics of ammonia detachment from reduced cobalt(III) complexes based on conductometric pulse radiolysis. Journal of the American Chemical Society, 96, 291.
31. UJJANI, B., LYMAN, S, WINKELMANN, D., ANTHOLINE, W., PETERING, D.H. & JONES, M.M. (1990). Enhancement of cytotoxicity of bleomycin by dithiocarbamates: formation of bis(dithiocarbamato) Cu(II). Journal of Inorganic Biochemistry, 38, 81.
32. WARE, D.C., PALMER, B.D., WILSON, W.R. & DENNY, W.A. (1993). Hypoxia-selective antitumor agents. 7. Metal complexes of aliphatic mustards are a new class of hypoxia-selective cytotoxins. Synthesis and evaluation of cobalt (III) complexes of bidentate mustards. Journal of Medicinal Chemistry, 36, 1839.
33. WILSON, W.R. (1992). Tumour hypoxia: challenges for cancer chemotherapy. In Cancer Biology and Medicine. Waring, M.J. & Ponder, B.A.J. (eds), Vol. 3, p. 87. Kluwer Academic Publishers: Lancaster.
34. WILSON, W.R., MOSELEN, J.W., CLIFFE, S., DENNY, W.A. & WARE, D.C. (1994). Exploiting tumor hypoxia through bioreductive release of diffusible cytotoxins: the cobalt(III)-nitrogen mustard complex SN 24771. International Journal of Radiation Oncology, Biology and Physics, 29, 323.
35. WILSON, W.R., DENNY, W.A, PULLEN, S.M., THOMPSON, K.M., LI, A.E., PATTERSON, L.H. & LEE, H.H. (1996). Tertiary amine N-oxides as bioreductive drugs: DACA N-oxide, nitracrine N-oxide and AQ4N. British Journal of Cancer, 74(Suppl. XXVII), S43.
36. WOON, T.C., MACKAY, M.F. & O'CONNOR, M.J. (1982). The preparation and characterisation of tris(pyrrole)-N-(carbodithioato)cobalt(III) hemikis dichloromethane. Crystal and molecular structure and solution properties. Inorganica Chimica Acta, 58, 5.