8
Views
2
CrossRef citations to date
0
Altmetric
Original Article

Reduction of Antitumour Mitosenes in Non-Aqueous and Aqueous Environment. An Electron Spin Resonance and Cyclic Voltammetry Study

, , , , , , & show all
Pages 109-121 | Received 04 Jul 1994, Published online: 07 Jul 2009

References

  • Hendriks H. R., Pizao P. E., Berger D. P., Kooistra K. L., Bibby M. C., Boven E., Dreef-van der Meulen H. C., Henrar R. E.C., Fiebig H. H., Double J. A., Hornstra H. W., Pinedo H. M., Workman P., Schwartsmann G. E09 - A novel bioreductive alkylating indoloquinone with preferential solid tumour activity and lack of bone marrow toxicity in preclinical models. Eur. J. Cancer 1993; 29A: 897–906
  • Franck R. W., Tomasz M. The chemistry of mitomycins. The Chemistry of Antitumour Agents, E. V. Wilman. Blackie & Son Limited, Glasgow 1990; 379–394
  • Tomasz M., Chowdary D., Lipman R., Shimotakahara S., Veiro D., Walker V., Verdine G. L. Reaction of DNA with chemically or enzymatically activated mitomycin C: Isolation and structure of the major covalent adduct. Proceedings of the National Academy of Sciences USA 1986; 83: 6702–6706
  • Tomasz M., Lipman R., McGuinness B. F., Nakanishi K. Isolation and characterization of a major adduct between mitomycin C and DNA. Journal of the American Chemical Society 1988; 110: 5892–5896
  • Tomasz M., Lipman R., Chowdary D., Pawlak J., Verdine G. L., Nakanishi K. Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Science 1987; 235: 1204–1208
  • Kohn K. W. Biological aspects of DNA damage by crosslinking agents. Molecular Aspects of Anti-Cancer Drug Action, S. Neidle, M. J. Waring. Verlag Chemie, Weinheim 1983; 315–361
  • Orlemans E. O.M., Verboom W., Scheltinga M. W., Reinhoudt D. N., Lelieveld P., Fiebig H. H., Winterhalter B. R., Double J. A., Bibby M. C. Synthesis, mechanism of action, and biological evaluation of mitosenes. Journal of Medicinal Chemistry 1989; 32: 1612–1620
  • Maliepaard M., de Mol N. J., Janssen L. H.M., van der Neut W., Verboom W., Reinhoudt D. N. Role of lipophilicity in the in vitro antitumour activity of a series of new mitosene compounds. Anti-Cancer Drug Design 1992; 7: 415–425
  • Maliepaard M., de Mol N. J., Janssen L. H.M., Hoogvliet J. C., van der Neut W., Verboom W., Reinhoudt D. N. Reductive activation of potential antitumor mitosene compounds. Journal of Medicinal Chemistry 1993; 36: 2091–2097
  • Wardman P. Bioreductive activation of quinones - Redox properties and thiol reactivity. Free Radical Research Communications 1990; 8: 219–229
  • Andrews P. A., Pan S.-S., Bachur N. R. Electrochemical reductive activation of mitomycin C. Journal of the American Chemical Society 1986; 108: 4158–4166
  • Powis G. Metabolism and reaction of quinoid anticancer agents. Pharmacology and Therapeutics 1987; 35: 57–162
  • Kappus H. Overview of enzyme systems involved in bioreduction of drugs and in redox cycling. Biochemical Pharmacology 1986; 35: 1–6
  • Guengerich F. P., Martin M. V. Purification of cytochrome P-450, NADPH-cytochrome P-450 reductase and epoxide hydratase from a single preparation of rat liver microsomes. Archives of Biochemistry and Biophysics 1980; 205: 365–379
  • Bansal S. K., Love J. H., Gurtoo H. L. Resolution by high-pressure liquid chromatography and partial characterization of multiple forms of cytochrome P-450 from hepatic microsomes of phenobarbital-treated rats. European Journal of Biochemistry 1985; 146: 23–33
  • Massey V., Hemmerich P. A photochemical procedure for reduction of oxidation-reduction proteins employing deazariboflavin as catalyst. Journal of Biological Chemistry 1977; 252: 5612–5614
  • Goeptar A. R., te Koppele J. M., van Maanen J. M.S., Zoetemelk C. E.M., Vermeulen N. P.E. One-electron reductive bioactivation of 2,3,5,6-tetramethyl-benzoquinone by cytochrome P450. Biochemical Pharmacology 1992; 43: 343–352
  • Goeptar A. R., te Koppele J. M., Lamme E. K., Piqué J. M., Vermeulen N. P.E. Cytochrome P450 2B7-mediated one-electron reduction of adriamycin: A study with rat liver microsomes and purified enzymes. Molecular Pharmacology 1993; 44: 1267–1277
  • Vromans R. M., van de Straat R., Groeneveld M., Vermeulen N. P.E. One-electron reduction of mitomycin C by rat liver: Role of cytochrome P-450 and NADPH-cytochrome P-450 reductase. Xenobiotica 1990; 20: 967–978
  • Nagata C., Matsuyama A. On the mechanism of action of the carcinostatic antibiotic mitomycin C. Progress in antibiotics and anticancer chemotherapy. Proceedings of the 6th International Congress on Chemotherapy, Tokyo, Volume II. 1970; 423–427
  • Kalyanaraman B., Peret-Reyes E., Mason R. P. Spin trapping and direct electron spin resonance investigations of the redox metabolism of quinone anticancer drugs. Biochimica Biophysica Acta 1980; 630: 119–130
  • Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. Journal of Physical and Chemical Reference Data 1989; 18: 1637–1755
  • Janssen L. H.M., van Til A. L., van Duijneveldt F. B. Reductive activation and radical formation in a series of substituted benzoquinones. Thermodynamic and quantum chemical studies. Bioelectrochemistry and Bioenergetics 1992; 27: 161–178
  • Cresteil T., Jaiswal A. K. High levels of expression of the NAD(P)H-quinone oxido-reductase (NQO1) gene in tumor cells compared to normal cells of the same origin. Biochemical Pharmacology 1991; 42: 1021–1027

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.