Literature DB >> 8195032

The role of specific reductases in the intracellular activation and binding of 2-nitroimidazoles.

P Joseph1, A K Jaiswal, C C Stobbe, J D Chapman.   

Abstract

PURPOSE: To determine the relative effectiveness of specific cellular reductases for the activation and binding of 2-nitroimidazoles in vivo. METHODS AND MATERIALS: Monkey kidney cells were transfected with recombinant plasmids to effect intracellular overexpression of P450 reductase and DT-diaphorase. The covalent binding of 2-nitroimidazoles to cellular macromolecules was measured as a function of time of cell incubation at various oxygen concentrations. The effect of allopurinol on cellular binding of radiolabeled 2-nitroimidazoles was also measured.
RESULTS: A 1,000-fold overexpression of DT-diaphorase resulted in a small but significant increase in 2-nitroimidazole binding rate. An 80-fold overexpression of cytochrome P450 reductase resulted in a 5-7-fold increase in the binding rate of 2-nitroimidazole. The inhibition of xanthine oxidase by allopurinol had no effect on 2-nitroimidazole binding rates. The amplification of P450 reductase activity within cells was always much larger than the resultant increase in 2-nitroimidazole binding rate, suggesting an enzyme kinetic process less than first order and possibly of 1/2-order.
CONCLUSION: These data suggest that cytochrome P450 reductase is the most important enzyme in these cells for reducing 2-nitroimidazoles to intermediates which can covalently bind to cellular macromolecules. Furthermore, since this cellular process demonstrates approximately 1/2-order kinetics, a tissue's capacity for binding 2-nitroimidazole drug in hypoxia should be proportional to the square root of its intracellular P450 reductase level.

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Year:  1994        PMID: 8195032     DOI: 10.1016/0360-3016(94)90288-7

Source DB:  PubMed          Journal:  Int J Radiat Oncol Biol Phys        ISSN: 0360-3016            Impact factor:   7.038


  8 in total

1.  Induction of DT-diaphorase by 1,2-dithiole-3-thione and increase of antitumour activity of bioreductive agents.

Authors:  A Begleiter; M K Leith; T J Curphey
Journal:  Br J Cancer Suppl       Date:  1996-07

2.  The relationship between tumour oxygenation determined by oxygen electrode measurements and magnetic resonance spectroscopy of the fluorinated 2-nitroimidazole SR-4554.

Authors:  E O Aboagye; R J Maxwell; M R Horsman; A D Lewis; P Workman; M Tracy; J R Griffiths
Journal:  Br J Cancer       Date:  1998       Impact factor: 7.640

Review 3.  Current issues in the utility of 19F nuclear magnetic resonance methodologies for the assessment of tumour hypoxia.

Authors:  Simon P Robinson; John R Griffiths
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2004-06-29       Impact factor: 6.237

4.  Anomalous patterns of nitroimidazole binding adjacent to necrosis in human glioma xenografts: possible role of decreased oxygen consumption.

Authors:  M B Parliament; A J Franko; M J Allalunis-Turner; B W Mielke; C L Santos; B G Wolokoff; J R Mercer
Journal:  Br J Cancer       Date:  1997       Impact factor: 7.640

5.  DT-diaphorase activity in NSCLC and SCLC cell lines: a role for fos/jun regulation.

Authors:  J K Kepa; D Ross
Journal:  Br J Cancer       Date:  1999-04       Impact factor: 7.640

6.  A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy.

Authors:  C P Lee; G S Payne; A Oregioni; R Ruddle; S Tan; F I Raynaud; D Eaton; M J Campbell; K Cross; G Halbert; M Tracy; J McNamara; B Seddon; M O Leach; P Workman; I Judson
Journal:  Br J Cancer       Date:  2009-12-01       Impact factor: 7.640

7.  Oxygen dependence of cellular uptake of EF5 [2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)a cet amide] : analysis of drug adducts by fluorescent antibodies vs bound radioactivity.

Authors:  C J Koch; S M Evans; E M Lord
Journal:  Br J Cancer       Date:  1995-10       Impact factor: 7.640

8.  In vivo evaluation of [18F]fluoroetanidazole as a new marker for imaging tumour hypoxia with positron emission tomography.

Authors:  H Barthel; H Wilson; D R Collingridge; G Brown; S Osman; S K Luthra; F Brady; P Workman; P M Price; E O Aboagye
Journal:  Br J Cancer       Date:  2004-06-01       Impact factor: 7.640

  8 in total

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