Literature DB >> 10682679

NADPH:cytochrome c (P450) reductase activates tirapazamine (SR4233) to restore hypoxic and oxic cytotoxicity in an aerobic resistant derivative of the A549 lung cancer cell line.

M P Saunders1, A V Patterson, E C Chinje, A L Harris, I J Stratford.   

Abstract

Tirapazamine (TPZ, SR4233, WIN 59075) is a bioreductive drug that is activated in regions of low oxygen tension to a cytotoxic radical intermediate. This labile metabolite shows high selective toxicity towards hypoxic cells, such as those found in solid tumours. Under aerobic conditions, redox cycling occurs with subsequent generation of superoxide radicals, which are also cytotoxic. NADPH:cytochrome c (P450) reductase (P450R) is a one-electron reducing enzyme that efficiently activates TPZ. Recently a derivative of the A549 non-small cell lung cancer cell line (A549c50) was generated that showed substantially reduced P450R activity compared to its parental line (Elwell et al (1997) Biochem Pharmacol 54: 249-257). Here, it is demonstrated that the A549c50 cells are markedly more resistant to TPZ under both aerobic and hypoxic conditions. In addition, these cells have a dramatically impaired ability to metabolize TPZ to its two-electron reduction product, SR4317, under hypoxic conditions when compared to wild-type cells. P450R activity in the A549c50 cells was reintroduced to similar levels as that seen in the parental A549 cells by transfection of the full-length cDNA for human P450R. These P450R over-expressing cells exhibit restored sensitivity to TPZ under both aerobic and hypoxic conditions, comparable to that found in the original parental A549 cells. Further, the ability of the transfected cells to metabolize TPZ to SR4317 under hypoxic conditions is also shown to be restored. This provides further evidence that P450R can play an important role in the activation, metabolism and toxicity of this lead bioreductive drug.

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Year:  2000        PMID: 10682679      PMCID: PMC2363339          DOI: 10.1054/bjoc.1999.0977

Source DB:  PubMed          Journal:  Br J Cancer        ISSN: 0007-0920            Impact factor:   7.640


  20 in total

1.  Expression of glutathione S-transferases and cytochrome P450 in normal and tumor breast tissue.

Authors:  L M Forrester; J D Hayes; R Millis; D Barnes; A L Harris; J J Schlager; G Powis; C R Wolf
Journal:  Carcinogenesis       Date:  1990-12       Impact factor: 4.944

2.  Potentiation by the hypoxic cytotoxin SR 4233 of cell killing produced by fractionated irradiation of mouse tumors.

Authors:  J M Brown; M J Lemmon
Journal:  Cancer Res       Date:  1990-12-15       Impact factor: 12.701

3.  Intermittent blood flow in a murine tumor: radiobiological effects.

Authors:  D J Chaplin; P L Olive; R E Durand
Journal:  Cancer Res       Date:  1987-01-15       Impact factor: 12.701

4.  Tumor-specific, schedule-dependent interaction between tirapazamine (SR 4233) and cisplatin.

Authors:  M J Dorie; J M Brown
Journal:  Cancer Res       Date:  1993-10-01       Impact factor: 12.701

5.  Initial characterization of the major mouse cytochrome P450 enzymes involved in the reductive metabolism of the hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1,4-di-N-oxide (tirapazamine, SR 4233, WIN 59075).

Authors:  R J Riley; S A Hemingway; M A Graham; P Workman
Journal:  Biochem Pharmacol       Date:  1993-03-09       Impact factor: 5.858

6.  Microsomal reduction of 3-amino-1,2,4-benzotriazine 1,4-dioxide to a free radical.

Authors:  R V Lloyd; D R Duling; G V Rumyantseva; R P Mason; P K Bridson
Journal:  Mol Pharmacol       Date:  1991-09       Impact factor: 4.436

Review 7.  Determinants of tumor blood flow: a review.

Authors:  R K Jain
Journal:  Cancer Res       Date:  1988-05-15       Impact factor: 12.701

Review 8.  The experimental development of bioreductive drugs and their role in cancer therapy.

Authors:  P Workman; I J Stratford
Journal:  Cancer Metastasis Rev       Date:  1993-06       Impact factor: 9.264

Review 9.  Enzymology of tirapazamine metabolism: a review.

Authors:  A V Patterson; M P Saunders; E C Chinje; L H Patterson; I J Stratford
Journal:  Anticancer Drug Des       Date:  1998-09

Review 10.  SR 4233 (tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours.

Authors:  J M Brown
Journal:  Br J Cancer       Date:  1993-06       Impact factor: 7.640

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  6 in total

1.  Hypoxia-activated cytotoxic agent tirapazamine enhances hepatic artery ligation-induced killing of liver tumor in HBx transgenic mice.

Authors:  Wei-Hsiang Lin; Shiou-Hwei Yeh; Kun-Huei Yeh; Kai-Wei Chen; Ya-Wen Cheng; Tung-Hung Su; Ping Jao; Lin-Chun Ni; Pei-Jer Chen; Ding-Shinn Chen
Journal:  Proc Natl Acad Sci U S A       Date:  2016-10-04       Impact factor: 11.205

Review 2.  Significance of Specific Oxidoreductases in the Design of Hypoxia-Activated Prodrugs and Fluorescent Turn off-on Probes for Hypoxia Imaging.

Authors:  Ewelina Janczy-Cempa; Olga Mazuryk; Agnieszka Kania; Małgorzata Brindell
Journal:  Cancers (Basel)       Date:  2022-05-29       Impact factor: 6.575

3.  Hypoxia-targeting by tirapazamine (TPZ) induces preferential growth inhibition of nasopharyngeal carcinoma cells with Chk1/2 activation.

Authors:  Bo Hong; Vivian W Y Lui; Edwin P Hui; Margaret H L Ng; Suk-Hang Cheng; Fion L Sung; Chi-Man Tsang; Sai-Wah Tsao; Anthony Tak-Cheung Chan
Journal:  Invest New Drugs       Date:  2009-12-16       Impact factor: 3.850

4.  Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated Hypoxia.

Authors:  Blake A Winn; Laxman Devkota; Bunnarack Kuch; Matthew T MacDonough; Tracy E Strecker; Yifan Wang; Zhe Shi; Jeni L Gerberich; Deboprosad Mondal; Alejandro J Ramirez; Ernest Hamel; David J Chaplin; Peter Davis; Ralph P Mason; Mary Lynn Trawick; Kevin G Pinney
Journal:  J Nat Prod       Date:  2020-03-20       Impact factor: 4.050

5.  The role of bioreductive activation of doxorubicin in cytotoxic activity against leukaemia HL60-sensitive cell line and its multidrug-resistant sublines.

Authors:  D Kostrzewa-Nowak; M J I Paine; C R Wolf; J Tarasiuk
Journal:  Br J Cancer       Date:  2005-07-11       Impact factor: 7.640

6.  Hypoxia-activated prodrugs and (lack of) clinical progress: The need for hypoxia-based biomarker patient selection in phase III clinical trials.

Authors:  Linda Spiegelberg; Ruud Houben; Raymon Niemans; Dirk de Ruysscher; Ala Yaromina; Jan Theys; Christopher P Guise; Jeffrey B Smaill; Adam V Patterson; Philippe Lambin; Ludwig J Dubois
Journal:  Clin Transl Radiat Oncol       Date:  2019-01-18
  6 in total

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