Literature DB >> 34156

NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals.

N R Bachur, S L Gordon, M V Gee, H Kon.   

Abstract

With NADPH as the electron donor, rat liver NADPH cytochrome P-450 reductase (NADPH:ferricytochrome oxidoreductase, EC 1.6.2.4) catalyzes the single-electron reduction of several quinone antibiotics to a semiquinone or free radical state. The benzanthraquinones adriamycin, daunorubicin, carminomycin, 7-O-methylnogalarol, and aclacinomycin A and the N-heterocyclic quinones streptonigrin and mitomycin C are activated to free radical intermediates which can transfer their single electron to molecular oxygen to form superoxide. The overall Km range for this electron transfer is 0.4 to 42.1 X 10(-4) M. We postulate that the formation of the "site-specific free radical/ intermediate is central to the cytotoxic action of these antibiotics.

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Year:  1979        PMID: 34156      PMCID: PMC383104          DOI: 10.1073/pnas.76.2.954

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  28 in total

1.  Anthracycline antibiotic augmentation of microsomal electron transport and free radical formation.

Authors:  N R Bachur; S L Gordon; M V Gee
Journal:  Mol Pharmacol       Date:  1977-09       Impact factor: 4.436

2.  DNA breaks in P288 tumor cells in mice after treatment with daunorubicin and adriamycin.

Authors:  H S Schwartz
Journal:  Res Commun Chem Pathol Pharmacol       Date:  1975-01

3.  A flavoprotein oxidizing NADPH isolated from liver microsomes.

Authors:  H NISHIBAYASHI; T OMURA; R SATO
Journal:  Biochim Biophys Acta       Date:  1963-03-12

4.  Strand scission of DNA by bound adriamycin and daunorubicin in the presence of reducing agents.

Authors:  J W Lown; S K Sim; K C Majumdar; R Y Chang
Journal:  Biochem Biophys Res Commun       Date:  1977-06-06       Impact factor: 3.575

5.  Generation of free radicals and lipid peroxidation by redox cycling of adriamycin and daunomycin.

Authors:  J Goodman; P Hochstein
Journal:  Biochem Biophys Res Commun       Date:  1977-07-25       Impact factor: 3.575

6.  Generation of free radicals of quinone group-containing anti-cancer chemicals in NADPH-microsome system as evidenced by initiation of sulfite oxidation.

Authors:  K Handa; S Sato
Journal:  Gan       Date:  1975-02

7.  The mechanism of the degradation of DNA by streptonigrin.

Authors:  R Cone; S K Hasan; J W Lown; A R Morgan
Journal:  Can J Biochem       Date:  1976-03

8.  MITOMYCINS AND PORFIROMYCIN: CHEMICAL MECHANISM OF ACTIVATION AND CROSS-LINKING OF DNA.

Authors:  V N IYER; W SZYBALSKI
Journal:  Science       Date:  1964-07-03       Impact factor: 47.728

9.  The coenzyme Q10 and vitamin K1 semiquinone free radicals.

Authors:  M S BLOIS; J E MALING
Journal:  Biochem Biophys Res Commun       Date:  1960-08       Impact factor: 3.575

10.  MITOMYCIN C: CHEMICAL AND BIOLOGICAL STUDIES ON ALKYLATION.

Authors:  H S SCHWARTZ; J E SODERGREN; F S PHILIPS
Journal:  Science       Date:  1963-11-29       Impact factor: 47.728

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  87 in total

1.  Depletion of topoisomerase II in isolated nuclei during a glucose-regulated stress response.

Authors:  J W Shen; J R Subjeck; R B Lock; W E Ross
Journal:  Mol Cell Biol       Date:  1989-08       Impact factor: 4.272

2.  Distinct roles of cytochrome P450 reductase in mitomycin C redox cycling and cytotoxicity.

Authors:  Yun Wang; Joshua P Gray; Vladimir Mishin; Diane E Heck; Debra L Laskin; Jeffrey D Laskin
Journal:  Mol Cancer Ther       Date:  2010-05-25       Impact factor: 6.261

3.  Probing the transmembrane structure and dynamics of microsomal NADPH-cytochrome P450 oxidoreductase by solid-state NMR.

Authors:  Rui Huang; Kazutoshi Yamamoto; Meng Zhang; Nataliya Popovych; Ivan Hung; Sang-Choul Im; Zhehong Gan; Lucy Waskell; Ayyalusamy Ramamoorthy
Journal:  Biophys J       Date:  2014-05-20       Impact factor: 4.033

4.  Genotoxicity in the hepatocyte/DNA repair test and toxicity to liver mitochondria of 1-hydroxyanthraquinone and several dihydroxyanthraquinones.

Authors:  K Kawai; H Mori; S Sugie; N Yoshimi; T Inoue; T Nakamaru; Y Nozawa; T Matsushima
Journal:  Cell Biol Toxicol       Date:  1986-12       Impact factor: 6.691

5.  The Effect of 5OH-1,4-Naphthoquinone on Norway Spruce Seeds during Germination.

Authors:  J Segura-Aguilar; I Hakman; J Rydström
Journal:  Plant Physiol       Date:  1992-12       Impact factor: 8.340

6.  Cytotoxicity of mitomycin C on clonogenic human carcinoma cells is not enhanced by hypoxia.

Authors:  C U Ludwig; Y M Peng; J N Beaudry; S E Salmon
Journal:  Cancer Chemother Pharmacol       Date:  1984       Impact factor: 3.333

Review 7.  Epirubicin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in cancer chemotherapy.

Authors:  G L Plosker; D Faulds
Journal:  Drugs       Date:  1993-05       Impact factor: 9.546

Review 8.  Doxorubicin cardiomyopathy.

Authors:  Kanu Chatterjee; Jianqing Zhang; Norman Honbo; Joel S Karliner
Journal:  Cardiology       Date:  2009-12-11       Impact factor: 1.869

9.  The influence of ranitidine on the pharmacokinetics and toxicity of doxorubicin in rabbits.

Authors:  N L Harris; D E Brenner; L B Anthony; J C Collins; S Halter; K R Hande
Journal:  Cancer Chemother Pharmacol       Date:  1988       Impact factor: 3.333

10.  The effect of chronic adriamycin treatment on heart kidney and liver tissue of male and female rat.

Authors:  R H Julicher; L Sterrenberg; G R Haenen; A Bast; J Noordhoek
Journal:  Arch Toxicol       Date:  1988       Impact factor: 5.153

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