Flavin-containing reductase: new perspective on the detoxification of nitrobenzodiazepine

Bibliography

• Childress SJ, Gluckman MI. 1,4-Benzodiazepines. J Pharm Sci 1964;53:577-90
   PubMed Web of Science ®Google Scholar
• Haefely WE. Central actions of benzodiazepines: general introduction. Br J Psychiatry 1978;133:231-8
   PubMed Web of Science ®Google Scholar
• Loew GH, Nienow JR, Poulsen M. Theoretical structure-activity studies of benzodiazepine analogues. Requirements for receptor affinity and activity. Mol Pharmacol 1984;26(1):19-34
   PubMed Web of Science ®Google Scholar
• Shader RI, Greenblatt DJ. Benzodiazepines: some aspects of their clinical pharmacology. Ciba Found Symp 1979;(74):141-55
   PubMedGoogle Scholar
• Robertson MD, Drummer OH. Postmortem distribution and redistribution of nitrobenzodiazepines in man. J Forensic Sci 1998;43(1):9-13
   PubMed Web of Science ®Google Scholar
• Mizuno K, Katoh M, Okumura H, Metabolic activation of benzodiazepines by CYP3A4. Drug Metab Dispos 2009;37(2):345-51
   PubMed Web of Science ®Google Scholar
• Darragh A, Lambe R, Brick I, Antagonism of the central effects of 3-methylclonazepam. Br J Clin Pharmacol 1982;14(6):871-2
   PubMed Web of Science ®Google Scholar
• Amir L, Waisman Y. Medical and toxicological aspects of drug facilitated sexual assault. Isr J Emerg Med 2006;6(3):62-6
   Google Scholar
• Gambi F, Conti CM, Grimaldi MR, Flunitrazepam a benzodiazepine most used among drug abusers. Int J Immunopathol Pharmacol 1999;12(3):157-9
   PubMed Web of Science ®Google Scholar
• Lane SD, Cherek DR, Nouvion SO. Modulation of human risky decision making by flunitrazepam. Psychopharmacology (Berl) 2008;196(2):177-88
   PubMed Web of Science ®Google Scholar
• Pirnay S, Megarbane B, Decleves X, Buprenorphine alters desmethylflunitrazepam disposition and flunitrazepam toxicity in rats. Toxicol Sci 2008;106(1):64-73
   PubMed Web of Science ®Google Scholar
• Kilicarslan T, Haining RL, Rettie AE, Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4. Drug Metab Dispos 2001;29(4 Pt 1):460-5
   PubMed Web of Science ®Google Scholar
• Hesse LM, Venkatakrishnan K, von Moltke LL, CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam. Drug Metab Dispos 2001;29(2):133-40
   PubMed Web of Science ®Google Scholar
• Saito H, Kobayashi H, Takeno S, In vivo and in vitro studies on fetal toxicity of benzodiazepines in rats. Res Commun Chem Pathol Pharmacol 1986;52(3):295-304
   PubMedGoogle Scholar
• De Silva JA, Puglisi CV, Munno N. Determination of clonazepam and flunitrazepam in blood and urine by electron-capture GLC. J Pharm Sci 1974;63(4):520-7
   PubMed Web of Science ®Google Scholar
• Ask K, Decologne N, Asare N, Distribution of nitroreductive activity toward nilutamide in rat. Toxicol Appl Pharmacol 2004;201(1):1-9
   PubMed Web of Science ®Google Scholar
• Peterson FJ, Mason RP, Hovsepian J, Oxygen-sensitive and -insensitive nitroreduction by Escherichia coli and rat hepatic microsomes. J Biol Chem 1979;254(10):4009-14
   PubMed Web of Science ®Google Scholar
• Takeno S, Sakai T. Involvement of the intestinal microflora in nitrazepam-induced teratogenicity in rats and its relationship to nitroreduction. Teratology 1991;44(2):209-14
   PubMedGoogle Scholar
• Robertson MD, Drummer OH. Postmortem drug metabolism by bacteria. J Forensic Sci 1995;40(3):382-6
   PubMed Web of Science ®Google Scholar
• Wilson WR, Hicks KO, Pullen SM, Bystander effects of bioreductive drugs: potential for exploiting pathological tumor hypoxia with dinitrobenzamide mustards. Radiat Res 2007;167(6):625-36
   PubMed Web of Science ®Google Scholar
• Rooseboom M, Commandeur JN, Vermeulen NP. Enzyme-catalyzed activation of anticancer prodrugs. Pharmacol Rev 2004;56(1):53-102
   PubMed Web of Science ®Google Scholar
• Sarlauskas J, Nemeikaite-Ceniene A, Anusevicius Z, Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: implications for their cytotoxicity. Arch Biochem Biophys 2004;425(2):184-92
   PubMed Web of Science ®Google Scholar
• Anlezark GM, Melton RG, Sherwood RF, The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954)–I. Purification and properties of a nitroreductase enzyme from Escherichia coli–a potential enzyme for antibody-directed enzyme prodrug therapy (ADEPT). Biochem Pharmacol 1992;44(12):2289-95
   PubMed Web of Science ®Google Scholar
• Fukinaga M, Ishizawa K, Kamei C. Anticonvulsant properties of 1,4-benzodiazepine derivatives in amygdaloid-kindled seizures and their chemical structure-related anticonvulsant action. Pharmacology 1998;57(5):233-41
   PubMed Web of Science ®Google Scholar
• Bogusz MJ, Maier RD, Kruger KD, Determination of flunitrazepam and its metabolites in blood by high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B Biomed Sci Appl 1998;713(2):361-9
   PubMedGoogle Scholar
• Druid H, Holmgren P, Ahlner J. Flunitrazepam: an evaluation of use, abuse and toxicity. Forensic Sci Int 2001;122(2-3):136-41
   PubMed Web of Science ®Google Scholar
• Berthault F, Kintz P, Mangin P. Simultaneous high-performance liquid chromatographic analysis of flunitrazepam and four metabolites in serum. J Chromatogr B Biomed Appl 1996;685(2):383-7
   PubMedGoogle Scholar
• Poisnel G, Dhilly M, Le Boisselier R, Comparison of five benzodiazepine-receptor agonists on buprenorphine-induced mu-opioid receptor regulation. J Pharmacol Sci 2009;110(1):36-46
   PubMed Web of Science ®Google Scholar
• Drummer OH, Syrjanen ML, Cordner SM. Deaths involving the benzodiazepine flunitrazepam. Am J Forensic Med Pathol 1993;14(3):238-43
   PubMed Web of Science ®Google Scholar
• Browne TR. Clonazepam. A review of a new anticonvulsant drug. Arch Neurol 1976;33(5):326-32
   PubMed Web of Science ®Google Scholar
• Lorizio A. Treatment of the epilepsy using clonazepam (RO 5-4023 – Rivotril). Riv Neurobiol 1972;18(3-4):233-40
   PubMedGoogle Scholar
• Negrusz A, Bowen AM, Moore CM, Deposition of 7-aminoclonazepam and clonazepam in hair following a single dose of Klonopin. J Anal Toxicol 2002;26(7):471-8
   PubMed Web of Science ®Google Scholar
• Gatzonis S, Karadimas P, Gatzonis S, Clonazepam associated retinopathy. Eur J Ophthalmol 2003;13(9-10):813-5
   PubMed Web of Science ®Google Scholar
• Koczerginski D, Kennedy SH, Swinson RP. Clonazepam and lithium–a toxic combination in the treatment of mania? Int Clin Psychopharmacol 1989;4(3):195-9
   PubMed Web of Science ®Google Scholar
• Witt DM, Ellsworth AJ, Leversee JH. Amiodarone-clonazepam interaction. Ann Pharmacother 1993;27(12):1463-4
   PubMed Web of Science ®Google Scholar
• Bittigau P, Sifringer M, Ikonomidou C. Antiepileptic drugs and apoptosis in the developing brain. Ann NY Acad Sci 2003;993:103-14; discussion 23-4
   PubMed Web of Science ®Google Scholar
• Eschenhof E. Studies on the disposition of the anticonvulsant clonazepam in the organisms of rat, dog, and man. Arzneimittelforschung 1973;23(3):390-400
   PubMedGoogle Scholar
• Sjo O, Hvidberg EF, Naestoft J, Pharmacokinetics and side-effects of clonazepam and its 7-amino-metabolite in man. Eur J Clin Pharmacol 1975;8(3-4):249-54
   PubMed Web of Science ®Google Scholar
• Ansseau M, Doumont A, Thiry D, Initial study of methylclonazepam in generalized anxiety disorder. Evidence for greater power in the cross-over design. Psychopharmacology (Berl) 1985;87(2):130-5
   PubMed Web of Science ®Google Scholar
• Thibaut JP, Monteiro LM, Leite LC, The effects of 3-methylclonazepam on Schistosoma mansoni musculature are not mediated by benzodiazepine receptors. Eur J Pharmacol 2009;606(1-3):9-16
   PubMed Web of Science ®Google Scholar
• O'Boyle C, Lambe R, Darragh A. Central effects in man of the novel schistosomicidal benzodiazepine meclonazepam. Eur J Clin Pharmacol 1985;29(1):105-8
   PubMed Web of Science ®Google Scholar
• Davies C, Levine S. A controlled comparison of nitrazepam (‘mogadon’) with sodium amylobarbitone as a sleep-inducing agent. Br J Psychiatry 1967;113(502):1005-8
   PubMed Web of Science ®Google Scholar
• Berman AJ, Pomina AC, Nepomuceno NR. Anticonvulsant properties of nitrazepam (mogadon). Electroencephalogr Clin Neurophysiol 1968;24(2):187
   PubMedGoogle Scholar
• Giri AK, Banerjee S. Genetic toxicology of four commonly used benzodiazepines: a review. Mutat Res 1996;340(2-3):93-108
   PubMed Web of Science ®Google Scholar
• Takeno S, Hirano Y, Kitamura A, Comparative developmental toxicity and metabolism of nitrazepam in rats and mice. Toxicol Appl Pharmacol 1993;121(2):233-8
   PubMed Web of Science ®Google Scholar
• Kishi K, Kanamori S, Maruyama T, Potential parameters of male reproductive toxicity: reproductive performance, histopathology and sperm evaluation in SD rats given nitrazepam. J Toxicol Sci 1995;20(3):329-39
   PubMedGoogle Scholar
• Saito H, Kobayashi H, Takeno S, Fetal toxicity of benzodiazepines in rats. Res Commun Chem Pathol Pharmacol 1984;46(3):437-47
   PubMedGoogle Scholar
• Yanagi Y, Haga F, Endo M, Comparative metabolic study of nimetazepam and its desmethyl derivative (nitrazepam) in rats. Xenobiotica 1975;5(4):245-7
   PubMed Web of Science ®Google Scholar
• Kuang H, Li Q, Shen C, A highly sensitive method for the determination of 7-aminonitrazepam, a metabolite of nitrazepam, in human urine using high-performance electrospray liquid chromatography tandem mass spectrometry. Biomed Chromatogr 2009;23(7):740-4
   PubMed Web of Science ®Google Scholar
• Kangas L. Determination of nitrazepam and its main metabolites in urine by gas–liquid chromatography: use of electron capture and nitrogen-selective detectors. J Chromatogr 1979;172:273-8
   PubMed Web of Science ®Google Scholar
• Yanagi Y, Haga F, Endo M, Comparative metabolic study of nimetazepam and its desmethyl derivative (nitrazepam) in dogs. Xenobiotica 1976;6(2):101-12
   PubMed Web of Science ®Google Scholar
• Sumirtapura YC, Aubert C, Coassolo P, Determination of 7-amino-flunitrazepam (Ro 20-1815) and 7-amino-desmethylflunitrazepam (Ro 5-4650) in plasma by high-performance liquid chromatography and fluorescence detection. J Chromatogr 1982;232(1):111-8
   PubMed Web of Science ®Google Scholar
• Petters I, Peng DR, Rane A. Quantitation of clonazepam and its 7-amino and 7-acetamido metabolites in plasma by high-performance liquid chromatography. J Chromatogr 1984;306:241-8
   PubMed Web of Science ®Google Scholar
• Elmer GW, Remmel RP. Role of the intestinal microflora in clonazepam metabolism in the rat. Xenobiotica 1984;14(11):829-40
   PubMed Web of Science ®Google Scholar
• Jonen HG. Enhancement of reductive metabolism of p-nitrobenzoate and nitrazepam in isolated perfused rat liver by ethanol. Drug Metab Dispos 1979;7(3):176-80
   PubMed Web of Science ®Google Scholar
• Hewick DS, Shaw V. The importance of the intestinal microflora in nitrazepam metabolism in the rat [proceedings]. Br J Pharmacol 1978;62(3):427P
   PubMed Web of Science ®Google Scholar
• Seree EJ, Pisano PJ, Placidi M, Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol 1993;7(2):69-75
   PubMed Web of Science ®Google Scholar
• Berson A, Wolf C, Berger V, Generation of free radicals during the reductive metabolism of the nitroaromatic compound, nilutamide. J Pharmacol Exp Ther 1991;257(2):714-9
   PubMed Web of Science ®Google Scholar
• Peng FC, Chaing HH, Tang SH, NADPH-cytochrome P-450 reductase is involved in flunitrazepam reductive metabolism in Hep G2 and Hep 3B cells. J Toxicol Environ Health A 2004;67(2):109-24
   PubMed Web of Science ®Google Scholar
• Leclerc H, Mossel DA, Edberg SC, Advances in the bacteriology of the coliform group: their suitability as markers of microbial water safety. Annu Rev Microbiol 2001;55:201-34
   PubMed Web of Science ®Google Scholar
• Roldan MD, Perez-Reinado E, Castillo F, Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev 2008;32(3):474-500
   PubMed Web of Science ®Google Scholar
• Rau J, Stolz A. Oxygen-insensitive nitroreductases NfsA and NfsB of Escherichia coli function under anaerobic conditions as lawsone-dependent Azo reductases. Appl Environ Microbiol 2003;69(6):3448-55
   PubMed Web of Science ®Google Scholar
• Liochev SI, Hausladen A, Fridovich I. Nitroreductase A is regulated as a member of the soxRS regulon of Escherichia coli. Proc Natl Acad Sci USA 1999;96(7):3537-9
   PubMed Web of Science ®Google Scholar
• Patel P, Young JG, Mautner V, A phase I/II clinical trial in localized prostate cancer of an adenovirus expressing nitroreductase with CB1954 [correction of CB1984]. Mol Ther 2009;17(7):1292-9
   PubMed Web of Science ®Google Scholar
• LinWu SW, Syu CJ, Chen YL, Characterization of Escherichia coli nitroreductase NfsB in the metabolism of nitrobenzodiazepines. Biochem Pharmacol 2009;78(1):96-103
   PubMed Web of Science ®Google Scholar
• Kaplan SA, Alexander K, Jack ML, Pharmacokinetic profiles of clonazepam in dog and humans and of flunitrazepam in dog. J Pharm Sci 1974;63(4):527-32
   PubMed Web of Science ®Google Scholar
• Moriya F, Hashimoto Y. Tissue distribution of nitrazepam and 7-aminonitrazepam in a case of nitrazepam intoxication. Forensic Sci Int 2003;131(2-3):108-12
   PubMed Web of Science ®Google Scholar
• Moreno SN, Mason RP, Docampo R. Reduction of nifurtimox and nitrofurantoin to free radical metabolites by rat liver mitochondria. Evidence of an outer membrane-located nitroreductase. J Biol Chem 1984;259(10):6298-305
   PubMed Web of Science ®Google Scholar
• Mason RP, Holtzman JL. The mechanism of microsomal and mitochondrial nitroreductase. Electron spin resonance evidence for nitroaromatic free radical intermediates. Biochemistry 1975;14(8):1626-32
   PubMed Web of Science ®Google Scholar
• Abou-Khalil S, Abou-Khalil WH, Yunis AA. Identification of a mitochondrial p-dinitrobenzene reductase activity in rat liver. Pharmacology 1985;31(6):301-8
   PubMed Web of Science ®Google Scholar
• Bartosek I, Mussini E, Saronio C, Studies on nitrazepam reduction in vitro. Eur J Pharmacol 1970;11(2):249-53
   PubMed Web of Science ®Google Scholar
• Koder RL, Haynes CA, Rodgers ME, Flavin thermodynamics explain the oxygen insensitivity of enteric nitroreductases. Biochemistry 2002;41(48):14197-205
   PubMed Web of Science ®Google Scholar
• Smyth GE, Orsi BA. Nitroreductase activity of NADH dehydrogenase of the respiratory redox chain. Biochem J 1989;257(3):859-63
   PubMed Web of Science ®Google Scholar
• Ghafourifar P, Cadenas E. Mitochondrial nitric oxide synthase. Trends Pharmacol Sci 2005;26(4):190-5
   PubMed Web of Science ®Google Scholar
• Ghafourifar P, Richter C. Nitric oxide synthase activity in mitochondria. FEBS Lett 1997;418(3):291-6
   PubMed Web of Science ®Google Scholar
• Stuehr DJ, Tejero J, Haque MM. Structural and mechanistic aspects of flavoproteins: electron transfer through the nitric oxide synthase flavoprotein domain. FEBS J 2009;276(15):3959-74
   PubMed Web of Science ®Google Scholar
• Chandor A, Dijols S, Ramassamy B, Metabolic activation of the antitumor drug 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) by NO synthases. Chem Res Toxicol 2008;21(4):836-43
   PubMed Web of Science ®Google Scholar
• Ask K, Dijols S, Giroud C, Reduction of nilutamide by NO synthases: implications for the adverse effects of this nitroaromatic antiandrogen drug. Chem Res Toxicol 2003;16(12):1547-54
   PubMed Web of Science ®Google Scholar
• Vella F, Ferry G, Delagrange P, NRH:quinone reductase 2: an enzyme of surprises and mysteries. Biochem Pharmacol 2005;71(1-2):1-12
   PubMed Web of Science ®Google Scholar
• Bianchet MA, Erdemli SB, Amzel LM. Structure, function, and mechanism of cytosolic quinone reductases. Vitam Horm 2008;78:63-84
   PubMed Web of Science ®Google Scholar
• Graves PR, Kwiek JJ, Fadden P, Discovery of novel targets of quinoline drugs in the human purine binding proteome. Mol Pharmacol 2002;62(6):1364-72
   PubMed Web of Science ®Google Scholar
• Dinkova-Kostova AT, Talalay P. Persuasive evidence that quinone reductase type 1 (DT diaphorase) protects cells against the toxicity of electrophiles and reactive forms of oxygen. Free Radic Biol Med 2000;29(3-4):231-40
   PubMed Web of Science ®Google Scholar
• Knox RJ, Jenkins TC, Hobbs SM, Bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by human NAD(P)H quinone oxidoreductase 2: a novel co-substrate-mediated antitumor prodrug therapy. Cancer Res 2000;60(15):4179-86
   PubMed Web of Science ®Google Scholar
• Jamieson D, Tung AT, Knox RJ, Reduction of mitomycin C is catalysed by human recombinant NRH:quinone oxidoreductase 2 using reduced nicotinamide adenine dinucleotide as an electron donating co-factor. Br J Cancer 2006;95(9):1229-33
   PubMed Web of Science ®Google Scholar
• Knox RJ, Boland MP, Friedlos F, The nitroreductase enzyme in Walker cells that activates 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to 5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide is a form of NAD(P)H dehydrogenase (quinone) (EC 1.6.99.2). Biochem Pharmacol 1988;37(24):4671-7
   PubMed Web of Science ®Google Scholar
• Choi JW, Lee J, Nishi K, Crystal structure of a minimal nitroreductase, ydjA, from Escherichia coli K12 with and without FMN cofactor. J Mol Biol 2008;377(1):258-67
   PubMed Web of Science ®Google Scholar
• Barak Y, Thorne SH, Ackerley DF, New enzyme for reductive cancer chemotherapy, YieF, and its improvement by directed evolution. Mol Cancer Ther 2006;5(1):97-103
   PubMed Web of Science ®Google Scholar
• Zhao Q, Modi S, Smith G, Crystal structure of the FMN-binding domain of human cytochrome P450 reductase at 1.93 A resolution. Protein Sci 1999;8(2):298-306
   PubMed Web of Science ®Google Scholar
• Xia C, Misra I, Iyanagi T, Kim JJ. Regulation of interdomain interactions by calmodulin in inducible nitric oxide synthase. J Biol Chem 2009;284(44):30708-17
   PubMed Web of Science ®Google Scholar
• Skelly JV, Sanderson MR, Suter DA, Crystal structure of human DT-diaphorase: a model for interaction with the cytotoxic prodrug 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954). J Med Chem 1999;42(21):4325-30
   PubMed Web of Science ®Google Scholar
• Parkinson GN, Skelly JV, Neidle S. Crystal structure of FMN-dependent nitroreductase from Escherichia coli B: a prodrug-activating enzyme. J Med Chem 2000;43(20):3624-31
   PubMed Web of Science ®Google Scholar
• Kobori T, Sasaki H, Lee WC, Structure and site-directed mutagenesis of a flavoprotein from Escherichia coli that reduces nitrocompounds: alteration of pyridine nucleotide binding by a single amino acid substitution. J Biol Chem 2001;276(4):2816-23
   PubMed Web of Science ®Google Scholar
• Holm L, Kaariainen S, Rosenstrom P, Searching protein structure databases with DaliLite v.3. Bioinformatics 2008;24(23):2780-1
   PubMed Web of Science ®Google Scholar
• Kolbeck B, May P, Schmidt-Goenner T, Connectivity independent protein-structure alignment: a hierarchical approach. BMC Bioinformatics 2006;7:510
   PubMedGoogle Scholar
• Vass SO, Jarrom D, Wilson WR, E. coli NfsA: an alternative nitroreductase for prodrug activation gene therapy in combination with CB1954. Br J Cancer 2009;100(12):1903-11
   PubMed Web of Science ®Google Scholar
• Amrein R, Leishman B, Bentzinger C, Flumazenil in benzodiazepine antagonism. Actions and clinical use in intoxications and anaesthesiology. Med Toxicol Adverse Drug Exp 1987;2(6):411-29
   PubMedGoogle Scholar
• Emptage CD, Knox RJ, Danson MJ, Nitroreductase from Bacillus licheniformis: a stable enzyme for prodrug activation. Biochem Pharmacol 2009;77(1):21-9
   PubMed Web of Science ®Google Scholar
• Gao D, Narasimhan DL, Macdonald J, Thermostable variants of cocaine esterase for long-time protection against cocaine toxicity. Mol Pharmacol 2009;75(2):318-23
   PubMed Web of Science ®Google Scholar
• Singlas E. Pharmacokinetics of flunitrazepam. Nouv Presse Med 1979;8(31):2519-23
   PubMedGoogle Scholar
• Hall PM, Stupans I, Burgess W, Immunohistochemical localization of NADPH-cytochrome P450 reductase in human tissues. Carcinogenesis 1989;10(3):521-30
   PubMed Web of Science ®Google Scholar
• Pan SS, Andrews PA, Glover CJ, Reductive activation of mitomycin C and mitomycin C metabolites catalyzed by NADPH-cytochrome P-450 reductase and xanthine oxidase. J Biol Chem 1984;259(2):959-66
   PubMed Web of Science ®Google Scholar
• Chat M, Bayol-Denizot C, Suleman G, Drug metabolizing enzyme activities and superoxide formation in primary and immortalized rat brain endothelial cells. Life Sci 1998;62(2):151-63
   PubMed Web of Science ®Google Scholar
• Schmalix WA, Lang D, Schneider A, Stable expression and coexpression of human cytochrome P450 oxidoreductase and cytochrome P450 1A2 in V79 Chinese hamster cells: sensitivity to quinones and biotransformation of 7-alkoxyresorufins and triazines. Drug Metab Dispos 1996;24(12):1314-9
   PubMed Web of Science ®Google Scholar
• Berger V, Berson A, Wolf C, Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol 1992;43(3):654-7
   PubMed Web of Science ®Google Scholar
• Navarro A, Boveris A. Mitochondrial nitric oxide synthase, mitochondrial brain dysfunction in aging, and mitochondria-targeted antioxidants. Adv Drug Deliv Rev 2008;60(13-14):1534-44
   PubMed Web of Science ®Google Scholar
• Garner AP, Paine MJ, Rodriguez-Crespo I, Nitric oxide synthases catalyze the activation of redox cycling and bioreductive anticancer agents. Cancer Res 1999;59(8):1929-34
   PubMed Web of Science ®Google Scholar
• Jiang HB, Ichikawa M, Furukawa A, Reductive activation of mitomycin C by neuronal nitric oxide synthase. Biochem Pharmacol 2000;60(4):571-9
   PubMed Web of Science ®Google Scholar
• Kobzik L, Bredt DS, Lowenstein CJ, Nitric oxide synthase in human and rat lung: immunocytochemical and histochemical localization. Am J Respir Cell Mol Biol 1993;9(4):371-7
   PubMed Web of Science ®Google Scholar
• Bachmann S, Bosse HM, Mundel P. Topography of nitric oxide synthesis by localizing constitutive NO synthases in mammalian kidney. Am J Physiol 1995;268(5 Pt 2):F885-98
   PubMed Web of Science ®Google Scholar
• Pou S, Pou WS, Bredt DS, Generation of superoxide by purified brain nitric oxide synthase. J Biol Chem 1992;267(34):24173-6
   PubMed Web of Science ®Google Scholar
• Geller DA, Lowenstein CJ, Shapiro RA, Molecular cloning and expression of inducible nitric oxide synthase from human hepatocytes. Proc Natl Acad Sci USA 1993;90(8):3491-5
   PubMed Web of Science ®Google Scholar
• Terenghi G, Riveros-Moreno V, Hudson LD, Immunohistochemistry of nitric oxide synthase demonstrates immunoreactive neurons in spinal cord and dorsal root ganglia of man and rat. J Neurol Sci 1993;118(1):34-7
   PubMed Web of Science ®Google Scholar
• Lowenstein CJ, Glatt CS, Bredt DS, Cloned and expressed macrophage nitric oxide synthase contrasts with the brain enzyme. Proc Natl Acad Sci USA 1992;89(15):6711-5
   PubMed Web of Science ®Google Scholar
• Ozuyaman B, Grau M, Kelm M, RBC NOS: regulatory mechanisms and therapeutic aspects. Trends Mol Med 2008;14(7):314-22
   PubMed Web of Science ®Google Scholar
• Joseph P, Long DJ, 2nd, Role of NAD(P)H:quinone oxidoreductase 1 (DT diaphorase) in protection against quinone toxicity. Biochem Pharmacol 2000;60(2):207-14
   PubMed Web of Science ®Google Scholar
• Jamieson D, Tung AT, Knox RJ, Reduction of mitomycin C is catalysed by human recombinant NRH:quinone oxidoreductase 2 using reduced nicotinamide adenine dinucleotide as an electron donating co-factor. Br J Cancer 2006;95(9):1229-33
   PubMed Web of Science ®Google Scholar
• Liao S, Dulaney JT, Williams-Ashman HG. Purification and properties of a flavoprotein catalyzing the oxidation of reduced ribosyl nicotinamide. J Biol Chem 1962;237:2981-7
   PubMed Web of Science ®Google Scholar
• Zenno S, Koike H, Kumar AN, Biochemical characterization of NfsA, the Escherichia coli major nitroreductase exhibiting a high amino acid sequence homology to Frp, a Vibrio harveyi flavin oxidoreductase. J Bacteriol 1996;178(15):4508-14
   PubMed Web of Science ®Google Scholar