Mutagenicity of nitrofuran derivatives: Review

Environmental MutagenesisVolume 5, Issue 5 p. 745-765 Reviews Mutagenicity of nitrofuran derivatives: Review D. R. McCalla, Corresponding Author D. R. McCalla Department of Biochemistry, McMaster University, Hamilton, Ontario, CanadaDepartment of Biochemistry, McMaster University, 1200 Main Street West, Hamilton, Ontario, Canada L8N 3Z5Search for more papers by this author D. R. McCalla, Corresponding Author D. R. McCalla Department of Biochemistry, McMaster University, Hamilton, Ontario, CanadaDepartment of Biochemistry, McMaster University, 1200 Main Street West, Hamilton, Ontario, Canada L8N 3Z5Search for more papers by this author First published: 1983 https://doi.org/10.1002/em.2860050512Citations: 137AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat References Adams GE, Fowler JF, Wardman P (eds) (1978): Hypoxic cell sensitizers in radiobiology and radiotherapy. Br J Cancer (Suppl 3) 37: 1–321. Google Scholar Asnis RE (1957): The reduction of furacin by cell-free extracts of furacin-resistant and parent-susceptible strains of Escherichia coli. Arch Biochem Biophys 66: 208–216. 10.1016/0003-9861(57)90551-9 CASPubMedWeb of Science®Google Scholar Baumeister M, Luetzen L (1979): Detection of the carcinogenic nitrofuran derivative VR-6 as a mutagen in the Salmonella/microsome test. Arch Toxicol 42(4): 259–264. 10.1007/BF00334839 CASPubMedWeb of Science®Google Scholar Bueding E, Jolliffe N (1946): Metabolism of trinitrotoluene (TNT) in vitro. J Pharmacol Exp Ther 80: 399–312. Google Scholar Blijleven WGH, Kortselius MJH, Kramers PGN (1977): Mutagenicity testing of H-193, AF-2 and Furazolidone in Drosophila melanogaster. Mutat Res 56: 95–100. 10.1016/0027-5107(77)90249-4 CASPubMedWeb of Science®Google Scholar Boyd JA, Barrett JC, Eling TE (1982): Prostaglandin endoperoxide synthetase-dependent co-oxidation of (+)-trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene in C3H/10T1/2 clone 8 cells. Cancer Res 42: 2628–2632. CASPubMedWeb of Science®Google Scholar Boyland E, Speyer BE (1970): Enzyme-catalysed reactions between some 2-substituted 5-nitrofuran derivatives and glutathione. Biochem J 119: 463–472. 10.1042/bj1190463 CASPubMedWeb of Science®Google Scholar Brawn K, Fridovich I (1981): DNA strand scission by enzymatically generated oxygen radicals. Arch Biochem Biophys 206: 414–419. 10.1016/0003-9861(81)90108-9 CASPubMedWeb of Science®Google Scholar Brunsche H, Krooth RS (1973): Studies on the xanthine oxidase activity of mammalian cells. Biochem Genet 8: 341–350. 10.1007/BF00487339 PubMedWeb of Science®Google Scholar GT Bryan (ed) (1978): " Nitrofurans: Carcinogenesis—A Comprehensive Survey Series." New York: Raven Press, Vol. 4. Google Scholar Bryant DW, McCalla DR (1980): Nitrofuran induced mutagenesis and error prone repair in Escherichia coli. Chem Biol Interact 31: 151–166. 10.1016/0009-2797(80)90002-2 CASPubMedWeb of Science®Google Scholar Bryant DW, McCalla DR, Leeksma M, Laneuville P (1981): Type I nitroreductases of Escherichia coli. Can J Microbiol 27: 81–86. 10.1139/m81-013 CASPubMedWeb of Science®Google Scholar Callen DF (1981): Comparison of the genetic activity of AF-2 and nitrofurantoin in log and stationary phase cells of Saccharomyces cerevisiae. Environ Mutagen 3: 651–658. 10.1002/em.2860030607 CASWeb of Science®Google Scholar Cerna M, Sram RJ (1980): Mutagenicity studies with nitrofurans II. Mutagenicity of nitrofurylacrylic acid for Salmonella typhimurium. Mutat Res 77: 1–12. 10.1016/0165-1218(80)90114-7 CASPubMedWeb of Science®Google Scholar Chatterjee SN, Ghosh S (1979): Mechanism of action of furazolidone inter-strand cross-linking in DNA and liquid holding recovery of Vibrio cholerae cells. Indian J Biochem Biophys 16: 125–130. CASPubMedWeb of Science®Google Scholar Claxton LD (1983): Characterization of automotive emissions by bacterial mutagenesis bioassay: A review. Environ Mutagen 5: 609–631. 10.1002/em.2860050410 CASPubMedWeb of Science®Google Scholar Cleaver JE, Bootsma D (1975): Xeroderma pigmentosum: Biochemical and genetic characteristics. Ann Rev Genet 9: 19–38. 10.1146/annurev.ge.09.120175.000315 CASPubMedWeb of Science®Google Scholar Cohen SM (1979): Toxicity and carcinogenicity of nitrofurans. In GT Bryan (ed): "Carcinogenesis—A Comprehensive Survey". New York: Raven Press, Vol 4, pp 171–232. Google Scholar Cohen SM, Zensen TV, Muraski G, Fukushima S, Mattammal MB, Rapp NS, Davis BB (1981): Aspirin inhibition of N-(4-(5-nitro-2-furyl)-2-thiazolyl) formamide-induced lesions of the urinary bladder correlated with inhibition of metabolism by bladder prostaglandin endoperoxide synthesis. Cancer Res 41: 3355–3359. CASPubMedWeb of Science®Google Scholar Coughlan MP (1980): Aldehyde oxidase, xanthine oxidase and xanthine dehydrogenase: Hydroxylases containing molybdenum, iron-sulphur and flavin: In MP Coughlan (ed): " Molybdenum and Molybdenum-Containing Enzymes," Oxford: Pergamon Press, pp 119–185. 10.1016/B978-0-08-024398-6.50009-2 Google Scholar Dershwitz M, Novak RF (1980): Lack of inhibition of glutathione reductase by unnitrated derivatives of nitrofurantoin. Biochem Biophys Res Commun 92: 1313–1319. 10.1016/0006-291X(80)90429-5 CASPubMedWeb of Science®Google Scholar Docampo R, Mason RP, Mottley C. Muniz RPA (1981): Generation of free radicals induced by nifurtimox in mammalian tissues. J Biol Chem 256: 10930–10933. 10.1016/S0021-9258(19)68534-0 CASPubMedWeb of Science®Google Scholar Docampo R, Stoppani AOM (1979): Generation of superoxide anion and hydrogen peroxide induced by nifurtimox in Trypanosoma cruzi. Arch Biochem Biophys 179: 317–321. 10.1016/0003-9861(79)90251-0 Web of Science®Google Scholar Ebringer L, Konicek J, Konichkova-Radochova M (1979): The mutagenic action of 5-nitro-2-furaldehyde on Mycobacterium phlei. Acta FRN Univ Comen Microbiol VII: 33–41. Google Scholar Ebringer L, Subik J, Lahitova N, Trubacik S, Horvathova R, Siekel P, Krajcovic J (1982): Mutagenic effects of two nitrofuran food preservatives. Neoplasma (Bratislava) 29: 675–684. CASPubMedWeb of Science®Google Scholar Fridovich I (1978): The biology of oxygen radicals. Science 201: 875–880. 10.1126/science.210504 CASPubMedWeb of Science®Google Scholar Fujii T (1980): Short communication. Somatic mutations induced by furylfuramide (AF-2) in maize and soybean. J Genet 55: 241–245. CASWeb of Science®Google Scholar Goodman DR, Hakkinen PJ, Nemenzo JH, Vore M (1977): Mutagenic evaluation of nitrofuran derivatives in Salmonella typhimurium, by the micronucleus test and by in vivo cytogenetics. Mutat Res 48: 295–306. 10.1016/0027-5107(77)90172-5 CASPubMedWeb of Science®Google Scholar Gounot AM, Brevet C, Videz S (1979): Les nitrofurannes: Mecanismes d'action. Ann Pharm Fr 37: 421–428. CASPubMedWeb of Science®Google Scholar Green MHL, Rogers AM, Muriel WJ, Ward AC, McCalla DR (1977): Use of a simplified fluctuation test to detect and characterize mutagenesis by nitrofurans. Mutat Res 44: 139–143. 10.1016/0027-5107(77)90122-1 CASPubMedWeb of Science®Google Scholar Hoener BA, Patterson SE (1981): Nitrofurantoin disposition. Clin Pharmacol Ther 29: 808–816. 10.1038/clpt.1981.115 CASPubMedWeb of Science®Google Scholar Holtzman JL (1981): Minireview. Role of reactive oxygen and metabolite binding in drug toxicity. Life Sci 30: 1–9. 10.1016/0024-3205(82)90629-4 Web of Science®Google Scholar Holtzman JL, Crankshaw DL, Peterson FJ, Polnaszek CF (1981): The kinetics of the aerobic reduction of nitrofurantoin by NADPH-cytochrome P-450(c) reductase. Mol Pharmacol 20: 669–673. CASPubMedWeb of Science®Google Scholar Howard PC, Beland FA (1982): Xanthine oxidase catalyzed binding of 1-nitropyrene to DNA. Biochem Biophys Res Commun 104: 727–732. 10.1016/0006-291X(82)90697-0 CASPubMedWeb of Science®Google Scholar Jenkins ST, Bennett PN (1976): Effect of mutations in DNA repair pathways on the sensitivity of E coli K12 strains to nitrofurantoin. J Bacteriol 125: 1214–1216. CASPubMedWeb of Science®Google Scholar Jonen HG, Kaufman I (1980): Enhanced biotransformation of nitrofurantoin rats after induction with 3-methylcholanthrene or naphthoflavone. Biochem Pharmacol 29: 263–266. 10.1016/0006-2952(80)90340-8 CASPubMedWeb of Science®Google Scholar Kalyanaraman B, Mason RP, Rowlett R, Kispert LD (1981): An electron spin resonance investigation and molecular orbital calculation of the anion radical intermediate in the enzymatic cis-trans isomerization of furylfuramide, a nitrofuran derivative of ethylene. Biochim Biophys Acta 660: 102–109. 10.1016/0005-2744(81)90114-5 CASPubMedWeb of Science®Google Scholar Karmali RA (1980): Prostaglandins and cancer. Prostaglandins Med 5: 11–28. 10.1016/0161-4630(80)90086-5 CASPubMedWeb of Science®Google Scholar Kato R, Takahashi A, Oshima T (1970): Characteristics of nitro reduction of the carcinogenic agent, 4-nitroquinoline N-oxide. Biochem Pharmacol 19: 45–55. 10.1016/0006-2952(70)90328-X PubMedGoogle Scholar Kelley M, Baden JM (1980): Oxygen mutagenicity. Mutat Res 77: 185–188. 10.1016/0165-1218(80)90137-8 CASPubMedWeb of Science®Google Scholar Knox RJ, Knight RC, Edwards DI (1981): Misonidazole-induced thymidine release from DNA. Biochem Pharmacol 30: 1925–1929. 10.1016/0006-2952(81)90201-X CASPubMedWeb of Science®Google Scholar Koch RL, Chrystal EJT, Beaulieu BB Jr, Goldman P (1979): Acetamide—A metabolite of metronidazole formed by the intestinal flora. Biochem Pharmacol 28: 3611–3615. 10.1016/0006-2952(79)90407-6 CASPubMedWeb of Science®Google Scholar Lu C, McCalla DR, Bryant DW (1979): Action of nitrofurans on E coli: Mutation and induction and repair of daughter-strand gaps in DNA. Mutat Res 67: 133–144. 10.1016/0165-1218(79)90124-1 CASPubMedWeb of Science®Google Scholar Lu C, McCalla DR (1978): Action of some nitrofuran derivatives on glucose metabolism, ATP levels, and macromolecule synthesis in Escherichia coli. Can J Microbiol 24: 650–657. 10.1139/m78-109 CASPubMedWeb of Science®Google Scholar Leskovac V, Popovic M (1980): Mechanism of reduction of nitrofurantoin on liver microsomes. Pharmacol Res Commun 12: 13–27. 10.1016/S0031-6989(80)80058-0 CASPubMedWeb of Science®Google Scholar Maher VM, Curren RD, Ouellette LM, McCormick JJ (1976): Effect of DNA repair on the frequency of mutations induced in human cells by ultraviolet irradiation and by chemical carcinogens. In P Magee, S Takayama, T Sugimura, T Matsushima (eds): " Fundamentals in Cancer Prevention." Tokyo: University of Tokyo Press, pp 363–382. Google Scholar Mahood JS, Willson RL (1981): Cytotoxicity of metronidazol (Flagyl) and misonidazole (Ro-07–0582): Enhancement by lactate. Br J Cancer 43: 350–354. 10.1038/bjc.1981.55 CASPubMedWeb of Science®Google Scholar Maier P, Philpot RM, Mohn GR, Mailing HV (1979): Influence of subcellular fractions of mammalian testes on the mutagenic activity of nitrofurans toward Escherichia coli. Mutat Res 63: 233–243. 10.1016/0027-5107(79)90056-3 CASPubMedWeb of Science®Google Scholar McCalla DR (1979): Nitrofurans. In FE Hahn (ed): " Mechanism of Action of Antibacterial Agents." Berlin: Springer Verlag, Vol 1, pp 176–213. 10.1007/978-3-642-46403-4_11 Google Scholar McCalla DR (1981): Metabolic activation of nitroheterocyclic compounds in bacterial and mammalian cells. In HP Stich, RHC San (eds): " Short-Term Tests for Chemical Carcinogens." Berlin: Springer-Verlag, pp 36–47. 10.1007/978-1-4612-5847-6_4 Google Scholar McCalla DR, Reuvers A, Kaiser C (1970): Mode of action of nitrofurazone. J Bacteriol 104: 1126–1134. 10.1128/jb.104.3.1126-1134.1970 CASPubMedWeb of Science®Google Scholar McCalla DR, Reuvers A, Kaiser C (1971): Breakage of bacterial DNA by nitrofuran derivatives. Cancer Res 31: 2184–2188. CASPubMedWeb of Science®Google Scholar McCalla DR, Voutsinos D, Olive PL (1975): Mutagen screening with bacteria: Niridazole and nitrofurans. Mutat Res 31: 31–37. 10.1016/0165-1161(75)90060-6 CASPubMedWeb of Science®Google Scholar McCalla DR, Olive P, Tu Y, Fan ML (1975): Nitrofurazone-reducing enzymes in E coli and their role in drug activation in vivo. Can J Microbiol 21: 1484–1491. 10.1139/m75-220 CASPubMedWeb of Science®Google Scholar McCalla DR, Arlett CR, Broughton B (1978a): The action of AF2 on cultured hamster and human cells under aerobic and hypoxic conditions. Chem Biol Interact 21: 89–102. 10.1016/0009-2797(78)90070-4 CASPubMedWeb of Science®Google Scholar McCalla DR, Kaiser C, Green MHL (1978b): The genetics of nitrofurazone resistance in Escherichia coli. J Bacteriol 133: 10–16. CASPubMedWeb of Science®Google Scholar McCalla DR, Voutsinos D (1974): On the mutagenicity of nitrofurans. Mutat Res 26: 3–16. 10.1016/S0027-5107(74)80065-5 CASPubMedWeb of Science®Google Scholar McCann J, Spingarn NE, Kobori J, Ames BN (1975): Detection of carcinogens as mutagens: Bacterial tester strains with R factor plasmids. Proc Natl Acad Sci USA 72: 979–983. 10.1073/pnas.72.3.979 CASPubMedWeb of Science®Google Scholar Mermelstein R, Kiriazides DK, Butler M, McCoy EC, Rosenkranz HS (1981): The extraordinary mutagenicity of nitropyrenes in bacteria. Mutat Res 89: 187–196. 10.1016/0165-1218(81)90236-6 CASPubMedWeb of Science®Google Scholar Messier F, Lu C, Andrews P, McCarry B, Quillium M, McCalla DR (1981): Metabolism of 1-nitropyrene and formation of DNA-adducts in Salmonella typhimurium. Carcinogenesis 2: 1007–1011. 10.1093/carcin/2.10.1007 CASPubMedWeb of Science®Google Scholar Mohindra JK, Rauth AM (1976): Increased cell killing by metronidazole and nitrofurazone of hypoxic compared to aerobic mammalian cells. Cancer Res 36: 930–936. CASPubMedWeb of Science®Google Scholar Moody CS, Hassan HM (1982): Mutagenicity of oxygen free radicals. Proc Natl Acad Sci USA 79: 2855–2859. 10.1073/pnas.79.9.2855 CASPubMedWeb of Science®Google Scholar Nakamura Y, Fukushima H, Tomita I, Kimura I (1982): Mutagenicity of nifurpirinol (P-7138) in Escherichia coli WP2 and Salmonella typhimurium TA 100. Mutat Res 104: 61–66. 10.1016/0165-7992(82)90121-X CASPubMedWeb of Science®Google Scholar Nocentini S, Coppey J, Buisson J-P, Royer R (1981): Inhibition of DNA synthesis in relation to enhanced survival of UV-damaged herpes virus in monkey cells treated by a variety of 2-nitronaphthofurans. Mutat Res 90: 125–135. 10.1016/0165-1218(81)90075-6 CASPubMedWeb of Science®Google Scholar Nuhrich A, Cantet P, Dargelos R, Devaux G (1978): Etude pharmacologique des arylpropenones nitrofuranniques: Quelques aspects de leur activite cytotoxique. Bull Soc Pharm Bordeaux 117: 102–114. Google Scholar Ohgake H, Matsukura N, Morino K, Kawachi T, Sugimura T, Morita K, Tokowa H, Hirota T (1982): Carcinogenicity in rats of the mutagenic compounds 1-nitropyrene and 3-nitrofluoranthene. Cancer Lett 15: 1–7. 10.1016/0304-3835(82)90068-4 PubMedWeb of Science®Google Scholar Ohnishi T, Ohashi Y, Nozu K, Inoki S (1980): Mutagenicity of Nifurtimox in Escherichia coli. Mutat Res 77: 241–244. 10.1016/0165-1218(80)90056-7 CASPubMedWeb of Science®Google Scholar Olivard J, Rose GM, Klein GM, Heotis JP (1976): Metabolic and photochemical hydroxylation of 5-nitro-2-furancarboxaldehyde derivatives. J Med Chem 19: 729–731. 10.1021/jm00227a032 CASPubMedWeb of Science®Google Scholar Olive PL, Durand RE (1981): Uptake and mutagenicity of AF-2 in Chinese hamster V-79 spheroids under aerobic and hypoxic conditions. Environ Mutagen 3: 659–670. 10.1002/em.2860030608 CASWeb of Science®Google Scholar Olive PL, McCalla DR (1975): Damage to mammalian cell DNA by nitrofurans. Cancer Res 35: 781–784. CASPubMedWeb of Science®Google Scholar Olive PL, McCalla DR (1977): Cytotoxicity and DNA damage to mammalian cells by nitrofurans. Chem Biol Interact 16: 223–233. 10.1016/0009-2797(77)90131-4 CASPubMedWeb of Science®Google Scholar Ong TM (1974): Mutagenicity of nitrofuran derivatives in Neurospora crassa. Mutat Res 26: 449. Web of Science®Google Scholar Ong TM, deSerres FJ (1981): Genetic analysis of ad-3 mutants induced by AF-2 and two other nitrofurans in Neurospora crassa. Environ Mutagen 3: 151–158. 10.1002/em.2860030206 CASPubMedWeb of Science®Google Scholar Paine AJ (1978): Excited states of oxygen in biology: Their possible involvement in cytochrome P450 linked oxidations as well as in the induction of the P450 system by many diverse compounds. Biochem Pharmacol 27: 1805–1813. 10.1016/0006-2952(78)90023-0 CASPubMedWeb of Science®Google Scholar Paterson MC, Smith PJ (1979): Ataxia telangiectasia: An inherited human disorder involving hyper-sensitivity to ionizing radiation and related DNA-damaging chemicals. Ann Rev Genet 13: 291–318. 10.1146/annurev.ge.13.120179.001451 CASPubMedWeb of Science®Google Scholar Peterson FJ, Mason RP, Hovsepian J, Holtzman JL (1979): Oxygen-sensitive and insensitive nitro reduction by Escherichia coli and rat hepatic microsomes. J Biol Chem 254: 4009–4014. CASPubMedWeb of Science®Google Scholar Pienta RJ, Lebhertz WB III, Takayama S (1978): Malignant transformation of cryopreserved early passage Syrian golden hamster cells by 2-(2-furyl)-3-(5-nitro-2-furyl)-acrylamide. Cancer Lett 5: 245–251. 10.1016/S0304-3835(78)80021-4 CASPubMedWeb of Science®Google Scholar Pitts JN Jr (1979): Photochemical and biological implications of the atmospheric reactions of amines and benzo(a)pyrene. Phil Trans R Soc Lond 290: 551–576. 10.1098/rsta.1979.0014 CASWeb of Science®Google Scholar Pitts JN Jr, Van Cauwenberghe KA, Grosjean D, Schmid JP, Fitz DR, Belser WL Jr, Knudson GB, Hynds PM (1978): Atmospheric reactions of polycyclic aromatic hydrocarbons: Facile formation of mutagenic nitro derivatives. Science 202: 515–519. 10.1126/science.705341 PubMedWeb of Science®Google Scholar Prior JT, Ferguson JH (1950): Cytotoxic effects of a nitrofuran on the rat testis. Cancer 3: 1062–1072. 10.1002/1097-0142(1950)3:6<1062::AID-CNCR2820030617>3.0.CO;2-C CASPubMedWeb of Science®Google Scholar Rosenkranz HS, McCoy EC, Sanders DR, Butler M, Kiriazides D, Mermelstein R (1980): Nitropyrenes: Isolation, identification and reduction of mutagenic impurities in carbon black and toners. Science 209: 1039–1043. 10.1126/science.6996095 CASPubMedWeb of Science®Google Scholar Rosenkranz HS, Speck T (1977): Activation of nitrofurantoin to a mutagen by rat liver nitroreductase. Biochem Pharmacol 25: 1555–1556. 10.1016/0006-2952(76)90080-0 PubMedWeb of Science®Google Scholar Rosin MP, Stich HF (1978): Inhibitory effect of cysteine on the mutagenic acitivities of several carcinogens. Mutat Res 54: 73–81. 10.1016/0165-1161(78)90137-1 CASPubMedWeb of Science®Google Scholar Roxe DM, Siew C, Siddiqui F, Lang I, Rao GS (1980): Mutagenic activity of urinary pigments from patients on antischistosomal therapy with niridazole. Mutat Res 77: 367–370. 10.1016/0165-1218(80)90010-5 CASPubMedWeb of Science®Google Scholar Russo P, Pala M, Nicolo G, Santi L, Parodi S (1982): DNA damage in liver of rats treated with nitrofurantoin. Mutat Res 105: 377–382. 10.1016/0165-7992(82)90110-5 CASPubMedWeb of Science®Google Scholar Salmeen I, Durisin AM, Prater TJ, Riley T, Schuetzle D (1982): Contribution of 1-nitropyrene to direct acting ames assay mutagenicities of diesel particulate extracts. Mutat Res 104: 17–23. 10.1016/0165-7992(82)90114-2 CASPubMedWeb of Science®Google Scholar Sasame HA, Boyd MR (1979): Superoxide and hydrogen peroxide production and NADPH oxidation stimulated by nitrofurantoin in lung microsomes: Possible implications for toxicity. Life Sci 24: 1091–1096. 10.1016/0024-3205(79)90042-0 CASPubMedWeb of Science®Google Scholar Saska J, Koukalova B, Ebringer L (1981): Mutagenic activities of simple nitrofuran derivatives. I. Comparison of related compounds in the phage inductest, chloroplast-bleaching and bacterial-repair and mutagenicity tests. Mutat Res 81: 21–26. PubMedWeb of Science®Google Scholar Shirai T, Wang CY (1980): Enhancement of sister-chromatid exchange in Chinese hamster ovary cells by nitrofurans. Mutat Res 79: 345–350. 10.1016/0165-1218(80)90159-7 CASPubMedWeb of Science®Google Scholar Slamenová D, Mazáriova O (1979): The influence of 5-nitro-2-furyl acrylic acid on human fibroblasts cultivated in vitro. Neoplasma 26: 267–274. PubMedWeb of Science®Google Scholar Spano MA, Takahashi CS (1918): Genetic effects of nifurtimox on Drosophila melanogaster. Wistar rats and Allium cepa. Rev Brasil Genet IV 3: 357–366. Google Scholar Spielberg SP, Gordon GB (1981): Nitrofurantoin cytotoxicity: In vitro assessment of risk based on glutathione metabolism. J Clin Invest 67: 37–41. 10.1172/JCI110030 CASPubMedWeb of Science®Google Scholar Sram RJ, Rossner P, Zhurkov VS, Kodytkova I (1979): Mutagenicity studies with nitrofurans. I. Mutagenicity of nitrofurylacrylic acid for mammals. Mutat Res 68: 367–380. 10.1016/0165-1218(79)90168-X CASPubMedWeb of Science®Google Scholar Steinhoff D, Grundmann E (1972): Test for carcinogenicity of nifurtimox on oral and subcutaneous administration to rats. Arzneim Forsch 22: 1607–1612. CASPubMedWeb of Science®Google Scholar Stirpe F, Della Corte E (1969): The regulation of rat liver xanthine oxidase: Conversion in vitro of the enzyme activity from dehydrogenase (type D) to oxidase (type O). J Biol Chem 244: 3855–3863. CASPubMedWeb of Science®Google Scholar Sturdik E, Drobnica L, Balaz S, Marko V (1979): Reaction of vinylfurans with sulphydryl and amino groups. Biochem Pharmacol 28: 2525–2530. 10.1016/0006-2952(79)90020-0 CASPubMedWeb of Science®Google Scholar Sugimura T, Okabe K, Nagao M (1966): The metabolism of 4-nitroquinoline-1-oxide. a carcinogen III. An enzyme catalyzing the conversion of 4-nitroquinoline-1-oxide to 4-hydroxyaminoquinoline-1-oxide in rat liver and hepatomas. Cancer Res 26: 1717–1721. CASPubMedWeb of Science®Google Scholar Swaminathan S, Erturk E, Bryan GT (1981): Mutagenicity, carcinogenicity, distribution and nitroreduction of 4-(5-nitro-2-furyl)thiazole in the rat. Cancer Res 41: 2648–2653. CASPubMedWeb of Science®Google Scholar Swaminathan S, Lower GM Jr, Bryan GT (1980): Reductive metabolism of the carcinogen 4-(5-nitro-2-furyl)thiazole to 1-(4-thiazolyl)-3-cyano-1-propanone by rat liver subcellular fractions. Biochem Pharmacol 29: 3285–3292. 10.1016/0006-2952(80)90305-6 CASPubMedWeb of Science®Google Scholar Tatsumi K, Doi T, Koga N, Yoshimura H, Koga H, Horiuchi T (1981): Studies on oxygen-insensitive nitrofuran reductase in Escherichia coli B/r. Jpn J Biochem 89: 855–859. CASPubMedWeb of Science®Google Scholar Tatsumi K, Koga N, Kitamura S, Yoshimura H, Wardman P, Kato Y (1979): Enzymic cis-trans isomerization of nitrofuran derivatives. Isomerizing activity of xanthine oxidase, lipoyl dehydrogenase. DT-diaphorase and liver microsomes. Biochem Biophys Acta 567: 75–87. 10.1016/0005-2744(79)90174-8 CASPubMedWeb of Science®Google Scholar Tatsumi K, Ou T, Yamada H, Yoshimura H, Koga H, Horiuchi T (1978): Isolation and identification of the metabolite of N-(5-nitro-2-furfurylidene)-3-amino-2-oxazolidone (furazolidone). J Pharm Dyn 1: 256–261. 10.1248/bpb1978.1.256 CASGoogle Scholar Tatsumi K, Yamada H, Yoshimura H, Kawazoe Y (1981): Metabolism of furazolidone by milk xanthine oxidase and rat liver 9000g supernatant: Formation of a unique nitrofuran metabolite and an aminofuran derivative. Arch Biochem Biophys 208: 167–174. 10.1016/0003-9861(81)90136-3 CASPubMedWeb of Science®Google Scholar Tatsumi K, Yamaguchi T, Yoshimura H (1973b): Metabolism of drugs. LXXX. The metabolic fate of nitrofuran derivatives. (3) Studies of enzymes in small intestinal mucosa of rat catalysing degradation of nitrofuran derivatives. Chem Pharmacol Bull 21: 622–628. 10.1248/cpb.21.622 CASPubMedWeb of Science®Google Scholar Tazima Y (1979): Consequences of the AF-2 incident in Japan. Environ Health Perspect 29: 183–187. 10.2307/3429062 CASPubMedWeb of Science®Google Scholar Tazima Y, Kada T, Murakami A (1975): Mutagenicity of nitrofuran derivatives, including furylfuramide, a food preservative. Mutat Res 32: 55–80. 10.1016/0165-1110(75)90011-1 CASPubMedWeb of Science®Google Scholar Thompson LH, Rubin JS, Cleaver JE, Whitmore GF, Brookman KA (1980): A screening method for isolating DNA repair-deficient mutants of CHO cells. Somat Cell Genet 6: 391–405. 10.1007/BF01542791 CASPubMedWeb of Science®Google Scholar Varghese AJ, Whitmore GF (1983): Modification of guanine derivatives by reduced 2-nitromidazolcs. Cancer Res 43: 78–82. CASPubMedWeb of Science®Google Scholar Wang CY, Behrens BC. Ichikawa M, Bryan GT (1974): Nitroreduction of 5-nitrofuran derivatives by rat liver xanthinc oxidase and reduced nicotinamide adeninc dinuclcotidc phosphate-cytochromc c reductase. Biochem Pharmacol 23: 3395–3404. 10.1016/0006-2952(74)90342-6 CASPubMedWeb of Science®Google Scholar Wang CY. Chiu CW, Kaiman B, Bryan GT (1975): Identification of 2-methyl-4-(5-amino-2-furyl)thiazole as the reduced metabolite of 2-methyl-4-(5-nitro-2-furyl)thiazolc. Biochcm Pharmacol 24: 291–293. 10.1016/0006-2952(75)90291-9 CASPubMedWeb of Science®Google Scholar Wang CY. Hayashida S. Pamukcu AM. Bryan GT (1976): Enhancing effect of allopurinol on the induction of bladder cancer in rats by N-(4-(5-nitro-2-furyl)-2-thiazolyl)formamidc. Cancer Res 36: 1551–1555. CASPubMedWeb of Science®Google Scholar Weill-Thevenet N. Buisson J-P. Royer R. Hofnung M (1982): Genetic toxicology studies with 2-nitro-benzofurans and 2-nitroaphthofurans. Mutat Res 104: 1–8. 10.1016/0165-7992(82)90112-9 CASPubMedWeb of Science®Google Scholar Wentzell B. McCalla DR (1980): Formation and excision of nitrofuran-DNA adducts in Escherichia coli. Chem Biol Interact 31: 133–150. 10.1016/0009-2797(80)90001-0 CASPubMedWeb of Science®Google Scholar Westfall BB (1943): The reduction of symmetrical trinitrotoluene by a succinic dehydrogenase preparation. J Pharmacol Exp Thcr 79: 23–26. CASGoogle Scholar Witkin EM (1976): Ultraviolet mutagcncsis and inducible DNA repair in Escherichia coli. Bacteriol Rev 40: 869–907. CASPubMedWeb of Science®Google Scholar Xu XB. Nachtman JP. Jin ZL. Wei ET. Rappaport SM. Burlingame AL (1982): Isolation and identification of mutagenic nitro-PAH in diesel-exhaust particulates. Anal Chim Acta 136: 163–174. 10.1016/S0003-2670(01)95375-9 CASWeb of Science®Google Scholar Yahagi T. Nagao M. Hara K. Matsushima T. Sugimura T. Bryan GT (1974): Relationships between the carcinogenic and mutagcnic or DNA-modifying effects of nitrofuran derivatives, including 2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide. a food additive. Cancer Res 34: 2266–2273. CASPubMedWeb of Science®Google Scholar Zenser TV. Mattammal MB. Davis BB (1980a): Mechanism of FANFT co-oxidation by prostaglandin endoperoxide synthetase. J Pharmacol Exp Ther 214: 312–317. CASPubMedWeb of Science®Google Scholar Zenser TV. Mattammal MB. Davis BB (1980b): Metabolism of N-(4-(5-nitro-2-furyl)-2-thiazolyl)formamide by prostaglandin endoperoxide synthetase. Cancer Res 40: 114–118. CASPubMedWeb of Science®Google Scholar Zenser TV. Mattammal MB. Armbrecht HJ. Davis BB (1980c): Benzidine binding to nucleic acids mediated by the peroxidative activity of prostaglandin endoperoxide synthetase. Cancer Res 40: 2839–2845. CASPubMedWeb of Science®Google Scholar Zenser TV. Balasubramanian TM. Mattammal MB. Davis BB (1981): Transport of the renal carcinogen 3-Hydroxymethyl-1-(3-(5-nitro-2-furyl)allydidene)amino)hydantoin by renal cortex and co-oxidative metabolism by prostaglandin endoperoxide synthetase. Cancer Res 41: 2032–2037. CASPubMedWeb of Science®Google Scholar Citing Literature Volume5, Issue51983Pages 745-765 ReferencesRelatedInformation