Skip to main content
PMC home page
Japanese Journal of Cancer Research : Gann logoLink to Japanese Journal of Cancer Research : Gann
. 1989 Aug;80(8):691–697. doi: 10.1111/j.1349-7006.1989.tb01698.x

Molecular Basis of 4‐Nitroquinoline 1‐Oxide Carcinogenesis

Bernard Bailleul 1, Pierre Daubersies 1, Sylvie Galiègue‐Zouitina 1, Marie‐Henriette Loucheux‐Lefebvre 1
PMCID: PMC5917829  PMID: 2511172

Full Text

The Full Text of this article is available as a PDF (436.5 KB).

REFERENCES

  • 1. ) Nakahara , W. , Fukuoka , F. and Sugimura , T.Carcinogenic action of 4‐nitroquinoline‐N‐oxide . Gann , 48 , 129 – 137 ( 1957. ). [PubMed] [Google Scholar]
  • 2. ) Mori , K. and Yasuno , A.Induction of pulmonary tumors in mice by subcutaneous injection of 4‐nitroquinoline N‐oxide . Gann , 52 , 52 – 149 ( 1961. ). [PubMed] [Google Scholar]
  • 3. ) Hayashi , Y. and Hasegawa , T.Experimental pancreatic tumor in rats after intravenous injection of 4‐hydroxy‐aminoquinoline 1‐oxide . Gann , 62 , 329 – 330 ( 1971. ). [PubMed] [Google Scholar]
  • 4. ) Mori , K.Carcinoma of the glandular stomach of mice by instillation of 4‐nitroquinoline 1‐oxide , Gann , 58 , 389 – 393 ( 1967. ). [PubMed] [Google Scholar]
  • 5. ) Endo , H. , Ono , T. and Sugimura , T.Chemistry and biological actions of 4‐nitroquinoline 1‐oxide . Recent Results Cancer Res. , 34 , 1 – 99 ( 1971. ). [Google Scholar]
  • 6. ) Sugimura , T.The nitroquinolines . In “ Carcinogenesis, A Comprehensive Survey ,“ Vol. 6 , pp. 1 – 153 ( 1981. ). Raven Press; , New York ). [PubMed] [Google Scholar]
  • 7. ) Nagao , M. and Sugimura , T.Molecular biology of the carcinogen, 4‐nitroquinoline 1‐oxide . Adv. Cancer Res. , 23 , 131 – 169 ( 1976. ). [DOI] [PubMed] [Google Scholar]
  • 8. ) Miller , J. A.Carcinogenesis by chemicals: an overview. G.H.A. Clowes Memorial Lecture . Cancer Res. , 30 , 559 – 576 ( 1970. ). [PubMed] [Google Scholar]
  • 9. ) Tada , M. and Tada , M.Main binding sites of the carcinogen, 4‐nitroquinoline 1‐oxide in nucleic acids . Biochim. Biophys. Acta , 454 , 558 – 566 ( 1976. ). [DOI] [PubMed] [Google Scholar]
  • 10. ) Ames , B. N. , Lee , F. D. and Durston , W. E.An improved bacterial test system for the detection and classification of mutagens and carcinogens . Proc. Natl. Acad. Sci. USA , 70 , 782 – 786 ( 1973. ). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 11. ) Coulondre , C. and Miller , J. M.Genetic studies of the lac represser. IV Mutagenic specificity in the lac I gene of Escherichia coll J. Mol Biol. , 117 , 577 – 606 ( 1977. ). [DOI] [PubMed] [Google Scholar]
  • 12. ) Prakash , L. , Stewart , J. W. and Sherman , F.Specific induction of transitions and transversions of G‐C base pairs by 4‐nitroquinoline‐1‐oxide in iso‐1‐cytochrome c mutants of yeast . J. Mol. Biol. , 85 , 51 – 65 ( 1974. ). [DOI] [PubMed] [Google Scholar]
  • 13. ) Reddy , E. P. , Reynolds , R. K. , Santos , E , and Barbacid , M.A point mutation is responsible for the acquisition of transforming properties by the T24 human bladder carcinoma . Nature , 300 , 149 – 152 ( 1982. ). [DOI] [PubMed] [Google Scholar]
  • 14. ) Bailleul , B. , Brown , K. , Ramsden , M. , Akhurst , R. J. , Fee , F. and Balmain , A.Chemical induction of oncogene mutations and growth factor activity in mouse skin Carcinogenesis . In “ Environmental Health Perspectives ,“ ed. Upton A. , Niehs Press; , North Carolina . In press . [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 15. ) Okabayashi , T. and Yoshimoto , A.Reduction of 4‐nitroquinoline 1‐oxide by microorganism . Chem. Pharm. Bull. , 10 , 1221 – 1226 ( 1962. ). [DOI] [PubMed] [Google Scholar]
  • 16. ) Shirasu , Y.Further studies on carcinogenic action of 4‐hydroxyaminoquinoline 1‐oxide . Gann , 54 , 487 – 495 ( 1963. ). [PubMed] [Google Scholar]
  • 17. ) Kato , R. , Takahashi , A. and Oshima , T.Characteristics of nitro reduction of the carcinogenic agent, 4‐nitroquinoline 1‐oxide . Biochem. Pharmacol. , 19 , 45 – 55 ( 1970. ). [DOI] [PubMed] [Google Scholar]
  • 18. ) Sugimura , T. , Okabe , K. and Nagao , M.The metabolism of 4‐nitroquinoline 1‐oxide, a carcinogen. III. An enzyme catalysing the conversion of 4‐nitroquinoline‐1‐oxide to 4‐hydroxyaminoquinoline 1‐oxide in rat liver and hepa‐tomas . Cancer Res. , 26 , 1717 – 1721 ( 1966. ). [PubMed] [Google Scholar]
  • 19. ) Mori , K. , Kondo , M. , Koibuchi , E. and Hashimoto , A.Induction of lung cancer in mice by injection of 4‐hydroxyaminoquinoline 1‐oxide . Gann , 58 , 105 – 106 ( 1961. ). [PubMed] [Google Scholar]
  • 20. ) Mori , K. and Ohta , A.Carcinoma of the glandular stomach of mice by 4‐hydroxyaminoquinoline 1‐oxide . Gann , 58 , 551 – 554 ( 1967. ). [PubMed] [Google Scholar]
  • 21. ) Tada , M. and Tada , M.Seryl‐tRNA synthetase and activation of the carcinogen 4‐nitroquinoline‐1‐oxide . Nature , 255 , 510 – 512 ( 1975. ). [DOI] [PubMed] [Google Scholar]
  • 22. ) Enomoto , M. , Sato , K. , Miller , E. C. and Miller , J. A.Reactivity of the diacetyl derivative of the carcinogen 4HAQO with DNA, RNA, and other nucleophiles . Life Sci. , 7 , 1025 – 1032 ( 1968. ). [DOI] [PubMed] [Google Scholar]
  • 23. ) Galiègue , S. , Bailleul , B. and Loucheux‐Lefebvre , M. H.Reactivity of the O,O'‐diacetyl derivative of the carcinogen 4‐hydroxyaminoquinoline 1‐oxide with DNA. Comparison with in vivo‐reacted DNA . Eur. J. Cancer , 16 , 1283 – 1287 ( 1980. ). [DOI] [PubMed] [Google Scholar]
  • 24. ) Bailleul , B. , Galiegue , S. and Loucheux‐Lefebvre , M. H.Adducts from the reaction of O,O'‐diacetyl or O‐acetyl derivatives of the carcinogen 4‐hydroxyaminoquinoline 1‐oxide with purine nucleosides . Cancer Res. , 41 , 4559 – 4565 ( 1981. ). [PubMed] [Google Scholar]
  • 25. ) Kawazoe , Y. , Ogawa , O. and Huang , G. F.Studies on chemical carcinogens. XVII. Structure of carcinogenic 4‐hydroxyaminoquinoline 1‐oxide derivatives . Tetrahedron , 36 , 2833 – 2838 ( 1980. ). [Google Scholar]
  • 26. ) Galiegue , S. , Bailleul , B. and Loucheux‐Lefebvre , M. H.In vitro DNA reaction with an ultimate carcinogen model of 4‐nitroquinoline 1‐oxide: the acetoxyaminoquinoline 1‐oxide. Enzymatic degradation of the modified DNA . Carcinogenesis , 4 , 249 – 254 ( 1983. ). [DOI] [PubMed] [Google Scholar]
  • 27. ) Galiègue‐Zouitina , S. , Bailleul , B. and Loucheux‐Lefebvre , M. H.Adducts from in vivo action of the carcinogen 4‐hydroxyaminoquinoline 1‐oxide in rats and from in vitro reaction of 4‐acetoxyaminoquinoline 1‐oxide with DNA and polynucleotides . Cancer Res. , 45 , 520 – 525 ( 1985. ). [PubMed] [Google Scholar]
  • 28. ) Kawazoe , Y. and Araki , M.Studies on chemical carcinogens. V. O,O'‐Diacetyl‐4‐hydroxyaminoquinoline 1‐oxide . Gann , 58 , 485 – 487 ( 1967. ). [PubMed] [Google Scholar]
  • 29. ) Kawazoe , Y.Chemistry of 4‐nitroquinoline 1‐oxide and related compounds . In “ Carcinogenesis, A Comprehensive Survey ,“ Vol. 6 . ed. Sugimura T. , pp. 1 – 24 ( 1981. ). Raven Press; , New York ). [PubMed] [Google Scholar]
  • 30. ) Kawazoe , Y. , Araki , M. , Huang , G. F. , Okamoto , T. , Tada , M , and Tada , M.Chemical structure of QAII, one of the covalently bound adducts of carcinogenic 4‐nitroquinoline 1‐oxide with nucleic acid bases of cellular nucleic acids . Chem. Phartn. Bull. , 23 , 3041 – 3043 ( 1975. ). [DOI] [PubMed] [Google Scholar]
  • 31. ) Tada , M. , Kohda , K. H. and Kawazoe , Y.Biomimetic preparation and structure determination of QG1, one of the quinoline‐DNA base adducts formed in cells treated with 4 ‐nitroquinoline 1‐oxide . Gann , 75 , 976 – 985 ( 1984. ). [PubMed] [Google Scholar]
  • 32. ) Galiègue‐Zouitina , S. , Bailleul , B. , Ginot , Y‐M. , Perly , B. , Vigny , P. and Loucheux‐Lefebvre , M. H.N‐2 guanyl and N‐6 adenyl arylation of chicken erythrocyte DNA by the ultimate carcinogen of 4‐nitroquinoline 1‐oxide . Cancer Res. , 46 , 1858 – 1863 ( 1986. ). [PubMed] [Google Scholar]
  • 33. ) Miller , E. C.Some current perspectives on chemical carcinogens in humans and experimental animals: presidential address . Cancer Res. , 38 , 1479 – 1496 ( 1978. ). [PubMed] [Google Scholar]
  • 34. ) Bailleul , B. , Galiègue , S. , Demeunynck , M. , Lhomme , M. F. , Lhomme , J. and Loucheux‐Lefebvre , M. H.Identification of 4‐acetoxyaminoquinoline from the hydrolysis of 1‐acetoxy‐4‐acetoxyimino‐ 1–4‐dihydroquinoline; in vitro and in vivo properties . Chem. Biol. Interact. , 43 , 87 – 98 ( 1983. ). [DOI] [PubMed] [Google Scholar]
  • 35. ) Purchase , I. F. , Longstaff , E. , Ashby , J. A. , Anderson , D. , Lefevre , P. A. and Westwood , F. R.Evaluation of six short term tests for detecting organic chemical carcinogens and recommendations for their use . Nature , 264 , 624 – 627 ( 1976. ). [DOI] [PubMed] [Google Scholar]
  • 36. ) Edwards , S. , Fielding , S. and Waters , R.The response to DNA damage induced by 4‐nitroquinoline 1‐oxide or its 3‐methyI derivative in xeroderma pigmentosum fibroblasts belonging to different complementation groups: evidence for different epistasis groups involved in the repair of large adducts in human DNA . Carcinogenesis , 9 , 1071 – 1075 ( 1987. ). [DOI] [PubMed] [Google Scholar]
  • 37. ) Mirzayans , R. and Waters , R.DNA damage and repair in human normal or xeroderma pigmentosum fibroblasts treated with 4‐nttroquinoline 1‐oxide or its 3‐methyl derivative . Carcinogenesis , 2 , 1359 – 1362 ( 1981. ). [DOI] [PubMed] [Google Scholar]
  • 38. ) Mirzayans , R. , Paterson , M. C. and Waters , R.Defective repair of a class of 4‐NQO‐induced alkali‐labile DNA lesions in xeroderma pigmentosum complementation group A fibroblasts . Carcinogenesis , 6 , 555 – 559 ( 1985. ). [DOI] [PubMed] [Google Scholar]
  • 39. ) Kohda , K , Tada , M. , Hakura , A. , Kasai , H. and Kawazoe , Y.Formation of 8‐hydroxyguanine residues in DNA treated with 4‐hydroxyaminoquinoline 1‐oxide and its related compounds in the presence of seryl‐AMP . Biochem. Biophys. Res. Commun. , 149 , 1141 – 1148 ( 1987. ). [DOI] [PubMed] [Google Scholar]
  • 40. ) Kohda , K. , Tada , M. , Kasai , H. , Nishimura , S. and Kawazoe , Y.Formation of 8‐hydroxyguanine residues in cellular DNA exposed to the carcinogen 4‐nitroquinoline 1‐oxide . Biochem. Biophys. Res. Commun. , 139 , 626 – 632 ( 1986. ). [DOI] [PubMed] [Google Scholar]
  • 41. ) Spodheim‐Maurizot , M. , Dreux , M. , Saint‐Ruf , G. and Leng , M.Alkaline stability of guanosine and some of its derivatives modified by the carcinogen N‐acetoxyacetyl‐aminofluorene . Nucleic Acids Res. , 7 , 2347 – 2356 ( 1979. ). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 42. ) Kriek , E. and Westra , J. G.Structural identification of the pyrimidine derivatives formed from N‐(deoxyguanosin‐8‐yl)‐2‐aminofluorene in aqueous solution at alkaline pH . Carcinogenesis , 1 , 459 – 68 ( 1980. ). [DOI] [PubMed] [Google Scholar]
  • 43. ) Kadlubar , F. F , Unruh , L. E. , Beland , F. A. , Straub , K. M. and Evans , F. E.In vitro reaction of the carcinogen N‐hydroxy‐2‐naphthylamine with DNA at the C‐8 and N2 atoms of guanine and at N6 atom of adenine . Carcinogenesis , 1 , 139 – 150 ( 1980. ). [DOI] [PubMed] [Google Scholar]
  • 44. ) Hertzog , P. G. , Lindsay‐Smith , J. R. and Garner , R. C.4NQO‐DNA Adducts and Biological Relevance Characterization of the imidazole ring‐opened forms of trans‐ 8,9‐dihydro ‐ 8 ‐ (7 ‐ guanyl) ‐ 9 ‐ hydroxyaflatoxin B1 . Carcinogenesis , 3 , 723 – 725 ( 1982. ). [DOI] [PubMed] [Google Scholar]
  • 45. ) Bailleul , B. , Galiègue‐Zouitina , S. , Perly , B. and Loucheux‐Lefebvre , M. H.Structural identification of the purine ring‐opened form of N‐(deoxyguanosin‐8‐yl)‐4‐aminoquinoline 1‐oxide . Carcinogenesis , 6 , 319 – 322 ( 1985. ). [DOI] [PubMed] [Google Scholar]
  • 46. ) Galiegue‐Zouitina , S. , Bailleul , B. and Loucheux‐Lefebvre , M. H.Guanyl‐C8‐arylamination of DNA by the ultimate carcinogen of 4‐nitroquinoline 1‐oxide: a spectrophoto‐metric titration . Anal. Biochem. , 138 , 454 – 457 ( 1984. ). [DOI] [PubMed] [Google Scholar]
  • 47. ) Fuchs , R. P. P.Arylamidation and arylation by the carcinogen N‐2‐fluorenyl‐acetamide; a sensitive and rapid chemical assay . Anal Biochem. , 91 , 663 – 673 ( 1978. ). [DOI] [PubMed] [Google Scholar]
  • 48. ) Walker , I. G.Alkaline sucrose sedimentation an analysis as an indicator of repair. Capability of xeroderma pigmentosum fibroblasts for repair of 4‐nitroquinoline 1‐oxide damage . Carcinogenesis , 2 , 691 – 695 ( 1981. ). [DOI] [PubMed] [Google Scholar]
  • 49. ) Bigalow , J. E. , Jacobson , B. E. and Nygaard , O. F.Metabolic reduction of 4‐nitroquinoline 1‐oxide and other radical‐producing drugs to oxygen‐reactive intermediates . Cancer Res. , 37 , 3306 – 3313 ( 1977. ). [PubMed] [Google Scholar]
  • 50. ) Walker , I. G.Lack of effect of 4‐nitroquinoline 1‐oxide on cellular NAD levels . Mutat. Res. , 139 , 155 – 159 ( 1984. ). [DOI] [PubMed] [Google Scholar]
  • 51. ) Regan , J. D. and Setlow , R. B.Two forms of repair in the DNA of human cells damaged by chemical carcinogens and mutagens . Cancel Res. , 34 , 3318 – 3325 ( 1974. ). [PubMed] [Google Scholar]
  • 52. ) Ikenaga , M. , Ichikawa‐Ryo , H. and Kondo , S.The major cause of inactivation and mutation by 4‐nitroquinoline‐1‐oxide in Escherichia coli: excisable 4NQO‐purine adducts . J. Mol. Biol. , 92 , 341 – 356 ( 1975. ). [DOI] [PubMed] [Google Scholar]
  • 53. ) Kuhnlein , V. , Penhoet , E. E. and Linn , S.An altered apurinic endonuclease activity in group A and group D xeroderma pigmentosum fibroblasts . Proc. Natl. Acad. Sci. USA , 73 , 1169 – 1173 ( 1976. ). [DOI] [PMC free article] [PubMed] [Google Scholar]
  • 54. ) Lindhal , T. and Anderson , A.Rate of chain breakage at apurinic sites in double‐stranded deoxyribonucleic acid . Biochemistry , 11 , 3618 ( 1972. ). [DOI] [PubMed] [Google Scholar]
  • 55. ) De Serres F. J. and Ashby ( ed ). “ Evaluation of Short‐term Tests for Carcinogens “ ( 1981. ). Elsevier/North Holland; , Amsterdam ). [Google Scholar]
  • 56. ) Fuchs , R. P. P. , Schwartz , N. and Daune , M. P.Hot spots of frameshift mutations induced by the ultimate carcinogen N‐acetoxy‐N‐ 2 ‐acetylaminofluorene . Nature , 294 , 657 – 659 ( 1981. ). [DOI] [PubMed] [Google Scholar]

Articles from Japanese Journal of Cancer Research : Gann are provided here courtesy of Wiley

RESOURCES