DNA adducts as biomarkers for oxidative and genotoxic stress from pesticides in crop plants

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 15, 2008, Pages 6751-6760

  Boerth, Donald W ^a   Eder, Erwin ^b   Stanks, John R ^a   Wanek, Paul ^b   Wacker, Mathias ^b   Gaulitz, Scott ^a   Skypeck, Daniel ^a   Pandolfo, Derek ^a   Yashin, Michael ^a  

^a UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

1,N 2 propanodeoxyguanosine adducts; 4 hydroxy 2 nonenal; 32P postlabeling; Carbaryl; Chlorothalonil; Diazinon; DNA adducts; Esfenvalerate; Genotoxicity; Hexenal; Oxidative stress; Pesticide; Pesticide formulation; Plant lipid peroxidation

Indexed keywords

BIOLOGICAL MARKER; MUTAGENIC AGENT; OXIDIZING AGENT; PESTICIDE; PHOSPHORUS;

ARTICLE; CROP; DNA ADDUCT; DRUG EFFECT; GENETICS; LIPID PEROXIDATION; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS;

BIOLOGICAL MARKERS; CROPS, AGRICULTURAL; DNA ADDUCTS; LIPID PEROXIDATION; MUTAGENS; OXIDANTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PESTICIDES; PHOSPHORUS RADIOISOTOPES;

CUCUMIS SATIVUS; CUCURBITA; GLYCINE MAX; VITACEAE;

EID: 50449089259     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf072816q     Document Type: Article

References (88)

1. McGregor, D. B.; Brown, L.; Cattanach, P.; Edwards, I.; McBride, D.; Riach, C.; Caspary, W. Responses of the L5178Y tk+/tk-mouse lymphoma cell forward mutation assay: III. 72 coded chemicals. Environ. Mol. Mutagen. 1988, 12, 85-154.
2. Beland, F. A.; Poirier, M. C. The pathobiology of neoplasia. In The Pathobiology of Neoplasia; Sirica, A. E., Ed.; Plenum: New York, 1989; pp 57-80.
3. Marnett, L. J.; Burcham, P. C. Endogenous DNA adducts: Potential and paradox. Chem. Res. Toxicol. 1993, 6, 771-785.
4. Bolognesi, C.; Taningher, M.; Parodi, S.; Santi, L. Quantitative predictivity of carcinogenicity of the autoradiographic repair test (primary hepatocyte cultures) for a group of 80 chemicals belonging to different chemical classes. Environ. Health Perspect. 1986, 70, 247-253.
5. Donalson, R. P.; Luster, D. G. Multiple forms of cytochromes P450. Plant Physiol. 1991, 96, 669-674.
6. Sandermann, H. Plant metabolism of xenobiotics. Trends Biochem. Sci. 1992, 17, 82-84.
7. 32P-postlabeling quantification of DNA adducts in vivo. Rec. Results Cancer Res. 1997, 143, 65-75.
8. Chaudhary, A. K.; Nokubo, M.; Reddy, G. R.; Yeola, S. N.; Morrow, J. D.; Blair, I. A.; Marnett, L. J. Detection of endogenous malondialdehyde- deoxyguanosine adducts in human liver. Science 1994, 265, 1580-1582.
9. Blair, I. A. Lipid hydroperoxide-mediated DNA damage. Exp. Gerontol. 2001, 36, 1473-1481.
10. Burcham, P. C. Genotoxic lipid peroxidation products: their DNA damaging properties and role in formation of endogenous DNA adducts. Mutagenesis 1998, 13, 565-574.
11. Carcinogenic Potency Database. Lawrence Berkeley Laboratory.
12. National Toxicology Program. National Cancer Institute.
13. 32P- Postlabeling detection of DNA adducts in mice treated with the herbicide Roundup. Environ. Mol. Mutagen. 1998, 31, 55-59.
14. Vulimiri, S. V.; Gupta, S.; Smith, C. V.; Moorthy, B.; Randerath, K. Rapid decreases in indigenous covalent DNA modifications (I-compounds) of male Fisher-344 rat liver DNA by diquat treatment. Chem.-Biol. Interact. 1995, 95, 1-16.
15. Munnia, A.; Puntoni, R.; Merlo, F.; Parodi, S.; Peluso, M. Exposure to agrochemicals and DNA adducts in Western Liguria, Italy. Environ. Mol. Mutagen. 1999, 34 (1), 52-56.
16. Andre, V.; Le Goff, J.; Pottier, D.; Lebailly, P.; Peluso, M.; Munnia, A.; Gauduchon, P. Evaluation of bulky DNA adduct levels after pesticide use: Comparison between open-field farmers and fruit growers. Toxicol. Environ. Chem. 2007, 89 (1), 125-139.
17. Dubois, M.; Grosse, Y.; Thome, J. P.; Kremers, P.; Pfohl-Leszkowicz, A. Metabolic activation and DNA-adducts detection as biomarkers of chlorinated pesticide exposures. Biomarkers 1997, 2 (1), 17-24.
18. Bolognesi, C.; Peluso, M.; Degan, P.; Rabboni, R.; Munnia, A.; Abbondandolo, A. Genotoxic effects of the carbamate insecticide, methomyl. II. In vivo studies with pure compound and the technical formulation, "Lannate 25. Environ. Mol. Mutagen. 1994, 24 (3), 235-242.
19. 32P-postlabeling. Mol. Cell. Biochem. 1997, 169 (1-2), 177-184.
20. Nelson, G. B.; Ross, J. A. DNA adduct formation by the pesticide Alachlor and its metabolite 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA). Bull. Environ. Contam. Toxicol. 1998, 60, 387-394.
21. Schneider, M.; Quistad, G. B.; Casida, J. E. N27-Bis(1-hydroxy-2- oxopropyl)-2′-dexyguanosine: Identical noncyclic adducts with 1,3-dichlorpropene epoxides and methylglyoxal. Chem. Res. Toxicol. 1998, 11, 1536-1542.
22. Brown, M.; Kimmel, E.; Casida, J. DNA adduct formation by alachlor metabolites. Life Sci. 1988, 43, 2087-2094.
23. Hedli, C. C.; Snyder, R.; Kinoshita, F. K.; Steinberg, M. Investigation of hepatic cytochrome P-450 enzyme induction and DNA adduct formation in male CD/1 mice following oral administration of toxaphene. J. Appl. Toxicol. 1998, 18 (3), 173-178.
24. Le Goff, J.; Andre, V.; Lebailly, P.; Pottier, D.; Perin, F.; Perin, O.; Gauduchon, P. Seasonal variations of DNA-adduct patterns in open field farmers handling pesticides. Mutat. Res. 2005, 587 (1-2), 90-102.
25. Laouedji, A.; Schenk, C.; Pfohl-Leszkowicz, A.; Keith, G.; Schontz, D.; Guillemaut, P.; Rether, B. Detection of DNA adducts in declining hop plants grown on fields formerly treated with heptachlor, a persistent insecticide. Environ. Pollut. 1995, 90 (3), 409-14.
26. Podwall, D.; Dresner, H. S.; Lipetz, J.; Steinberg, J. J. Variation in the deoxynucleotide composition between organic and nonorganic strawberries. Ecotoxicol. Environ. Saf. 1999, 44, 259-270.
27. Muniz, J. F.; McCauley, L.; Scherer, J.; Lasarev, M.; Koshy, M.; Kow, Y. W.; Nazar-Stewart, V.; Kisby, G. E. Biomarkers of oxidative stress and DNA damage in agricultural workers: A pilot study. Toxicol. Appl. Pharmacol. 2008, 227 (1), 97-107.
28. Treshow, M.; Anderson, F. K. Plant Stress from Air Pollution; John Wiley and Sons: New York, 1989; pp 87-120.
29. Weber-Lofti, F.; Obrecht-Pflumio, S.; Guillemaut, P.; Kleinpeter, J.; Dietrich, A. Specific plant DNA adducts as molecular biomarkers of genotoxic atmospheric environments. Mutat. Res. 2005, 581, 55-67.
30. Kuhns, L. J.; Haramaki, C.; Thompson, V. D. Screening herbicides for use on peach seed beds. Proc. Annu. Meet. Northeast Weed Sci. Soc. 1981, 35, 186-189.
31. Cain, N. P. Effect of selected herbicides on cranberry vine growth, yield and weed control. Proc. 40th Annu. Meet. Northeastern Weed Sci. Soc. 1986, 156.
32. Devlin, R. M.; Demoranville, I. E. Influence of the herbicide R-74565 on cranberry fruit development. Hort. Sci. 1973, 8, 400.
33. Devlin, R. M.; Demoranville, I. E. Influence of dichlobenil and three experimental herbicides on bud break, terminal growth, and root development of cranberry cuttings. Abstr. 1974 Meet. Weed Sci. Soc. Am. 1974, 14-15.
34. Devlin, R. M.; Deubert, K. H.; Demoranville, I. E. Poison ivy control on cranberry bogs. Proc. Northeast Weed Control Conf. 1969, 23, 58-62.
35. Jeffers, S. N. Effects of fungicides applied during bloom on yield, yield components, and storage rots of cranberry. Plant Dis. 1991, 75, 244.
36. Soczek, Z.; Mackiewicz, M.; Luczak, F.; Kowalski, R. Preliminary evaluation of some herbicides applied in young non-fruiting cranberry plantation. Acta Hortic. 1977, 61, 309-313.
37. Shawa, A. Y. Control of aster and birdsfoot trefoil in cranberries with napropamide. Weed Sci. 1982, 30, 369-371.
38. Reddy, K. N.; Singh, M. Response of citrus (Citrus spp.) rootstock seedlings to soil-applied herbicides. J. Environ. Hortic. 1993, 11, 39-40.
39. Neal, J. C.; Pritts, M. P.; A. F., S. Evaluation of preemergent herbicide phytoxicity to tissue culture-propagated 'Heritage' red raspberry. J. Am. Soc. Hortic. Sci. 1990, 115, 416-422.
40. Argerich, C. A.; Bradford, K. J.; Ashton, F. M. Influence of seed vigor and plant herbicides on emergence growth, and yield of tomato. Hort. Sci. 1990, 25, 288-291.
41. Glaze, N. C.; Hall, M. R. Cultivation and herbicides for weed control in sweet potato (Ipomoea batatas). Weed Technol. 1990, 4, 518-523.
42. Chernicky, J. P.; Gast, R.; Slife, F. W. The effect of sethoxydim on corn (Zea mays) and giant foxtail (Setaria faberi). Weed Sci. 1989, 37, 600-603.
43. Gillespie, G. R.; Nalewaja, J. D. Postemergence grass control herbicides applied to the soil. Weed Sci. 1986, 34 (6), 942-947.
44. 32P-postlabeling test for srucrurally diverse DNA adducts. Carcinogenesis 1986, 7, 1543-1551.
45. 2-propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal in vivo. Chem. Res. Toxicol. 2000, 13, 1165-1173.
46. 32P-Postlabelling test for DNA damage. Proc. Natl. Acad. Sci. 1981, 78, 6126-6129.
47. 2-(1,3-propano)-2′- deoxyguanosine 3′-phosphate adducts formed from 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 1997, 10, 1259-1265.
48. Maekawa, M.; Kawai, K.; Takahashi, Y.; Nakamura, H.; Watanabe, T.; Sawa, R.; Hachisuka, K.; Kasai, H. Identification of 4-oxo-2-hexenal and other direct mutagens formed in model lipid peroxidation reactions as dGuo adducts. Chem. Res. Toxicol. 2006, 19 (1), 130-138.
49. Pollack, M.; Yang, I.-Y.; Kim, H.-Y. H.; Blair, I. A.; Moriya, M. Translesion DNA synthesis across the heptanone-etheno-2′-deoxycytidine adduct in cells. Chem. Res. Toxicol. 2006, 19 (8), 1074-1079.
50. Rouzer, C. A.; Marnett, L. J. Mechanism of free radical oxygenation of polyunsaturated fatty acids by cyclooxygenases. Chem. Rev. 2003, 103, 2239-2304.
51. Brash, A. R. Lipoxygenases: Occurence, function, catalysis, and acquisition of substrate. J. Biol. Chem. 1999, 274, 23679-23682.
52. 6-etheno-2′-deoxyadenosine adduct by lipid hydorperoxide-mediated generation of 4-oxo-2-nonenal. Chem. Res. Toxicol. 2000, 13, 846-852.
53. Cheeseman, K. H. Mechanisms and effects of lipid peroxidation. Mol. Aspects Med. 1993, 14 (3), 191-197.
54. Dix, T. A.; Aikens, J. Mechanisms and biological relevance of lipid peroxidation initiation. Chem. Res. Toxicol. 1993, 6 (1), 2-18.
55. Girotti, A. W. Mechanisms of lipid peroxidation. J. Free Radical Biol. Med. 1985, 1 (2), 87-95.
56. Horton, A. A.; Fairhurst, S. Lipid peroxidation and mechanism of toxicity. Crit. Rev. Toxicol. 1987, 18 (1), 27-29.
57. Sevanian, A.; Hochcstein, P. Mechanisms and consequences of lipid peroxidation in biological systems. Annu. Rev. Nutr. 1985, 5, 365-390.
58. Weber-Lotfi, F.; Pfohl-Leszkowicz, A.; Keith, G.; Pillay, D. T. N.; Dietrich, A.; Rether, B.; Guillemaut, P. Formation of abnormal hypermodified nucleotides on plant DNA upon xenobiotic action. Plant Sci. 1992, 86, 13-19.
59. Imlay, J. A.; Linn, S. DNA damage and oxygen radical toxicity. Science 1988, 240, 1302-1309.
60. Menghini, R. Genotoxicity of active oxygen species in mammalian cells. Mutat. Res. 1988, 195, 215-230.
61. Benson, E. E. Free radical damage in stored plant germplasm. Int. Board Plant Genet. Resour. 1990, 9-34.
62. Salmon, T. B.; Evert, B. A.; Song, B.; Doetsch, P. W. Biological consequences of oxidative stress-induced DNA damage in Saccharomyces cerevisiae. Nucleic Acids Res. 2004, 32 (12), 3712-3723.
63. Vaca, C. E.; Wilhelm, J. Interaction of lipid peroxidation products with DNA. A review. Mutat. Res. 1988, 195 (2), 137-149.
64. Hatanaka, A.; Kajiwara, T.; Sekiya, J. Fatty acid hydroperoxide lyase in plant tissues: Volatile aldehyde formation from linoleic and linolenic acid. In Biogeneration of Aromas; Parliament, T. H., Croteau, R., Eds.; American Chemical Society: Washington, DC, 1986; pp 167-175.
65. 2-(1,3-propano)-2′-deoxyguanosine adducts in mammalian cells. Chem. Res. Toxicol. 1996, 9, 1207-1213.
66. 2- propanodeoxyguanosine in DNA. Chem. Res. Toxicol. 2006, 19 (4), 563-570.
67. Eder, E.; Hoffman, C. Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners. Chem. Res. Toxicol. 1993, 6, 486-494.
68. 2- propano adducts of 2′-deoxyguanosine with 4-hydroxynonenal and other α,β-unsaturated aldehydes. Chem. Res. Toxicol. 1994, 7, 511-518.
69. Winter, C. K.; Segall, H. J.; Haddon, W. F. Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro. Cancer Res. 1986, 46 (11), 5682-5686.
70. Del Rio, D.; Stewart, A. J.; Pellegrini, N. A review of recent studies on malondialdehyde as toxic molecule and biological marker of oxidative stress. Nutr. Metab. Cardiovasc. Dis. 2005, 15 (4), 316-328.
71. Eder, E.; Wacker, M.; Lutz, U.; Nair, J.; Fang, X.; Bartsch, H.; Beland, F. A.; Schlatter, J.; Lutz, W. K. Oxidative stress related DNA adducts in the liver of female rats fed with sunflower-, rapeseed-, olive- or coconut oil supplemented diets. Chem.-Biol. Interact. 2006, 159 (2), 81-89.
72. 2- propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal and cell proliferation in the colonic mucosa of healthy volunteers. Cancer Epidemiol. Biomarkers Prev. 2002, 11 (9), 915-920.
73. 2-propanodeoxyguanosine adduct levels. Cancer Epidemiol Biomarkers Prev. 2001, 10 (8), 883-888.
74. 2- propanodeoxyguanosine adducts of 2-hexenal in vivo. Arch Toxicol. 2000, 74 (10), 642-648.
75. Taylor, N. L.; Day, D. A.; Millar, A. H. Environmental stress causes oxidative damage to plant mitochondria leading to inhibition of glycine decarboxylase. J. Biol. Chem. 2002, 277 (45), 42603-42668.
76. Winger, A. M.; Taylor, N. L.; Heazlewood, J. L.; Day, D. A.; Millar, A. H. The Cytotoxic lipid peroxidation product 4-hydroxy-2-nonenal covalently modifies a selective range of proteins linked to respiratory function in plant mitochondria. J. Biol. Chem. 2007, 282 (52), 37436-37447.
77. Branzei, D.; Foiani, M. The Rad53 signal transduction pathway: Replication fork stabilization, DNA repair, and adaptation. Exp. Cell Res. 2006, 312 (14), 2654-2659.
78. Ames, B. N.; Shigenaga, M. K.; Gold, L. S. DNA lesions, inducible DNA repair, and cell division: Three key factors in mutagenesis and carcinogenesis. Environ. Health Perspect. 1993, 101 (5), 35-44.
79. Saxowsky, T. T.; Doetsch, P. W. RNA polymerase encounters with DNA damage: Transcription-coupled repair or transcriptional mutagenesis. Chem. Rev. 2006, 106 (2), 474-488.
80. Takao, M.; Yasui, A. DNA repair initiated by glycosylases in the nucleus and mitochondria of mammalian cells; how our cells respond to a flood of oxidative DNA damage. J. Dermatol. Sci., Suppl. 2005, 1 (2), S9-S19.
81. Dukan, S.; Farewell, A.; Balksteros, M.; Taddei, F.; Radman, M.; Nystrom, T. Protein oxidation in response to increased transcriptional or translational errors. Proc. Natl. Acad Sci. U.S.A. 2000, 97 (11), 5746-5749.
82. Lindsey-Boltz, L. A.; Sancar, A. Nucleotide excision repair in eukaryotes. Encycl. Biol. Chem. 2004, 3, 130-133.
83. Holmquist, G. P. Cell-selfish modes of evolution and mutations directed after transcriptional bypass. Mutat. Res. 2002, 510 (1,2), 141-152.
84. Engelward, B. P.; Dreslin, A.; Christensen, J.; Huszar, D.; Kurahara, C.; Samson, L. Repair-deficient 3-methyladenine DNA glycosylase homozygous mutant mouse cells have increased sensitivity to alkylation-induced chromosome damage and cell killing. EMBO J. 1996, 15 (4), 945-952.
85. Sarasin, A.; Bounacer, A.; Lepage, F.; Schlumberger, M.; Suarez, H. G. Mechanisms of mutagenesis in mammalian cells. Application to human thyroid tumours. C. R. Acad. Sci., Ser. III 1999, 322 (2-3), 143-149.
86. Daube, S. S.; Tomer, G.; Livneh, Z. Translesion replication by DNA polymerase delta depends on processivity accessory proteins and differs in specificity from DNA polymerase beta. Biochemistry 2000, 39 (2), 348-355.
87. Rajalakshmi, S.; Sarma, D. S. R. Replication of hepatic DNA in rats treated with dimethylmtrosamine. Chem-Biol. Interact. 1975, 11 (4), 245-252.
88. Sweder, K. Nucleotide excision repair in yeast. Curr. Genet. 1994, 27 (1), 1-16.