Structures of acrolein-guanine adducts: A semi-empirical self- consistent field and nuclear magnetic resonance spectral study

Chemical Research in Toxicology

Volumn 11, Issue 4, 1998, Pages 284-294

  Boerth, Donald W ^a   Eder, Erwin ^b   Hussain, Sazzad ^a   Hoffman, Christian ^b  

^a UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; ACROLEIN DERIVATIVE; ALPHA CHLOROACROLEIN; CHLORO 11 HYDROXYTETRAHYDROPYRIMIDINOGUANINE; CHLORO 13 HYDROXYTETRAHYDROPYRIMIDINOGUANINE; CROTONALDEHYDE; GUANINE; GUANINE DERIVATIVE; HYDROXY 11 METHYLTETRAHYDROPYRIMIDINOGUANINE; HYDROXY 13 METHYLTETRAHYDROPYRIMIDINOGUANINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CONFORMATION; CYCLIZATION; DNA ADDUCT; DNA DAMAGE; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; TOXIN ANALYSIS; TOXIN STRUCTURE;

ACROLEIN; ALDEHYDES; DNA ADDUCTS; GUANINE; MAGNETIC RESONANCE SPECTROSCOPY; MUTAGENS;

EID: 0031901709     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970152g     Document Type: Article

References (79)

1. Schauenstein, E., Esterbauer, H., and Zollner, H. (1977) Aldehydes with specific biological functions. Aldehydes in Biological Systems. Their Natural Occurrence and Biological Activities, pp 172-200, Methuen Inc., New York.
2. Witz, G. (1988) Biological interactions of α,β-unsaturated aldehydes. Free Radical Biol. 7, 333-349.
3. Eder, E., Scheckenbach, S., Deininger, C., and Hoffman, C. (1993) The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis. Toxicol. Lett. 67, 87-103.
4. Eder, E., Deininger, C., Neudecker, T., and Deininger, D. (1992) Mutagenicity of β-alkyl substituted acrolein congeners in the Salmonella typhimurium strain TA 100 and genotoxicity testing in the SOS-chromotest. Environ. Mol. Mutagen, 19, 338-345.
5. Eder, E., Huffman, C., Bastian, H., Deininger, C., and Scheckenbach, S. (1990) Molecular mechanisms of DNA damage initiated by α,α-unsaturated carbonyl compounds as criteria for genotoxicity and mutagenicity. Environ. Health Perspect. 88, 99-106.
6. Kronberg, L., and Franzen, R. (1993) Determination of chlorinated furanones, hydroxyfuranones and butenoic acid in chlorine treated water and in pulp bleaching liquor. Environ. Sci. Technol. 27, 1811-1816.
7. Franzen, R., and Kronberg, L. (1994) Determination of chlorinated 5-methyl-5-hydroxyfuranones in drinking water, in chlorinated hurnic water, and in pulp bleaching liquor. Environ. Sci. Technol. 28, 2222-2227.
8. Kronberg, L., and Vartiainen, T. (1988) Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)5-hydroxy-2(5H)-furanone and of its geometric isomer CS)-2chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. Mutat. Res. 206, 177-182.
9. Horth, H. (1990) Identification of mutagens in water. J. Fr. Hydrol.21, 135-145.
10. Cantor, K. P., Hoover, R., Hartge, P., Mason, T. J., Silverman, D. T., Altman, R., Austin, D. F., Child, M. A., Key, C. R., Marrett, L. D., Myers, M. H., Narayana, A. S., Levin, L. I., Sullivan, J. W., Swanson, G. M., Thomas, D. B., and West, D. W. (1987) Bladder cancer, drinking water source and tap water consumption: A case-control study. J. Natl. Cancer Inst. 79, 1269-1279.
11. (U) Knasmüller, S., Zohrer, E., Kronberg, L., Kundi, M., Franzen, R., and Schulte-Hermann, R. (1996) Mutational spectra of Salmonella typhimurium revertants induced by chlorohydroxyfuranones, byproducts of chlorine disinfection of drinking water. Chem. Res. Toxicol. 9, 374-381.
12. Munter, T., Kronberg, L., and Sjöholm, R. (1996) Identification of adducts formed in reaction of adenosine with 3-chloro-4-methyl-5-hydroxy-2(5H)-furanone, a bacterial mutagen present in chlorine disinfected drinking water. Chem. Res. Toxicol. 9, 703-708.
13. Eiter, K. (1970) Insekten Sexuallockstoffe. In Chemie der Pflanzen und Schadlingsbekampfungmittel I (Wegler, R., Ed.) pp 497-522, Springer, Berlin.
14. Schildknecht, H., Holonbek, K., Weis, K. H., and Vetter H. (1961) Über Insekten- und Pflanzenabwehrstoffe, ihre Isolierung und Strukturauiklärung. (Insect and Plant Defense Substances, Isolation and Structure Determination.) Angew. Chem. 73, 629.
15. Marnett, L., Hurd, H. K., Hollstein, M. C., Levin, D. E., Esterbauer, H., and Ames, B. N. (1985) Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat. Res. 148, 25-34.
16. IARC. (1985) Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 36, pp 133-177, IARC, Lyon, France.
17. Draminski, W., Eder, E., and Henschler, D. (1983) New pathway of acrolein metabolism in rats. Arch. Toxicol. 52, 243-247.
18. Neudecker, T., Eder, E., Deininger, C., and Henschler, D. (1989) Crotonaldeyhde is mutagenic in Salmonella typhimurium TA 100. Environ. Mol. Mutagen. 14, 146-148.
19. Neudecker, T., Eder, E., Deininger, C., Huffman, C., and Henschler, D. (1989) Mutagenicity of methylvinyl ketone in Salmonella typhimurium TA100 -indication for epoxidation as an activation mechanism. Mutat. Res. 227, 131-134.
20. IARC. (1979) Evaluation of the Carcinogenic Risk of Chemicals to Humans, Monograph 19, pp 479-494, IARC, Lyon, France.
21. Trietman, R. D., Burgess, W. A., and Gold, A. (1980) Air contaminants encountered by firefighters. Am. Ind. Hyg. Assoc. J. 41, 796-802.
22. Graedel, T. E. (1979) Chemical Compounds in the Atmosphere, Academic Press, New York.
23. Izard, C., and Liberman, C. (1978) Acrolein. Mutat. Res. 47, 115-138.
24. Wynder, E. L., Goodman, D. A., and Hoffmann, D. (1965) Ciliatoxic compounds in cigarette smoke. II. Carboxylic acids and aldehydes. Cancer 18, 505-509.
25. Baker, R. R., Dymond, H. F., and Shilabear, P. K. (1984) Determination of α,β-unsaturated compounds formed by burning cigarette. Anal. Proc. (London) 21, 135-137.
26. 2-Ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans4-hydroxy-2-nonenal. Cancer Res. 48, 320-323.
27. 2propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. SCi. U.S.A. 91, 7491-7495.
28. Chaudhary, A. K., Nokubo, M., Reddy, G. R., Yeola, S. N., Morrow, J. D., Blair, I. A., and Maraett, L. J. (1994) Detection of endogenous malondialdehyde- deoxyguanosine adducts in human liver. Science 265, 1580-1582.
29. Marnett, L. J. (1994) DNA Adducts of α,β-unsaturated aldehydes and dicarbonyl compounds. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerback, D., and Bartsch, H., Eds.) Publication No. 125, pp 151-163, IARC, Lyon, France.
30. Lutz, D., Eder, E., Neudecker, T., and Henschler, D. (1982) Structure-mutagenicity relationship in α,β-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 93, 305-315.
31. Beauchamp, R. O., Jr., Andjelkovich, D. A., Kligerman, A. D., Morgan, K. T., and Heck, H. d'A. (1985) A Critical Review of the Literature on Acrolein Toxicity. CRC Crit. Rev. Toxicol. 14, 309-380.
32. Eder, E., Henschler, D., and Neudecker, T. (1982) Mutagenic properties of allylic and α,β-unsaturated compounds: consideration of alkylating mechanisms. Xenobiotica 12, 831-848.
33. Neudecker, T., Lutz, D., Eder, E., and Henschler, D. (1981) Crotonaldehyde is mutagenic in a modified Salmonella typhimurium mutagenicity testing system. Mutat. Res. 91, 27-31.
34. Henschler, D., and Eder, E. (1986) Structure-activity relation-ships of α,β-unsaturated carbonyl compounds. In The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis (Singer, B., and Bartsch, H., Eds.) Publication No. 70, pp 198-205, IARC, Lyon, France.
35. Haworth, S., Lawler, T., Mortelmans, K., Speck, W., and Zeiger, E. (1983) Salmonella mutagenicity test results for 250 chemicals. Environ. Mutagen Suppl. 1, 3-142.
36. Basu, A., and Marnett, L. J. (1984) Molecular requirements for the mutagenicity of malondialdehyde and related acroleins. Cancer Res. 44, 2848-2854.
37. 2-(l,3-propano)-2′-deoxyguanosine adducts in mammalian cells. Chem. Res. Toxicol. 9, 1207-1213.
38. Chung, F. L., Tanaka, T., and Hecht, S. S. (1986) Induction of liver tumors in F344 rats by crotonaldehyde. Cancer Res. 46, 1285-1289.
39. 32P postlabeling quantification of DNA adducts in vivo. Recent Results Cancer Res. 143, 65-75.
40. Deininger, C., Eder, E., Neudecker, T., and Huffman, C. (1990) Mutagenicity and genotoxicity of ethylvinyl ketone in bacterial tests. J. Appl. Toxicol. 10, 167-171.
41. Neudecker, T., Eder, E., Deininger, C., and Henschler, D. (1991) Mutagenicity of 2-methylacrolein, 2-ethylacrolein and 2-propylacrolein in Salmonella typhimurium TA100. A comparative study. Mutat. Res. 264, 193-196.
42. Basu, A. K., Marnett, L. J., and Romano, L. J. (1984) Dissociation of malondialdehyde mutagenicity in Salmonella typhimurium from its ability to induce interstrand DNA cross-links. Mutat. Res. 129, 39-46.
43. Basu, A. K., O'Hara, S. M., Valladier, P., Stone, K., Mols, O., and Marnett, L. J. (1988) Identification of adducts formed by reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes. Chem. Res. Toxicol. 1, 53-59.
44. Mukai, F. H., and Goldstein, B. D. (1976) Mutagenicity of malondialdehyde, a decomposition product of peroxidized polyunsaturated fatty acids. Science 191, 868-869.
45. Marnett, L. J., and Tuttle, M. A. (1980) Comparison of the mutagenicities of malondialdehyde and side products formed during its chemical synthesis. Cancer Res. 40, 276-282.
46. Basu, A. K., and Marnett, L. J. (1983) Unequivocal demonstration that malondialdehyde is a mutagen. Carcinogenesis 4, 331-333.
47. Yau, T. M. (1979) Mutagenicity and cytotoxicity of malondialdehyde in mammalian cells. Mech. Aging Dev. 11, 137-144.
48. Spalding, J. W. (1988) Toxicology and carcinogenesis studies of malondialdehyde sodium salt (3-hydroxy-2-propenal, sodium salt) in F344/N rats and B6C3F1 mice. Natl. Toxicol. Program Technol. Rep. Ser. 331, 5-13.
49. Goda, Y., and Marnett, L. J. (1991) High-performance liquid chromatography with electrochemical detection for determination of the major malondialdehyde-guanine adduct. Chem. Res. Toxicol. 4, 520-524.
50. Stone, K., Ksebati, M. B., and Marnett, L. J. (1990) Investigation of the adducts formed by reaction of malondialdehyde with adenosine. Chem. Res. Toxicol. 3, 33-38.
51. Chenna, A., and Iden, C. R. (1993) Characterization of 2′deoxycytidine and 2′-deoxyuridine adducts formed in reactions with acrolein and 2-bromoacrolein. Chem. Res. Toxicol. 6, 261-268.
52. Rosen, J. D., Segall, Y., and Casida, J. E. (1980) Mutagenic potency of haloacroleins and related compounds. Mutat. Res. 78, 113-119.
53. Eder, E., Deininger, C., Deininger, D., and Weinfurtner, E. (1994) Genotoxicity of 2-halosubstituted enals and 2-chloroacrylonitrile in the Ames test and the SOS-chromotest. Mutat. Res. 322, 321-328.
54. Eder, E., Huffman, C., Sporer, S., and Scheckenbach, S. (1993) Biomonitoring studies and susceptibility markers for acrolein congeners and allylic and benzyl compounds. Environ. Health Perspect. 99, 245-247.
55. Eder, E., Hoffman, C., and Deininger, C. (1991) Identification and characterization of deoxyguanosine adducts of methyl vinyl ketone and ethyl vinyl ketone. Genotoxicity of the ketones in the SOS chromtest. Chem. Res. Toxicol. 4, 50-57.
56. 2.S-bis-cyclic adducts. Chem. Res. Toxicol. 5, 802-808.
57. Eder, E., and Hoffman, C. (1993) Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners. Chem. Res. Toxicol. 6, 486-494.
58. Hoffman, C. (1990) Studies of the reactivity of α,β-unsaturated carbonyl compounds with nucleosides and nucleotides; model substances for DNA binding studies. Doctoral Dissertation, Julius-Maximilians University, Würzburg, Germany.
59. 2-Cyclic deoxyguanosine adducts and guanine adducts of 2-haloacroleins. Isolation, characterization, isomerization and stability. Arch. Toxicol. 68, 471479.
60. Marnett, L. J., Basu, A. K., O'Hara, S., Weller, P. E., Maqsudur, R., and Oliver, J. P. (1986) Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region. J. Am. Chem. Soc. 108, 1348-1350.
61. Reddy, G. R., and Marnett, L. J. (1996) Mechanism of reaction of β-(aryloxy)acroleins with nucleosides. Chem. Res. Toxicol. 9, 12-15.
62. 2-propanodeoxyguanosine adducts in DNA upon reaction with 3-(N-carbethoxy-N-nitrosamino) propionaldehyde. Chem. Res. Toxicol. 7, 62-67.
63. Chen, H.-J. C., and Chung, F.-L. (1994) Formation of etheno adducts in reactions of enals via autoxidation. Chem. Res. Toxicol. 7, 857-860.
64. 2-(l,3-propano)-2′-deoxyguanosine and incorpora-tion into oligodexoynucleotides: a model for exocyclic acrolein-DNA adducts. Chem. Res. Toxicol. 3, 49-58.
65. 6adenosinyl)ethenoadenosine derivatives. Chem. Res. Toxicol. 8, 841-846.
66. 2-hydroxybromopropanode-oxyguanosine isomers upon reaction of 2-bromoacrolein with 2′deoxyguanosine. J. Org. Chem. 53, 30-35.
67. Stewart, J. J. P. (1989) Optimization of parameters for semiempirical methods II. Applications. J. Comput. Chem. 10, 221-264.
68. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P. (1985) AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
69. Dewar, M. J. S., and Thiel, W. (1977) Ground states of molecules. 38. the MNDO method. Approximations and parameters. J. Am. Chem. Soc. 99, 4899-4906.
70. Dewar, M. J. S., and Thiel, W. (1977) Ground states of molecules. 39. MNDO results for molecules containing hydrogen, carbon, nitrogen, and oxygen. J. Am. Chem. Soc. 99, 4907-4915.
71. Stewart, J. J. P. (1990) MOPAC version 6.0, Quantum Chemistry Program Exchange No. 455.
72. Pulay, P. (1980) Convergence accelaration of iterative sequences. Chem. Phys. Lett. 73, 393.
73. Burkert, U., and Allinger, N. L. (1982) Molecular Mechanics, ACS Monograph No. 177, American Chemical Society, Washington, DC.
74. Tai, J. C., and Allinger, N. L. (1988) Molecular mechanics calculations on conjugated nitrogen-containing heterocycles. J. Am. Chem. Soc. 110, 2050-2055.
75. Allinger, N. L., and Yuh, Y. (1980) Quantum Chemistry Program Exchange No. 395.
76. Günther, H. (1980) NMR Spectroscopy. An Introduction, pp 106-107, 256-257, 386, John Wiley and Sons, Chichester, U.K.
77. Kemp, W. (1991) Organic Spectroscopy, pp 152-155, W. H. Freeman and Co., New York, NY.
78. Jackman, L. M., and Sternhell, S. (1969) Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, pp 238-241, 281-283, 286-289, Pergamon Press, Braunschweig, FRG.
79. Eliel, E. L., Allinger, N. L., Angyal, S. J., and Morrison, G. A. (1981) Conformational Analysis, pp 375-377, 411, American Chemical Society, Washington, DC.