Simple and α,β-unsaturated aldehydes: Correct prediction of genotoxic activity through structure-activity relationship models

Environmental and Molecular Mutagenesis

Volumn 46, Issue 4, 2005, Pages 268-280

  Benigni, Romualdo ^a   Conti, Luigi ^a   Crebelli, Riccardo ^a   Rodomonte, Andrea ^a   Vari, Maria Rosaria ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

DNA adduct; Priority setting; QSAR; Risk; SOS Chromotest

Indexed keywords

ALDEHYDE;

ALLERGENICITY; ARTICLE; CARCINOGENICITY; CHEMICAL STRUCTURE; DNA ADDUCT; GENOTOXICITY; HEALTH HAZARD; MUTAGENICITY; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SOS CHROMOTEST;

ALDEHYDES; COMPUTER SIMULATION; DNA ADDUCTS; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; MUTAGENS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SALMONELLA;

EID: 30844471959     PISSN: 08936692     EISSN: 10982280     Source Type: Journal    
DOI: 10.1002/em.20158     Document Type: Article

References (35)

1. Benigni R. 2003a. SARs and QSARs of mutagens and carcinogens: understanding action mechanisms and improving risk assessment. In: Benigni R, editor. Quantitative Structure-Activity Relationship (QSAR) Models of Mutagens and Carcinogens. Boca Raton: CRC Press, pp 259-282.
2. Benigni R. (Ed.) 2003b. Quantitative Structure-Activity Relationship (QSAR) Models of Mutagens and Carcinogens. Boca Raton: CRC Press.
3. Benigni R. 2005. Structure-activity relationship studies of chemical mutagens and carcinogens: mechanistic investigations and prediction approaches. Chem Rev 105:1767-1800.
4. Benigni R, Passerini L. 2002. Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment. Mutat Res Revs 511:191-206.
5. Benigni R, Zito R. 2004. The second National Toxicology Program comparative exercise on the prediction of rodent carcinogenicity: definitive results. Mutat Res Revs 566:49-63.
6. Benigni R, Andreoli C, Conti L, Tafani P, Cotta-Ramusino M, Carere A, Crebelli R. 1993. Quantitave structure-activity relationship models correctly predict the toxic and aneuploidizing properties of six halogenated methanes in Aspergillus nidulans. Mutagenesis 8:301-305.
7. Benigni R, Giuliani A, Franke R, Gruska A. 2000. Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines. Chem Rev 100:3697-3714.
8. Benigni R, Passerini L, Rodomonte A. 2003. Structure-activity relationships for the mutagenicity and carcinogenicity of simple and α-β unsaturated aldehydes. Environ Mol Mutagen 42:136-143.
9. Crebelli R, Andreoli C, Carere A, Conti L, Crochi B, Cotta-Ramusino M, Benigni R. 1995. Toxicology of halogenated aliphatic hydrocarbons: structural and molecular determinants for the disturbance of chromosome segregation induction of lipid peroxidation. Chem Biol Interact 98:113-129.
10. Dillon D, Combes R, Zeiger E. 1998. The effectiveness of Salmonella strains TA100, TA102 and TA104 for detecting mutagenicity of some aldehydes and peroxides. Mutagenesis 13:19-26.
11. Eder E, Deininger C. 2001. Mutagenicity of 2-alkylpropenals in Salmonella typhimurium strain TA 100: structural influences. Environ Mol Mutagen 37:324-328.
12. Eder E, Deininger C, Neudecker T, Deininger D. 1992. Mutagenicity of β-alkyl substituted acrolein congeners in the Salmonella typhimurium strain TA100 and genotoxicity testing in the SOS chromotest. Environ Mol Mutagen 19:338-345.
13. Eder E, Scheckenbach S, Deininger C, Hoffman C. 1993. The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis. Toxicol Lett 67:87-103.
14. Eder E, Deininger C, Deininger D, Weinfurtner E. 1994a. Genotoxicity of 2-halocinnamaldehydes in two bacterial assays. Induction of SOS repair and frame-shift mutation. Mutagenesis 9:473-476.
15. Eder E, Deininger C, Deininger D, Weinfurtner E. 1994b. Genotoxicity of 2-halosubstituted enals and 2-chloroacrylonitrile in the Ames test and the SOS-chromotest. Mutat Res 322:321-328.
16. Eriksson L, Jaworska JS, Worth AP, Cronin MTD, McDowell RM, Gramatica P. 2003. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ Health Perspect 111:1361-1375.
17. Feron VJ, Til HP, de Vrijer F, Woutersen RA, Cassee FR, van Bladeren PJ. 1991. Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat Res 259:363-385.
18. Franke R, Gruska A. 2003. General introduction to QSAR. In: Benigni R, editor. Quantitative Structure-Activity Relationhsip (QSAR) Models of Mutagens and Carcinogens. Boca Raton: CRC Press, pp 1-40.
19. Franke R, Gruska A, Giuliani A, Benigni R. 2001. Prediction of rodent carcinogenicity of aromatic amines: a quantitative structure-activity relationships model. Carcinogenesis 22:1561-1571.
20. Friedberg EC, Walker GC, Siede W. 1995. DNA Repair and Mutagenesis. Washington, DC: American Society for Microbiology Press.
21. Hansch C. 1977. On the predictive value of QSAR. In: Keverling Buisman JA, editor. Biological Activity and Chemical Structure. Amsterdam: Elsevier.
22. Hansch C, Leo A. 1995. Exploring QSAR. 1. Fundamentals and Applications in Chemistry and Biology. Washington, DC: American Chemical Society.
23. Kalinowski HO, Berger S, Broun S. 1988. Carbon-13 NMR Spectroscopy. New York: Wiley.
24. LaLonde RT, Cook GP, Perakyla H, Dence CW, Babish JG. 1991. Salmonella typhimurium (TA100) mutagenicity of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)- furanone and its open- and closed-ring analogs. Environ Mol Mutagen 17:40-48.
25. March J. 2001. Advanced Organic Chemistry. New York: Wiley Interscience.
26. Maron DM, Ames BN. 1983. Revised methods for the Salmonella mutagenicity test. Mutat Res 113:173-215.
27. OECD.Bacterial Reverse Mutation Test. OECD Guidelines for Testing of Chemicals 471, Paris, 1997.
28. Oki M. 1983. Recent advances in atropoisomerism. In: Topics in Stereochemistry. New York: Wiley. pp 1-81.
29. Passerini L. 2003. QSARs for individual classes of chemical mutagens and carcinogens. In: Benigni R, editor. Quantitative Structure-Activity Relationship (QSAR) Models of Chemical Mutagens and Carcinogens. Boca Raton: CRC Press. pp 81-124.
30. Patlewicz GY, Wright ZM, Basketter DA, Pease CK, Lepoittevin JP, Gimenez AE. 2002. Structure-activity relationships for selected fragrance allergens. Contact Dermatitis 47:219-226.
31. Quillardet P, Hofnung M. 1985. The SOS chromostest: a colrimetric bacterial assay for genotoxins procedures. Mutat Res 147:65-78.
32. 32P-post-labeling technique. Carcinogenesis 20:1345-1350.
33. Stewart JJP. 1990. MOPAC: a semiempirical molecular orbital program. J Comput Aided Mol Design 4:1-105.
34. Stewart JJP. 1999. MOPAC200 Manual. St. Louis, MO: Fujitsu Ltd.
35. Zhang L, Sannes K, Shusterman AJ, Hansch C. 1992. The structure-activity relationships of skin carcinogenicity of aromatic hydrocarbons and heterocycles. Chem Biol Interact 81:149-180.