Mutagenicity of acrolein and acrolein-induced DNA adducts

References

• Arif JM, Dresler C, Clapper ML, Gairola CG, Srinivasan C, Lubet RA, Gupta RC. 2006. Lung DNA adducts detected in human smokers are unrelated to typical polyaromatic carcinogens. Chem Res Toxicol 19:295–299.
   PubMed Web of Science ®Google Scholar
• Au W, Sokova OI, Kopnin B, Arrighi FE. 1980. Cytogenetic toxicity of cyclophosphamide and its metabolites in vitro. Cytogenet Cell Genet 26:108–116.
   PubMedGoogle Scholar
• Barros AR, Comendador MA, Sierra LM. 1994. Acrolein genotoxicity in Drosophila melanogaster. II. Influence of mus201 and mus308 mutations. Mutat Res 306:1–8.
   PubMedGoogle Scholar
• Basu AK, Marnett LJ. 1984. Molecular requirements for the mutagenicity of malondialdehyde and related acroleins. Cancer Res 44:2848–2854.
   PubMed Web of Science ®Google Scholar
• Besaratinia A. 2009. Acrolein: excessive cytotoxicity or potent mutagenicity? Chem Res Toxicol 22:751–753; author reply 753–754.
   PubMed Web of Science ®Google Scholar
• Cai Y, Wu MH, Ludeman SM, Grdina DJ, Dolan ME. 1999. Role of O6-alkylguanine-DNA alkyltransferase in protecting against cyclophosphamide-induced toxicity and mutagenicity. Cancer Res 59:3059–3063.
   PubMed Web of Science ®Google Scholar
• Chen PY, Moldoveanu SC. 2003. Mainstream smoke chemical analyses for 2R4F Kentucky reference cigarette. Beiträge zur Tabakforschung Int 20:448–458.
   Google Scholar
• Chung FL, Komninou D, Zhang L, Nath R, Pan J, Amin S, Richie J. 2005. Glutathione depletion enhances the formation of endogenous cyclic DNA adducts derived from t-4-hydroxy-2-nonenal in rat liver. Chem Res Toxicol 18:24–27.
   PubMed Web of Science ®Google Scholar
• Chung FL, Nath RG, Nagao M, Nishikawa A, Zhou GD, Randerath K. 1999. Endogenous formation and significance of 1,N2-propanodeoxyguanosine adducts. Mutat Res 424:71–81.
   PubMed Web of Science ®Google Scholar
• Chung FL, Roy KR, Hecht SS. 1988. Study of reactions of alpha, beta-unsaturated carbonyl compounds with deoxyguanosine. J Org Chem 53:14–17.
   Web of Science ®Google Scholar
• Chung FL, Young R, Hecht SS. 1984. Formation of cyclic 1,N2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res 44:990–995.
   PubMed Web of Science ®Google Scholar
• Cohen SM, Garland EM, St John M, Okamura T, Smith RA. 1992. Acrolein initiates rat urinary bladder carcinogenesis. Cancer Res 52:3577–3581.
   PubMed Web of Science ®Google Scholar
• Curren RD, Yang LL, Conklin PM, Grafstrom RC, Harris CC. 1988. Mutagenesis of xeroderma pigmentosum fibroblasts by acrolein. Mutat Res 209:17–22.
   PubMed Web of Science ®Google Scholar
• de los Santos C, Zaliznyak T, Johnson F. 2001. NMR characterization of a DNA duplex containing the major acrolein-derived deoxyguanosine adduct gamma -OH-1,-N2-propano-2’-deoxyguanosine. J Biol Chem 276:9077–9082.
   PubMed Web of Science ®Google Scholar
• Facchinetti F, Amadei F, Geppetti P, Tarantini F, Di Serio C, Dragotto A, Gigli PM, Catinella S, Civelli M, Patacchini R. 2007. Alpha,beta-unsaturated aldehydes in cigarette smoke release inflammatory mediators from human macrophages. Am J Respir Cell Mol Biol 37:617–623.
   PubMed Web of Science ®Google Scholar
• Falletti O, Cadet J, Favier A, Douki T. 2007. Trapping of 4-hydroxynonenal by glutathione efficiently prevents formation of DNA adducts in human cells. Free Radic Biol Med 42:1258–1269.
   PubMed Web of Science ®Google Scholar
• Feng Z, Hu W, Hu Y, Tang MS. 2006. Acrolein is a major cigarette-related lung cancer agent: preferential binding at p53 mutational hotspots and inhibition of DNA repair. Proc Natl Acad Sci USA 103:15404–15409.
   PubMed Web of Science ®Google Scholar
• Feron VJ, Til HP, Vrijer Fd, Woutersen RA, Cassee FR, Bladeren PJV. 1991. Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat Res 259:363–385.
   PubMed Web of Science ®Google Scholar
• Finkelstein EI, Nardini M, van der Vliet A. 2001. Inhibition of neutrophil apoptosis by acrolein: a mechanism of tobacco-related lung disease? Am J Physiol Lung Cell Mol Physiol 281:L732–L739.
   PubMed Web of Science ®Google Scholar
• Finkelstein EI, Ruben J, Koot CW, Hristova M, van der Vliet A. 2005. Regulation of constitutive neutrophil apoptosis by the alpha,beta-unsaturated aldehydes acrolein and 4-hydroxynonenal. Am J Physiol Lung Cell Mol Physiol 289:L1019–L1028.
   Web of Science ®Google Scholar
• Florin I, Rutberg L, Curvall M, Curt RB. 1980. Screening of tobacco smoke constituents for mutagenicity using the Ames’ test. Toxicology 18:219–232.
   Web of Science ®Google Scholar
• Foiles PG, Akerkar SA, Chung F-L. 1989. Application of an immunoassay for cyclic acrolein deoxyguanosine adducts to assess their formation in DNA of Salmonella typhimurium under conditions of mutation induction by acrolein. Carcinogenesis 10:87–90.
   PubMed Web of Science ®Google Scholar
• Foiles PG, Akerkar SA, Miglietta LM, Chung FL. 1990. Formation of cyclic deoxyguanosine adducts in Chinese hamster ovary cells by acrolein and crotonaldehyde. Carcinogenesis 11:2059–2061.
   PubMed Web of Science ®Google Scholar
• Galloway SM, Armstrong MJ, Reuben C, Colman S, Brown B, Cannon C, Bloom AD, Nakamura F, Ahmed M, Duk S. 1987. Chromosome aberrations and sister chromatid exchanges in Chinese hamster ovary cells: evaluations of 108 chemicals. Environ Mol Mutagen 10(Suppl 10):1–175.
   PubMed Web of Science ®Google Scholar
• Grafstrom RC, Dypbukt JM, Willey JC, Sundqvist K, Edman C, Atzori L, Harris CC. 1988. Pathobiological effects of acrolein in cultured human bronchial epithelial cells. Cancer Res 48:1717–1721.
   PubMed Web of Science ®Google Scholar
• Hales BF. 1982. Comparison of the mutagenicity and teratogenicity of cyclophosphamide and its active metabolites, 4-hydroxycyclophosphamide, phosphoramide mustard, and acrolein. Cancer Res 42:3016–3021.
   PubMed Web of Science ®Google Scholar
• Hansen RJ, Nagasubramanian R, Delaney SM, Samson LD, Dolan ME. 2007. Role of O6-methylguanine-DNA methyltransferase in protecting from alkylating agent-induced toxicity and mutations in mice. Carcinogenesis 28:1111–1116.
   PubMed Web of Science ®Google Scholar
• Haworth S, Lawlor T, Mortelmans K, Speck W, Zeiger E. 1983. Salmonella mutagenicity test results for 250 chemicals. Environ Mutagen 5:3–142.
   Web of Science ®Google Scholar
• Hemminki K, Falck K, Vainio H. 1980. Comparison of alkylation rates and mutagenicity of directly acting industrial and laboratory chemicals: epoxides, glycidyl ethers, methylating and ethylating agents, halogenated hydrocarbons, hydrazine derivatives, aldehydes, thiuram and dithiocarbamate derivatives. Arch Toxicol 46:277–285.
   PubMed Web of Science ®Google Scholar
• Johnson WS, He Q-Y, Tomasz M. 1995. Selective recognition of the m5CpG dinucleotide sequence in DNA by mitomycin C for alkylation and cross-linking. Bioorg Med Chem 3:851–860.
   PubMed Web of Science ®Google Scholar
• Kanuri M, Minko IG, Nechev LV, Harris TM, Harris CM, Lloyd RS. 2002. Error prone translesion synthesis past gamma-hydroxypropano deoxyguanosine, the primary acrolein-derived adduct in mammalian cells. J Biol Chem 277:18257–18265.
   PubMed Web of Science ®Google Scholar
• Kawanishi M, Matsuda T, Nakayama A, Takebe H, Matsui S, Yagi T. 1998. Molecular analysis of mutations induced by acrolein in human fibroblast cells using supF shuttle vector plasmids. Mutat Res 417:65–73.
   PubMed Web of Science ®Google Scholar
• Kehrer JH, Biswal SS. 2000. The molecular effects of acrolein. Toxicol Sci 57:6–15.
   PubMed Web of Science ®Google Scholar
• Kern JC, Kehrer JP. 2002. Acrolein-induced cell death: a caspase-influenced decision between apoptosis and oncosis/necrosis. Chem Biol Interact 139:79–95.
   PubMed Web of Science ®Google Scholar
• Kim HY, Voehler M, Harris TM, Stone MP. 2002. Detection of an interchain carbinolamine cross-link formed in a CpG sequence by the acrolein DNA adduct gamma-OH-1,N( 2)-propano-2’-deoxyguanosine. J Am Chem Soc 124:9324–9325.
   PubMed Web of Science ®Google Scholar
• Kim SI, Pfeifer GP, Besaratinia A. 2007. Lack of mutagenicity of acrolein-induced DNA adducts in mouse and human cells. Cancer Res 67:11640–11647.
   PubMed Web of Science ®Google Scholar
• Klaunig JE, Kamendulis LM. 2004. The role of oxidative stress in carcinogenesis. Annu Rev Pharmacol Toxicol 44:239–267.
   PubMed Web of Science ®Google Scholar
• Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, Harris TM. 2003. DNA interchain cross-links formed by acrolein and crotonaldehyde. J Am Chem Soc 125:50–61.
   PubMed Web of Science ®Google Scholar
• Kozekov ID, Nechev LV, Sanchez A, Harris CM, Lloyd RS, Harris TM. 2001. Interchain cross-linking of DNA mediated by the principal adduct of acrolein. Chem Res Toxicol 14:1482–1485.
   PubMed Web of Science ®Google Scholar
• Kurtz AJ, Lloyd RS. 2003.1,N2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage. J Biol Chem 278:5970–5976.
   PubMed Web of Science ®Google Scholar
• Li L, Jiang L, Geng C, Cao J, Zhong L. 2008. The role of oxidative stress in acrolein-induced DNA damage in HepG2 cells. Free Radic Res 42:354–361.
   PubMed Web of Science ®Google Scholar
• Lijinsky W, Andrews AW. 1980. Mutagenicity of vinyl compounds in Salmonella Typhimurium. Teratogen Carcinogen Mutagen 1:259–267.
   PubMedGoogle Scholar
• Lijinsky W, Reuber MD. 1987. Chronic carcinogenesis studies of acrolein and related compounds. Toxicol Ind Health 3:337–345.
   PubMed Web of Science ®Google Scholar
• Liu X, Lovell MA, Lynn BC. 2005. Development of a method for quantification of acrolein-deoxyguanosine adducts in DNA using isotope dilution-capillary LC/MS/MS and its application to human brain tissue. Anal Chem 77:5982–5989.
   PubMed Web of Science ®Google Scholar
• Loquet C, Toussaint G, Letalaer JY. 1981. Study on mutagenic constituents of apple brandy and various alcoholic beverages collected in western France, a high incidence area for oesophageal cancer. Mutat Res 88:155–164.
   PubMedGoogle Scholar
• Lutz D, Eder E, Neudecker T, Henschler D. 1982. Structure-mutagenicity relationship in α,β-unsaturated carbonyl compounds and their corresponding allylic alcohols. Mutat Res 93:305–315.
   Web of Science ®Google Scholar
• Marnett LJ, Hurd HK, Hollstein MC, Levin DE, Esterbauer H, Ames BN. 1985. Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat Res 148:25–34.
   PubMed Web of Science ®Google Scholar
• Minko IG, Kozekov ID, Kozekova A, Harris TM, Rizzo CJ, Lloyd RS. 2008a. Mutagenic potential of DNA-peptide crosslinks mediated by acrolein-derived DNA adducts. Mutat Res 637:161–172.
   PubMed Web of Science ®Google Scholar
• Minko IG, Yamanaka K, Kozekov ID, Kozekova A, Indiani C, O’Donnell ME, Jiang Q, Goodman MF, Rizzo CJ, Lloyd RS. 2008b. Replication bypass of the acrolein-mediated deoxyguanine DNA-peptide cross-links by DNA polymerases of the DinB family. Chem Res Toxicol 21:1983–1990.
   PubMed Web of Science ®Google Scholar
• Nair U, Bartsch H, Nair J. 2007. Lipid peroxidation-induced DNA damage in cancer-prone inflammatory diseases: a review of published adduct types and levels in humans. Free Radic Biol Med 43:1109–1120.
   PubMed Web of Science ®Google Scholar
• Nath RG, Chen HJ, Nishikawa A, Young-Sciame R, Chung FL. 1994. A 32P-postlabeling method for simultaneous detection and quantification of exocyclic etheno and propano adducts in DNA. Carcinogenesis 15:979–984.
   PubMed Web of Science ®Google Scholar
• Nath RG, Chung FL. 1994. Detection of exocyclic 1,N2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc Natl Acad Sci USA 91:7491–7495.
   PubMed Web of Science ®Google Scholar
• Nath RG, Ocando JE, Chune F-L. 1996. Detection of 1,N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res 56:452–456.
   PubMed Web of Science ®Google Scholar
• Nath RG, Ocando JE, Guttenplan JB, Chung FL. 1998.1,N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. Cancer Res 58:581–584.
   PubMed Web of Science ®Google Scholar
• Noll DM, Mason TM, Miller PS. 2006. Formation and repair of interstrand cross-links in DNA. Chem Rev 106:277–301.
   PubMed Web of Science ®Google Scholar
• Nunoshiba T, Yamamoto K. 1999. Role of glutathione on acrolein-induced cytotoxicity and mutagenicity in Escherichia coli. Mutat Res 442:1–8.
   PubMed Web of Science ®Google Scholar
• O’Toole TE, Zheng YT, Hellmann J, Conklin DJ, Barski O, Bhatnagar A. 2009. Acrolein activates matrix metalloproteinases by increasing reactive oxygen species in macrophages. Toxicol Appl Pharmacol 236:194–201.
   PubMed Web of Science ®Google Scholar
• Parent RA, Caravello HE, Christian MS, Hoberman AM. 1993. Developmental toxicity of acrolein in New Zealand white rabbits. Fundam Appl Toxicol 20:248–256.
   PubMedGoogle Scholar
• Parent RA, Caravello HE, Harbell JW. 1991. Gene mutation assay of acrolein in the CHO/HGPRT test system. J Appl Toxicol 11:91–95.
   PubMed Web of Science ®Google Scholar
• Parent RA, Caravello HE, Long JE. 1992a. Two-year toxicity and carcinogenicity study of acrolein in rats. J Appl Toxicol 12:131–139.
   PubMed Web of Science ®Google Scholar
• Parent RA, Caravello HE, San RHC. 1996. Mutagenic activity of acrolein in S. typhimurium and E. coli. J Appl Toxicol 16:103–108.
   PubMed Web of Science ®Google Scholar
• Parent RA, Caravelloz HE, Balmer MF, Shellenberger TE, Long JE. 1992b. One-year toxicity of orally administered acrolein to the beagle dog. J Appl Toxicol 12:311–316.
   PubMed Web of Science ®Google Scholar
• Rodgman A. 2003. The composition of cigarette smoke: problems with lists of tumorigens. Beiträge zur Tabakforschung Int 20:402–437.
   Google Scholar
• Rodgman A, Green CR. 2003. Toxic chemicals in cigarette mainstream smoke—hazard and hoopla. Beiträge zur Tabakforschung Int 20:481–543.
   Google Scholar
• Rudra PK, Krokan HE. 1999. Acrolein cytotoxicity and glutathione depletion in n-3 fatty acid sensitive- and resistant human tumor cells. Anticancer Res 19:461–469.
   PubMed Web of Science ®Google Scholar
• Sanchez AM, Minko IG, Kurtz AJ, Kanuri M, Moriya M, Lloyd RS. 2003. Comparative evaluation of the bioreactivity and mutagenic spectra of acrolein-derived alpha-HOPdG and gamma-HOPdG regioisomeric deoxyguanosine adducts. Chem Res Toxicol 16:1019–1028.
   PubMed Web of Science ®Google Scholar
• Sasaki Y, Endo R. 1978. Mutagenicity of aldehydes in Salmonella. Mutat Res 27:251–252.
   Google Scholar
• Sierra LM, Barros AR, Garcia M, Ferreiro JA, Comendador MA. 1991. Acrolein genotoxicity in Drosophila melanogaster. I. Somatic and germinal mutagenesis under proficient repair conditions. Mutat Res 260:247–256.
   PubMed Web of Science ®Google Scholar
• Smith PA, Cohen SM, Lawson TA. 1990. Acrolein mutagenicity in the V79 assay. Carcinogenesis 11:497–498.
   PubMed Web of Science ®Google Scholar
• Stone MP, Cho YJ, Huang H, Kim HY, Kozekov ID, Kozekova A, Wang H, Minko IG, Lloyd RS, Harris TM, Rizzo CJ. 2008. Interstrand DNA cross-links induced by alpha,beta-unsaturated aldehydes derived from lipid peroxidation and environmental sources. Acc Chem Res 41:793–804.
   PubMed Web of Science ®Google Scholar
• Takabe W, Niki E, Uchida K, Yamada S, Satoh K, Noguchi N. 2001. Oxidative stress promotes the development of transformation: involvement of a potent mutagenic lipid peroxidation product, acrolein. Carcinogenesis 22:935–941.
   PubMed Web of Science ®Google Scholar
• Tanel A, Averill-Bates DA. 2005. The aldehyde acrolein induces apoptosis via activation of the mitochondrial pathway. Biochim Biophys Acta 1743:255–267.
   PubMed Web of Science ®Google Scholar
• Tanel A, Averill-Bates DA. 2007a. Activation of the death receptor pathway of apoptosis by the aldehyde acrolein. Free Radic Biol Med 42:798–810.
   PubMed Web of Science ®Google Scholar
• Tanel A, Averill-Bates DA. 2007b. Inhibition of acrolein-induced apoptosis by the antioxidant N-acetylcysteine. J Pharmacol Exp Ther 321:73–83.
   PubMed Web of Science ®Google Scholar
• Tanel A, Averill-Bates DA. 2007c. P38 and ERK mitogen-activated protein kinases mediate acrolein-induced apoptosis in Chinese hamster ovary cells. Cell Signal 19:968–977.
   PubMed Web of Science ®Google Scholar
• van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ. 1997. Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact 108:67–78.
   PubMed Web of Science ®Google Scholar
• VanderVeen LA, Hashim MF, Nechev LV, Harris TM, Harris CM, Marnett LJ. 2001. Evaluation of the mutagenic potential of the principal DNA adduct of acrolein. J Biol Chem 276: 9066–9070.
   PubMed Web of Science ®Google Scholar
• Vogel EW, Nivard MJ. 1993. Performance of 181 chemicals in a Drosophila assay predominantly monitoring interchromosomal mitotic recombination. Mutagenesis 8:57–81.
   PubMed Web of Science ®Google Scholar
• Wang HT, Zhang S, Hu Y, Tang MS. 2009. Mutagenicity and sequence specificity of acrolein-DNA adducts. Chem Res Toxicol 22:511–517.
   PubMed Web of Science ®Google Scholar
• Washington MT, Minko IG, Johnson RE, Haracska L, Harris TM, Lloyd RS, Prakash S, Prakash L. 2004a. Efficient and error-free replication past a minor-groove N2-guanine adduct by the sequential action of yeast Rev1 and DNA polymerase zeta. Mol Cell Biol 24:6900–6906.
   PubMed Web of Science ®Google Scholar
• Washington MT, Minko IG, Johnson RE, Wolfle WT, Harris TM, Lloyd RS, Prakash S, Prakash L. 2004b. Efficient and error-free replication past a minor-groove DNA adduct by the sequential action of human DNA polymerases iota and kappa. Mol Cell Biol 24:5687–5693.
   PubMed Web of Science ®Google Scholar
• Wilmer JL, Erexson GL, Kligerman AD. 1990. Effect of acrolein on phosphoramide mustard-induced sister chromatid exchanges in cultured human lymphocytes. Cancer Res 50:4635–4638.
   PubMed Web of Science ®Google Scholar
• Wilson VL, Foiles PG, Chung FL, Povey AC, Frank AA, Harris CC. 1991. Detection of acrolein and crotonaldehyde DNA adducts in cultured human cells and canine peripheral blood lymphocytes by 32P-postlabeling and nucleotide chromatography. Carcinogenesis 12:1483–1490.
   PubMed Web of Science ®Google Scholar
• Yang IY, Chan G, Miller H, Huang Y, Torres MC, Johnson F, Moriya M. 2002a. Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. Biochemistry 41:13826–13832.
   PubMed Web of Science ®Google Scholar
• Yang IY, Hossain M, Miller H, Khullar S, Johnson F, Grollman A, Moriya M. 2001. Responses to the major acrolein-derived deoxyguanosine adduct in Escherichia coli. J Biol Chem 276:9071–9076.
   PubMed Web of Science ®Google Scholar
• Yang IY, Johnson F, Grollman AP, Moriya M. 2002b. Genotoxic mechanism for the major acrolein-derived deoxyguanosine adduct in human cells. Chem Res Toxicol 15:160–164.
   PubMed Web of Science ®Google Scholar
• Yang IY, Miller H, Wang Z, Frank EG, Ohmori H, Hanaoka F, Moriya M. 2003. Mammalian translesion DNA synthesis across an acrolein-derived deoxyguanosine adduct. Participation of DNA polymerase eta in error-prone synthesis in human cells. J Biol Chem 278:13989–13994.
   PubMed Web of Science ®Google Scholar
• Zhang S, Villalta PW, Wang M, Hecht SS. 2007. Detection and quantitation of acrolein-derived 1,N2-propanodeoxyguanosine adducts in human lung by liquid chromatography–electrospray ionization–tandem mass spectrometry. Chem Res Toxicol 20:565–571.
   PubMed Web of Science ®Google Scholar
• Zimmering S, Mason JM, Valencia R. 1989. Chemical mutagenesis testing in Drosophila. VII. Results of 22 coded compounds tested in larval feeding experiments. Environ Mol Mutagen 14:245–251.
   PubMed Web of Science ®Google Scholar
• Zimmering S, Mason JM, Valencia R, Woodruff RC. 1985. Chemical mutagenesis testing in Drosophila. II. Results of 20 coded compounds tested for the National Toxicology Program. Environ Mutagen 7:87–100.
   PubMedGoogle Scholar