丙烯醛-DNA加合物的研究进展

尹瑞川, 汪海林. 丙烯醛-DNA加合物的研究进展[J]. 环境化学, 2011, 30(1): 179-188.
引用本文: 尹瑞川, 汪海林. 丙烯醛-DNA加合物的研究进展[J]. 环境化学, 2011, 30(1): 179-188.
YIN Ruichuan, WANG Hailin. REVIEW:THE FORMATION AND MUTAGENESIS OF ACROLEIN-DNA ADDUCTS[J]. Environmental Chemistry, 2011, 30(1): 179-188.
Citation: YIN Ruichuan, WANG Hailin. REVIEW:THE FORMATION AND MUTAGENESIS OF ACROLEIN-DNA ADDUCTS[J]. Environmental Chemistry, 2011, 30(1): 179-188.

丙烯醛-DNA加合物的研究进展

  • 基金项目:

    973计划项目(2007CB407305,2009CB421605)

    863计划项目(2007AA06A407)

    国家自然科学基金(20877091,20737003)资助.

REVIEW:THE FORMATION AND MUTAGENESIS OF ACROLEIN-DNA ADDUCTS

  • Fund Project:
  • 摘要: 丙烯醛是一种活泼的α,β不饱和醛,在环境中广泛存在,香烟烟气和厨房油烟是人体丙烯醛暴露的主要环境来源.另一方面机体内丙烯醛可以通过脂质过氧化、氨基酸氧化等多种途径自发生成.进入人体后,丙烯醛和DNA发生加合生成丙烯醛-DNA加合物.目前研究最多的是丙烯醛-dG加合物,包括α-OH-PdG和γ-OH-PdG,其中γ-OH-PdG是主要dG加合物,可引起基因突变 (约1%),以G→T突变为主,而次要加合物α-OH-PdG的突变概率高于γ-OH-PdG(约8%),同样以G→T突变为主,并且这些加合物与一些癌症密切相关,如吸烟相关肺癌和膀胱癌等.此外,丙烯醛可以与其它碱基发生加合,生成其它类型的DNA加合物,包括丙烯醛-dA、dC和dT加合物,其中一些加合物的结构已表征,并在体外反应中存在.
  • 加载中
  • [1] Feng Z H, Hu W W, Hu Y, et al. Acrolein is a major cigarette-related lung cancer agent: Preferential binding at p53 mutational hotspots and inhibition of DNA repair [J]. Proc Natl Acad Sci USA, 2006, 103:15404-15409
    [2] Stevens J F, Maier C S. Acrolein: Sources, metabolism, and biomolecular interactions relevant to human health and disease [J].Mol Nutr Food Res, 2008, 52:7-25
    [3] Minko I G, Kozekov I D, Kozekova A, et al. Mutagenic potential of DNA-peptide crosslinks mediated by acrolein-derived DNA adducts [J].Mutation Research, 2008, 637:161-172
    [4] Chung F L, Young R,Hecht S S. Formation of cyclic 1, N2-propanodeoxyguanosine adducts in DMA upon reaction with acrolein or crotonaldehyde [J].Cancer Research, 1984, 44:990-995
    [5] Nath R G and Chung F L. Detection of exocyclic 1,N2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans [J].Proc Natl Acad Sci USA, 1994, 91:7491-7495
    [6] Nath R G, Ocando J E, Guttenplan J B, et al. 1,N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking induced DNA damage in human oral tissue [J]. Cancer Research, 1998, 58:581-584
    [7] Zhang S Y,Villalta P W, Wang M Y, et al. Detection and quantitation of acrolein-derived 1,N2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry [J]. Chem Res Toxicol, 2007, 20:565-571
    [8] Sodum R S, Shapiao D. Reaction of acrolein with cytosine and adenine derivatives [J]. Biorganic Chemistry, 1988,16:272-282
    [9] Smith R A,Williamson D S, Cerny R L, et al. Detection of 1,N6-propanodeoxyadenosine in acrolein-modified polydeoxyadenylic acid and DNA by32P postlabeling [J].Cancer Research, 1990,50:3005-3012
    [10] Pawiowicz A J, Munter T, Klika K D, et al. Reaction of acrolein with 2'-deoxyadenosine and 9-ethyladenine-Formation of cyclic adducts [J].Bioorganic Chemistry, 2006, 34:39-48
    [11] Pawowicz A J, Munter T, Zhao Y, et al. Formation of acrolein adducts with 2'-deoxyadenosine in calf thymus DNA [J]. Chem Res Toxicol, 2006, 19:571-576
    [12] Kawai Y, Furuhata A, Toyokuni S, et al. Formation of acrolein-derived 2'-deoxyadenosine adduct in an iron-induced carcinogenesis model [J].Journal of Biological Chimestry, 2003, 278:50346-50354
    [13] Smith R A, Williamson D S, Cohen S M. Identification of 3,N4-propanodeoxycytidine 5'-monophosphate formed by the reaction of acrolein with deoxycytidine 5'-monop hosp hate [J]. Chem Res Toxicol, 1989, 2:267-271
    [14] Chenna A and Iden C R. Characterization of 2'-deoxycytidine and 2'-deoxyuridine adducts formed in reactions with acrolein and 2-bromoacrolein [J]. Chem Res Toxicol, 1993,6:261-268
    [15] Pawowicz A J, Klika K D, Kronberg L. The structural identification and conformational analysis of the products from the reaction of acrolein with 2'-deoxycytidine, 1-methylcytosine and calf thymus DNA [J]. Eur J Org Chem, 2007:1429-1437
    [16] Chenna A, Rieger R A and Iden C R. Characterization of thymidine adducts formed by acrolein and 2-bromoacrolein [J]. Carcinogenesis, 1992, 13:2361-2365
    [17] Pawlowicz A J and Kronberg L. Characterization of adducts formed in reactions of acrolein with thymidine and calf thymus DNA [J].Chemistry and Biodiversity,2008,5:177-188
    [18] Hecht S S. Smoking and lung cancer-a new role for an old toxicant? [J]. Proc Natl Acad Sci USA, 2006,103:15725-15726
    [19] Gomes R,Meek M E, Eggleton M. Concise international chemical assessment document No.43.World Health Organization, Geneva, 2002
    [20] Foiles P G, Akerkar S A, Miglietta L M, et al. Formation of cyclic deoxyguanosine adducts in Chinese hamster ovary cells by acrolein and crotonaldehyde [J]. Carcinogenesis, 1990,11:2059-2061
    [21] Wilson V L,Foiles P G,Chung F L, et al. Detection of acrolein and crotonaldehyde DNA adducts in cultured human cells and canine peripheral blood lymphocytes by32P-postlabeling and nucleotide chromatography [J]. Carcinogenesis, 1991,12: 1483-1490
    [22] Nath R G, Ocando J, Chung F L. Detection of 1,N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues [J]. Cancer Research, 1996,56: 452-456
    [23] Pan J S, Davis W, Trushin N, Amin S, et al. A solid-phase extraction/high-performance liquid chromatography-based 32P-postlabeling method for detection of cyclic 1, N2-propanodeoxyguanosine adducts derived from enals [J]. Analytical Biochemistry, 2006,348:15-23
    [24] Liu X L, Lovell M A, Lynn B C. 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 [J].Anal Chem, 2005, 77:5982-5989
    [25] Chen C H, Lin W P. Simultaneous quantification of 1,N2-propano-2'-deoxyguanosine adducts derived from acrolein and crotonaldehyde in human placenta and leukocytes by isotope dilution nanoflow LC nanospray ionization tandem mass spectrometry [J].Anal Chem, 2009, 81:9812-9818
    [26] Foiles P G, Chung F L, Hecht S S. Development of a monoclonal antibody-based immunoassay for cyclic DNA adducts resulting from exposure to crotonaldehyde [J].Cancer Research,1987,47:360-363
    [27] Foiles P G, Akerkar S A, Chung F L. 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 [J].Carcinogenesis, 1989,10:87-90
    [28] McDiarmid M A, Iype T, Kolodner K, Kram D J, et al. Evidence for acrolein-modified DNA in peripheral blood leukocytes of cancer patients treated with cyclophosphamide [J].Mutation Research, 1991, 248:93-99
    [29] Akatsuka S,Aung T T,Dutta K K,et al. Contrasting genome-wide distribution of 8-Hydroxyguanine and acrolein-modified adenine during oxidative stress-induced renal carcinogenesis [J]. The American Journal of Pathology, 2006, 169:1328-1342
    [30] Marnett L J, Hurd H K, Hollstein M C, et al. Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104 [J]. Mutation Research, 1985, 148:25-34
    [31] Curren R D,Yang L L,Conkin P M, et al. Mutagenesis of xeroderma pigmentosum fibroblasts by acrolein [J]. Mutation Research, 1988, 209:17-22
    [32] Kawanishi M, Matsuda T, Nakayama A, et al. Molecular analysis of mutations induced by acrolein in human fibroblast cells using supF shuttle vector plasmids [J]. Mutation Research, 1998, 417:65-73
    [33] Wang H T, Zhang S Z, Hu Y, et al. Mutagenicity and sequence specificity of acrolein-DNA adducts [J].Chem Res Toxicol, 2009, 22:511-517
    [34] Kim S, Pfeifer G P, Besaratinia A. Lack of mutagenicity of acrolein-Induced DNA adducts in mouse and human cells [J].Cancer Res, 2007,67:11640-11647
    [35] Khullar S, Varaprasad C V, Johnson F. Postsynthetic generation of a major acrolein adduct of 2'-deoxyguanosine in oligomeric DNA [J]. J Med Chem, 1999, 42:947-950
    [36] Nechev L V, Harris C M, Harris T M. Synthesis of nucleosides and oligonucleotides containing adducts of acrolein and vinyl chloride [J].Chem Res Toxicol, 2000, 13:421-429
    [37] Huang Y H, Torres M C, Iden C R, et al. Synthesis of the minor acrolein adducts of 2'-deoxyguanosine and their generation in oligomeric DNA [J]. Bioorganic Chemistry, 2003,31:136-148
    [38] VanderVeen L A, Hashim M F, Nechev L V, et al. Evaluation of the mutagenic potential of the principal DNA adduct of acrolein [J].Journal of Biological Chemistry, 2001, 276:9066-9070
    [39] Yang I Y, Hossain M, Miller H, et al. Responses to the major acrolein-derived deoxyguanosine adduct in escherichia coli [J].Journal of Biological Chemistry, 2001,276:9071-9076
    [40] Yang I Y, Johnson F, Grollman A P, et al. Genotoxic mechanism for the major acrolein-derived deoxyguanosine adduct in human cells [J]. Chem Res Toxicol, 2002, 15:160-164
    [41] Yang I Y, Chan G,Miller H, et al. Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells [J]. Biochemistry, 2002,41:13826-13832
    [42] Kanuri M, Minko I G, Nechev L V, et al. Error prone translesion synthesis past γ-hydroxypropano deoxyguanosine, the primary acrolein-derived adduct in mammalian cells [J]. Journal of Biological Chemistry, 2002, 277:18257-18265
    [43] Sanchez A M, Minko I G, Kurtz A J, et al. Comparative evaluation of the bioreactivity and mutagenic spectra of acrolein-derived α-HOPdG and γ-HOPdG regioisomeric deoxyguanosine adducts [J].Chem Res Toxicol, 2003, 16:1019-1028
    [44] Minko I G, Washington M T, Kanuri M, et al. Translesion synthesis past acrolein-derived DNA adduct, γ-hydroxypropanodeoxyguanosine, by yeast and human DNA polymerase η [J]. Journal of Biological Chemistry, 2003, 278: 784-790
    [45] Santos C, Zaliznyak T, Johnson F. NMR characterization of a DNA duplex containing the major acrolein derived deoxyguanosine adduct γ-OH-1,-N2-propano-2'-deoxyguanosine [J]. Journal of Biological Chemistry, 2001,276: 9077-9082
    [46] Minko I G,Kozekov I D, Harris T M, et al. Chemistry and biology of DNA containing 1,N2-deoxyguanosine adducts of the α, β-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal [J]. Chem Res Toxicol, 2009, 22:759-778
    [47] Stone M P,Cho Y J,Huang H, et al. Interstrand DNA cross-links induced by α, β-unsaturated aldehydes derived from lipid peroxidation and environmental sources [J].Accounts of Chemical Research, 2008,41: 793-804
    [48] VanderVeen L V, Harris T M,Jacobson L J,et al. Formation of DNA-protein cross-links betweenγ-hydroxypropanodeoxyguanosine and EcoRI [J]. Chem Res Toxicol, 2008, 21:1733-1738
    [49] Cohen S M,Garland E M,John M S, et al. Acrolein initiates rat urinary bladder carcinogenesis [J].Cancer Research, 1992,52:3577-3581
    [50] Sakata T, Smith R A, Garland E M, et al. Rat urinary bladder epithelial lesions induced by acrolein [J]. J Exp Pathol Toxicol Oncol, 1989, 9: 159-170
    [51] Irving C C, Murphy W M, Cox R. The effects of intravesical instillation of acrolein on the urothelium of the rat [J]. Proc Am Assoc Cancer Res, 1987, 28: 109
    [52] Cohen S M. The pathology of bladder cancer [M]. Boca Raton, FL: CRC Press, Inc,1983, 2:1-40
    [53] Wang H and Tang M S. Acrolein: excessive cytotoxicity or potent mutagenicity? [J]. Chem Res Toxicol, 2009, 22:753-754
  • 加载中
计量
  • 文章访问数:  1332
  • HTML全文浏览数:  1295
  • PDF下载数:  248
  • 施引文献:  0
出版历程
  • 收稿日期:  2010-08-06
尹瑞川, 汪海林. 丙烯醛-DNA加合物的研究进展[J]. 环境化学, 2011, 30(1): 179-188.
引用本文: 尹瑞川, 汪海林. 丙烯醛-DNA加合物的研究进展[J]. 环境化学, 2011, 30(1): 179-188.
YIN Ruichuan, WANG Hailin. REVIEW:THE FORMATION AND MUTAGENESIS OF ACROLEIN-DNA ADDUCTS[J]. Environmental Chemistry, 2011, 30(1): 179-188.
Citation: YIN Ruichuan, WANG Hailin. REVIEW:THE FORMATION AND MUTAGENESIS OF ACROLEIN-DNA ADDUCTS[J]. Environmental Chemistry, 2011, 30(1): 179-188.

丙烯醛-DNA加合物的研究进展

  • 1. 中国科学院生态环境研究中心环境化学与生态毒理学国家重点实验室, 北京, 100085
基金项目:

973计划项目(2007CB407305,2009CB421605)

863计划项目(2007AA06A407)

国家自然科学基金(20877091,20737003)资助.

摘要: 丙烯醛是一种活泼的α,β不饱和醛,在环境中广泛存在,香烟烟气和厨房油烟是人体丙烯醛暴露的主要环境来源.另一方面机体内丙烯醛可以通过脂质过氧化、氨基酸氧化等多种途径自发生成.进入人体后,丙烯醛和DNA发生加合生成丙烯醛-DNA加合物.目前研究最多的是丙烯醛-dG加合物,包括α-OH-PdG和γ-OH-PdG,其中γ-OH-PdG是主要dG加合物,可引起基因突变 (约1%),以G→T突变为主,而次要加合物α-OH-PdG的突变概率高于γ-OH-PdG(约8%),同样以G→T突变为主,并且这些加合物与一些癌症密切相关,如吸烟相关肺癌和膀胱癌等.此外,丙烯醛可以与其它碱基发生加合,生成其它类型的DNA加合物,包括丙烯醛-dA、dC和dT加合物,其中一些加合物的结构已表征,并在体外反应中存在.

English Abstract

参考文献 (53)

返回顶部

目录

/

返回文章
返回