Evaluation of the noncovalent binding interactions between polycyclic aromatic hydrocarbon metabolites and human p53 cDNA

Science of the Total Environment

Volumn 408, Issue 24, 2010, Pages 6285-6290

  Wei, Yin ^a   Lin, Yuan ^b   Zhang, Ai Qian ^b   Guo, Liang Hong ^a   Cao, Jie ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

DNA binding; Intercalation; P53 complementary DNA; Polycyclic aromatic hydrocarbon metabolites

Indexed keywords

1-HYDROXYPYRENE; 2-NAPHTHOLS; AROMATIC RINGS; BENZO [A] PYRENE; BINDING AFFINITIES; DISPLACEMENT METHOD; DISSOCIATION CONSTANT; DNA ADDUCTS; DNA BASE PAIRS; DNA BASIS; DNA BINDING; GROOVE BINDING; HYDROXYL GROUPS; IN-VIVO; INTERCALATORS; MOLECULAR DOCKING; NONCOVALENT BINDING; NONCOVALENT BINDING INTERACTIONS; P53 COMPLEMENTARY DNA; PHENYL RINGS; POLYCYCLIC AROMATICS; SEQUENCE SELECTIVITY;

AROMATIC HYDROCARBONS; AROMATIZATION; BINDING ENERGY; BIOMOLECULES; DISSOCIATION; FUNCTIONAL GROUPS; HYDROGEN; HYDROGEN BONDS; METABOLISM; METABOLITES; PHENOLS; POLYCYCLIC AROMATIC HYDROCARBONS; TERNARY SYSTEMS;

DNA;

1 HYDROXYPYRENE; 2 FLUORENOL; 2 HYDROXYBENZO[C]PHENANTHRENE; 2 NAPHTHOL; 3 HYDROXYBENZO[A]PYRENE; 3 HYDROXYBENZO[C]PYRENE; 7,8 DIHYDROXYBENZO[A]PYRENE 9,10 OXIDE; 9 PHENANTHROL; BENZ[A]ANTHRACENE 8,9 DIHYDRODIOL 10,11 OXIDE; BENZENE DERIVATIVE; BENZO[A]PYRENE 4,5 DIHYDROEPOXIDE; CHRYSENE 1,2 DIHYDRODIOL 3,4 EPOXIDE; COMPLEMENTARY DNA; DIBENZ[A,C]ANTHRACENE 10,11 DIHYDRODIOL 12,13 EPOXIDE; FUNCTIONAL GROUP; HYDROGEN; POLYCYCLIC AROMATIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROTEIN P53; UNCLASSIFIED DRUG;

CARCINOGEN; CHEMICAL BINDING; DNA; METABOLITE; PAH;

ARTICLE; BASE PAIRING; BINDING AFFINITY; CARCINOGEN DNA INTERACTION; CARCINOGENICITY; CONTROLLED STUDY; COVALENT BOND; DISSOCIATION CONSTANT; FLUORESCENCE ANALYSIS; HUMAN; HYDROGEN BOND; INTERCALATION COMPLEX; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR STABILITY; PRIORITY JOURNAL;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; BENZO(A)PYRENE; BENZOPYRENES; DNA DAMAGE; DNA, COMPLEMENTARY; ENVIRONMENTAL POLLUTANTS; HUMANS; MUTAGENS; POLYCYCLIC HYDROCARBONS, AROMATIC; PYRENES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 77958108219     PISSN: 00489697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2010.09.024     Document Type: Article

References (29)

1. Aranda R., Villalba K., Ravina E., Masaguer C.F., Brea J., Areias F., et al. Synthesis, binding affinity, and molecular docking analysis of new benzofuranone derivatives as potential antipsychotics. J Med Chem 2008, 51:6085-6094.
2. Dipple A., Pigott M.A., Agarwal S.K., Yagi H., Sayer J.M., Jerina D.M. Optically active benzo[c]phenanthrene diol-epoxides bind extensively to adenine in DNA. Nature 1987, 327:535-536.
3. Feng Z., Hu W., Chen J.X., Pao A., Li H., Rom W., et al. Preferential DNA damage and poor repair determine ras gene mutational hotspot in human cancer. J Natl Cancer Inst 2002, 94:1527-1536.
4. Fields W.R., Desiderio J.G., Leonard R.M., Burger E.E., Brown B.G., Doolittle D.J. Differential c-myc expression profiles in normal human bronchial epithelial cells following treatment with benzo[a]pyrene, benzo[a]pyrene-4, 5 epoxide, and benzo[a]pyrene-7, 8-9, 10 diol epoxide. Mol Carcinog 2004, 40:79-89.
5. Geacintov N.E., Yoshida H., Ibanez V., Harvey R.G. Non-covalent intercalative binding of 7, 8-dihydroxy-9, 10-epoxybenzo(a)pyrene to DNA. Biochem Biophys Res Commun 1981, 100:1569-1577.
6. Geacintov N.E., Gagliano A.G., Ibanez V., Harvey R.G. Spectroscopic characterizations and comparisons of the structures of the covalent adducts derived from the reactions of 7, 8-dihydroxy-7, 8, 9, 10-tetrahydrobenzo[a]pyrene-9, 10-oxide, and the 9, 10-epoxides of 7, 8, 9, 10-tetrahydrobenzo[a]pyrene and 9, 10, 11, 12-tetrahydrobenzo[e]pyrene with DNA. Carcinogenesis 1982, 3:247-253.
7. Geacintov N.E., Yoshida H., Ibanez V., Harvey R.G. Noncovalent binding of 7, 8-dihydroxy-9,10-epoxytetrahydrobenzo[a]pyrene to DNA and its catalytic effect on the hydrolysis of the diol epoxide to tetrol. Biochemistry 1982, 21:1864-1869.
8. Geacintov N.E., Cosman M., Mao B., Alfano A., Ibanez V., Harvey R.G. Spectroscopic characteristics and site I/site II classification of cis and trans benzo[a]pyrene diolepoxide enantiomer-guanosine adducts in oligonucleotides and polynucleotides. Carcinogenesis 1991, 12:2099-2108.
9. Hainaut P., Pfeifer G.P. Patterns of p53 GT transversions in lung cancers reflect the primary mutagenic signature of DNA-damage by tobacco smoke. Carcinogenesis 2001, 22:367-374.
10. Hainaut P., Soussi T., Shomer B., Hollstein M., Greenblatt M., Hovig E., et al. Database of p53 gene somatic mutations in human tumors and cell lines: updated compilation and future prospects. Nucleic Acids Res 1997, 25:151-157.
11. Hainaut P., Olivier M., Pfeifer G.P. TP53 mutational spectrum in lung cancers and mutagenic signature of components of tobacco smoke: lessons from the IARC TP53 mutation database. Mutagenesis 2001, 16:551-553.
12. Harris C.C. p53: at the crossroads of molecular carcinogenesis and risk assessment. Science 1993, 262:1980-1981.
13. Harvey R.G. Polycyclic aromatic hydrocarbons, chemistry and carcinogenicity 1991, 11-87. Cambridge Univ. Press, Cambridge, UK.
14. Holt P.A., Chaires J.B., Trent J.O. Molecular docking of intercalators and groove-binders to nucleic acids using autodock and surflex. J Chem Inf Model 2008, 48:1602-1615.
15. IARC IARC monographs on the evaluation of carcinogenic risks to humans 2009, Lyon, France.
16. Jerina D.M., Chadha A., Cheh A.M., Schurdak M.E., Wood A.W., Sayer J.M. Covalent bonding of bay region diol epoxides to nucleic acids. Biological Reactive Intermediates IV 1991, 533-553. Plenum Press, New York. C.M. Witmer, R. Snyder, D.J. Jollow, G.F. Kalf, J.J. Koscis, I.G. Sipes (Eds.).
17. Lamb P., Crawford L. Characterization of the human p53 gene. Mol Cell Biol 1986, 6:1379-1385.
18. Lane D.P., Benchimol S. p53: oncogene or anti-oncogene?. Genes Dev 1990, 4:1-8.
19. Levine A.J. p53, the cellular gatekeeper for growth and division. Cell 1997, 88:323-331.
20. Meehan T., Gamper H., Becker J.F. Characterization of reversible, physical binding of benzo[a]pyrene derivatives to DNA. J Biol Chem 1982, 257:10479-10485.
21. Miller E.C., Miller J.A. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 1981, 47:2327-2345.
22. Miller C.W., Simon K., Aslo A., Kok K., Yokota J., Buys C.H.C.M., et al. p53 mutations in human lung tumors. Cancer Res 1992, 52:1695-1698.
23. Pirogov N., Shafirovich V., Kolbanovskiy A., Solntsev K., Courtney S.A., Amin S., et al. Role of hydrophobic effects in the reaction of a polynuclear aromatic diol epoxide with oligodeoxynucleotides in aqueous solutions. Chem Res Toxicol 1998, 11:381-388.
24. Rodríguez F.A., Cai Y., Lin C., Tang Y., Kolbanovskiy A., Amin S., et al. Exocyclic amino groups of flanking guanines govern sequence-dependent adduct conformations and local structural distortions for minor groove-aligned benzo[a]pyrenyl-guanine lesions in a GG mutation hotspot context. Nucleic Acids Res 2007, 35:1555-1568.
25. Shahbaz M., Geacintov N.E., Harvey R.G. Noncovalent intercalative complex formation and kinetic flow linear dichroism of racemic syn- and anti-benzo[a]pyrenediol epoxide-DNA solutions. Biochemistry 1986, 25:3290-3296.
26. Smith L.E., Denissenko M.F., Bennett W.P., Li H., Amin S., Tang M., et al. Targeting of lung cancer mutational hotspots by polycyclic aromatic hydrocarbons. J Natl Cancer Inst 2000, 92:803-811.
27. Urano S., Price H.L., Fetzer S.M., Briedis A.V., Milliman A., LeBreton P.R. Photoemission probes of hydrocarbon-DNA interactions: A comparison of DNA influences on the reactivities of (±)-trans-7, 8-dihydroxy-anti-9, 10-epoxy-7, 8, 9, 10-tetrahydrobenzo[a]pyrene, benzo[a]pyrene 4, 5-oxide, and benz[a]anthracene 5, 6-Oxide. J Am Chem Soc 1991, 113:3881-3893.
28. Wei Y., Guo L.H. Binding interaction between polycyclic aromatic compounds and DNA by fluorescence displacement method. Environ Toxicol Chem 2009, 28:940-945.
29. WHO Selected non-heterocyclic polycyclic aromatic hydrocarbons; Environmental Health Criteria 202, Geneva 1998.