Comparative analysis of binding affinities between styrene and mammalian CYP2E1 by bioinformatics approaches

Ecotoxicology

Volumn 20, Issue 5, 2011, Pages 1041-1046

  Wu, Bing ^a   Sun, Jie ^a   Cheng, Shu Pei ^a   Gu, Ji Dong ^b   Li, Ai Min ^a   Zhang, Xu Xiang ^a  

^a NANJING UNIVERSITY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Cytochrome P450 2E1; Homology modeling; Mammal; Molecular docking; Styrene

Indexed keywords

AMINO ACID; CYTOCHROME P450 2E1; POLYSTYRENE; STYRENE;

AMINO ACID; COMPARATIVE STUDY; CRYSTAL STRUCTURE; CYTOCHROME; ENZYME ACTIVITY; HOMOLOGY; MAMMAL; METABOLISM;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; BIOINFORMATICS; COMPARATIVE STUDY; CONTROLLED STUDY; CRYSTAL STRUCTURE; HUMAN; MOLECULAR DOCKING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE ALIGNMENT; SWISS-PROT;

ANIMALS; COMPUTATIONAL BIOLOGY; CYTOCHROME P-450 CYP2E1; ENVIRONMENTAL POLLUTANTS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STYRENE;

MAMMALIA; RUMEX;

EID: 79960333804     PISSN: 09639292     EISSN: 15733017     Source Type: Journal    
DOI: 10.1007/s10646-011-0643-z     Document Type: Article

References (25)

1. L Bordoli F Kiefer K Arnold P Benkert J Battey T Schwede 2009 Protein structure homology modeling using SWISS-MODEL workspace Nat Protoc 4 1 1 13 10.1038/nprot.2008.197 1:CAS:528:DC%2BD1cXhsFCkurfP
2. GP Carlson 2004 Comparison of the susceptibility of wild-type and CYP2E1 knockout mice to the hepatotoxic and pneumotoxic effects of styrene and styrene oxide Toxicol Lett 150 3 335 339 10.1016/j.toxlet.2004.02.004 1:CAS:528:DC%2BD2cXjsVWrtrY%3D (Pubitemid 38510585)
3. L Celik JDD Lund B Schiott 2008 Exploring interactions of endocrine-disrupting compounds with different conformations of the human estrogen receptor alpha ligand binding domain: a molecular docking study Chem Res Toxicol 21 11 2195 2206 10.1021/tx800278d 1:CAS:528:DC%2BD1cXht1CltbbF
4. R Chenna H Sugawara T Koike R Lopez TJ Gibson DG Higgins JD Thompson 2003 Multiple sequence alignment with the Clustal series of programs Nucleic Acids Res 31 13 3497 3500 10.1093/nar/gkg500 1:CAS:528:DC%2BD3sXltVWjsrg%3D (Pubitemid 37442184)
5. JK Chung W Yuan G Liu J Zheng 2006 Investigation of bioactivation and toxicity of styrene in CYP2E1 transgenic cells Toxicology 226 2-3 99 106 10.1016/j.tox.2006.06.001 1:CAS:528:DC%2BD28XoslOhsL8%3D (Pubitemid 44287159)
6. G Cruzan GP Carlson M Turner W Mellert 2005 Ring-oxidized metabolites of styrene contribute to styrene-induced Clara-cell toxicity in mice J Toxicol Environ Health A 68 3 229 237 10.1080/15287390590890464 1:CAS:528: DC%2BD2MXot1eiug%3D%3D (Pubitemid 40070925)
7. Goodsell DS, David S (2005) Representing structural information with RasMol. Curr Protoc Bioinformatics, Chap 5: Unit 5.4
8. N Guex MC Peitsch 1997 SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18 15 2714 2723 10.1002/elps.1150181505 1:CAS:528:DyaK1cXhvFaks70%3D (Pubitemid 28059943)
9. LM Henderson G Speit 2005 Review of the genotoxicity of styrene in humans Mutat Res Rev Mutat Res 589 3 158 191 1:CAS:528:DC%2BD2MXjvVOntLY%3D (Pubitemid 40616863)
10. C Hofmann TH Faller GA Csanady JG Filser 2005 Metabolism of styrene to styrene-7, 8-oxide in ventilated, perfused lungs of mice and rats Naunyn Schmiedebergs Arch Pharmacol 371 415
11. PA Holt JB Chaires JO Trent 2008 Molecular docking of intercalators and groove-binders to nucleic acids using Autodock and Surflex J Chem Inf Model 48 8 1602 1615 10.1021/ci800063v 1:CAS:528:DC%2BD1cXoslCrsbs%3D
12. AN Jain 2007 Surflex-Dock 2.1: robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search J Comput Aided Mol Des 21 5 281 306 10.1007/s10822-007-9114-2 1:CAS:528:DC%2BD2sXksVOgt78%3D (Pubitemid 46630055)
13. M Karlsson A Strid A Sirsjo LA Eriksson 2008 Homology models and molecular modeling of human retinoic acid metabolizing enzymes cytochrome P450 26A1 (CYP26A1) and P450 26131 (CYP26B1) J Chem Theory Comput 4 6 1021 1027 10.1021/ct800033x 1:CAS:528:DC%2BD1cXltlamt70%3D
14. RA Laskowski MW Macarthur DS Moss JM Thornton 1993 Procheck-a program to check the stereochemical quality of protein structures J Appl Crystallogr 26 283 291 10.1107/S0021889892009944 1:CAS:528:DyaK3sXit12lurY%3D
15. DFV Lewis BG Lake MG Bird GD Loizou M Dickins PS Goldfarb 2003 Homology modelling of human CYP2E1 based on the CYP2C5 crystal structure: investigation of enzyme-substrate and enzyme-inhibitor interactions Toxicol In Vitro 17 1 93 105 10.1016/S0887-2333(02)00098-X 1:CAS:528:DC%2BD3sXltVKqsw%3D%3D (Pubitemid 36106496)
16. WH Li Y Tang H Liu JG Cheng WL Zhu HL Jiang 2008 Probing ligand binding modes of human cytochrome P450 2J2 by homology modeling, molecular dynamics simulation, and flexible molecular docking Proteins: Struct Funct Bioinform 71 2 938 949 10.1002/prot.21778 1:CAS:528:DC%2BD1cXkt1amuro%3D (Pubitemid 351436336)
17. G Lutfullah F Amin Z Khan N Azhar MK Azim S Noor K Shoukat 2008 Homology modeling of hemagglutinin/protease [HA/P (vibriolysin)] from Vibrio cholerae: sequence comparison, residue interactions and molecular mechanism Protein J 27 2 105 114 10.1007/s10930-007-9113-0 1:CAS:528:DC%2BD1cXkt12nt7o%3D (Pubitemid 351661106)
18. ER Nestmann BS Lynch F Ratpan 2005 Perspectives on the genotoxic risk of styrene J Toxicol Environ Health B 8 2 95 107 10.1080/10937400590908988 1:CAS:528:DC%2BD2MXis1Wjtrw%3D (Pubitemid 40364845)
19. PR Porubsky KM Meneely EE Scott 2008 Structures of human cytochrome P-450 2E1 insights into the binding of inhibitors and both small molecular weight and fatty acid substrates J Biol Chem 283 48 33698 33707 10.1074/jbc.M805999200 1:CAS:528:DC%2BD1cXhsVSgt7jO
20. J Rueff JP Teixeira LS Santos JF Gaspar 2009 Genetic effects and biotoxicity monitoring of occupational styrene exposure Clin Chim Acta 399 1-2 8 23 10.1016/j.cca.2008.09.012 1:CAS:528:DC%2BD1cXhsVOis77P
21. R Sarangapani JG Teeguarden G Cruzan HJ Clewell ME Andersen 2002 Physiologically based pharmacokinetic modeling of styrene and styrene oxide respiratory-tract dosimetry in rodents and humans Inhalation Toxicol 14 8 789 834 10.1080/08958370290084647 1:CAS:528:DC%2BD38XmsFaksbY%3D
22. G Speit L Henderson 2005 Review of the in vivo genotoxicity tests performed with styrene Mutat Res Rev Mutat Res 589 1 67 79 1:CAS:528: DC%2BD2MXis1WksA%3D%3D (Pubitemid 40094592)
23. H Van Brussel J Wyns P Valckenaers L Bongaerts P Peeters 1998 Reference architecture for holonic manufacturing systems: PROSA Comput Ind 37 3 255 274 10.1016/S0166-3615(98)00102-X (Pubitemid 128419944)
24. MAM Wenker S Kezic AC Monster FA de Wolff 2000 Metabolism of styrene-7, 8-oxide in human liver in vitro: interindividual variation and stereochemistry Toxicol Appl Pharmacol 169 1 52 58 10.1006/taap.2000.9038 1:CAS:528: DC%2BD3cXnvFyrtr0%3D
25. WH Yang YS Mu JP Giesy AQ Zhang HX Yu 2009 Anti-androgen activity of polybrominated diphenyl ethers determined by comparative molecular similarity indices and molecular docking Chemosphere 75 9 1159 1164 10.1016/j.chemosphere. 2009.02.047 1:CAS:528:DC%2BD1MXlsVGqtr4%3D