Molecular docking and comparative molecular similarity indices analysis of estrogenicity of polybrominated diphenyl ethers and their analogues

Environmental Toxicology and Chemistry

Volumn 29, Issue 3, 2010, Pages 660-668

  Yang, Weihua ^a,b   Liu, Xiaohua ^a   Liu, Hongling ^a   Wu, Yang ^a   Giesy, John P ^a,c,d,e   Yu, Hongxia ^a  

^a NANJING UNIVERSITY   (China)

^b JIANGSU NORMAL UNIVERSITY   (China)

^c UNIVERSITY OF SASKATCHEWAN   (Canada)

^d MICHIGAN STATE UNIVERSITY   (United States)

^e CITY UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Endocrine disrupting activity; Ligand receptor interaction mechanism; Receptor based; Surflex dock; Three dimensional quantitative structure activity relationships

Indexed keywords

CHEMICAL ENGINEERING; DOCKING; DOCKS; ENDOCRINOLOGY; ENZYME INHIBITION; ETHERS; HYDRAULIC STRUCTURES; HYDROGEN BONDS; LIGANDS; MOLECULAR MODELING; ORGANIC COMPOUNDS; PHENOLS; SULFUR COMPOUNDS;

3D-QSAR; BISPHENOL A; BISPHENOLS; COMPARATIVE-MOLECULAR-SIMILARITY-INDICES ANALYSIS; ENDOCRINE-DISRUPTING ACTIVITY; ESTROGENIC ACTIVITIES; ESTROGENICITY; HUMAN ESTROGEN RECEPTORS; HYDROGEN BONDINGS; HYDROXYLATED POLYBROMINATED DIPHENYL ETHERS; INTERACTION MECHANISMS; LEAVE-ONE-OUT; LIGAND-RECEPTOR INTERACTIONS; MOLECULAR CONFORMATION; MOLECULAR DOCKING; POLYBROMINATED DIPHENYL ETHERS; STRUCTURAL CHARACTERISTICS; TEST SETS; THREE-DIMENSIONAL QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TRAINING SETS;

THREE DIMENSIONAL;

1,4 HYDROXYLATED POLYBROMINATED DIPHENYL ETHER; BROMINATED BISPHENOL A; ESTROGEN RECEPTOR ALPHA; POLYBROMINATED DIPHENYL ETHER; UNCLASSIFIED DRUG; DIPHENYL ETHER DERIVATIVE; ENDOCRINE DISRUPTOR; ESTROGEN RECEPTOR BETA;

ENDOCRINE DISRUPTOR; ESTROGENIC COMPOUND; HYDROGEN; LIGAND; MOLECULAR ANALYSIS; PBDE;

ARTICLE; BINDING SITE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; ECOTOXICOLOGY; ESTROGEN ACTIVITY; HUMAN; HYDROGEN BOND; MOLECULAR DOCKING; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR BINDING; STRUCTURE ANALYSIS; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECTS; METABOLISM; TOXICITY;

RUMEX;

ENDOCRINE DISRUPTORS; ESTROGEN RECEPTOR BETA; HALOGENATED DIPHENYL ETHERS; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77951144249     PISSN: 07307268     EISSN: 15528618     Source Type: Journal    
DOI: 10.1002/etc.70     Document Type: Article

References (25)

1. Darnerud PO, Gunnar ES, Johannesson T, Larsen PB, Viluksela M. 2001. Polybrominated diphenyl ethers: occurrence, dietary exposure and toxicology. Environ Health Perspect 109:49-68. (Pubitemid 32303230)
2. Hites RA. 2004. Polybrominated diphenyl ethers in the environment and in people: A meta-analysis of concentrations. Environ Sci Technol 38:945-956. (Pubitemid 38228706)
3. He JZ, Robrock KR, Alvarez-Cohen L. 2006. Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs). Environ Sci Technol 40:4429-4434. (Pubitemid 44092377)
4. Mai BX, Chen SJ, Luo XJ, Chen LG, Yang QS, Sheng GY, Peng PA, Fu JM, Zeng EY. 2005. Distribution of polybrominated diphenyl ethers in sediments of the Pearl River Delta and adjacent South China Sea. Environ Sci Technol 39:3521-3527. (Pubitemid 40705473)
5. Qiu XH, Bigsby RM, Hites RA. 2009. Hydroxylated metabolites of polybrominated diphenyl ethers inhumanblood samples from the United States. Environ Health Perspect 117:93-98.
6. Toms LM, Harden FA, Symons RK, Burniston D, Fürst P, Müller JF. 2007. Polybrominated diphenyl ethers (PBDEs) in human milk from Australia. Chemosphere 68:797-803. (Pubitemid 46602513)
7. Meerts IA, Letcher RJ, Hoving S, Marsh G, Bergman A, Lemmen JG, van der Burg B, Brouwer A. 2001. In vitro estrogenicity of polybrominated diphenyl ethers, hydroxylated PDBEs, and polybrominated bisphenol A compounds. Environ Health Perspect 109:399-407.
8. Hamers T, Kamstra JH, Sonneveld E, Murk AJ, Kester MHA, Andersson PL, Legler J, Brouwer A. 2006. In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol Sci 92:157-173.
9. Wang YW, Liu HX, Zhao CY, Liu HX, Cai ZW, Jiang GB. 2005. Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners. Environ Sci Technol 39:4961-4966.
10. Harju M, Hamers T, Kamstra JH, Sonneveld E, Boon JP, Tysklind M, Andersson PL. 2007. Quantitative structure-activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants. Environ Toxicol Chem 26:816-826. (Pubitemid 46663284)
11. Tamura H, Ishimoto Y, Fujikawa T, Aoyama H, Yoshikawa H, Akamatsu M. 2006. Structural basis for androgen receptor agonists and antagonists: Interaction of SPEED 98-listed chemicals and related compounds with the androgen receptor based on an in vitro reporter gene assay and 3D-QSAR. Bioorg Med Chem 14:7160-7174. (Pubitemid 44404243)
12. Klebe G, Abraham U, Mietzner T. 1994. Molecular similarity indexes in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37:4130-4146. (Pubitemid 24379702)
13. Jójárt B, Martinek TA, Márki Á. 2005. The 3D structure of the binding pocket of the human oxytocin receptor for benzoxazine antagonists, determined by molecular docking, scoring functions and 3D-QSAR methods. J Comput Aided Mol Des 19:341-356. (Pubitemid 41440001)
14. Gilbert KM, Boos TL, Dersch CM, Greiner E, Jacobson AE, Lewis D, Mateck D, Prisinzano TE, Zhang Y, Rothman RB, Rice KC, Venanzia CA. 2007. DAT/SERT selectivity of flexible GBR 12909 analogs modeled using 3D-QSAR methods. Bioorg Med Chem 15:1146-1159. (Pubitemid 44895501)
15. Novellino E, Fattorusso C, Greco G. 1995. Use of comparative molecular field analysis and cluster analysis in series design. Pharm Acta Helv 70:149-154.
16. Kubinyi H, Hamprecht FA, Mietzner T. 1998. Three-dimensional quantitative similarity-activity relationships (3D QSAR) from SEAL similarity matrices. J Med Chem 41:2553-2564. (Pubitemid 28321904)
17. 2! J Mol Graph Model 20:269-276.
18. Fang H, Tong WD, Shi LM, Blair R, Perkins R, Branham W, Hass BS, Xie Q, Dial SL, Moland CL, Sheehan DM. 2001. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem Res Toxicol 14:280-294. (Pubitemid 32238488)
19. Mercado-Feliciano M, Bigsby RM. 2008. Hydroxylated metabolites of the polybrominated diphenyl ether mixture DE-71 are weak estrogen receptor alpha ligands. Environ Health Perspect 116:1315-1321.
20. Anstead GM, Carlson KE, Katzenellenbogen JA. 1997. The estradiol pharmacophore: Ligand structure - estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 62:268-303.
21. Sun H, Xu XL, Qu JH, Hong X, Wang YB, Xu LC, Wang XR. 2008. 4-Alkylphenols and related chemicals show similar effect on the function of human and rat estrogen receptor a in reporter gene assay. Chemosphere 71:582-588. (Pubitemid 351625271)
22. Fang H, Tong WD, Perkins R, Soto AM, Prechtl NV, Sheehan DM. 2000. Quantitative comparisons of in vitro assays for estrogenic activities. Environ Health Perspect 108:723-729.
23. Celik L, Lund JDD, Schiøtt B. 2008. Exploring Interactions of endocrine-disrupting compounds with different conformations of the human estrogen receptor a ligand binding domain: A molecular docking study. Chem Res Toxicol 21:2195-2206.
24. Layton AC, Sanseverino J, Gregory BW, Easter JP, Sayler GS, Schultz TW. 2002. In vitro estrogen receptor binding of PCBs: Measured activity and detection of hydroxylated metabolites in a recombinant yeast assay. Toxicol Appl Pharmacol 180:157-163.
25. Aptula AO, Roberts DW, Cronin MTD, Schultz TW. 2005. Chemistry-toxicity relationships for the effects of diand trihydroxybenzenes to Tetrahymena pyriformis. Chem Res Toxicol 18:844-854.