Activation of the aryl hydrocarbon receptor by carbaryl: Computational evidence of the ability of carbaryl to assume a planar conformation

Environmental Toxicology and Chemistry

Volumn 25, Issue 12, 2006, Pages 3141-3147

  Casado, Susana ^a   Alonso, Mercedes ^b   Herradón, Bernardo ^b   Tarazona, José V ^a   Navas, José Ma ^a  

^a INIA   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Aryl hydrocarbon receptor; Carbaryl; Computational modeling; Cytochrome P4501A

Indexed keywords

ACTIVATION ANALYSIS; BINDING ENERGY; COMPUTATIONAL METHODS; COMPUTER SIMULATION; CONFORMATIONS; HYDROGEN BONDS; MOLECULAR STRUCTURE;

ARYL HYDROCARBON RECEPTOR (AHR); CARBARYL MOLECULES; COPLANAR CONFORMATIONS; CYTOCHROME P4501A; LIGAND BINDING;

AROMATIC HYDROCARBONS;

AROMATIC HYDROCARBON RECEPTOR; BETA NAPHTHOFLAVONE; CARBARIL; CYTOCHROME P450 1A; HYDROFLUORIC ACID; NAPHTHALENE;

CYTOCHROME; HYDROCARBON; LIGAND; MODELING;

ANIMAL CELL; ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; GENETIC TRANSFECTION; HYDROGEN BOND; LIGAND BINDING; LUMINESCENCE; MODEL; MOLECULAR INTERACTION; MOLECULAR MECHANICS; NONHUMAN; PRIORITY JOURNAL; QUANTUM CHEMISTRY; RAT;

ANIMALS; CARBARYL; CELL LINE, TUMOR; COMPUTER SIMULATION; GENE EXPRESSION; GENES, REPORTER; HYDROFLUORIC ACID; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RATS; RECEPTORS, ARYL HYDROCARBON;

RATTUS;

EID: 33846206467     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/06-131R.1     Document Type: Article

References (32)

1. Ledirac N, Delescluse C, Sousa G, Plalavorio M, Lesca P, Amichot M, Bergé JB, Rahmani R. 1997. Carbaryl induces P4501A1 gene expression in HepG2 and HaCaT cells but is not a ligand of the human hepatic Ah receptor. Toxicol Appl Pharmacol 144: 177-182.
2. Delescluse C, Ledirac N, Li R, Piechocki MP, Hines RN, Gidrol X, Rahmani R. 2001. Induction of cytochrome CYP1A1 gene expression, oxidative stress, and genotoxicity by carbaryl and thiabendazole in transfected human HepG2 and lymphoblastoid cells. Biochem Pharmacol 61:399-407.
3. Stegeman JJ, Hahn ME. 1994. Biochemistry and molecular biology of monooxygenases: Current perspectives on forms, functions, and regulation of cytochrome P450 in aquatic species. In Malins DC, Ostrander GK, eds, Aquatic Toxicology. CRC, Boca Raton, FL, USA, pp 87-206.
4. Denison MS, Whitlock JP Jr. 1995. Xenobiotic-inducible transcription of cytochrome P450 genes. J Biol Chem 270:18175-18178.
5. Ma Q, Whitlock JP Jr. 1997. A novel cytoplasmic protein that interacts with the Ah receptor, contains a tetratricopeptide repeat motif, and augments the transcriptional response to 2,3,7,8-tetrachlorodibenzo-p-dioxin. J Biol Chem 27:8878-8884.
6. Dubey RK, Jackson EK. 2001. Estrogen-induced cardiorenal protection: Potential cellular, biochemical, and molecular mechanisms. Am J Physiol Renal Physiol 280:F365-F388.
7. Pollenz RS, Sattler CA, Poland A. 1994. The aryl hydrocarbon receptor and aryl hydrocarbon receptor nuclear translocator protein show distinct subcellular localizations in Hepa 1c1c7 cells by immunofluorescence microscopy. Mol Pharmacol 45:428-438.
8. Rowlands JC, Gustafsson JA. 1997. Aryl hydrocarbon receptor-mediated signal transduction. Crit Rev Toxicol 27:109-134.
9. Safe S. 1990. Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and related compounds: Environmental and mechanistic considerations which support the development of toxic equivalency factors (TEFs). Crit Rev Toxicol 21:51-88.
10. Waller CL, McKinney JD. 1995. Three-dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: Model validation and Ah receptor characterization. Chem Res Toxicol 8:847-858.
11. Mekenyan OG, Veith VD, Call DJ, Ankley GT 1996. A QSAR evaluation of Ah receptor binding of halogenated aromatic xenobiotics. Environ Health Perspect 104:1302-1310.
12. Kafafi SA, Afeefy HY, Ali AH, Said HK, Kafafi AG. 1993. Binding of polychlorinated biphenyls to the aryl hydrocarbon receptor. Environ Health Perspect 101:422-428.
13. Chana A, Concejero MA, de Frutos J, Gonzalez MJ, Herradón B. 2002. Computational studies on biphenyl derivatives. Analysis of the conformational mobility, molecular electrostatic potential, and dipole moment of chlorinated biphenyls: Searching for the rationalization of the selective toxicity of polychlorinated biphenyls. Chem Res Toxicol 15:1514-1526.
14. Mhin BJ, Lee JE, Choi W. 2002. Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: Chlorination pattern and molecular quadrupole moment. J Am Chem Soc 124:144-148.
15. Sandoz C, Lesca P, Carpy A, Laguionie M, Narbonne JF. 1998. Effects of carbaryl and naphthalene on rat hepatic CYPIA1/2: Potential binding to Ah receptor and 4S benzo[a]pyrene-binding protein. Int J Mol Med 2:615-623.
16. Sandoz C, Lesca P, Narbonne JN, Carpy A. 2000. Molecular characteristics of carbaryl, a CYP1A1 gene inducer. Arch Biochem Biophys 373:275-280.
17. Denison MS, Phelan D, Winter GM, Ziccardi MH. 1998. Carbaryl, a carbamate insecticide, is a ligand for the hepatic Ah (dioxin) receptor. Toxicol Appl Pharmacol 152:406-414.
18. Navas JM, Chana A, Herradón B, Segner H. 2003. Induction of CYP1A by the noncoplanar compound, 1-benzylimidazole. Environ Toxicol Chem 22:830-836.
19. Navas JM, Chana A, Herradón B, Segner H. 2004. Induction of cytochrome P4501A (CYP1A) by clotrimazole, a nonplanar aromatic compound. Computational studies on structural features of clotrimazole and related imidazole derivatives. Life Sci 76: 699-714.
20. Babín M, Casado S, Chana A, Herradón B, Segner H, Tarazona JV, Navas JM. 2005. Cytochrome P4501A induction caused by the imidazole derivative Procloraz in a rainbow trout cell line. Toxicol In Vitro 19:899-902.
21. Murk AJ, Legler J, Denison MS, Giesy JP, van de Guchte C, Brouwer A. 1996. Chemical-activated luciferase gene expression (CALUX): A novel in vitro bioassay for Ah receptor active compounds in sediments and pore water. Fundam Appl Toxicol 33: 149-160.
22. Kennedy SW, Jones SP, Bastien LJ. 1995. Efficient analysis of cytochrome P4501A catalytic activity, porphyrins, and total proteins in chicken embryo hepatocytes cultures with a fluorescence plate reader. Anal Biochem 226:362-370.
23. Halgren TA. 1996. Merck molecular force field. 1. Basis, form, scope, parameterization, and performance of MMFF94. Journal of Computational Chemistry 17:490-519.
24. Saunders M. 1987. Stochastic exploration of molecular mechanics energy surfaces-Hunting for the global minimum. J Am Chem Soc 109:3150-3152.
25. Becke AD. 1993. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648-5652.
26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. 2003. Gaussian 03, Revision B.04. Gaussian, Pittsburgh, PA, USA.
27. Denison MS, Pandini A, Nagy SR, Baldwin EP, Bonati L. 2002. Ligand binding and activation of the Ah receptor. Chem-Biol Interact 141:3-24.
28. Laaksonen L. 1992. A graphics program for the analysis and display of molecular dynamics trajectories. J Mol Graph Model 10:33-34.
29. Lewars E. 2003. Computacional Chemistry: Introduction to the Theory and Applications of Molecular and Quantum Mechanics. Kluwer Academic, Boston, MA, USA.
30. Boys SF, Bernardi F. 1970. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Molecular Physics 19:553-556.
31. Denison MS, Nagy SR. 2003. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu Rev Pharmacol Toxicol 43:309-334.
32. Murray JS, Evans P, Politzer P. 1990. A comparative analysis of the electrostatic potential of some structural analogues of 2,3,7,8- tetrachlorodibenzo-p-dioxin and of related aromatic systems. Int J Quantum Chem 37:271-289.