Theoretical targets for TCDD: A bioinformatics approach

Chemosphere

Volumn 80, Issue 10, 2010, Pages 1160-1166

  Olivero Verbel, Jesús ^a   Cabarcas Montalvo, María ^a   Ortega Zúñiga, Carlos ^a  

^a UNIVERSIDAD DE CARTAGENA   (Colombia)

Author keywords

AhR; Protein; TarFisDock; Virtual screening

Indexed keywords

BIOINFORMATICS; CHEMICAL ACTIVATION; ORGANIC POLLUTANTS; PROTEINS;

2 ,3 ,7 ,8 TETRACHLORODIBENZO P DIOXINS; ARYL HYDROCARBON RECEPTOR; METALLOPEPTIDASES; OXIDOSQUALENE CYCLASES; PATHOLOGICAL EFFECTS; TARFISDOCK; THEORETICAL TARGETS; VIRTUAL SCREENING;

BINDING SITES;

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; LANOSTEROL SYNTHASE; MYELOPEROXIDASE; NEUTROPHIL COLLAGENASE; STROMELYSIN;

BIOCHEMISTRY; BIOINFORMATICS; DIABETES; PATHOLOGY; POLLUTION EXPOSURE; PROTEIN; TCDD; TOXIC SUBSTANCE; VISUAL ANALYSIS;

ANIMAL EXPERIMENT; ARTICLE; BINDING SITE; BIOINFORMATICS; DIABETES MELLITUS; ENDOMETRIOSIS; ENVIRONMENTAL EXPOSURE; INFLAMMATION; LIVER INJURY; MOUSE; NONHUMAN; THEORETICAL MODEL;

EID: 77955428597     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2010.06.020     Document Type: Article

References (69)

1. Agrawal H., Kumar A., Chandra-Bal N., Imran-Siddiqia M., Arora A. Ligand based virtual screening and biological evaluation of inhibitors of chorismate mutase (Rv1885c) from Mycobacterium tuberculosis H37Rv. Bioorg. Med. Chem Lett. 2007, 17:3053-3058.
2. Akahoshi E., Yoshimura S., Uruno S., Ishihara-Sugano M. Effect of dioxins on regulation of tyrosine hydroxylase gene expression by aryl hydrocarbon receptor: a neurotoxicology study. Environ. Health 2009, 8:24.
3. Allport J.R., Lim Y.C., Shipley J.M., Senior R.M., Shapiro S.D., Matsuyoshi N., Vestweber D., Luscinskas F.W. Neutrophils from MMP-9- or neutrophil elastase-deficient mice show no defect in transendothelial migration under flow in vitro. J. Leukocyte Biol. 2002, 71:821-828.
4. Apfel R., Benbrook D., Lernhardt E., Ortiz M.A., Salbert G., Pfahl M. A novel orphan receptor specific for a subset of thyroid hormone-responsive elements and its interaction with the retinoid/thyroid hormone receptor subfamily. Mol. Cell. Biol. 1994, 14:7025-7035.
5. Arima A., Kato H., Ooshima Y., Tateishi T., Inoue A., Muneoka A., Ihara T., Kamimura S., Fukusato T., Kubota S., Sumida H., Yasuda M. In utero and lactational exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) induces a reduction in epididymal and ejaculated sperm number in rhesus monkeys. Reprod. Toxicol. 2009, 28:495-502.
6. Berrin J.G., McLauchlan W.R., Needs P., Williamson G., Puigserver A., Kroon P.A., Juge N. Functional expression of human liver cytosolic β-glucosidase in Pichia pastoris: insights into its role in the metabolism of dietary glucosides. Eur. J. Biochem. 2002, 269:249-258.
7. Boutros P.C., Yan R., Moffat I.D., Pohjanvirta R., Okey A.B. Transcriptomic responses to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in liver: comparison of rat and mouse. BMC Genom. 2008, 9:419.
8. Brinckerhoff C.E., Rutter J.L., Benbow U. Interstitial collagenases as markers of tumor progression. Clin. Cancer Res. 2000, 6:4823-4830.
9. Bryant P.L., Schmid J.E., Fenton S.E., Buckalew A.R., Abbott B.D. Teratogenicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (tcdd) in mice lacking the expression of egf and/or tgf-α. Toxicol. Sci. 2001, 62:103-114.
10. Castrignano T., De Meo P.D., Cozzetto D., Talamo I.G., Tramontano A. The PMDB protein model database. Nucleic Acids Res. 2006, 34:306-309.
11. Chan C.Y.Y., Kim P.M., Winn L.M. TCDD affects DNA double strand-break repair. Toxicol. Sci. 2004, 81:133-138.
12. Cortés V., Quezadaa N., Rigott A., Maiz A. Nuevos receptores nucleares heterodiméricos: reguladores metabólicos con impacto en fisiopatología y su proyección terapéutica en dislipidemias y diabetes mellitus. Rev. Méd. Chile 2005, 133:1483-1492.
13. Cox K.E., Piva M., Sharpe-Timms K.L. Differential regulation of matrix metalloproteinase-3 gene expression in endometriotic lesions compared with endometrium. Biol. Reprod. 2001, 65:1297-1303.
14. Daniels L.B., Coyle P.J., Chiao Y.B., Glew R.H., Labow R.S. Purification and characterization of a cytosolic broad specificity β-glucosidase from human liver. J. Biol. Chem. 1981, 256:13004-13013.
15. Enan E., Matsumura F. Evidence for a second pathway in the action mechanism of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). Significance of Ah-receptor mediated activation of protein kinase under cell-free conditions. Biochem. Pharmacol. 1995, 49:249-261.
16. Fernandez-Salguero P.M., Hilbert D.M., Rudikoff S., Ward J.M., Gonzalez F.J. Aryl-hydrocarbon receptor-deficient mice are resistant to 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced toxicity. Toxicol. Appl. Pharmacol. 1996, 140:173-179.
17. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., 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 J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., Pople J.A. Gaussian 03. Revision B.02 2003, Gaussian, Inc., Pittsburgh PA.
18. Gogal R.M., Holladay S.D. Perinatal TCDD exposure and the adult onset of autoimmune disease. J. Immunotoxicol. 2008, 5:413-418.
19. Guha R., Howard M.T., Hutchison G.R., Murray-Rust P., Rzepa H., Steinbeck C., Wegner J., Willighagen E.L. The blue obelisk-interoperability in chemical informatics. J. Chem. Inf. Model. 2006, 46:991-998.
20. Hutz R.J. Reproductive endocrine disruption by environmental xenobiotics that modulate the estrogen-signaling pathway, particularly tetrachlorodibenzo-p-dioxin (TCDD). J. Reprod. Develop. 1999, 45:1-12.
21. Jin S.L.C., Lan L., Zoudilova M., Conti M. Specific role of phosphodiesterase 4b in lipopolysaccharide-induced signaling in mouse macrophages. J. Immunol. 2005, 175:1523-1531.
22. Jin M.H., Hong C.H., Lee H.Y., Kang H.J., Han S.W. Enhanced TGF-beta1 is involved in 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) induced oxidative stress in C57BL/6 mouse testis. Toxicol. Lett. 2008, 178:202-209.
23. Jin M.H., Ko H.K., Hong C.H., Han S.W. In utero exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin affects the development of reproductive system in mouse. Yonsei Med. J. 2008, 49:843-850.
24. Kerkvliet N.I. Immunological effects of chlorinated dibenzo-p-dioxins. Environ. Health Perspect. 1995, 103:47-53.
25. Khedkar S.A., Malde A.K., Coutinho E.C., Srivastava S. Pharmacophore modeling in drug discovery and development: an overview. Med. Chem. 2007, 3:187-197.
26. Knerr S., Schrenk D. Carcinogenicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in experimental models. Mol. Nutr. Food Res. 2006, 50:897-907.
27. Kobayashi D., Ahmed S., Ishida M., Kasai S., Kikuchi H. Calcium/calmodulin signaling elicits release of cytochrome c during 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced apoptosis in the human lymphoblastic T-cell line. L-MAT Toxicol. 2009, 258:25-32.
28. Kobayashi S., Okamoto H., Iwamoto T., Toyama Y., Tomatsu T., Yamanaka H., Momohara S. A role for the aryl hydrocarbon receptor and the dioxin TCDD in rheumatoid arthritis. Rheumatology 2008, 47:1317-1322.
29. Kortagere S., Ekins S., We W.J. Halogenated ligands and their interactions with amino acids: Implications for structure-activity and structure-toxicity relationships. J. Mol. Graph. Model. 2008, 27:170-177.
30. Kramer M.A. Focus on Cholesterol Research 2006, New York, Nova Science Publishers, Inc.
31. Kumar A., Imran-Siddiqi M., Miertus S. New molecular scaffolds for the design of Mycobacterium tuberculosis type II dehydroquinase inhibitors identified using ligand and receptor based virtual screening. J. Mol. Model. 2009, 16:693-712.
32. Lewis S.N., Bassaganya-Riera J., Bevan D.R. Virtual screening as a technique for PPAR modulator discovery. PPAR Res. 2009, 2010:861238.
33. Li H., Gao Z., Kang L., Zhang H., Yang K., Yu K., Luo X., Zhu W., Chen K., Shen J., Wang X., Jiang H. TarFisDock: a web server for identifying drug targets with docking approach. Nucleic Acids Res. 2006, 34:W219-W224.
34. Lugnier C. Cyclic nucleotide phosphodiesterase (PDE) superfamily: a new target for the development of specific therapeutic agents. Pharmacol. Therapeut. 2006, 109:366-398.
35. Lyne P.D. Structure-based virtual screening: an overview. Drug Discov. Today 2002, 7:1047-1055.
36. Matsuki H., Fujimoto N., Iwata K., Knauper V., Okada Y., Hayakawa T. A one-step sandwich enzyme immunoassay for human matrix metalloproteinase 8 (neutrophil collagenase) using monoclonal antibodies. Clin. Chim. Acta 1996, 244:129-143.
37. Mimura J., Fujii-Kuriyama Y. Functional role of AhR in the expression of toxic effects by TCDD. Biochim. Biophys. Acta 2003, 1619:263-268.
38. Mimura J., Yamashita K., Nakamura K., Morita M., Takagi T.N., Nakao K., Ema M., Sogawa K., Yasuda M., Katsuki M., Fujii-Kuriyama Y. Loss of teratogenic response to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking the Ah (dioxin) receptor. Genes Cells 1997, 2:645-654.
39. Murphy S.D. Toxic effects of pesticides in Casarett and Doull's toxicology. The Basic Science of Poisons 1986, Macmillan Publishing Company, New York. third ed. C. Klaassen, M. Amdur, D. John (Eds.).
40. Nukaya M., Moran S., Bradfield C.A. The role of the dioxin-responsive element cluster between the Cyp1a1 and Cyp1a2 loci in aryl hydrocarbon receptor biology. Proc. Natl. Acad. Sci. USA 2009, 106:4923-4928.
41. Nwomeh B.C., Liang H.X., Cohen I.K., Yager D.R. MMP-8 is the predominant collagenase in healing wounds and nonhealing ulcers. J. Surg. Res. 1999, 81:189-195.
42. Palackal N.T., Lee S.H., Harvey R.G., Blair I.A., Penning T.M. Activation of polycyclic aromatic hydrocarbon trans-dihydrodiol proximate carcinogens by human aldo-keto reductase (AKR1C) enzymes and their functional overexpression in human lung carcinoma (A549) cells. J. Biol. Chem. 2002, 277:24799-24808.
43. Pandini A., Soshilov A.A., Song Y., Zhao J., Bonati L., Denison M.S. Detection of the TCDD binding-fingerprint within the Ah receptor ligand binding domain by structurally driven mutagenesis and functional analysis. Biochemistry 2009, 48:5972-5983.
44. Park S.J., Yoon W.K., Kim H.J., Son H.Y., Cho S.W., Jeong K.S., Kim T.H., Kim S.H., Kim S.R., Ryu S.Y. 2,3,7,8-Tetrachlorodibenzo-p-dioxin activates ERK and p38 mitogen-activated protein kinases in RAW 264.7 cells. Anticancer Res. 2005, 25:2831-2836.
45. Park J.H., Hahn E.J., Kong J.H., Cho H.J., Yoon C.S., Cheong S.W., Oh G.S., Youn H.J. TCDD-induced apoptosis in EL-4 cells deficient of the aryl hydrocarbon receptor and down-regulation of IGFBP-6 prevented the apoptotic cell death. Toxicol. Lett. 2003, 145:55-68.
46. Penning T.M., Drury J.E. Human aldo-keto reductases: function, gene regulation, and single nucleotide polymorphisms. Arch. Biochem. Biophys. 2007, 464:241-250.
47. Pérez-Nueno V.I., Pettersson S., Ritchie D.W., Borrell J.I., Teixidó J. Discovery of novel HIV entry inhibitors for the CXCR4 receptor by prospective virtual screening. J. Chem. Inf. Model. 2009, 49:810-823.
48. Pohjanvirta R., Tuomisto J. Short-term toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin in laboratory animals: effects, mechanisms, and animal models. Pharmacol. Rev. 1994, 46:483-549.
49. Pauwels A., Schepens P.J., D́Hooghe T., Delbeke L., Dhont M., Brouwer A., Weyler J. The risk of endometriosis and exposure to dioxins and polychlorinated biphenyls: a case-control study of infertile women. Human Reprod. 2001, 16:2050-2055.
50. Porpora M.G., Medda E., Abballe A., Bolli S., De Angelis I., di Domenico A., Ferro A., Ingelido A.M., Maggi A., Panici P.B., De Felip E. Endometriosis and organochlorinated environmental pollutants: a case-control study on Italian women of reproductive age. Environ. Health Perspect. 2009, 117:1070-1075.
51. Ratjen F., Hartog C.M., Paul K., Wermelt J., Braun J. Matrix metalloproteases in BAL fluid of patients with cystic fibrosis and their modulation by treatment with dornase. Thorax 2002, 57:930-934.
52. Sahlberg C., Peltonen E., Lukinmaa P.L., Alaluusua S. Dioxin alters gene expression in mouse embryonic tooth explants. J. Dent. Res. 2007, 86:600-605.
53. Sato S., Shirakawa H., Tomita S., Ohsaki Y., Haketa K., Tooi O., Santo N., Tohkin M., Furukawa Y., Gonzalez F.J., Komai M. Low-dose dioxins alter gene expression related to cholesterol biosynthesis, lipogenesis, and glucose metabolism through the aryl hydrocarbon receptor-mediated pathway in mouse liver. Toxicol. Appl. Pharm. 2008, 229:10-19.
54. Shetty K., Paliyath G., Pometto A., Levin R.E. Food Biotechnology 2006, CRC Press, Taylor & Francis Group, Cleveland.
55. Smialowicz R.J., DeVito M.J., Williams W.C., Birnbaum L.S. Relative potency based on hepatic enzyme induction predicts immunosuppressive effects of a mixture of PCDDS/PCDFS and PCBS. Toxicol. Appl. Pharm. 2008, 227:477-484.
56. Stahura F.L., Bajorath J. New methodologies for ligand-based virtual screening. Curr. Pharm. Design. 2005, 11:1189-1202.
57. Stockwell B.R. Chemical genetics: ligand-based discovery of gene function. Nat. Rev. Genet. 2000, 1:116-125.
58. Swanson H.I., Bradfield C.A. The AH-receptor: genetics, structure and function. Pharmacogenetics 1993, 3:213-230.
59. Thackaberry E.A., Jiang Z., Johnson C.D., Ramos K.S., Walker M.K. Toxicogenomic profile of 2,3,7,8-tetrachlorodibenzo-p-dioxin in the murine fetal heart: modulation of cell cycle and extracellular matrix genes. Toxicol. Sci. 2005, 88:231-241.
60. Torphy T.J. Phosphodiesterase isozymes: molecular targets for novel antiasthma agents. Am. J. Resp. Crit. Care 1998, 157:351-370.
61. Urban P., Pelclová D., Lukás E., Kupka K., Preiss J., Fenclová Z., Smerhovský Z. Neurological and neurophysiological examinations on workers with chronic poisoning by 2,3,7,8-TCDD: follow-up 35 years after exposure. Eur. J. Neurol. 2007, 14:213-218.
62. Van den Berg M., Birnbaum L.S., Denison M., De Vito M., Farland W., Feeley M., Fiedler H., Hakansson H., Hanberg A., Haws L., Rose M., Safe S., Schrenk D., Tohyama C., Tritscher A., Tuomisto J., Tysklind M., Walker N., Peterson R.E. The 2005 World Health Organization reevaluation of human and Mammalian toxic equivalency factors for dioxins and dioxin-like compounds. Toxicol. Sci. 2006, 93:223-241.
63. Van den Berg M., Birnbaum L., Bosveld A.T., Brunström B., Cook P., Feeley M., Giesy J.P., Hanberg A., Hasegawa R., Kennedy S.W., Kubiak T., Larsen J.C., van Leeuwen F.X., Liem A.K., Nolt C., Peterson R.E., Poellinger L., Safe S., Schrenk D., Tillitt D., Tysklind M., Younes M., Waern F., Zacharewski T. Toxic equivalency factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife. Environ. Health Perspect. 1998, 106:775-792.
64. Van Themsche C., Potworowski E.F., ST-Pierre Y. Stromelysin-1 (MMP-3) is inducible in T lymphoma cells and accelerates the growth of lymphoid tumors in vivo. Biochem. Biophys. Res. Commun. 2004, 315:884-891.
65. Villano C.M., Murphy K.A., Akintobi A., White L.A. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) induces matrix metalloproteinase (MMP) expression and invasion in A2058 melanoma cells. Toxicol. Appl. Pharm. 2006, 210:212-224.
66. Wittsiepe J., Kullmann Y., Schrey P., Selenka F., Wilhelm M. Myeloperoxidase-catalyzed formation of PCDD/F from chlorophenols. Chemosphere 2000, 40:963-968.
67. Wolber G., Langer T. LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J. Chem. Inf. Model. 2005, 45:160-169.
68. Yoshizawa K., Walker N.J., Jokinen M.P., Brix A.E., Sells D.M., Marsh T., Wyde M.E., Orzech D., Haseman J.K., Nyska A. Gingival carcinogenicity in female harlan sprague-dawley rats following two-year oral treatment with 2,3,7,8-tetrachlorodibenzo-p-dioxin and dioxin-like compounds. Toxicol. Sci. 2005, 83:64-77.
69. Yu J., Wang Y., Zhou W.H., Wang L., He Y.Y., Li D.J. Combination of estrogen and dioxin is involved in the pathogenesis of endometriosis by promoting chemokine secretion and invasion of endometrial stromal cells. Hum. Reprod. 2008, 23:1614-1626.