Novel 2-amino-isoflavones exhibit aryl hydrocarbon receptor agonist or antagonist activity in a species/cell-specific context

Toxicology

Volumn 297, Issue 1-3, 2012, Pages 26-33

  Wall, Richard J ^a   He, Guochun ^b   Denison, Michael S ^b   Congiu, Cenzo ^c   Onnis, Valentina ^c   Fernandes, Alwyn ^d   Bell, David R ^e   Rose, Martin ^d   Rowlands, J Craig ^f   Balboni, Gianfranco ^c   Mellor, Ian R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CAGLIARI   (Italy)

^d FOOD AND ENVIRONMENT RESEARCH AGENCY   (United Kingdom)

^e EUROPEAN CHEMICALS AGENCY   (Finland)

^f DOW CHEMICAL COMPANY   (United States)

Author keywords

Aryl hydrocarbon receptor (AhR); Dioxin; Isoflavone; Species specific

Indexed keywords

2 AMINO 3 (4' CHLOROPHENYL) 7 METHOXYCHROMEN 4 ONE; 2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; 6 CHLORO 3 (4' METHOXY)PHENYLCOUMARIN; AROMATIC HYDROCARBON RECEPTOR; ISOFLAVONE DERIVATIVE; LIGAND; LUCIFERASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG ACTIVITY; HUMAN; HUMAN CELL; LIGAND BINDING; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RAT; REAL TIME POLYMERASE CHAIN REACTION;

ANIMALS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; HEP G2 CELLS; HUMANS; ISOFLAVONES; MICE; RATS; RECEPTORS, ARYL HYDROCARBON; SPECIES SPECIFICITY;

RATTUS;

EID: 84860617066     PISSN: 0300483X     EISSN: 18793185     Source Type: Journal    
DOI: 10.1016/j.tox.2012.03.011     Document Type: Article

References (41)

1. Aarts J.M.M.J.G., Denison M.S., Cox M.A., Schalk M.A.C., Garrison P.M., Tullis K., de Hann L.H.J., Brouwer A. Species-specific antagonism of Ah receptor action by 2,2',5,5'-tetrachloro- and 2,2',3,3',4,4'-hexachlorobiphenyl. Eur. J. Pharmacol. Environ. Toxicol. 1995, 293(4):463-474.
2. Adachi J., Mori Y., Matsui S., Takigami H., Fujino J., Kitagawa H., Miller C.A., Kato T., Saeki K., Matsuda T. Indirubin and indigo are potent Aryl hydrocarbon receptor ligands present in human urine. J. Biol. Chem. 2001, 276(34):31475-31478.
3. Amakura Y., Tsutsumi T., Sasaki K., Yoshida T., Maitani T. Screening of the inhibitory effect of vegetable constituents on the Aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biol. Pharm. Bull. 2003, 26(12):1754-1760.
4. Bazzi R., Bradshaw T.D., Rowlands J.C., Stevens M.F.G., Bell D.R. 2-(4-Amino-3-methylphenyl)-5-fluorobenzothiazole is a ligand and shows species-specific partial agonism of the Aryl hydrocarbon receptor. Toxicol. Appl. Pharmacol. 2009, 237(1):102-110.
5. Balboni G., Congiu C., Onnis V., Maresca A., Scozzafava A., Winum J.Y., Maietti A., Supuran C.T. Flavones and structurally related 4-chromenones inhibit carbonic anhydrases by a different mechanism of action compared to coumarins. Bioorg. Med. Chem. Lett. 2012, In press.
6. Bell D.R., Clode S., Fan M.Q., Fernandes A., Foster P.M.D., Jiang T., Loizou G., MacNicoll A., Miller B.G., Rose M., Tran L., White S. Relationships between tissue levels of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), mRNAs, and toxicity in the developing male Wistar(han) rat. Toxicol. Sci. 2007, 99(2):591-604.
7. Bell D.R., Poland A. Binding of Aryl hydrocarbon receptor (AhR) to AhR-interacting protein: the role of hsp90. J. Biol. Chem. 2000, 275:36407-36414.
8. Budinsky R.A., LeCluyse E.L., Ferguson S.S., Rowlands J.C., Simon T. Human and rat primary hepatocyte CYP1A1 and 1A2 induction with 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzofuran, and 2,3,4,7,8-pentachlorodibenzofuran. Toxicol. Sci. 2010, 118(1):224-235.
9. Choi E., Kim T. Daidzein modulates induction of hepatic CYP1A1, 1B1, and AhR by 7,12-dimethylbenz[a]anthracene in mice. Arch. Pharmacal Res. 2008, 31(9):1115-1119.
10. Ciolino H.P., Daschner P.J., Yeh G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem. J. 1999, 340(3):715-722.
11. Ciolino H.P., Yeh G.C. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br. J. Cancer 1999, 79(9/10):1340-1346.
12. Connor K.T., Harris M.A., Edwards M.R., Budinsky R.A., Clark G.C., Chu A.C., Finley B.L., Rowlands J.C. Ah receptor agonist activity in human blood measured with a cell-based bioassay: evidence for naturally occurring AH receptor ligands in vivo. J. Expo. Sci. Environ. Epidemiol. 2008, 18(4):369-380.
13. Denison M.S., Nagy S.R. Activation of the Aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 2003, 43:309-334.
14. Denison M.S., Seidel S.D., Rogers W.J., Ziccardi M., Winter G.M., Heath-Pagliuso S. Natural and synthetic ligands for the Ah receptor. Molecular Biology Approaches to Toxicology 1999, 393-410. Taylor & Francis, Philadelphia. A. Puga, K.B. Wallace (Eds.).
15. Denison M.S., Pandini A., Nagy S.R., Baldwin E.P., Bonati L. Ligand binding and activation of the Ah receptor. Chem. Biol. Interact. 2002, 141(1-2):3-24.
16. Denison M.S., Soshilov A.A., He G., DeGroot D.E., Zhao B. Exactly the same but different: promiscuity and diversity in the molecular mechanisms of action of the Aryl hydrocarbon (dioxin) receptor. Toxicol. Sci. 2011, 124(1):1-22.
17. Fernandes A., White S., D'Silva K., Rose M. Simultaneous determination of PCDDs, PCDFs, PCBs and PBDEs in food. Talanta 2004, 63(5):1147-1155.
18. Garrison P.M., Tullis K., Aarts J.M.M.J.G., Brouwer A., Giesy J.P., Denison M.S. Species-specific recombinant cell lines as bioassay systems for the detection of 2,3,7,8-tetrachlorodibenzo-p-dioxin-like chemicals. Fundam. Appl. Toxicol. 1996, 30:194-203.
19. Gasiewicz T.A., Kende A.S., Rucci G., Whitney B., Willey J.J. Analysis of structural requirements for Ah receptor antagonist activity. Ellipticines, flavones and related compounds. Biochem. Pharmacol. 1996, 52:1787-1803.
20. Hahn M.E., Karchner S.I., Shapiro M.A., Perera S.A. Molecular evolution of two vertebrate Aryl hydrocarbon (dioxin) receptors (AHR1 and AHR2) and the PAS family. Proc. Natl. Acad. Sci. U. S. A. 1997, 94(25):13743-13748.
21. Han D.-H., Nagy S.R., Denison M.S. Comparison of recombinant cell bioassays for the detection of Ah receptor agonists. Biofactors 2004, 20:11-22.
22. Hankinson O. The aryl hydrocarbon receptor complex. Annu. Rev. Pharmacol. Toxicol. 1995, 35:307-340.
23. Haws L.C., Su S.H., Harris M., Devito M.J., Walker N.J., Farland W.H., Finley B., Birnbaum L.S. Development of a refined database of mammalian relative potency estimates for dioxin-like compounds. Toxicol. Sci. 2006, 89(1):4-30.
24. Hellemans J., Mortier G., Paepe A.D., Speleman F., Vandesompele J. qBase relative quantification framework and software for management and automated analysis of real-time quantitative PCR data. Genome Biol. 2007, 8(2):1-14.
25. Henry E.C., Kende A.S., Rucci G., Totleben M.J., Willey J.J., Dertinger S.D., Pollenz R.S., Jones J.P., Gasiewicz T.A. Flavone antagonists bind competitively with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) to the Aryl hydrocarbon receptor but inhibit nuclear uptake and transformation. Mol. Pharmacol. 1999, 55:716-725.
26. Iwanari M., Nakajima M., Kizu R., Hayakawa K., Yokoi T. Induction of CYP1A1, CYP1A2, and CYP1B1 mRNAs by nitropolycyclic aromatic hydrocarbons in various human tissue-derived cells: chemical-, cytochrome P450 isoform-, and cell-specific differences. Arch. Toxicol. 2002, 76:287-298.
27. Jung J., Ishida K., Nishikawa J., Nishihara T. Inhibition of estrogen action by 2-phenylchromone as AhR agonist in MCF-7 cells. Life Sci. 2007, 81(19-20):1446-1451.
28. Lu Y.-F., Santostefano M., Cunningham B.D.M., Threadgill M.D., Safe S. Substituted flavones as aryl hydrocarbon (Ah) receptor agonists and antagonists. Biochem. Pharmacol. 1996, 51:1077-1087.
29. Medjakovic S., Jungbauer A. Red clover isoflavones biochanin A and formononetin are potent ligands of the human Aryl hydrocarbon receptor. J. Steroid Biochem. Mol. Biol. 2008, 108(1-2):171-177.
30. Nguyen L.P., Bradfield C.A. The search for endogenous activators of the Aryl hydrocarbon receptor. Chem. Res. Toxicol. 2008, 21:102-106.
31. 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.
32. Quezada E., Delogu G., Picciau C., Santana L., Podda G., Borges F., Garcia-Morales V., Vina D., Orallo F. Synthesis and vasorelaxant and platelet antiaggregatory activities of a new series of 6-halo-3-phenylcoumarins. Molecules 2010, 15:270-279.
33. Schecter A.J., Sheu S.U., Birnbaum L.S., DeVito M.J., Denison M.S., Papke O. A comparison and discussion of two different methods of measuring dioxin-like compounds: gas chromatography-mass spectrometry and the CALUX bioassay-implications for health studies. Organohalogen Compd. 1999, 40:247-250.
34. Shertzer H.G., Puga A., Chang C.-Y., Smith P., Nebert D.W., Setchell K.D.R., Dalton T.P. Inhibition of CYP1A1 enzyme activity in mouse hepatoma cell culture by soybean isoflavones. Chem. Biol. Interact. 1999, 123(1):31-49.
35. Stejskalova L., Dvorak Z., Pavek P. Endogenous and exogenous ligands of the Aryl hydrocarbon receptor: current state of art. Curr. Drug Metab. 2011, 12(2):198-212.
36. Van der Heiden E., Bechoux N., Sergent T., Schneider Y.-J., Muller M., Maghuin-Rogister G., Scippo M.-L. Aryl hydrocarbon receptor-mediated agonist/antagonist/synergic activities of food polyphenols are species- and tissue-dependent. Organohalogen Compd. 2007, 69:365-368.
37. Vanden Heuvel J.P., Clark G.C., Kohn M.C., Tritscher A.M., Greenlee W.E., Lucier G.W., Bell D.A. Dioxin-responsive genes: examination of dose-response relationships using quantitative reverse transcriptase-polymerase chain reaction. Cancer Res. 1994, 54:62-68.
38. Vandesompele J., De Preter K., Pattyn F., Poppe B., Van Roy N., De Paepe A., Speleman F. Accurate normalization of real-time quantitative RT-PCR data by geometric averaging of multiple internal control genes. Genome Biol. 2002, 3(7):1-12.
39. Whitlock J.P. Induction of cytochrome P4501A1. Annu. Rev. Pharmacol. Toxicol. 1999, 39:103-125.
40. Xu L., Li A.P., Kaminski D.L., Ruh M.F. 2,3,7,8-Tetrachlorodibenzo-p-dioxin induction of cytochrome P4501A in cultured rat and human hepatocytes. Chem. Biol. Interact. 2000, 124(3):173-189.
41. Zhang S., Qin C., Safe S.H. Flavonoids as Aryl hydrocarbon receptor agonists/antagonists. Effects of structure and cell context. Environ. Health Perspect. 2003, 111:1877-1882.