Discovery and biological characterization of 1-(1H-indol-3-yl)-9H-pyrido[3, 4-b]indole as an aryl hydrocarbon receptor activator generated by photoactivation of tryptophan by sunlight

Chemico-Biological Interactions

Volumn 193, Issue 2, 2011, Pages 119-128

  Diani Moore, Silvia ^a   Ma, Yuliang ^a   Labitzke, Erin ^a,b   Tao, Hui ^a,c   David Warren, J ^a   Anderson, Jared ^a   Chen, Qiuying ^a   Gross, Steven S ^a   Rifkind, Arleen B ^a  

^a WEILL CORNELL MEDICAL COLLEGE   (United States)

^b Genetica DNA Laboratories Inc   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

1 (1H indol 3 yl) 9H pyrido 3,4 b indole (IPI); 6 Formylindolo 3,2 b carbazole (FICZ); Aryl hydrocarbon receptor; Cytochrome P4501A; Mass spectrometry; Tryptophan photoproduct

Indexed keywords

1 (1H INDOL 3 YL) 9H PYRIDO[3,4 B]INDOLE; 2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; 6 FORMYLINDOLO[3,2 B]CARBAZOLE; AROMATIC HYDROCARBON RECEPTOR; CHEMICAL COMPOUND; CYTOCHROME P450 1A; ETHOXYRESORUFIN DEETHYLASE; INDOLE DERIVATIVE; MESSENGER RNA; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ASCIDIACEA; BIOLOGICAL ACTIVITY; CELL METABOLISM; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHICK EMBRYO; CONTROLLED STUDY; CYTOCHROME P450 1A GENE; EMBRYO; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SYNTHESIS; GENE; GENE EXPRESSION REGULATION; GLUCONEOGENESIS; GLUCOSE TRANSPORT; LABORATORY TEST; LIVER CELL CULTURE; MASS SPECTROMETRY; NONHUMAN; PHOSPHOENOLPYRUVATE CARBOXYKINASE GENE; PHOTOACTIVATION; SUNLIGHT;

ANIMALS; CARBAZOLES; CARBOLINES; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CELLS, CULTURED; CHICK EMBRYO; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CULTURE MEDIA; CULTURE MEDIA, CONDITIONED; CYTOCHROME P-450 CYP1A1; DOSE-RESPONSE RELATIONSHIP, DRUG; GENE EXPRESSION; GLUCONEOGENESIS; GLUCOSE; HEPATOCYTES; LIVER NEOPLASMS; MICE; MOLECULAR STRUCTURE; PHOSPHOENOLPYRUVATE CARBOXYKINASE (GTP); PHOTOCHEMICAL PROCESSES; RECEPTORS, ARYL HYDROCARBON; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUNLIGHT; TETRACHLORODIBENZODIOXIN; TRYPTOPHAN;

ASCIDIA; MAMMALIA;

EID: 79960997888     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2011.05.010     Document Type: Article

References (33)

1. J. Abel, T. Haarmann-Stemmann, An introduction to the molecular basics of aryl hydrocarbon receptor biology, Biol. Chem. 391 (2010) 1235-1248.
2. Y. Fujii-Kuriyama, K. Kawajiri, Molecular mechanisms of the physiological functions of the aryl hydrocarbon (dioxin) receptor, a multifunctional regulator that senses and responds to environmental stimuli, Proc. Jpn. Acad. Ser. B Phys. Biol. Sci. 86 (2010) 40-53.
3. A. Poland, J.C. Knutson, 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity, Annu. Rev. Pharmacol. Toxicol. 22 (1982) 517-554.
4. S. Diani-Moore, P. Ram, X. Li, P. Mondal, D.Y. Youn, A.A. Sauve, A.B. Rifkind, Identification of the aryl hydrocarbon receptor target gene TiPARP as a mediator of suppression of hepatic gluconeogenesis by 2,3,7,8- tetrachlorodibenzo-p-dioxin and of nicotinamide as a corrective agent for this effect, J. Biol. Chem. 285 (2010) 38801-38810.
5. M.S. Denison, S.R. Nagy, Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals, Annu. Rev. Pharmacol. Toxicol. 43 (2003) 309-334. (Pubitemid 37372644)
6. Y.H. Chen, J. Riby, P. Srivastava, J. Bartholomew, M. Denison, L. Bjeldanes, Regulation of CYP1A1 by indolo[3,2-b]carbazole in murine hepatoma cells, J. Biol. Chem. 270 (1995) 22548-22555.
7. E. Fritsche, C. Schafer, C. Calles, T. Bernsmann, T. Bernshausen, M. Wurm, U. Hubenthal, J.E. Cline, H. Hajimiragha, P. Schroeder, L.O. Klotz, A. Rannug, P. Furst, H. Hanenberg, J. Abel, J. Krutmann, Lightening up the UV response by identification of the arylhydrocarbon receptor as a cytoplasmatic target for ultraviolet B radiation, Proc. Natl. Acad. Sci. USA 104 (2007) 8851-8856. (Pubitemid 47175400)
8. S. Diani-Moore, E. Labitzke, R. Brown, A. Garvin, L. Wong, A.B. Rifkind, Sunlight generates multiple tryptophan photoproducts eliciting high efficacy CYP1A induction in chick hepatocytes and in vivo, Toxicol. Sci. 90 (2006) 96-110.
9. M. Mukai, S.A. Tischkau, Effects of tryptophan photoproducts in the circadian timing system: searching for a physiological role for aryl hydrocarbon receptor, Toxicol. Sci. 95 (2007) 172-181.
10. Y.D. Wei, H. Helleberg, U. Rannug, A. Rannug, Rapid and transient induction of CYP1A1 gene expression in human cells by the tryptophan photoproduct 6-formylindolo[3,2-b]carbazole, Chem. Biol. Interact. 110 (1998) 39-55.
11. K.J. Livak, T.D. Schmittgen, Analysis of relative gene expression data using realtime quantitative PCR and the 2(-Delta Delta C(T)) Method, Methods 25 (2001) 402-408. (Pubitemid 34164012)
12. G. Poch, S.N. Pancheva, Calculating slope and ED50 of additive dose-response curves and application of these tabulated parameter values, J. Pharmacol. Toxicol. Methods 33 (1995) 137-145.
13. A. Badre, A. Boulanger, E. Abou-Mansour, B. Banaigs, G. Combaut, C. Francisco, Eudistomin U and isoeudistomin U, new alkaloids from the Caribbean ascidian Lissoclinum fragile, J. Nat. Prod. 57 (1994) 528-533. (Pubitemid 24152912)
14. J.D. Panarese, S.P. Waters, Room-temperature aromatization of tetrahydro-beta-carbolines by 2-iodoxybenzoic acid: utility in a total synthesis of eudistomin U, Org. Lett. 12 (2010) 4086-4089.
15. P. Molina, P.M. Fresneda, S. Garcia-Zafra, An iminophosphorane-mediated efficeint synthesis of the alkaloid Eudistomin U of marine origin, Tetrahedron Lett. 36 (1995) 3581-3582.
16. P. Rocca, F. Marsais, A. Godard, G. Queguiner, L. Adams, B. Alo, New syntheses of the marine alkaloids eudistomins D and U, Tetrahedron Lett. 36 (1995) 7085-7088.
17. G. Massiot, S. Nazabadioko, C. Bliard, Structural revision of isoeudistomin U by total synthesis, J. Nat. Prod. 58 (1995) 1636-1639.
18. K. Nakai, A.M. Ward, M. Gannon, A.B. Rifkind, Beta-naphthoflavone induction of a cytochrome P-450 arachidonic acid epoxygenase in chick embryo liver distinct from the aryl hydrocarbon hydroxylase and from phenobarbital-induced arachidonate epoxygenase, J. Biol. Chem. 267 (1992) 19503-19512.
19. M. Oberg, L. Bergander, H. Hakansson, U. Rannug, A. Rannug, Identification of the tryptophan photoproduct 6-formylindolo[3,2-b]carbazole in cell culture medium, as a factor that controls the background aryl hydrocarbon receptor activity, Toxicol. Sci. 85 (2005) 935-943.
20. T.A. Kocarek, E.G. Schuetz, P.S. Guzelian, Transient induction of cytochrome P450 1A1 mRNA by culture medium component in primary cultures of adult rat hepatocytes, In Vitro Cell Dev. Biol. 29A (1993) 62-66. (Pubitemid 23082643)
21. H.J. Geyer, K.W. Schramm, E.A. Feicht, A. Behechti, C. Steinberg, R. Bruggemann, H. Poiger, B. Henkelmann, A. Kettrup, Half-lives of tetra-,penta-, hexa-, hepta-, and octachlorodibenzo-p-dioxin in rats, monkeys, and humans - a critical review, Chemosphere 48 (2002) 631-644.
22. D. Creed, The photophysics and photochemistry of the near-UV absorbing amino acids. 1. Tryptophan and its simple derivatives, Photochem. Photobiol. 39 (1984) 537-562.
23. B. Lucas, M. Barat, J.A. Fayeton, M. Perot, C. Jouvet, G. Gregoire, S. Brondsted Nielsen, Mechanisms of photoinduced Calpha[Single Bond]Cbeta bond breakage in protonated aromatic amino acids, J. Chem. Phys. 128 (2008) 164-302.
24. E. Marklova, Where does indolylacrylic acid come from?, Amino Acids 17 (1999) 401-413 (Pubitemid 30025829)
25. R. Cao, W. Peng, Z. Wang, A. Xu, Beta-Carboline alkaloids: biochemical and pharmacological functions, Curr. Med. Chem. 14 (2007) 479-500.
26. B.E. McIntosh, J.B. Hogenesch, C.A. Bradfield, Mammalian Per-Arnt-Sim proteins in environmental adaptation, Annu. Rev. Physiol. 72 (2010) 625-645.
27. S.G. Furness, M.J. Lees, M.L. Whitelaw, The dioxin (aryl hydrocarbon) receptor as a model for adaptive responses of bHLH/PAS transcription factors, FEBS Lett. 581 (2007) 3616-3625. (Pubitemid 47086313)
28. K. Kawajiri, Y. Kobayashi, F. Ohtake, T. Ikuta, Y. Matsushima, J. Mimura, S. Pettersson, R.S. Pollenz, T. Sakaki, T. Hirokawa, T. Akiyama, M. Kurosumi, L. Poellinger, S. Kato, Y. Fujii-Kuriyama, Aryl hydrocarbon receptor suppresses intestinal carcinogenesis in ApcMin/+ mice with natural ligands, Proc. Natl. Acad. Sci. USA 106 (2009) 13481-13486.
29. T.W. Kensler, J.G. Chen, P.A. Egner, J.W. Fahey, L.P. Jacobson, K.K. Stephenson, L. Ye, J.L. Coady, J.B. Wang, Y. Wu, Y. Sun, Q.N. Zhang, B.C. Zhang, Y.R. Zhu, G.S. Qian, S.G. Carmella, S.S. Hecht, L. Benning, S.J. Gange, J.D. Groopman, P. Talalay, Effects of glucosinolate-rich broccoli sprouts on urinary levels of aflatoxin-DNA adducts and phenanthrene tetraols in a randomized clinical trial in He Zuo township, Qidong, People's Republic of China, Cancer Epidemiol. Biomarkers Prev. 14 (2005) 2605-2613. (Pubitemid 41752722)
30. S. Nair, V.D. Kekatpure, B.L. Judson, A.B. Rifkind, R.D. Granstein, J.O. Boyle, K. Subbaramaiah, J.B. Guttenplan, A.J. Dannenberg, UVR exposure sensitizes keratinocytes to DNA adduct formation, Cancer Prev. Res. 2 (2009) 895-902.
31. G. Gaitanis, P. Magiatis, K. Stathopoulou, I.D. Bassukas, E.C. Alexopoulos, A. Velegraki, A.L. Skaltsounis, AhR ligands, malassezin and indolo[3,2-b]carbazole are selectively produced by Malassezia furfur strains isolated from seborrheic dermatitis, J. Invest. Dermatol. 128 (2008) 1620-1625.
32. M. Veldhoen, K. Hirota, A.M. Westendorf, J. Buer, L. Dumoutier, J.C. Renauld, B. Stockinger, The aryl hydrocarbon receptor links TH17-cell-mediated autoimmunity to environmental toxins, Nature 453 (2008) 106-109. (Pubitemid 351630329)
33. (H)17 cell differentiation by the aryl hydrocarbon receptor, Nature 453 (2008) 65-71.