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Volumn 29, Issue 1, 2016, Pages 75-86

Evidence for New Light-Independent Pathways for Generation of the Endogenous Aryl Hydrocarbon Receptor Agonist FICZ

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; AROMATIC HYDROCARBON RECEPTOR; CARBAZOLE DERIVATIVE; CYTOCHROME P450 1A1; CYTOCHROME P450 INHIBITOR; INDOLE DERIVATIVE; PYRUVIC ACID; TRYPTOPHAN; 6-FORMYLINDOLO(3,2-B)CARBAZOLE; CYP1A1 PROTEIN, HUMAN; ENZYME INHIBITOR;

EID: 84955298717     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/acs.chemrestox.5b00416     Document Type: Article
Times cited : (101)

References (80)
  • 1
    • 0017145975 scopus 로고
    • Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase
    • Poland, A., Glover, E., and Kende, A. S. (1976) Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase J. Biol. Chem. 251, 4936-4946
    • (1976) J. Biol. Chem. , vol.251 , pp. 4936-4946
    • Poland, A.1    Glover, E.2    Kende, A.S.3
  • 2
    • 84922377460 scopus 로고    scopus 로고
    • The aryl hydrocarbon receptor in barrier organ physiology, immunology, and toxicology
    • Esser, C. and Rannug, A. (2015) The aryl hydrocarbon receptor in barrier organ physiology, immunology, and toxicology Pharmacol. Rev. 67, 259-279 10.1124/pr.114.009001
    • (2015) Pharmacol. Rev. , vol.67 , pp. 259-279
    • Esser, C.1    Rannug, A.2
  • 3
    • 84922481111 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor ligands in cancer: Friend and foe
    • Murray, I. A., Patterson, A. D., and Perdew, G. H. (2014) Aryl hydrocarbon receptor ligands in cancer: friend and foe Nat. Rev. Cancer 14, 801-814 10.1038/nrc3846
    • (2014) Nat. Rev. Cancer , vol.14 , pp. 801-814
    • Murray, I.A.1    Patterson, A.D.2    Perdew, G.H.3
  • 4
    • 84896935541 scopus 로고    scopus 로고
    • The aryl hydrocarbon receptor: Multitasking in the immune system
    • Stockinger, B., Di Meglio, P., Gialitakis, M., and Duarte, J. H. (2014) The aryl hydrocarbon receptor: multitasking in the immune system Annu. Rev. Immunol. 32, 403-432 10.1146/annurev-immunol-032713-120245
    • (2014) Annu. Rev. Immunol. , vol.32 , pp. 403-432
    • Stockinger, B.1    Di Meglio, P.2    Gialitakis, M.3    Duarte, J.H.4
  • 5
    • 84896268602 scopus 로고    scopus 로고
    • The Ah receptor in stem cell cycling, regulation, and quiescence
    • Gasiewicz, T. A., Singh, K. P., and Bennett, J. A. (2014) The Ah receptor in stem cell cycling, regulation, and quiescence Ann. N. Y. Acad. Sci. 1310, 44-50 10.1111/nyas.12361
    • (2014) Ann. N. Y. Acad. Sci. , vol.1310 , pp. 44-50
    • Gasiewicz, T.A.1    Singh, K.P.2    Bennett, J.A.3
  • 6
    • 84883139105 scopus 로고    scopus 로고
    • Role of the aryl hydrocarbon receptor in carcinogenesis and potential as a drug target
    • Safe, S., Lee, S. O., and Jin, U. H. (2013) Role of the aryl hydrocarbon receptor in carcinogenesis and potential as a drug target Toxicol. Sci. 135, 1-16 10.1093/toxsci/kft128
    • (2013) Toxicol. Sci. , vol.135 , pp. 1-16
    • Safe, S.1    Lee, S.O.2    Jin, U.H.3
  • 7
    • 38949097735 scopus 로고    scopus 로고
    • The search for endogenous activators of the aryl hydrocarbon receptor
    • Nguyen, L. P. and Bradfield, C. A. (2008) The search for endogenous activators of the aryl hydrocarbon receptor Chem. Res. Toxicol. 21, 102-116 10.1021/tx7001965
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 102-116
    • Nguyen, L.P.1    Bradfield, C.A.2
  • 8
    • 0023616773 scopus 로고
    • Certain photooxidized derivatives of tryptophan bind with very high affinity to the Ah receptor and are likely to be endogenous signal substances
    • Rannug, A., Rannug, U., Rosenkranz, H. S., Winqvist, L., Westerholm, R., Agurell, E., and Grafstrom, A. K. (1987) Certain photooxidized derivatives of tryptophan bind with very high affinity to the Ah receptor and are likely to be endogenous signal substances J. Biol. Chem. 262, 15422-15427
    • (1987) J. Biol. Chem. , vol.262 , pp. 15422-15427
    • Rannug, A.1    Rannug, U.2    Rosenkranz, H.S.3    Winqvist, L.4    Westerholm, R.5    Agurell, E.6    Grafstrom, A.K.7
  • 9
    • 0029418619 scopus 로고
    • Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands
    • Rannug, U., Rannug, A., Sjoberg, U., Li, H., Westerholm, R., and Bergman, J. (1995) Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands Chem. Biol. 2, 841-845 10.1016/1074-5521(95)90090-X
    • (1995) Chem. Biol. , vol.2 , pp. 841-845
    • Rannug, U.1    Rannug, A.2    Sjoberg, U.3    Li, H.4    Westerholm, R.5    Bergman, J.6
  • 10
    • 0031895561 scopus 로고    scopus 로고
    • Rapid and transient induction of CYP1A1 gene expression in human cells by the tryptophan photoproduct 6-formylindolo[3,2-b]carbazole
    • Wei, Y. D., Helleberg, H., Rannug, U., and Rannug, A. (1998) 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, 39-55 10.1016/S0009-2797(97)00111-7
    • (1998) Chem.-Biol. Interact. , vol.110 , pp. 39-55
    • Wei, Y.D.1    Helleberg, H.2    Rannug, U.3    Rannug, A.4
  • 11
    • 0034326289 scopus 로고    scopus 로고
    • Regulation of CYP1A1 transcription via the metabolism of the tryptophan-derived 6-formylindolo[3,2-b]carbazole
    • Wei, Y. D., Bergander, L., Rannug, U., and Rannug, A. (2000) Regulation of CYP1A1 transcription via the metabolism of the tryptophan-derived 6-formylindolo[3,2-b]carbazole Arch. Biochem. Biophys. 383, 99-107 10.1006/abbi.2000.2037
    • (2000) Arch. Biochem. Biophys. , vol.383 , pp. 99-107
    • Wei, Y.D.1    Bergander, L.2    Rannug, U.3    Rannug, A.4
  • 12
    • 12244269085 scopus 로고    scopus 로고
    • Characterization of in vitro metabolites of the aryl hydrocarbon receptor ligand 6-formylindolo[3,2-b]carbazole by liquid chromatography-mass spectrometry and NMR
    • Bergander, L., Wahlstrom, N., Alsberg, T., Bergman, J., Rannug, A., and Rannug, U. (2003) Characterization of in vitro metabolites of the aryl hydrocarbon receptor ligand 6-formylindolo[3,2-b]carbazole by liquid chromatography-mass spectrometry and NMR Drug Metab. Dispos. 31, 233-241 10.1124/dmd.31.2.233
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 233-241
    • Bergander, L.1    Wahlstrom, N.2    Alsberg, T.3    Bergman, J.4    Rannug, A.5    Rannug, U.6
  • 14
    • 59149105791 scopus 로고    scopus 로고
    • The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formylindolo[3,2-b]carbazole is present in humans
    • Wincent, E., Amini, N., Luecke, S., Glatt, H., Bergman, J., Crescenzi, C., Rannug, A., and Rannug, U. (2009) The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formylindolo[3,2-b]carbazole is present in humans J. Biol. Chem. 284, 2690-2696 10.1074/jbc.M808321200
    • (2009) J. Biol. Chem. , vol.284 , pp. 2690-2696
    • Wincent, E.1    Amini, N.2    Luecke, S.3    Glatt, H.4    Bergman, J.5    Crescenzi, C.6    Rannug, A.7    Rannug, U.8
  • 15
    • 84858626055 scopus 로고    scopus 로고
    • Inhibition of cytochrome P4501-dependent clearance of the endogenous agonist FICZ as a mechanism for activation of the aryl hydrocarbon receptor
    • Wincent, E., Bengtsson, J., Bardbori, A. M., Alsberg, T., Luecke, S., Rannug, U., and Rannug, A. (2012) Inhibition of cytochrome P4501-dependent clearance of the endogenous agonist FICZ as a mechanism for activation of the aryl hydrocarbon receptor Proc. Natl. Acad. Sci. U. S. A. 109, 4479-4484 10.1073/pnas.1118467109
    • (2012) Proc. Natl. Acad. Sci. U. S. A. , vol.109 , pp. 4479-4484
    • Wincent, E.1    Bengtsson, J.2    Bardbori, A.M.3    Alsberg, T.4    Luecke, S.5    Rannug, U.6    Rannug, A.7
  • 16
    • 0021954494 scopus 로고
    • Mutations affecting the regulation of transcription of the cytochrome P1-450 gene in the mouse Hepa-1 cell line
    • Hankinson, O., Andersen, R. D., Birren, B. W., Sander, F., Negishi, M., and Nebert, D. W. (1985) Mutations affecting the regulation of transcription of the cytochrome P1-450 gene in the mouse Hepa-1 cell line J. Biol. Chem. 260, 1790-1795
    • (1985) J. Biol. Chem. , vol.260 , pp. 1790-1795
    • Hankinson, O.1    Andersen, R.D.2    Birren, B.W.3    Sander, F.4    Negishi, M.5    Nebert, D.W.6
  • 17
    • 0026376260 scopus 로고
    • Proposed role of drug-metabolizing enzymes: Regulation of steady state levels of the ligands that effect growth, homeostasis, differentiation, and neuroendocrine functions
    • Nebert, D. W. (1991) Proposed role of drug-metabolizing enzymes: regulation of steady state levels of the ligands that effect growth, homeostasis, differentiation, and neuroendocrine functions Mol. Endocrinol. 5, 1203-1214 10.1210/mend-5-9-1203
    • (1991) Mol. Endocrinol. , vol.5 , pp. 1203-1214
    • Nebert, D.W.1
  • 18
    • 0017184668 scopus 로고
    • Effect of amino acids and inducers on the activity of the microsomal mono-oxygenase system in rat liver cell culture
    • Paine, A. J. (1976) Effect of amino acids and inducers on the activity of the microsomal mono-oxygenase system in rat liver cell culture Chem.-Biol. Interact. 13, 307-315 10.1016/0009-2797(76)90083-1
    • (1976) Chem.-Biol. Interact. , vol.13 , pp. 307-315
    • Paine, A.J.1
  • 20
    • 0028986235 scopus 로고
    • Possible involvement of the Ah receptor in the induction of cytochrome P-450IA1 under conditions of hydrodynamic shear in microcarrier-attached hepatoma cell lines
    • Mufti, N. A., Bleckwenn, N. A., Babish, J. G., and Shuler, M. L. (1995) Possible involvement of the Ah receptor in the induction of cytochrome P-450IA1 under conditions of hydrodynamic shear in microcarrier-attached hepatoma cell lines Biochem. Biophys. Res. Commun. 208, 144-152 10.1006/bbrc.1995.1316
    • (1995) Biochem. Biophys. Res. Commun. , vol.208 , pp. 144-152
    • Mufti, N.A.1    Bleckwenn, N.A.2    Babish, J.G.3    Shuler, M.L.4
  • 21
    • 33846572931 scopus 로고    scopus 로고
    • The aryl hydrocarbon receptor is activated by modified low-density lipoprotein
    • McMillan, B. J. and Bradfield, C. A. (2007) The aryl hydrocarbon receptor is activated by modified low-density lipoprotein Proc. Natl. Acad. Sci. U. S. A. 104, 1412-1417 10.1073/pnas.0607296104
    • (2007) Proc. Natl. Acad. Sci. U. S. A. , vol.104 , pp. 1412-1417
    • McMillan, B.J.1    Bradfield, C.A.2
  • 22
  • 23
    • 67651091550 scopus 로고    scopus 로고
    • Characterization and potential environmental risks of leachate from shredded rubber mulches
    • Kanematsu, M., Hayashi, A., Denison, M. S., and Young, T. M. (2009) Characterization and potential environmental risks of leachate from shredded rubber mulches Chemosphere 76, 952-958 10.1016/j.chemosphere.2009.04.026
    • (2009) Chemosphere , vol.76 , pp. 952-958
    • Kanematsu, M.1    Hayashi, A.2    Denison, M.S.3    Young, T.M.4
  • 24
    • 0032948372 scopus 로고    scopus 로고
    • UV-induced CYP1A1 gene expression in human cells is mediated by tryptophan
    • Wei, Y. D., Rannug, U., and Rannug, A. (1999) UV-induced CYP1A1 gene expression in human cells is mediated by tryptophan Chem.-Biol. Interact. 118, 127-140 10.1016/S0009-2797(98)00118-5
    • (1999) Chem.-Biol. Interact. , vol.118 , pp. 127-140
    • Wei, Y.D.1    Rannug, U.2    Rannug, A.3
  • 26
    • 77949912531 scopus 로고    scopus 로고
    • Cytochrome P450 1A1 gene regulation by UVB involves crosstalk between the aryl hydrocarbon receptor and nuclear factor kappaB
    • Luecke, S., Wincent, E., Backlund, M., Rannug, U., and Rannug, A. (2010) Cytochrome P450 1A1 gene regulation by UVB involves crosstalk between the aryl hydrocarbon receptor and nuclear factor kappaB Chem.-Biol. Interact. 184, 466-473 10.1016/j.cbi.2010.01.038
    • (2010) Chem.-Biol. Interact. , vol.184 , pp. 466-473
    • Luecke, S.1    Wincent, E.2    Backlund, M.3    Rannug, U.4    Rannug, A.5
  • 27
    • 33845631590 scopus 로고    scopus 로고
    • Effects of tryptophan photoproducts in the circadian timing system: Searching for a physiological role for aryl hydrocarbon receptor
    • Mukai, M. and Tischkau, S. A. (2006) Effects of tryptophan photoproducts in the circadian timing system: searching for a physiological role for aryl hydrocarbon receptor Toxicol. Sci. 95, 172-181 10.1093/toxsci/kfl126
    • (2006) Toxicol. Sci. , vol.95 , pp. 172-181
    • Mukai, M.1    Tischkau, S.A.2
  • 28
    • 78649853496 scopus 로고    scopus 로고
    • Induction of long interspersed nucleotide element-1 (L1) retrotransposition by 6-formylindolo[3,2-b]carbazole (FICZ), a tryptophan photoproduct
    • Okudaira, N., Iijima, K., Koyama, T., Minemoto, Y., Kano, S., Mimori, A., and Ishizaka, Y. (2010) Induction of long interspersed nucleotide element-1 (L1) retrotransposition by 6-formylindolo[3,2-b]carbazole (FICZ), a tryptophan photoproduct Proc. Natl. Acad. Sci. U. S. A. 107, 18487-18492 10.1073/pnas.1001252107
    • (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 18487-18492
    • Okudaira, N.1    Iijima, K.2    Koyama, T.3    Minemoto, Y.4    Kano, S.5    Mimori, A.6    Ishizaka, Y.7
  • 29
    • 60549095448 scopus 로고    scopus 로고
    • Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of Th17 T cells
    • Veldhoen, M., Hirota, K., Christensen, J., O'Garra, A., and Stockinger, B. (2009) Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of Th17 T cells J. Exp. Med. 206, 43-49 10.1084/jem.20081438
    • (2009) J. Exp. Med. , vol.206 , pp. 43-49
    • Veldhoen, M.1    Hirota, K.2    Christensen, J.3    O'Garra, A.4    Stockinger, B.5
  • 30
    • 47749107262 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor regulates Stat1 activation and participates in the development of Th17 cells
    • Kimura, A., Naka, T., Nohara, K., Fujii-Kuriyama, Y., and Kishimoto, T. (2008) Aryl hydrocarbon receptor regulates Stat1 activation and participates in the development of Th17 cells Proc. Natl. Acad. Sci. U. S. A. 105, 9721-9726 10.1073/pnas.0804231105
    • (2008) Proc. Natl. Acad. Sci. U. S. A. , vol.105 , pp. 9721-9726
    • Kimura, A.1    Naka, T.2    Nohara, K.3    Fujii-Kuriyama, Y.4    Kishimoto, T.5
  • 31
    • 84856237141 scopus 로고    scopus 로고
    • The aryl hydrocarbon receptor regulates gut immunity through modulation of innate lymphoid cells
    • Qiu, J., Heller, J. J., Guo, X., Chen, Z. M., Fish, K., Fu, Y. X., and Zhou, L. (2012) The aryl hydrocarbon receptor regulates gut immunity through modulation of innate lymphoid cells Immunity 36, 92-104 10.1016/j.immuni.2011.11.011
    • (2012) Immunity , vol.36 , pp. 92-104
    • Qiu, J.1    Heller, J.J.2    Guo, X.3    Chen, Z.M.4    Fish, K.5    Fu, Y.X.6    Zhou, L.7
  • 32
    • 67651171182 scopus 로고    scopus 로고
    • Identification of a human helper T cell population that has abundant production of interleukin 22 and is distinct from T(H)-17, T(H)1 and T(H)2 cells
    • Trifari, S., Kaplan, C. D., Tran, E. H., Crellin, N. K., and Spits, H. (2009) Identification of a human helper T cell population that has abundant production of interleukin 22 and is distinct from T(H)-17, T(H)1 and T(H)2 cells Nat. Immunol. 10, 864-871 10.1038/ni.1770
    • (2009) Nat. Immunol. , vol.10 , pp. 864-871
    • Trifari, S.1    Kaplan, C.D.2    Tran, E.H.3    Crellin, N.K.4    Spits, H.5
  • 33
    • 84908551224 scopus 로고    scopus 로고
    • Allergic responses and aryl hydrocarbon receptor novel pathway of mast cell activation
    • Sibilano, R., Pucillo, C. E., and Gri, G. (2015) Allergic responses and aryl hydrocarbon receptor novel pathway of mast cell activation Mol. Immunol. 63, 69-73 10.1016/j.molimm.2014.02.015
    • (2015) Mol. Immunol. , vol.63 , pp. 69-73
    • Sibilano, R.1    Pucillo, C.E.2    Gri, G.3
  • 37
    • 79959918506 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor-induced signals up-regulate IL-22 production and inhibit inflammation in the gastrointestinal tract
    • Monteleone, I., Rizzo, A., Sarra, M., Sica, G., Sileri, P., Biancone, L., MacDonald, T. T., Pallone, F., and Monteleone, G. (2011) Aryl hydrocarbon receptor-induced signals up-regulate IL-22 production and inhibit inflammation in the gastrointestinal tract Gastroenterology 141, 237-248 10.1053/j.gastro.2011.04.007
    • (2011) Gastroenterology , vol.141 , pp. 237-248
    • Monteleone, I.1    Rizzo, A.2    Sarra, M.3    Sica, G.4    Sileri, P.5    Biancone, L.6    MacDonald, T.T.7    Pallone, F.8    Monteleone, G.9
  • 38
    • 84861874740 scopus 로고    scopus 로고
    • FICZ, a tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma
    • Jeong, K. T., Hwang, S. J., Oh, G. S., and Park, J. H. (2012) FICZ, a tryptophan photoproduct, suppresses pulmonary eosinophilia and Th2-type cytokine production in a mouse model of ovalbumin-induced allergic asthma Int. Immunopharmacol. 13, 377-385 10.1016/j.intimp.2012.04.014
    • (2012) Int. Immunopharmacol. , vol.13 , pp. 377-385
    • Jeong, K.T.1    Hwang, S.J.2    Oh, G.S.3    Park, J.H.4
  • 39
    • 84893407131 scopus 로고    scopus 로고
    • Differential consequences of two distinct AhR ligands on innate and adaptive immune responses to influenza A virus
    • Wheeler, J. L., Martin, K. C., Resseguie, E., and Lawrence, B. P. (2014) Differential consequences of two distinct AhR ligands on innate and adaptive immune responses to influenza A virus Toxicol. Sci. 137, 324-334 10.1093/toxsci/kft255
    • (2014) Toxicol. Sci. , vol.137 , pp. 324-334
    • Wheeler, J.L.1    Martin, K.C.2    Resseguie, E.3    Lawrence, B.P.4
  • 41
    • 20544441002 scopus 로고    scopus 로고
    • 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
    • Öberg, M., Bergander, L., Hakansson, H., Rannug, U., and Rannug, A. (2005) 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, 935-943 10.1093/toxsci/kfi154
    • (2005) Toxicol. Sci. , vol.85 , pp. 935-943
    • Öberg, M.1    Bergander, L.2    Hakansson, H.3    Rannug, U.4    Rannug, A.5
  • 42
    • 33144477599 scopus 로고    scopus 로고
    • Sunlight generates multiple tryptophan photoproducts eliciting high efficacy CYP1A induction in chick hepatocytes and in vivo
    • Diani-Moore, S., Labitzke, E., Brown, R., Garvin, A., Wong, L., and Rifkind, A. B. (2005) Sunlight generates multiple tryptophan photoproducts eliciting high efficacy CYP1A induction in chick hepatocytes and in vivo Toxicol. Sci. 90, 96-110 10.1093/toxsci/kfj065
    • (2005) Toxicol. Sci. , vol.90 , pp. 96-110
    • Diani-Moore, S.1    Labitzke, E.2    Brown, R.3    Garvin, A.4    Wong, L.5    Rifkind, A.B.6
  • 43
    • 84861778637 scopus 로고    scopus 로고
    • Blunted epidermal L-tryptophan metabolism in vitiligo affects immune response and ROS scavenging by Fenton chemistry, part 2: Epidermal H2O2/ONOO(-)-mediated stress in vitiligo hampers indoleamine 2,3-dioxygenase and aryl hydrocarbon receptor-mediated immune response signaling
    • Schallreuter, K. U., Salem, M. A., Gibbons, N. C., Maitland, D. J., Marsch, E., Elwary, S. M., and Healey, A. R. (2012) Blunted epidermal L-tryptophan metabolism in vitiligo affects immune response and ROS scavenging by Fenton chemistry, part 2: Epidermal H2O2/ONOO(-)-mediated stress in vitiligo hampers indoleamine 2,3-dioxygenase and aryl hydrocarbon receptor-mediated immune response signaling FASEB J. 26, 2471-2485 10.1096/fj.11-201897
    • (2012) FASEB J. , vol.26 , pp. 2471-2485
    • Schallreuter, K.U.1    Salem, M.A.2    Gibbons, N.C.3    Maitland, D.J.4    Marsch, E.5    Elwary, S.M.6    Healey, A.R.7
  • 45
    • 0037310739 scopus 로고    scopus 로고
    • The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine
    • Yu, A. M., Granvil, C. P., Haining, R. L., Krausz, K. W., Corchero, J., Kupfer, A., Idle, J. R., and Gonzalez, F. J. (2003) The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine J. Pharmacol. Exp. Ther. 304, 539-546 10.1124/jpet.102.043786
    • (2003) J. Pharmacol. Exp. Ther. , vol.304 , pp. 539-546
    • Yu, A.M.1    Granvil, C.P.2    Haining, R.L.3    Krausz, K.W.4    Corchero, J.5    Kupfer, A.6    Idle, J.R.7    Gonzalez, F.J.8
  • 46
    • 4544271437 scopus 로고    scopus 로고
    • Synthesis of Metabolites of the Ah Receptor Ligand 6-Formylindolo[3,2-b]carbazole
    • Wahlström, N., Romero, I., and Bergman, J. (2004) Synthesis of Metabolites of the Ah Receptor Ligand 6-Formylindolo[3,2-b]carbazole Eur. J. Org. Chem. 2004, 2593-2602 10.1002/ejoc.200400087
    • (2004) Eur. J. Org. Chem. , vol.2004 , pp. 2593-2602
    • Wahlström, N.1    Romero, I.2    Bergman, J.3
  • 47
    • 0031765393 scopus 로고    scopus 로고
    • Decreased susceptibility of Malassezia furfur to UV light by synthesis of tryptophane derivatives
    • Mayser, P. and Pape, B. (1998) Decreased susceptibility of Malassezia furfur to UV light by synthesis of tryptophane derivatives Antonie van Leeuwenhoek 73, 315-319 10.1023/A:1001500310537
    • (1998) Antonie van Leeuwenhoek , vol.73 , pp. 315-319
    • Mayser, P.1    Pape, B.2
  • 48
    • 73849102810 scopus 로고    scopus 로고
    • Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid
    • Chowdhury, G., Dostalek, M., Hsu, E. L., Nguyen, L. P., Stec, D. F., Bradfield, C. A., and Guengerich, F. P. (2009) Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid Chem. Res. Toxicol. 22, 1905-1912 10.1021/tx9000418
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 1905-1912
    • Chowdhury, G.1    Dostalek, M.2    Hsu, E.L.3    Nguyen, L.P.4    Stec, D.F.5    Bradfield, C.A.6    Guengerich, F.P.7
  • 49
    • 85137874192 scopus 로고    scopus 로고
    • Inhibition of drug metabolizing enzymes: Molecular and biochemical aspects
    • (Woolf, T. F. Ed.) pp, Marcel Dekker, New York
    • Guengerich, F. P. (1999) Inhibition of drug metabolizing enzymes: molecular and biochemical aspects, in Handbook of Drug Metabolism (Woolf, T. F., Ed.) pp 203-277, Marcel Dekker, New York.
    • (1999) Handbook of Drug Metabolism , pp. 203-277
    • Guengerich, F.P.1
  • 50
    • 50449100139 scopus 로고
    • The Carbon Monoxide-Binding Pigment of Liver Microsomes. II. Solubilization, Purification, and Properties
    • Omura, T. and Sato, R. (1964) The Carbon Monoxide-Binding Pigment of Liver Microsomes. Ii. Solubilization, Purification, and Properties J. Biol. Chem. 239, 2379-2385
    • (1964) J. Biol. Chem. , vol.239 , pp. 2379-2385
    • Omura, T.1    Sato, R.2
  • 51
    • 84988050310 scopus 로고
    • Synthesis and reaction of oxazolones from L-tryptophan and a-haloacetic anhydrides
    • Bergman, J., Lidgren, G., and Gogoll, A. (1992) Synthesis and reaction of oxazolones from L-tryptophan and a-haloacetic anhydrides Bull. Soc. Chim. Belg. 101, 643-660 10.1002/bscb.19921010712
    • (1992) Bull. Soc. Chim. Belg. , vol.101 , pp. 643-660
    • Bergman, J.1    Lidgren, G.2    Gogoll, A.3
  • 52
    • 0001689685 scopus 로고
    • The reaction of some indoles and indolines with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
    • Bergman, J., Carlsson, R., and Misztal, S. (1976) The reaction of some indoles and indolines with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Acta Chem. Scand. 30b, 853-862 10.3891/acta.chem.scand.30b-0853
    • (1976) Acta Chem. Scand. , vol.30 , pp. 853-862
    • Bergman, J.1    Carlsson, R.2    Misztal, S.3
  • 53
    • 0002294807 scopus 로고
    • Condensation of 3-hydroxymethylindoles with 3-substituted indoles. Formation of 2,3′-methylennediidole-derivatives
    • Amat-Guerri, F., Martinez-Utrilla, and Pascual, C. (1984) Condensation of 3-hydroxymethylindoles with 3-substituted indoles. Formation of 2,3′-methylennediidole-derivatives J. Chem. Res. Synop. 160-161
    • (1984) J. Chem. Res. Synop. , pp. 160-161
    • Amat-Guerri, F.1    Martinez-Utrilla2    Pascual, C.3
  • 54
    • 0033595871 scopus 로고    scopus 로고
    • Syntheses of 6,12-disubstituted 5,11-dihydroindolo[3,2-b]carbazoles, including 5,11-dihydroindolo[3,2-b]carbazole-6,12-dicarbaldehyde, an extremely efficient ligand for the TCDD (Ah) receptor
    • Tholander, J. and Bergman, J. (1999) Syntheses of 6,12-disubstituted 5,11-dihydroindolo[3,2-b]carbazoles, including 5,11-dihydroindolo[3,2-b]carbazole-6,12-dicarbaldehyde, an extremely efficient ligand for the TCDD (Ah) receptor Tetrahedron 55, 12577-12594 10.1016/S0040-4020(99)00733-4
    • (1999) Tetrahedron , vol.55 , pp. 12577-12594
    • Tholander, J.1    Bergman, J.2
  • 55
    • 84865589572 scopus 로고    scopus 로고
    • Tryptamine serves as a proligand of the AhR transcriptional pathway whose activation is dependent of monoamine oxidases
    • Vikstrom Bergander, L., Cai, W., Klocke, B., Seifert, M., and Pongratz, I. (2012) Tryptamine serves as a proligand of the AhR transcriptional pathway whose activation is dependent of monoamine oxidases Mol. Endocrinol. 26, 1542-1551 10.1210/me.2011-1351
    • (2012) Mol. Endocrinol. , vol.26 , pp. 1542-1551
    • Vikstrom Bergander, L.1    Cai, W.2    Klocke, B.3    Seifert, M.4    Pongratz, I.5
  • 56
    • 84897374287 scopus 로고    scopus 로고
    • Microbiome-derived tryptophan metabolites and their aryl hydrocarbon receptor-dependent agonist and antagonist activities
    • Jin, U. H., Lee, S. O., Sridharan, G., Lee, K., Davidson, L. A., Jayaraman, A., Chapkin, R. S., Alaniz, R., and Safe, S. (2014) Microbiome-derived tryptophan metabolites and their aryl hydrocarbon receptor-dependent agonist and antagonist activities Mol. Pharmacol. 85, 777-788 10.1124/mol.113.091165
    • (2014) Mol. Pharmacol. , vol.85 , pp. 777-788
    • Jin, U.H.1    Lee, S.O.2    Sridharan, G.3    Lee, K.4    Davidson, L.A.5    Jayaraman, A.6    Chapkin, R.S.7    Alaniz, R.8    Safe, S.9
  • 57
    • 0042856465 scopus 로고    scopus 로고
    • Aspartate aminotransferase generates proagonists of the aryl hydrocarbon receptor
    • Bittinger, M. A., Nguyen, L. P., and Bradfield, C. A. (2003) Aspartate aminotransferase generates proagonists of the aryl hydrocarbon receptor Mol. Pharmacol. 64, 550-556 10.1124/mol.64.3.550
    • (2003) Mol. Pharmacol. , vol.64 , pp. 550-556
    • Bittinger, M.A.1    Nguyen, L.P.2    Bradfield, C.A.3
  • 58
    • 84891329790 scopus 로고    scopus 로고
    • Nucleotide specificity of DNA binding of the aryl hydrocarbon receptor:ARNT complex is unaffected by ligand structure
    • DeGroot, D. E. and Denison, M. S. (2014) Nucleotide specificity of DNA binding of the aryl hydrocarbon receptor:ARNT complex is unaffected by ligand structure Toxicol. Sci. 137, 102-113 10.1093/toxsci/kft234
    • (2014) Toxicol. Sci. , vol.137 , pp. 102-113
    • DeGroot, D.E.1    Denison, M.S.2
  • 59
    • 79551688725 scopus 로고    scopus 로고
    • Kynurenic acid is a potent endogenous aryl hydrocarbon receptor ligand that synergistically induces interleukin-6 in the presence of inflammatory signaling
    • DiNatale, B. C., Murray, I. A., Schroeder, J. C., Flaveny, C. A., Lahoti, T. S., Laurenzana, E. M., Omiecinski, C. J., and Perdew, G. H. (2010) Kynurenic acid is a potent endogenous aryl hydrocarbon receptor ligand that synergistically induces interleukin-6 in the presence of inflammatory signaling Toxicol. Sci. 115, 89-97 10.1093/toxsci/kfq024
    • (2010) Toxicol. Sci. , vol.115 , pp. 89-97
    • DiNatale, B.C.1    Murray, I.A.2    Schroeder, J.C.3    Flaveny, C.A.4    Lahoti, T.S.5    Laurenzana, E.M.6    Omiecinski, C.J.7    Perdew, G.H.8
  • 62
    • 0016573535 scopus 로고
    • Effects of dietary constituents on the metabolism of chemical carcinogens
    • Wattenberg, L. W. (1975) Effects of dietary constituents on the metabolism of chemical carcinogens Cancer Res. 35, 3326-3331
    • (1975) Cancer Res. , vol.35 , pp. 3326-3331
    • Wattenberg, L.W.1
  • 63
    • 83855160821 scopus 로고    scopus 로고
    • Natural aryl hydrocarbon receptor ligands control organogenesis of intestinal lymphoid follicles
    • Kiss, E. A., Vonarbourg, C., Kopfmann, S., Hobeika, E., Finke, D., Esser, C., and Diefenbach, A. (2011) Natural aryl hydrocarbon receptor ligands control organogenesis of intestinal lymphoid follicles Science 334, 1561-1565 10.1126/science.1214914
    • (2011) Science , vol.334 , pp. 1561-1565
    • Kiss, E.A.1    Vonarbourg, C.2    Kopfmann, S.3    Hobeika, E.4    Finke, D.5    Esser, C.6    Diefenbach, A.7
  • 64
    • 80155164160 scopus 로고    scopus 로고
    • Exogenous Stimuli Maintain Intraepithelial Lymphocytes via Aryl Hydrocarbon Receptor Activation
    • Li, Y., Innocentin, S., Withers, D. R., Roberts, N. A., Gallagher, A. R., Grigorieva, E. F., Wilhelm, C., and Veldhoen, M. (2011) Exogenous Stimuli Maintain Intraepithelial Lymphocytes via Aryl Hydrocarbon Receptor Activation Cell 147, 629-640 10.1016/j.cell.2011.09.025
    • (2011) Cell , vol.147 , pp. 629-640
    • Li, Y.1    Innocentin, S.2    Withers, D.R.3    Roberts, N.A.4    Gallagher, A.R.5    Grigorieva, E.F.6    Wilhelm, C.7    Veldhoen, M.8
  • 65
    • 0026046412 scopus 로고
    • Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: Comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin
    • Bjeldanes, L. F., Kim, J. Y., Grose, K. R., Bartholomew, J. C., and Bradfield, C. A. (1991) Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin Proc. Natl. Acad. Sci. U. S. A. 88, 9543-9547 10.1073/pnas.88.21.9543
    • (1991) Proc. Natl. Acad. Sci. U. S. A. , vol.88 , pp. 9543-9547
    • Bjeldanes, L.F.1    Kim, J.Y.2    Grose, K.R.3    Bartholomew, J.C.4    Bradfield, C.A.5
  • 69
    • 84988360143 scopus 로고    scopus 로고
    • Malassezia infections in humans and animals: Pathophysiology, detection, and treatment
    • Velegraki, A., Cafarchia, C., Gaitanis, G., Iatta, R., and Boekhout, T. (2015) Malassezia infections in humans and animals: pathophysiology, detection, and treatment PLoS Pathog. 11, e1004523 10.1371/journal.ppat.1004523
    • (2015) PLoS Pathog. , vol.11 , pp. e1004523
    • Velegraki, A.1    Cafarchia, C.2    Gaitanis, G.3    Iatta, R.4    Boekhout, T.5
  • 70
    • 22144449295 scopus 로고    scopus 로고
    • New Tryptophan Metabolites from Cultures of the Lipophilic Yeast Malassezia furfur
    • Irlinger, B., Bartsch, A., Krämer, H.-J., Mayser, P., and Steglich, W. (2005) New Tryptophan Metabolites from Cultures of the Lipophilic Yeast Malassezia furfur Helv. Chim. Acta 88, 1472-1485 10.1002/hlca.200590118
    • (2005) Helv. Chim. Acta , vol.88 , pp. 1472-1485
    • Irlinger, B.1    Bartsch, A.2    Krämer, H.-J.3    Mayser, P.4    Steglich, W.5
  • 71
    • 80053017405 scopus 로고    scopus 로고
    • Influence of light on aryl hydrocarbon receptor signaling and consequences in drug metabolism, physiology and disease
    • Ma, Q. (2011) Influence of light on aryl hydrocarbon receptor signaling and consequences in drug metabolism, physiology and disease Expert Opin. Drug Metab. Toxicol. 7, 1267-1293 10.1517/17425255.2011.614947
    • (2011) Expert Opin. Drug Metab. Toxicol. , vol.7 , pp. 1267-1293
    • Ma, Q.1
  • 72
    • 79960997888 scopus 로고    scopus 로고
    • 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
    • Diani-Moore, S., Ma, Y., Labitzke, E., Tao, H., David Warren, J., Anderson, J., Chen, Q., Gross, S. S., and Rifkind, A. B. (2011) 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 Chem.-Biol. Interact. 193, 119-128 10.1016/j.cbi.2011.05.010
    • (2011) Chem.-Biol. Interact. , vol.193 , pp. 119-128
    • Diani-Moore, S.1    Ma, Y.2    Labitzke, E.3    Tao, H.4    David Warren, J.5    Anderson, J.6    Chen, Q.7    Gross, S.S.8    Rifkind, A.B.9
  • 73
    • 84866434831 scopus 로고    scopus 로고
    • Quercetin, resveratrol, and curcumin are indirect activators of the aryl hydrocarbon receptor (AHR)
    • Mohammadi-Bardbori, A., Bengtsson, J., Rannug, U., Rannug, A., and Wincent, E. (2012) Quercetin, resveratrol, and curcumin are indirect activators of the aryl hydrocarbon receptor (AHR) Chem. Res. Toxicol. 25, 1878-1884 10.1021/tx300169e
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 1878-1884
    • Mohammadi-Bardbori, A.1    Bengtsson, J.2    Rannug, U.3    Rannug, A.4    Wincent, E.5
  • 74
    • 84155196846 scopus 로고    scopus 로고
    • Exactly the same but different: Promiscuity and diversity in the molecular mechanisms of action of the aryl hydrocarbon (dioxin) receptor
    • Denison, M. S., Soshilov, A. A., He, G., Degroot, D. E., and Zhao, B. (2011) Exactly the same but different: promiscuity and diversity in the molecular mechanisms of action of the aryl hydrocarbon (dioxin) receptor Toxicol. Sci. 124, 1-22 10.1093/toxsci/kfr218
    • (2011) Toxicol. Sci. , vol.124 , pp. 1-22
    • Denison, M.S.1    Soshilov, A.A.2    He, G.3    Degroot, D.E.4    Zhao, B.5
  • 75
    • 84897476165 scopus 로고    scopus 로고
    • Ligand promiscuity of aryl hydrocarbon receptor agonists and antagonists revealed by site-directed mutagenesis
    • Soshilov, A. A. and Denison, M. S. (2014) Ligand promiscuity of aryl hydrocarbon receptor agonists and antagonists revealed by site-directed mutagenesis Mol. Cell. Biol. 34, 1707-1719 10.1128/MCB.01183-13
    • (2014) Mol. Cell. Biol. , vol.34 , pp. 1707-1719
    • Soshilov, A.A.1    Denison, M.S.2
  • 76
    • 0034551667 scopus 로고    scopus 로고
    • Hydrogen peroxide in the human body
    • Halliwell, B., Clement, M. V., and Long, L. H. (2000) Hydrogen peroxide in the human body FEBS Lett. 486, 10-13 10.1016/S0014-5793(00)02197-9
    • (2000) FEBS Lett. , vol.486 , pp. 10-13
    • Halliwell, B.1    Clement, M.V.2    Long, L.H.3
  • 77
  • 78
    • 33745631769 scopus 로고    scopus 로고
    • Cell signaling. H2O2, a necessary evil for cell signaling
    • Rhee, S. G. (2006) Cell signaling. H2O2, a necessary evil for cell signaling Science 312, 1882-1883 10.1126/science.1130481
    • (2006) Science , vol.312 , pp. 1882-1883
    • Rhee, S.G.1
  • 79
    • 84951299778 scopus 로고    scopus 로고
    • NADPH Oxidase-Dependent Mechanism Explains How Arsenic and Other Oxidants Can Activate Aryl Hydrocarbon Receptor Signaling
    • Mohammadi-Bardbori, A., Vikstrom Bergander, L., Rannug, U., and Rannug, A. (2015) NADPH Oxidase-Dependent Mechanism Explains How Arsenic and Other Oxidants Can Activate Aryl Hydrocarbon Receptor Signaling Chem. Res. Toxicol. 28, 2278-2286 10.1021/acs.chemrestox.5b00415
    • (2015) Chem. Res. Toxicol. , vol.28 , pp. 2278-2286
    • Mohammadi-Bardbori, A.1    Vikstrom Bergander, L.2    Rannug, U.3    Rannug, A.4
  • 80
    • 45349105125 scopus 로고    scopus 로고
    • AhR ligands, malassezin, and indolo[3,2-b]carbazole are selectively produced by Malassezia furfur strains isolated from seborrheic dermatitis
    • Gaitanis, G., Magiatis, P., Stathopoulou, K., Bassukas, I. D., Alexopoulos, E. C., Velegraki, A., and Skaltsounis, A. L. (2008) AhR ligands, malassezin, and indolo[3,2-b]carbazole are selectively produced by Malassezia furfur strains isolated from seborrheic dermatitis J. Invest. Dermatol. 128, 1620-1625 10.1038/sj.jid.5701252
    • (2008) J. Invest. Dermatol. , vol.128 , pp. 1620-1625
    • Gaitanis, G.1    Magiatis, P.2    Stathopoulou, K.3    Bassukas, I.D.4    Alexopoulos, E.C.5    Velegraki, A.6    Skaltsounis, A.L.7


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