The Intersection Between the Aryl Hydrocarbon Receptor (AhR)- and Retinoic Acid-Signaling Pathways

Vitamins and Hormones

Volumn 75, Issue , 2007, Pages 33-67

  Murphy, Kyle A ^a   Quadro, Loredana ^b   White, Lori A ^a  

^a The State University of New Jersey   (United States)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; RETINOIC ACID; RETINOIC ACID RECEPTOR; TRANSCRIPTION FACTOR;

ANIMAL; CHEMISTRY; GENE EXPRESSION REGULATION; HUMAN; METABOLISM; PHYSIOLOGY; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; RECEPTORS, ARYL HYDROCARBON; RECEPTORS, RETINOIC ACID; SIGNAL TRANSDUCTION; TRANSCRIPTION FACTORS; TRETINOIN;

EID: 33947184743     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0083-6729(06)75002-6     Document Type: Review

References (189)

1. Abbott B.D., and Birnbaum L.S. Retinoic acid-induced alterations in the expression of growth factors in embryonic mouse palatal shelves. Teratology 42 (1990) 597-610
2. Abbott B.D., and Buckalew A.R. Embryonic palatal responses to teratogens in serum-free organ culture. Teratology 45 (1992) 369-382
3. Achkar C.C., Derguini F., Blumberg B., Langston A., Levin A.A., Speck J., Evans R.M., Bolado Jr. J., Nakanishi K., Buck J., and Gudas L.J. 4-Oxoretinol, a new natural ligand and transactivator of the retinoic acid receptors. Proc. Natl. Acad. Sci. USA 93 (1996) 4879-4884
4. Ahmad M., Nicholls P.J., Smith H.J., and Ahmadi M. Effect of P450 isozyme-selective inhibitors on in-vitro metabolism of retinoic acid by rat hepatic microsomes. J. Pharm. Pharmacol. 52 (2000) 311-314
5. Ahmed S., Shibazaki M., Takeuchi T., and Kikuchi H. Protein kinase Ctheta activity is involved in the 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced signal transduction pathway leading to apoptosis in L-MAT, a human lymphoblastic T-cell line. FEBS J. 272 (2005) 903-915
6. Andreola F., Fernandez-Salguero P.M., Chiantore M.V., Petkovich M.P., Gonzalez F.J., and De Luca L.M. Aryl hydrocarbon receptor knockout mice (AHR-/-) exhibit liver retinoid accumulation and reduced retinoic acid metabolism. Cancer Res. 57 (1997) 2835-2838
7. Andreola F., Calvisi D.F., Elizondo G., Jakowlew S.B., Mariano J., Gonzalez F.J., and De Luca L.M. Reversal of liver fibrosis in aryl hydrocarbon receptor null mice by dietary vitamin A depletion. Hepatology 39 (2004) 157-166
8. Aoki Y. Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters-what we have learned from Yusho disease. Environ. Res. 86 (2001) 2-11
9. Baniahmad A. Nuclear hormone receptor co-repressors. J. Steroid Biochem. Mol. Biol. 93 (2005) 89-97
10. Bank P.A., Salyers K.L., and Zile M.H. Effect of tetrachlorodibenzo-p-dioxin (TCDD) on the glucuronidation of retinoic acid in the rat. Biochim. Biophys. Acta 993 (1989) 1-6
11. Beischlag T.V., Wang S., Rose D.W., Torchia J., Reisz-Porszasz S., Muhammad K., Nelson W.E., Probst M.R., Rosenfeld M.G., and Hankinson O. Recruitment of the NCoA/SRC-1/p160 family of transcriptional coactivators by the aryl hydrocarbon receptor/aryl hydrocarbon receptor nuclear translocator complex. Mol. Cell. Biol. 22 (2002) 4319-4333
12. Bertazzi P.A., Zocchetti C., Pesatori A.C., Guercilena S., Sanarico M., and Radice L. Mortality in an area contaminated by TCDD following an industrial incident. Med. Lav. 80 (1989) 316-329
13. Bertazzi P.A., Consonni D., Bachetti S., Rubagotti M., Baccarelli A., Zocchetti C., and Pesatori A.C. Health effects of dioxin exposure: A 20-year mortality study. Am. J. Epidemiol. 153 (2001) 1031-1044
14. Birnbaum L.S., Harris M.W., Stocking L.M., Clark A.M., and Morrissey R.E. Retinoic acid and 2,3,7,8-tetrachlorodibenzo-p-dioxin selectively enhance teratogenesis in C57BL/6N mice. Toxicol. Appl. Pharmacol. 98 (1989) 487-500
15. Blaner W.S. Cellular metabolism and actions of 13-cis-retinoic acid. J. Am. Acad. Dermatol. 45 (2001) S129-S135
16. Blumberg B., Bolado Jr. J., Derguini F., Craig A.G., Moreno T.A., Chakravarti D., Heyman R.A., Buck J., and Evans R.M. Novel retinoic acid receptor ligands in Xenopus embryos. Proc. Natl. Acad. Sci. USA 93 (1996) 4873-4878
17. Boerman M.H., and Napoli J.L. Cholate-independent retinyl ester hydrolysis. Stimulation by Apo-cellular retinol-binding protein. J. Biol. Chem. 266 (1991) 22273-22278
18. Boerman M.H., and Napoli J.L. Cellular retinol-binding protein-supported retinoic acid synthesis. Relative roles of microsomes and cytosol. J. Biol. Chem. 271 (1996) 5610-5616
19. Brinckerhoff C.E., and Matrisian L.M. Matrix metalloproteinases: A tail of a frog that became a prince. Nat. Rev. Mol. Cell. Biol. 3 (2002) 207-214
20. Brouwer A., Hakansson H., Kukler A., Van den Berg K.J., and Ahlborg U.G. Marked alterations in retinoid homeostasis of Sprague-Dawley rats induced by a single i.p. dose of 10 micrograms/kg of 2,3,7,8-tetrachlorodibenzo-p-dioxin. Toxicology 58 (1989) 267-283
21. Carver L.A., and Bradfield C.A. Ligand-dependent interaction of the aryl hydrocarbon receptor with a novel immunophilin homolog in vivo. J. Biol. Chem. 272 (1997) 11452-11456
22. Carver L.A., LaPres J.J., Jain S., Dunham E.E., and Bradfield C.A. Characterization of the Ah receptor-associated protein, ARA9. J. Biol. Chem. 273 (1998) 33580-33587
23. Chambon P. A decade of molecular biology of retinoic acid receptors. FASEB J. 10 (1996) 940-954
24. Chen H., and Juchau M.R. Glutathione S-transferases act as isomerases in isomerization of 13-cis-retinoic acid to all-trans-retinoic acid in vitro. Biochem. J. 327 Pt. 3 (1997) 721-726
25. Chen H., and Juchau M.R. Biotransformation of 13-cis- and 9-cis-retinoic acid to all-trans-retinoic acid in rat conceptal homogenates. Evidence for catalysis by a conceptal isomerase. Drug Metab. Dispos. 26 (1998) 222-228
26. Chen H., and Juchau M.R. Recombinant human glutathione S-transferases catalyse enzymic isomerization of 13-cis-retinoic acid to all-trans-retinoic acid in vitro. Biochem. J. 336 Pt. 1 (1998) 223-226
27. Chen H., Howald W.N., and Juchau M.R. Biosynthesis of all-trans-retinoic acid from all-trans-retinol: Catalysis of all-trans-retinol oxidation by human P-450 cytochromes. Drug Metab. Dispos. 28 (2000) 315-322
28. Chen J.D. Steroid/nuclear receptor coactivators. Vitam. Horm. 58 (2000) 391-448
29. Chen J.D., and Li H. Coactivation and corepression in transcriptional regulation by steroid/nuclear hormone receptors. Crit. Rev. Eukaryot. Gene Expr. 8 (1998) 169-190
30. Choudhary D., Jansson I., Schenkman J.B., Sarfarazi M., and Stoilov I. Comparative expression profiling of 40 mouse cytochrome P450 genes in embryonic and adult tissues. Arch. Biochem. Biophys. 414 (2003) 91-100
31. Choudhary D., Jansson I., Stoilov I., Sarfarazi M., and Schenkman J.B. Expression patterns of mouse and human CYP orthologs (families 1-4) during development and in different adult tissues. Arch. Biochem. Biophys. 436 (2005) 50-61
32. Chu I., Lecavalier P., Hakansson H., Yagminas A., Valli V.E., Poon P., and Feeley M. Mixture effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin and polychlorinated biphenyl congeners in rats. Chemosphere 43 (2001) 807-814
33. Crews S.T., and Fan C.M. Remembrance of things PAS: Regulation of development by bHLH-PAS proteins. Curr. Opin. Genet. Dev. 9 (1999) 580-587
34. Denison M.S., Pandini A., Nagy S.R., Baldwin E.P., and Bonati L. Ligand binding and activation of the Ah receptor. Chem. Biol. Interact. 141 (2002) 3-24
35. DeVito M.J., Birnbaum L.S., Farland W.H., and Gasiewicz T.A. Comparisons of estimated human body burdens of dioxinlike chemicals and TCDD. Environ. Health Perspect. 103 (1995) 820-831
36. Dragnev K.H., Rigas J.R., and Dmitrovsky E. The retinoids and cancer prevention mechanisms. Oncologist 5 (2000) 361-368
37. Du L., Neis M.M., Ladd P.A., Lanza D.L., Yost G.S., and Keeney D.S. Effects of the differentiated keratinocyte phenotype on expression levels of CYP1-4 family genes in human skin cells. Toxicol. Appl. Pharmacol. 213 2 (2005) 135-144
38. Duester G. Families of retinoid dehydrogenases regulating vitamin A function: Production of visual pigment and retinoic acid. Eur. J. Biochem. 267 (2000) 4315-4324
39. Fiorella P.D., Olson J.R., and Napoli J.L. 2,3,7,8-Tetrachlorodibenzo-p-dioxin induces diverse retinoic acid metabolites in multiple tissues of the Sprague-Dawley rat. Toxicol. Appl. Pharmacol. 134 (1995) 222-228
40. Fisher G.J., and Voorhees J.J. Molecular mechanisms of retinoid actions in skin. FASEB J. 10 (1996) 1002-1013
41. FitzGerald C.T., Fernandez-Salguero P., Gonzalez F.J., Nebert D.W., and Puga A. Differential regulation of mouse Ah receptor gene expression in cell lines of different tissue origins. Arch. Biochem. Biophys. 333 (1996) 170-178
42. Fletcher N., Hanberg A., and Hakansson H. Hepatic vitamin a depletion is a sensitive marker of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) exposure in four rodent species. Toxicol. Sci. 62 (2001) 166-175
43. Fletcher N., Giese N., Schmidt C., Stern N., Lind P.M., Viluksela M., Tuomisto J.T., Tuomisto J., Nau H., and Hakansson H. Altered retinoid metabolism in female Long-Evans and Han/Wistar rats following long-term 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-treatment. Toxicol. Sci. 86 (2005) 264-272
44. Fujii-Kuriyama Y., Imataka H., Sogawa K., Yasumoto K., and Kikuchi Y. Regulation of CYP1A1 expression. FASEB J. 6 (1992) 706-710
45. Gamble M.V., Shang E., Zott R.P., Mertz J.R., Wolgemuth D.J., and Blaner W.S. Biochemical properties, tissue expression, and gene structure of a short chain dehydrogenase/reductase able to catalyze cis-retinol oxidation. J. Lipid Res. 40 (1999) 2279-2292
46. Gambone C.J., Hutcheson J.M., Gabriel J.L., Beard R.L., Chandraratna R.A., Soprano K.J., and Soprano D.R. Unique property of some synthetic retinoids: Activation of the aryl hydrocarbon receptor pathway. Mol. Pharmacol. 61 (2002) 334-342
47. Garrison P.M., Tullis K., Aarts J.M., Brouwer A., Giesy J.P., and 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. 30 (1996) 194-203
48. Genchi G., Wang W., Barua A., Bidlack W.R., and Olson J.A. Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim. Biophys. Acta 1289 (1996) 284-290
49. Ghyselinck N.B., Bavik C., Sapin V., Mark M., Bonnier D., Hindelang C., Dierich A., Nilsson C.B., Hakansson H., Sauvant P., Azais-Braesco V., Frasson M., et al. Cellular retinol-binding protein I is essential for vitamin A homeostasis. EMBO J. 18 (1999) 4903-4914
50. Glass C.K., Rosenfeld M.G., Rose D.W., Kurokawa R., Kamei Y., Xu L., Torchia J., Ogliastro M.H., and Westin S. Mechanisms of transcriptional activation by retinoic acid receptors. Biochem. Soc. Trans. 25 (1997) 602-605
51. Gonzalez F.J., and Fernandez-Salguero P. The aryl hydrocarbon receptor: Studies using the AHR-null mice. Drug Metab. Dispos. 26 (1998) 1194-1198
52. Goodman D.S. The metabolism of chylomicron cholesterol ester in the rat. J. Clin. Invest. 41 (1962) 1886-1896
53. Goodman D.W., Huang H.S., and Shiratori T. Tissue distribution and metabolism of newly absorbed vitamin a in the rat. J. Lipid Res. 6 (1965) 390-396
54. Hakansson H., and Ahlborg U.G. The effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on the uptake, distribution and excretion of a single oral dose of [11,12-3H]retinyl acetate and on the vitamin A status in the rat. J. Nutr. 115 (1985) 759-771
55. Hakansson H., and Hanberg A. The distribution of [14C]-2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and its effect on the vitamin A content in parenchymal and stellate cells of rat liver. J. Nutr. 119 (1989) 573-580
56. Hakansson H., Waern F., and Ahlborg U.G. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the lactating rat on maternal and neonatal vitamin A status. J. Nutr. 117 (1987) 580-586
57. Hakansson H., Johansson L., Manzoor E., and Ahlborg U.G. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on the vitamin A status of Hartley guinea pigs, Sprague-Dawley rats, C57Bl/6 mice, DBA/2 mice, and Golden Syrian hamsters. J. Nutr. Sci. Vitaminol. (Tokyo) 37 (1991) 117-138
58. Hakansson H., Manzoor E., Trossvik C., Ahlborg U.G., Chu I., and Villenueve D. Effect on tissue vitamin A levels in the rat following subchronic exposure to four individual PCB congeners (IUPAC 77, 118, 126, and 153). Chemosphere 29 (1994) 2309-2313
59. Hanberg A., Kling L., and Hakansson H. Effect of 2,3,7,8-tetrachlorodibenzo-P-dioxin (TCDD) on the hepatic stellate cell population in the rat. Chemosphere 32 (1996) 1225-1233
60. Hankinson O. The aryl hydrocarbon receptor complex. Ann. Rev. Pharmacol. Toxicol. 35 (1995) 307-340
61. Hankinson O. Role of coactivators in transcriptional activation by the aryl hydrocarbon receptor. Arch. Biochem. Biophys. 433 (2005) 379-386
62. Herr F.M., and Ong D.E. Differential interaction of lecithin-retinol acyltransferase with cellular retinol binding proteins. Biochemistry 31 (1992) 6748-6755
63. Hoegberg P., Schmidt C.K., Nau H., Ross A.C., Zolfaghari R., Fletcher N., Trossvik C., Nilsson C.B., and Hakansson H. 2,3,7,8-Tetrachlorodibenzo-p-dioxin induces lecithin: Retinol acyltransferase transcription in the rat kidney. Chem. Biol. Interact. 145 (2003) 1-16
64. Hoegberg P., Schmidt C.K., Fletcher N., Nilsson C.B., Trossvik C., Gerlienke Schuur A., Brouwer A., Nau H., Ghyselinck N.B., Chambon P., and Hakansson H. Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem. Biol. Interact. 156 (2005) 25-39
65. Hoffer A., Chang C.Y., and Puga A. Dioxin induces transcription of fos and jun genes by Ah receptor-dependent and -independent pathways. Toxicol. Appl. Pharmacol. 141 (1996) 238-247
66. Honkakoski P., and Negishi M. Regulation of cytochrome P450 (CYP) genes by nuclear receptors. Biochem. J. 347 (2000) 321-337
67. Imai S., Okuno M., Moriwaki H., Muto Y., Murakami K., Shudo K., Suzuki Y., and Kojima S. 9,13-di-cis-Retinoic acid induces the production of tPA and activation of latent TGF-beta via RAR alpha in a human liver stellate cell line, LI90. FEBS Lett. 411 (1997) 102-106
68. Jamsa T., Viluksela M., Tuomisto J.T., Tuomisto J., and Tuukkanen J. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on bone in two rat strains with different aryl hydrocarbon receptor structures. J. Bone Miner. Res. 16 (2001) 1812-1820
69. Jurek M.A., Powers R.H., Gilbert L.G., and Aust S.D. The effect of TCDD on acyl CoA:retinol acyltransferase activity and vitamin A accumulation in the kidney of male Sprague-Dawley rats. J. Biochem. Toxicol. 5 (1990) 155-160
70. Kalin J.R., Wells M.J., and Hill D.L. Effects of phenobarbital, 3-methylcholanthrene, and retinoid pretreatment on disposition of orally administered retinoids in mice. Drug Metab. Dispos. 12 (1984) 63-67
71. Kazlauskas A., Sundstrom S., Poellinger L., and Pongratz I. The hsp90 chaperone complex regulates intracellular localization of the dioxin receptor. Mol. Cell. Biol. 21 (2001) 2594-2607
72. Kelley S.K., Nilsson C.B., Green M.H., Green J.B., and Hakansson H. Use of model-based compartmental analysis to study effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A kinetics in rats. Toxicol. Sci. 44 (1998) 1-13
73. Kelley S.K., Nilsson C.B., Green M.H., Green J.B., and Hakansson H. Mobilization of vitamin A stores in rats after administration of 2,3,7,8-tetrachlorodibenzo-p-dioxin: A kinetic analysis. Toxicol. Sci. 55 (2000) 478-484
74. Kessler F.K., and Ritter J.K. Induction of a rat liver benzo[a]pyrene-trans-7,8-dihydrodiol glucuronidating activity by oltipraz and beta-naphthoflavone. Carcinogenesis 18 (1997) 107-114
75. Ko H.P., Okino S.T., Ma Q., and Whitlock Jr. J.P. Transactivation domains facilitate promoter occupancy for the dioxin-inducible CYP1A1 gene in vivo. Mol. Cell. Biol. 17 (1997) 3497-3507
76. Kobayashi A., Numayama-Tsuruta K., Sogawa K., and Fujii-Kuriyama Y. CBP/p300 functions as a possible transcriptional coactivator of Ah receptor nuclear translocator (Arnt). J. Biochem. (Tokyo) 122 (1997) 703-710
77. Kojima R., Fujimori T., Kiyota N., Toriya Y., Fukuda T., Ohashi T., Sato T., Yoshizawa Y., Takeyama K., Mano H., Soiching M., and Kato S. In vivo isomerization of retinoic acids. Rapid isomer exchange and gene expression. J. Biol. Chem. 269 (1994) 32700-32707
78. Kolluri S.K., Weiss C., Koff A., and Gottlicher M. p27(Kip1) induction and inhibition of proliferation by the intracellular Ah receptor in developing thymus and hepatoma cells. Genes Dev. 13 (1999) 1742-1753
79. Kondraganti S.R., Fernandez-Salguero P., Gonzalez F.J., Ramos K.S., Jiang W., and Moorthy B. Polycyclic aromatic hydrocarbon-inducible DNA adducts: Evidence by 32P-postlabeling and use of knockout mice for Ah receptor-independent mechanisms of metabolic activation in vivo. Int. J. Cancer 103 (2003) 5-11
80. Krig S.R., and Rice R.H. TCDD suppression of tissue transglutaminase stimulation by retinoids in malignant human keratinocytes. Toxicol. Sci. 56 (2000) 357-364
81. Kumar M.B., Tarpey R.W., and Perdew G.H. Differential recruitment of coactivator RIP140 by Ah and estrogen receptors. Absence of a role for LXXLL motifs. J. Biol. Chem. 274 (1999) 22155-22164
82. Lampen A., Meyer S., Arnhold T., and Nau H. Metabolism of vitamin A and its active metabolite all-trans-retinoic acid in small intestinal enterocytes. J. Pharmacol. Exp. Ther. 295 (2000) 979-985
83. LaPres J.J., Glover E., Dunham E.E., Bunger M.K., and Bradfield C.A. ARA9 modifies agonist signaling through an increase in cytosolic aryl hydrocarbon receptor. J. Biol. Chem. 275 (2000) 6153-6159
84. Leo M.A., Iida S., and Lieber C.S. Retinoic acid metabolism by a system reconstituted with cytochrome P-450. Arch. Biochem. Biophys. 234 (1984) 305-312
85. Li H., Leo C., Schroen D.J., and Chen J.D. Characterization of receptor interaction and transcriptional repression by the corepressor SMRT. Mol. Endocrinol. 11 (1997) 2025-2037
86. Lind P.M., Larsson S., Johansson S., Melhus H., Wikstrom M., Lindhe O., and Orberg J. Bone tissue composition, dimensions and strength in female rats given an increased dietary level of vitamin A or exposed to 3,3′,4,4′,5-pentachlorobiphenyl (PCB126) alone or in combination with vitamin C. Toxicology 151 (2000) 11-23
87. Lindros K.O., Oinonen T., Kettunen E., Sippel H., Muro-Lupori C., and Koivusalo M. Aryl hydrocarbon receptor-associated genes in rat liver: Regional coinduction of aldehyde dehydrogenase 3 and glutathione transferase Ya. Biochem. Pharmacol. 55 (1998) 413-421
88. Long W.P., Pray-Grant M., Tsai J.C., and Perdew G.H. Protein kinase C activity is required for aryl hydrocarbon receptor pathway-mediated signal transduction. Mol. Pharmacol. 53 (1998) 691-700
89. Lorick K.L., Toscano D.L., and Toscano Jr. W.A. 2,3,7,8-Tetrachlorodibenzo-p-dioxin alters retinoic acid receptor function in human keratinocytes. Biochem. Biophys. Res. Commun. 243 (1998) 749-752
90. Loudig O., Babichuk C., White J., Abu-Abed S., Mueller C., and Petkovich M. Cytochrome P450RAI(CYP26) promoter: A distinct composite retinoic acid response element underlies the complex regulation of retinoic acid metabolism. Mol. Endocrinol. 14 (2000) 1483-1497
91. Mahon M.J., and Gasiewicz T.A. Ah receptor phosphorylation: Localization of phosphorylation sites to the C-terminal half of the protein. Arch. Biochem. Biophys. 318 (1995) 166-174
92. Malik N., and Owens I.S. Genetic regulation of bilirubin-UDP-glucuronosyltransferase induction by polycyclic aromatic compounds and phenobarbital in mice. Association with aryl hydrocarbon (benzo[a]pyrene) hydroxylase induction. J. Biol. Chem. 256 (1981) 9599-9604
93. Mangelsdorf D.J., Thummel C., Beato M., Herrlich P., Schutz G., Umesono K., Blumberg B., Kastner P., Mark M., Chambon P., and Evans R.M. The nuclear receptor superfamily: The second decade. Cell 83 (1995) 835-839
94. Marchetti M.N., Sampol E., Bun H., Scoma H., Lacarelle B., and Durand A. In vitro metabolism of three major isomers of retinoic acid in rats. Intersex and interstrain comparison. Drug Metab. Dispos. 25 (1997) 637-646
95. Mark M., Ghyselinck N.B., Wendling O., Dupe V., Mascrez B., Kastner P., and Chambon P. A genetic dissection of the retinoid signalling pathway in the mouse. Proc. Nutr. Soc. 58 (1999) 609-613
96. Martini R., and Murray M. Retinal dehydrogenation and retinoic acid 4-hydroxylation in rat hepatic microsomes: Developmental studies and effect of foreign compounds on the activities. Biochem. Pharmacol. 47 (1994) 905-909
97. Matikainen T., Perez G.I., Jurisicova A., Pru J.K., Schlezinger J.J., Ryu H.Y., Laine J., Sakai T., Korsmeyer S.J., Casper R.F., Sherr D.H., and Tilly J.L. Aromatic hydrocarbon receptor-driven Bax gene expression is required for premature ovarian failure caused by biohazardous environmental chemicals. Nat. Genet. 28 (2001) 355-360
98. Matsushita N., Sogawa K., Ema M., Yoshida A., and Fujii-Kuriyama Y. A factor binding to the xenobiotic responsive element (XRE) of P-4501A1 gene consists of at least two helix-loop-helix proteins, Ah receptor and Arnt. J. Biol. Chem. 268 (1993) 21002-21006
99. McSorley L.C., and Daly A.K. Identification of human cytochrome P450 isoforms that contribute to all-trans-retinoic acid 4-hydroxylation. Biochem. Pharmacol. 60 (2000) 517-526
100. Mimura J., and Fujii-Kuriyama Y. Functional role of AhR in the expression of toxic effects by TCDD. Biochim. Biophys. Acta 1619 (2003) 263-268
101. Moise A.R., Kuksa V., Blaner W.S., Baehr W., and Palczewski K. Metabolism and transactivation activity of 13,14-dihydroretinoic acid. J. Biol. Chem. 280 (2005) 27815-27825
102. Morgan J.E., and Whitlock Jr. J.P. Transcription-dependent and transcription-independent nucleosome disruption induced by dioxin. Proc. Natl. Acad. Sci. USA 89 (1992) 11622-11626
103. Morita A., and Nakano K. Change in vitamin A content in tissues of rats fed on a vitamin A-free diet. J. Nutr. Sci. Vitaminol. (Tokyo) 28 (1982) 343-350
104. Morse D.C., and Brouwer A. Fetal, neonatal, and long-term alterations in hepatic retinoid levels following maternal polychlorinated biphenyl exposure in rats. Toxicol. Appl. Pharmacol. 131 (1995) 175-182
105. Mukerjee D. Health impact of polychlorinated dibenzo-p-dioxins: A critical review. J. Air Waste Manage. Assoc. 48 (1998) 157-165
106. Munzel P.A., Bruck M., and Bock K.W. Tissue-specific constitutive and inducible expression of rat phenol UDP-glucuronosyltransferase. Biochem. Pharmacol. 47 (1994) 1445-1448
107. Munzel P.A., Schmohl S., Heel H., Kalberer K., Bock-Hennig B.S., and Bock K.W. Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells. Drug Metab. Dispos. 27 (1999) 569-573
108. Murphy K.A., Villano C.M., Dorn R., and White L.A. Interaction between the aryl hydrocarbon receptor and retinoic acid pathways increases matrix metalloproteinase-1 expression in keratinocytes. J. Biol. Chem. 279 (2004) 25284-25293
109. Nagpal S., and Chandraratna R.A. Recent developments in receptor-selective retinoids. Curr. Pharm. Des. 6 (2000) 919-931
110. Napoli J.L. Interactions of retinoid binding proteins and enzymes in retinoid metabolism. Biochim. Biophys. Acta 1440 (1999) 139-162
111. Nebert D.W., and Russell D.W. Clinical importance of the cytochromes P450. Lancet 360 (2002) 1155-1162
112. Nelson D.R., Koymans L., Kamataki T., Stegeman J.J., Feyereisen R., Waxman D.J., Waterman M.R., Gotoh O., Coon M.J., Estabrook R.W., Gunsalus I.C., and Nebert D.W. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6 (1996) 1-42
113. Nguyen T.A., Hoivik D., Lee J.E., and Safe S. Interactions of nuclear receptor coactivator/corepressor proteins with the aryl hydrocarbon receptor complex. Arch. Biochem. Biophys. 367 (1999) 250-257
114. Nilsson A., Troen G., Petersen L.B., Reppe S., Norum K.R., and Blomhoff R. Retinyl ester storage is altered in liver stellate cells and in HL60 cells transfected with cellular retinol-binding protein type I. Int. J. Biochem. Cell Biol. 29 (1997) 381-389
115. Nilsson C.B., and Hakansson H. The retinoid signaling system-a target in dioxin toxicity. Crit. Rev. Toxicol. 32 (2002) 211-232
116. Nilsson C.B., Hoegberg P., Trossvik C., Azais-Braesco V., Blaner W.S., Fex G., Harrison E.H., Nau H., Schmidt C.K., van Bennekum A.M., and Hakansson H. 2,3,7,8-Tetrachlorodibenzo-p-dioxin increases serum and kidney retinoic acid levels and kidney retinol esterification in the rat. Toxicol. Appl. Pharmacol. 169 (2000) 121-131
117. Oberg M., Bergander L., Hakansson H., Rannug U., and Rannug A. 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
118. O'Byrne S.M., Wongsiriroj N., Libien J., Vogel S., Goldberg I.J., Baehr W., Palczewski K., and Blaner W.S. Retinoid absorption and storage is impaired in mice lacking lecithin:retinol acyltransferase (LRAT). J. Biol. Chem. 280 (2005) 35647-35657
119. Okuno M., Sato T., Kitamoto T., Imai S., Kawada N., Suzuki Y., Yoshimura H., Moriwaki H., Onuki K., Masushige S., Muto Y., Friedman S.L., et al. Increased 9,13-di-cis-retinoic acid in rat hepatic fibrosis: Implication for a potential link between retinoid loss and TGF-beta mediated fibrogenesis in vivo. J. Hepatol. 30 (1999) 1073-1080
120. Ott M.G., and Zober A. Cause specific mortality and cancer incidence among employees exposed to 2,3,7,8-TCDD after a 1953 reactor accident. Occup. Environ. Med. 53 (1996) 606-612
121. Park J.H., Hahn E.J., Kong J.H., Cho H.J., Yoon C.S., Cheong S.W., Oh G.S., and 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. 145 (2003) 55-68
122. Park K.T., Mitchell K.A., Huang G., and Elferink C.J. The aryl hydrocarbon receptor predisposes hepatocytes to Fas-mediated apoptosis. Mol. Pharmacol. 67 (2005) 612-622
123. 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., and 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. 25 (2005) 2831-2836
124. Peters J.M., Narotsky M.G., Elizondo G., Fernandez-Salguero P.M., Gonzalez F.J., and Abbott B.D. Amelioration of TCDD-induced teratogenesis in aryl hydrocarbon receptor (AhR)-null mice. Toxicol. Sci. 47 (1999) 86-92
125. Pijnappel W.W., Folkers G.E., de Jonge W.J., Verdegem P.J., de Laat S.W., Lugtenburg J., Hendriks H.F., van der Saag P.T., and Durston A.J. Metabolism to a response pathway selective retinoid ligand during axial pattern formation. Proc. Natl. Acad. Sci. USA 95 (1998) 15424-15429
126. Pollenz R.S. The mechanism of AH receptor protein down-regulation (degradation) and its impact on AH receptor-mediated gene regulation. Chem. Biol. Interact. 141 (2002) 41-61
127. Puga A., Nebert D.W., and Carrier F. Dioxin induces expression of c-fos and c-jun proto-oncogenes and a large increase in transcription factor AP-1. DNA Cell Biol. 11 (1992) 269-281
128. Quadro L., Blaner W.S., Salchow D.J., Vogel S., Piantedosi R., Gouras P., Freeman S., Cosma M.P., Colantuoni V., and Gottesman M.E. Impaired retinal function and vitamin A availability in mice lacking retinol-binding protein. EMBO J. 18 (1999) 4633-4644
129. Radominska A., Little J.M., Lehman P.A., Samokyszyn V., Rios G.R., King C.D., Green M.D., and Tephly T.R. Glucuronidation of retinoids by rat recombinant UDP: Glucuronosyltransferase 1.1 (bilirubin UGT). Drug Metab. Dispos. 25 (1997) 889-892
130. Raner G.M., Vaz A.D., and Coon M.J. Metabolism of all-trans, 9-cis, and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhibition of retinoid oxidation by citral. Mol. Pharmacol. 49 (1996) 515-522
131. Ray W.J., Bain G., Yao M., and Gottlieb D.I. CYP26, a novel mammalian cytochrome P450, is induced by retinoic acid and defines a new family. J. Biol. Chem. 272 (1997) 18702-18708
132. Renaud J.P., and Moras D. Structural studies on nuclear receptors. Cell. Mol. Life Sci. 57 (2000) 1748-1769
133. Reyes H., Reisz-Porszasz S., and Hankinson O. Identification of the Ah receptor nuclear translocator protein (Arnt) as a component of the DNA binding form of the Ah receptor. Science 256 (1992) 1193-1195
134. Roberts E.S., Vaz A.D., and Coon M.J. Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol. Pharmacol. 41 (1992) 427-433
135. Rolland R.M. A review of chemically-induced alterations in thyroid and vitamin A status from field studies of wildlife and fish. J. Wildl. Dis. 36 (2000) 615-635
136. Rowlands J.C., McEwan I.J., and Gustafsson J.A. Trans-activation by the human aryl hydrocarbon receptor and aryl hydrocarbon receptor nuclear translocator proteins: Direct interactions with basal transcription factors. Mol. Pharmacol. 50 (1996) 538-548
137. Rubin A.L., and Rice R.H. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and polycyclic aromatic hydrocarbons suppress retinoid-induced tissue transglutaminase in SCC-4 cultured human squamous carcinoma cells. Carcinogenesis 9 (1988) 1067-1070
138. Rushing S.R., and Denison M.S. The silencing mediator of retinoic acid and thyroid hormone receptors can interact with the aryl hydrocarbon (Ah) receptor but fails to repress Ah receptor-dependent gene expression. Arch. Biochem. Biophys. 403 (2002) 189-201
139. Saarikoski S.T., Rivera S.P., Hankinson O., and Husgafvel-Pursiainen K. CYP2S1: A short review. Toxicol. Appl. Pharmacol. 207 (2005) 62-69
140. Safe S. Molecular biology of the Ah receptor and its role in carcinogenesis. Toxicol. Lett. 120 (2001) 1-7
141. Sanders J.M., Burka L.T., Smith C.S., Black W., James R., and Cunningham M.L. Differential expression of CYP1A, 2B, and 3A genes in the F344 rat following exposure to a polybrominated diphenyl ether mixture or individual components. Toxicol. Sci. 88 (2005) 127-133
142. Schmidt C.K., Volland J., Hamscher G., and Nau H. Characterization of a new endogenous vitamin A metabolite. Biochim. Biophys. Acta 1583 (2002) 237-251
143. Schmidt C.K., Hoegberg P., Fletcher N., Nilsson C.B., Trossvik C., Hakansson H., and Nau H. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) alters the endogenous metabolism of all-trans-retinoic acid in the rat. Arch. Toxicol. 77 (2003) 371-383
144. Schule R., Rangarajan P., Yang N., Kliewer S., Ransone L.J., Bolado J., Verma I.M., and Evans R.M. Retinoic acid is a negative regulator of AP-1-responsive genes. Proc. Natl. Acad. Sci. USA 88 (1991) 6092-6096
145. Shertzer H.G., Nebert D.W., Puga A., Ary M., Sonntag D., Dixon K., Robinson L.J., Cianciolo E., and Dalton T.P. Dioxin causes a sustained oxidative stress response in the mouse. Biochem. Biophys. Res. Commun. 253 (1998) 44-48
146. Sogawa K., Iwabuchi K., Abe H., and Fujii-Kuriyama Y. Transcriptional activation domains of the Ah receptor and Ah receptor nuclear translocator. J. Cancer Res. Clin. Oncol. 121 (1995) 612-620
147. Song J., Clagett-Dame M., Peterson R.E., Hahn M.E., Westler W.M., Sicinski R.R., and DeLuca H.F. A ligand for the aryl hydrocarbon receptor isolated from lung. Proc. Natl. Acad. Sci. USA 99 (2002) 14694-14699
148. Soprano D.R., and Soprano K.J. Pharmacological doses of some synthetic retinoids can modulate both the aryl hydrocarbon receptor and retinoid receptor pathways. J. Nutr. 133 (2003) 277S-281S
149. Soprano D.R., Gambone C.J., Sheikh S.N., Gabriel J.L., Chandraratna R.A., Soprano K.J., and Kochhar D.M. The synthetic retinoid AGN 193109 but not retinoic acid elevates CYP1A1 levels in mouse embryos and Hepa-1c1c7 cells. Toxicol. Appl. Pharmacol. 174 (2001) 153-159
150. Sporn M.B., and Suh N. Chemoprevention of cancer. Carcinogenesis 21 (2000) 525-530
151. Sporn M.B., Roberts A.B., and Goodman D.S. "The Retinoids: Biology, Chemistry, and Medicine." (1994), Raven Press, New York
152. Stohs S.J. Oxidative stress induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). Free Radic. Biol. Med. 9 (1990) 79-90
153. Stohs S.J., Abbott B.D., Lin F.H., and Birnbaum L.S. Induction of ethoxyresorufin-O-deethylase and inhibition of glucocorticoid receptor binding in skin and liver of haired and hairless HRS/J mice by topically applied 2,3,7,8-tetrachlorodibenzo-p-dioxin. Toxicology 65 (1990) 123-136
154. Sundaresan P.R., and Bhat P.V. Ion-pair high-pressure liquid chromatography of cis-trans isomers of retinoic acid in tissues of vitamin A-sufficient rats. J. Lipid Res. 23 (1982) 448-455
155. Sutter T.R., Guzman K., Dold K.M., and Greenlee W.F. Targets for dioxin: Genes for plasminogen activator inhibitor-2 and interleukin-1 beta. Science 254 (1991) 415-418
156. Swanson H.I., and Yang J.H. The aryl hydrocarbon receptor interacts with transcription factor IIB. Mol. Pharmacol. 54 (1998) 671-677
157. Thacher S.M., Vasudevan J., and Chandraratna R.A. Therapeutic applications for ligands of retinoid receptors. Curr. Pharm. Des. 6 (2000) 25-58
158. Thunberg T., Ahlborg U.G., and Johnsson H. Vitamin A (retinol) status in the rat after a single oral dose of 2,3,7,8-tetrachlorodibenzo-p-dioxin. Arch. Toxicol. 42 (1979) 265-274
159. Thunberg T., Ahlborg U.G., Hakansson H., Krantz C., and Monier M. Effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on the hepatic storage of retinol in rats with different dietary supplies of vitamin A (retinol). Arch. Toxicol. 45 (1980) 273-285
160. Tijet N., Boutros P.C., Moffat I.D., Okey A.B., Tuomisto J., and Pohjanvirta R. Aryl hydrocarbon receptor regulates distinct dioxin-dependent and dioxin-independent gene batteries. Mol. Pharmacol. 69 (2006) 140-153
161. Tohkin M., Fukuhara M., Elizondo G., Tomita S., and Gonzalez F.J. Aryl hydrocarbon receptor is required for p300-mediated induction of DNA synthesis by adenovirus E1A. Mol. Pharmacol. 58 (2000) 845-851
162. Tomita S., Okuyama E., Ohnishi T., and Ichikawa Y. Characteristic properties of a retinoic acid synthetic cytochrome P-450 purified from liver microsomes of 3-methylcholanthrene-induced rats. Biochim. Biophys. Acta 1290 (1996) 273-281
163. Urbach J., and Rando R.R. Isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. Biochem. J. 299 Pt. 2 (1994) 459-465
164. Urbach J., and Rando R.R. Thiol dependent isomerization of all-trans-retinoic acid to 9-cis-retinoic acid. FEBS Lett. 351 (1994) 429-432
165. Van Birgelen A.P., Smit E.A., Kampen I.M., Groeneveld C.N., Fase K.M., Van der Kolk J., Poiger H., Van den Berg M., Koeman J.H., and Brouwer A. Subchronic effects of 2,3,7,8-TCDD or PCBs on thyroid hormone metabolism: Use in risk assessment. Eur. J. Pharmacol. 293 (1995) 77-85
166. Van Birgelen A.P., Van der Kolk J., Fase K.M., Bol I., Poiger H., Brouwer A., and Van den Berg M. Subchronic dose-response study of 2,3,7,8-tetrachlorodibenzo-p-dioxin in female Sprague-Dawley rats. Toxicol. Appl. Pharmacol. 132 (1995) 1-13
167. Van Wauwe J.P., Coene M.C., Goossens J., Cools W., and Monbaliu J. Effects of cytochrome P-450 inhibitors on the in vivo metabolism of all-trans-retinoic acid in rats. J. Pharmacol. Exp. Ther. 252 (1990) 365-369
168. Vanden Bossche H., Willemsens G., and Janssen P.A. Cytochrome-P-450-dependent metabolism of retinoic acid in rat skin microsomes: Inhibition by ketoconazole. Skin Pharmacol. 1 (1988) 176-185
169. Vane F.M., Stoltenborg J.K., and Bugge C.J. Determination of 13-cis-retinoic acid and its major metabolite, 4-oxo-13-cis-retinoic acid, in human blood by reversed-phase high-performance liquid chromatography. J. Chromatogr. 227 (1982) 471-484
170. Vecchini F., Lenoir-Viale M.C., Cathelineau C., Magdalou J., Bernard B.A., and Shroot B. Presence of a retinoid responsive element in the promoter region of the human cytochrome P4501A1 gene. Biochem. Biophys. Res. Commun. 201 (1994) 1205-1212
171. Villano C.M., Murphy K.A., Akintobi A., and White L.A. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) induces matrix metalloproteinase (MMP) expression and invasion in A2058 melanoma cells. Toxicol. Appl. Pharmacol. 210 (2006) 212-224
172. Vincenti M.P., White L.A., Schroen D.J., Benbow U., and Brinckerhoff C.E. Regulating expression of the gene for matrix metalloproteinase-1 (MMP-1): Mechanisms that control enzyme activity, transcription and mRNA stability. Crit. Rev. Eukaryot. Gene Expr. 6 (1996) 391-411
173. Vogel S., Gamble M.V., and Blaner W.S. Biosynthesis, absorption, metabolism and transport of retinoids. In: Nau H., and Blaner W.S. (Eds). "Handbook of Experimental Pharmacology. Retinoids. The Biochemical and Molecular Basis of Vitamin A and Retinoid Action" (1999), Springer Verlag, Heidelberg, Germany 31-95
174. Wang S., and Hankinson O. Functional involvement of the Brahma/SWI2-related gene 1 protein in cytochrome P4501A1 transcription mediated by the aryl hydrocarbon receptor complex. J. Biol. Chem. 277 (2002) 11821-11827
175. Wang X., Sperkova Z., and Napoli J.L. Analysis of mouse retinal dehydrogenase type 2 promoter and expression. Genomics 74 (2001) 245-250
176. Wanner R., Panteleyev A., Henz B.M., and Rosenbach T. Retinoic acid affects the expression rate of the differentiation-related genes aryl hydrocarbon receptor, ARNT and keratin 4 in proliferative keratinocytes only. Biochim. Biophys. Acta 1317 (1996) 105-111
177. Watson A.J., and Hankinson O. Dioxin- and Ah receptor-dependent protein binding to xenobiotic responsive elements and G-rich DNA studied by in vivo footprinting. J. Biol. Chem. 267 (1992) 6874-6878
178. Watt K., Jess T.J., Kelly S.M., Price N.C., and McEwan I.J. Induced alpha-helix structure in the aryl hydrocarbon receptor transactivation domain modulates protein-protein interactions. Biochemistry 44 (2005) 734-743
179. Wei L.N. Retinoid receptors and their coregulators. Annu. Rev. Pharmacol. Toxicol. 43 (2003) 47-72
180. Weston W.M., Nugent P., and Greene R.M. Inhibition of retinoic-acid-induced gene expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biochem. Biophys. Res. Commun. 207 (1995) 690-694
181. Widerak M., Ghoneim C., Dumontier M.F., Quesne M., Corvol M.T., and Savouret J.F. The aryl hydrocarbon receptor activates the retinoic acid receptoralpha through SMRT antagonism. Biochimie 88 3-4 (2005) 387-397
182. Yang Y.M., Huang D.Y., Liu G.F., Zhong J.C., Du K., Li Y.F., and Song X.H. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice. J. Biochem. Mol. Toxicol. 19 (2005) 327-335
183. Yao T.P., Ku G., Zhou N., Scully R., and Livingston D.M. The nuclear hormone receptor coactivator SRC-1 is a specific target of p300. Proc. Natl. Acad. Sci. USA 93 (1996) 10626-10631
184. Yin H., Li Y., and Sutter T.R. Dioxin-enhanced expression of interleukin-1 beta in human epidermal keratinocytes: Potential role in the modulation of immune and inflammatory responses. Exp. Clin. Immunogenet. 11 (1994) 128-135
185. Yoh S.M., and Privalsky M.L. Transcriptional repression by thyroid hormone receptors. A role for receptor homodimers in the recruitment of SMRT corepressor. J. Biol. Chem. 276 (2001) 16857-16867
186. Yueh M.F., Huang Y.H., Hiller A., Chen S., Nguyen N., and Tukey R.H. Involvement of the xenobiotic response element (XRE) in Ah receptor-mediated induction of human UDP-glucuronosyltransferase 1A1. J. Biol. Chem. 278 (2003) 15001-15006
187. Yueh M.F., Kawahara M., and Raucy J. Cell-based high-throughput bioassays to assess induction and inhibition of CYP1A enzymes. Toxicol. In Vitro 19 (2005) 275-287
188. Zhang Q.Y., Dunbar D., and Kaminsky L. Human cytochrome P-450 metabolism of retinals to retinoic acids. Drug Metab. Dispos. 28 (2000) 292-297
189. Zile M.H., Emerick R.J., and DeLuca H.F. Identification of 13-cis retinoic acid in tissue extracts and its biological activity in rats. Biochim. Biophys. Acta 141 (1967) 639-641