Summary: Organic compounds containing a BENZENE ring attached to a flavone group. Some of these are potent arylhydrocarbon hydroxylase inhibitors. They may also inhibit the binding of NUCLEIC ACIDS to BENZOPYRENES and related compounds. The designation includes all isomers; the 7,8-isomer is most frequently encountered.

Top Publications

  1. Kurelec B, Krca S, Garg A, Gupta R. The potential of carp to bioactivate benzo[a]pyrene to metabolites that bind to DNA. Cancer Lett. 1991;57:255-60 pubmed
    ..o. treatment. These results indicate that carp can biotransform polycyclic aromatic hydrocarbons such as benzo[a]pyrene to 'reactive' metabolites that bind to DNA. ..
  2. Shankar S, Zalutsky M, Friedman H, Vaidyanathan G. Molecular imaging of alkylguanine-DNA alkyltransferase: further evaluation of radioiodinated derivatives of O6-benzylguanine. Nucl Med Biol. 2006;33:399-407 pubmed
    ..However, its uptake, like that of [125I]IBdG, was blocked by dipyridamole. Taken together, these results suggest that labeled agents that are more specific for cellular AGT and that are more metabolically stable are needed. ..
  3. Lin P, Lin C, Huang C, Chuang M, Lin P. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) induces oxidative stress, DNA strand breaks, and poly(ADP-ribose) polymerase-1 activation in human breast carcinoma cell lines. Toxicol Lett. 2007;172:146-58 pubmed
  4. Anderson K, Cooper J, Haswell S, Marshall D, Yin H, Zhang X. Microfluidic-based measurements of cytochrome P450 enzyme activity of primary mammalian hepatocytes. Analyst. 2010;135:1282-7 pubmed publisher
    ..The EROD activity was determined with 3-methylcholanthrene (3-MC)-induced hepatocytes. The inhibition effect of alpha-naphthoflavone was also examined on EROD activity resulting in an IC(50) value of 12.98 microM. ..
  5. Whitelaw M, McGuire J, Picard D, Gustafsson J, Poellinger L. Heat shock protein hsp90 regulates dioxin receptor function in vivo. Proc Natl Acad Sci U S A. 1995;92:4437-41 pubmed
    ..Thus, these data suggest that hsp90 is a critical determinant of conditional regulation of dioxin receptor function in vivo via the ligand-binding domain. ..
  6. Bu H, Knuth K, Magis L, Teitelbaum P. High-throughput cytochrome P450 (CYP) inhibition screening via a cassette probe-dosing strategy. V. Validation of a direct injection/on-line guard cartridge extraction--tandem mass spectrometry method for CYP1A2 inhibition assessment. Eur J Pharm Sci. 2001;12:447-52 pubmed
    ..The IC(50) values (120 nM for alpha-naphthoflavone and 5.1 microM for furafylline) measured by the new method are in agreement with the literature values. ..
  7. Gelardi A, Morini F, Dusatti F, Penco S, Ferro M. Induction by xenobiotics of phase I and phase II enzyme activities in the human keratinocyte cell line NCTC 2544. Toxicol In Vitro. 2001;15:701-11 pubmed
    ..The exposure (24 h) of the cells to four hair dyes used in cosmetic formulations resulted in a marked increase in ECOD activity. All data give sustained evidence for the suitability of NCTC 2544 cell line to skin toxicology studies. ..
  8. Shao Y, Zhao P, Li Z, Liu M, Liu P, Huang M, et al. The molecular basis for the inhibition of human cytochrome P450 1A2 by oroxylin and wogonin. Eur Biophys J. 2012;41:297-306 pubmed publisher
  9. Rosenberg D. Tissue-specific induction of the carcinogen inducible cytochrome P450 isoform, P450IAI, in colonic epithelium. Arch Biochem Biophys. 1991;284:223-6 pubmed

More Information

Publications113 found, 100 shown here

  1. Charles G, Bartels M, Zacharewski T, Gollapudi B, Freshour N, Carney E. Activity of benzo[a]pyrene and its hydroxylated metabolites in an estrogen receptor-alpha reporter gene assay. Toxicol Sci. 2000;55:320-6 pubmed
    ..This cytotoxic response was completely inhibited by alpha-NF, suggesting that 7,8-OH B[a]P was being further metabolized to one or more cytotoxic metabolites. ..
  2. Cho U, Ahn H, Park E, Dong M, Kim K. Influence of ligand binding to human cytochrome P-450 1A2: conformational activation and stabilization by alpha-naphthoflavone. Biochim Biophys Acta. 2001;1546:412-21 pubmed
    ..The conformation of P-450 1A2 was also stabilized by ANF, resulting in an approx. 5 degrees C increase in thermal stability. ..
  3. Thompson K, Bourguet S, Christian P, Benedict J, Sipes I, Flaws J, et al. Differences between rats and mice in the involvement of the aryl hydrocarbon receptor in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss. Toxicol Appl Pharmacol. 2005;203:114-23 pubmed
    ..Whereas, AhR appears to be involved in rats, no evidence for a similar role in mice was obtained. Overall, these findings point out that there can be mechanistic species differences in ovarian responses to xenobiotic chemicals. ..
  4. Monostory K, Tamasi V, Vereczkey L, Perjesi P. A study on CYP1A inhibitory action of E-2-(4'-methoxybenzylidene)-1-benzosuberone and some related chalcones and cyclic chalcone analogues. Toxicology. 2003;184:203-10 pubmed
  5. Kang H, Kim H, Cho C, Hu Y, Li R, Bae I. BRCA1 transcriptional activity is enhanced by interactions between its AD1 domain and AhR. Cancer Chemother Pharmacol. 2008;62:965-75 pubmed publisher
    ..We speculate that the normal functioning of this interaction could play a role in BRCA1's tumor suppressing ability. ..
  6. Wormhoudt L, Ploemen J, Commandeur J, Van Ommen B, van Bladeren P, Vermeulen N. Cytochrome P450 catalyzed metabolism of 1,2-dibromoethane in liver microsomes of differentially induced rats. Chem Biol Interact. 1996;99:41-53 pubmed
  7. Ainbinder E, Bergelson S, Pinkus R, Daniel V. Regulatory mechanisms involved in activator-protein-1 (AP-1)-mediated activation of glutathione-S-transferase gene expression by chemical agents. Eur J Biochem. 1997;243:49-57 pubmed
    ..Furthermore, we find that activation by phorbol 12-myristate 13-acetate, which uses both protein kinase C and protein-tyrosine kinase activities, may share a common pathway with these chemicals downstream of Ras. ..
  8. Mense S, Singh B, Remotti F, Liu X, Bhat H. Vitamin C and alpha-naphthoflavone prevent estrogen-induced mammary tumors and decrease oxidative stress in female ACI rats. Carcinogenesis. 2009;30:1202-8 pubmed publisher
    ..Taken together, these results suggest that E(2) metabolism and oxidant stress are critically involved in estrogen-induced breast carcinogenesis. ..
  9. Xu D, Hu J, De Bruyne E, Menu E, Schots R, Vanderkerken K, et al. Dll1/Notch activation contributes to bortezomib resistance by upregulating CYP1A1 in multiple myeloma. Biochem Biophys Res Commun. 2012;428:518-24 pubmed publisher
    ..Our data provide a potential strategy to overcome bortezomib resistance by Notch inhibition in MM therapy. ..
  10. Tomita S, Okuyama E, Ohnishi T, Ichikawa Y. Characteristic properties of a retinoic acid synthetic cytochrome P-450 purified from liver microsomes of 3-methylcholanthrene-induced rats. Biochim Biophys Acta. 1996;1290:273-81 pubmed
    ..These results further support that the purified P-450 is P-450 1A1. This paper describes that P-450 1A1 was purified and characterized as a retinoic acid synthetic P-450. ..
  11. Dhawan K, Kumar S, Sharma A. Suppression of alcohol-cessation-oriented hyper-anxiety by the benzoflavone moiety of Passiflora incarnata Linneaus in mice. J Ethnopharmacol. 2002;81:239-44 pubmed
    ..incarnata. The chronic administration of P. incarnata with alcohol had better preventive effects than the single acute treatment with P. incarnata in alcohol-dependent mice...
  12. Cui X, Palamanda J, Norton L, Thomas A, Lau Y, White R, et al. A high-throughput cell-based reporter gene system for measurement of CYP1A1 induction. J Pharmacol Toxicol Methods. 2002;47:143-51 pubmed
    ..This reporter-gene system may be useful in eliminating compounds that can cause CYP1A1 induction at an early stage of drug discovery. ..
  13. Li Q, Bessems J, Commandeur J, Adams B, Vermeulen N. Mechanism of protection of ebselen against paracetamol-induced toxicity in rat hepatocytes. Biochem Pharmacol. 1994;48:1631-40 pubmed
    ..Reduction of NAPQI, the reactive metabolite of paracetamol, by ebselen selenol is discussed in terms of the mechanism of cytoprotection. ..
  14. Patel M, Bhat H. Differential oxidant potential of carcinogenic and weakly carcinogenic estrogens: Involvement of metabolic activation and cytochrome P450. J Biochem Mol Toxicol. 2004;18:37-42 pubmed
    ..Our data support the hypothesis that metabolic activation and subsequent generation of oxidative stress may play critical roles in estrogen-induced carcinogenesis. ..
  15. Hsiao G, Chang C, Shen M, Chou D, Tzeng S, Chen T, et al. alpha-Naphthoflavone, a potent antiplatelet flavonoid, is mediated through inhibition of phospholipase C activity and stimulation of cyclic GMP formation. J Agric Food Chem. 2005;53:5179-86 pubmed
    ..These results strongly indicate that alpha-NF appears to represent a novel and potent antiplatelet agent for treatment of arterial thromboembolism. ..
  16. Li Y, Jaiswal A. Regulation of human NAD(P)H:quinone oxidoreductase gene. Role of AP1 binding site contained within human antioxidant response element. J Biol Chem. 1992;267:15097-104 pubmed
    ..The supershift assays using antibodies against specific proteins of the AP1 family identified Jun-D and c-Fos as two members in the hARE-protein complex observed in band shift assays. ..
  17. Shizu M, Itoh Y, Sunahara R, Chujo S, Hayashi H, Ide Y, et al. Cigarette smoke condensate upregulates the gene and protein expression of proinflammatory cytokines in human fibroblast-like synoviocyte line. J Interferon Cytokine Res. 2008;28:509-21 pubmed publisher
    ..These results support the epidemiological studies indicating a strong association between heavy cigarette smoking and pathogenesis of RA. ..
  18. Jeon Y, Youk E, Lee S, Suh J, Na Y, Kim H. Polychlorinated biphenyl-induced apoptosis of murine spleen cells is aryl hydrocarbon receptor independent but caspases dependent. Toxicol Appl Pharmacol. 2002;181:69-78 pubmed
    ..Based on our findings, the most likely mechanism that can account for this biological effect involves the induction of caspase-dependent apoptotic cell death. ..
  19. Kawamura T, Yamashita I. Aryl hydrocarbon receptor is required for prevention of blood clotting and for the development of vasculature and bone in the embryos of medaka fish, Oryzias latipes. Zoolog Sci. 2002;19:309-19 pubmed
    ..Complementary DNA fragments encoding AHR homologs were cloned from medaka embryos. AHR-specific mRNA was ubiquitously expressed in embryos and adult tissues. ..
  20. Sansen S, Yano J, Reynald R, Schoch G, Griffin K, Stout C, et al. Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem. 2007;282:14348-55 pubmed
    ..This report provides the first structure of a microsomal P450 from family 1 and offers a template to study further structure-function relationships of alternative substrates and other cytochrome P450 family 1 members. ..
  21. Pesonen M, Celander M, Förlin L, Andersson T. Comparison of xenobiotic biotransformation enzymes in kidney and liver of rainbow trout (Salmo gairdneri). Toxicol Appl Pharmacol. 1987;91:75-84 pubmed
    ..In the liver, a 2-fold increase of this activity was seen 3 days after the treatment. The results indicate that the rainbow trout kidney in addition to the liver is of great importance in biotransformation of lipophilic xenobiotics. ..
  22. Cvrk T, Hodek P, Strobel H. Identification and characterization of cytochrome P4501A1 amino acid residues interacting with a radiolabeled photoaffinity diazido-benzphetamine analogue. Arch Biochem Biophys. 1996;330:142-52 pubmed
    ..The other two peptides were located on the surface of the protein with the label bound specifically to Lys residues that were predicted to be involved in reductase-P450 interaction. ..
  23. Wong S, Kobus S, McNamee J, Marks G. Gender differences in N-alkyl protoporphyrin IX production in rats after the administration of porphyrinogenic xenobiotics. Drug Metab Dispos. 1998;26:739-44 pubmed
    ..Because males produced markedly more N-ethylPP than females, and males have P4502C11 in addition to P4502C6, we conclude that P4502C11 is the major source of N-ethylPP in males, whereas P4502C6 may also be a significant contributor. ..
  24. Skene D, Papagiannidou E, Hashemi E, Snelling J, Lewis D, Fernandez M, et al. Contribution of CYP1A2 in the hepatic metabolism of melatonin: studies with isolated microsomal preparations and liver slices. J Pineal Res. 2001;31:333-42 pubmed
    ..Collectively, all the above data provide strong experimental evidence that CYP1A2 is an important catalyst of the 6-hydroxylation of melatonin. ..
  25. Traber P, McDonnell W, Wang W, Florence R. Expression and regulation of cytochrome P-450I genes (CYP1A1 and CYP1A2) in the rat alimentary tract. Biochim Biophys Acta. 1992;1171:167-75 pubmed
    ..In addition, these data suggest that the aromatic hydrocarbon receptor, which mediates transcriptional induction of multiple genes by xenobiotics, is expressed through the alimentary tract. ..
  26. Takamura T, Harama D, Fukumoto S, Nakamura Y, Shimokawa N, Ishimaru K, et al. Lactobacillus bulgaricus OLL1181 activates the aryl hydrocarbon receptor pathway and inhibits colitis. Immunol Cell Biol. 2011;89:817-22 pubmed publisher
    ..This strain of lactic acid bacterium has therefore the potential to activate the AhR pathway, which may be able to suppress colitis. ..
  27. Villard P, Sampol E, Elkaim J, Puyoou F, Casanova D, Seree E, et al. Increase of CYP1B1 transcription in human keratinocytes and HaCaT cells after UV-B exposure. Toxicol Appl Pharmacol. 2002;178:137-43 pubmed
    ..Taken together, these data demonstrated that UV-B induces CYP1B1 gene expression after an activation of its transcription, which involves Ah receptor. ..
  28. Coller J, Somogyi A, Bochner F. Flunitrazepam oxidative metabolism in human liver microsomes: involvement of CYP2C19 and CYP3A4. Xenobiotica. 1999;29:973-86 pubmed
    ..1-2.7 respectively. CYP2C19, CYP3A4 and CYP1A2 mediated the formation of both 3'-hydroxyflunitrazepam and desmethylflunitrazepam. Investigators need carefully to consider the choice of organic solvent to avoid false CYP identification. ..
  29. Jeurissen S, Bogaards J, Boersma M, ter Horst J, Awad H, Fiamegos Y, et al. Human cytochrome p450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol. Chem Res Toxicol. 2006;19:111-6 pubmed
    ..Especially lifestyle factors such as smoking (induces P450 1A) and the use of barbiturates (induces P450 2C) can increase the susceptibility for adverse effects of methyleugenol. ..
  30. Di Folco S, Stammati A, Vittozzi L, Zucco F. Studies of cytotoxicity and metabolic competence with the rat intestinal cell line IEC-17. Drug Chem Toxicol. 1990;13:221-8 pubmed
    ..Induction of xenobiotic metabolism by beta-naphthoflavone seems also to elicit the toxicity of 9,10-dimethyl-1,2-benzathracene (DBA) but not that one of cyclophosphamide (CPA). ..
  31. Komura K, Hayashi S, Makino I, Poellinger L, Tanaka H. Aryl hydrocarbon receptor/dioxin receptor in human monocytes and macrophages. Mol Cell Biochem. 2001;226:107-18 pubmed
  32. Hu Y, Yao T. Induction of diphenytriazol on cytochrome CYP1A. Acta Pharmacol Sin. 2004;25:528-33 pubmed
    ..These results reveal that diphenytriazol is a novel inducer of CYP1A. ..
  33. Dubuisson M, de Wergifosse B, Kremers P, Marchand Brynaert J, Trouet A, Rees J. Protection against nitrofurantoin-induced oxidative stress by coelenterazine analogues and their oxidation products in rat hepatocytes. Free Radic Res. 2001;34:285-96 pubmed
  34. Cavret S, Feidt C. Intestinal metabolism of PAH: in vitro demonstration and study of its impact on PAH transfer through the intestinal epithelium. Environ Res. 2005;98:22-32 pubmed
    ..These findings suggested that intestinal metabolism might play a key role in intestinal barrier permeability and thus in the bioavailability of tested micropollutants. ..
  35. Mortensen A, Arukwe A. Targeted salmon gene array (SalArray): a toxicogenomic tool for gene expression profiling of interactions between estrogen and aryl hydrocarbon receptor signalling pathways. Chem Res Toxicol. 2007;20:474-88 pubmed publisher
    ..Thus, the inhibitory ER-AhR interactions can be used to further investigate specific genes found to be affected in our targeted SalArray chip that are important for the reproductive effects of endocrine disruptors...
  36. Chambers J, Forsyth C. Lack of inducibility of brain monooxygenase activities including parathion desulfuration. J Biochem Toxicol. 1989;4:65-70 pubmed
    ..This lack of inducibility could serve to protect the animal against environmentally enhanced increases in the activation of xenobiotics to neurotoxic metabolites, such as parathion desulfuration to paraoxon. ..
  37. Ptak A, Ludewig G, Gregoraszczuk E. A low halogenated biphenyl (PCB3) increases CYP1A1 expression and activity via the estrogen receptor beta in the porcine ovary. J Physiol Pharmacol. 2008;59:577-88 pubmed
    ..Changes in the expression level of CYP1A1 not only alter the intensity of the activity of PCB3, but also the activity of estrogen in the ovary. ..
  38. Reed C, Lock E, De Matteis F. Olfactory cytochrome P-450. Studies with suicide substrates of the haemoprotein. Biochem J. 1988;253:569-76 pubmed
  39. Monteiro P, Gilot D, Langouet S, Fardel O. Activation of the aryl hydrocarbon receptor by the calcium/calmodulin-dependent protein kinase kinase inhibitor 7-oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid (STO-609). Drug Metab Dispos. 2008;36:2556-63 pubmed publisher
    ..Such data, therefore, make unlikely any contribution of CaMKK activity to the AhR pathway and, moreover, suggest that caution may be required when using STO-609 as a specific inhibitor of CaMKKs. ..
  40. Dostalek M, Pistovcakova J, Jurica J, Sulcova A, Tomandl J. The effect of St John's wort (hypericum perforatum) on cytochrome p450 1a2 activity in perfused rat liver. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2011;155:253-7 pubmed publisher
    ..It remains to be determined whether the co-administration of St John's wort extract and other medications or substrates for cytochrome P450 1A2 could result in significant drug interactions. ..
  41. Karkola S, Wahala K. The binding of lignans, flavonoids and coumestrol to CYP450 aromatase: a molecular modelling study. Mol Cell Endocrinol. 2009;301:235-44 pubmed publisher
    ..Sets of phytoestrogens, such as lignans, flavonoids/isoflavonoids and coumestrol, were docked into the aromatase active site and the binding modes were studied. ..
  42. Liu Z, Zeng S. Cytotoxicity of ginkgolic acid in HepG2 cells and primary rat hepatocytes. Toxicol Lett. 2009;187:131-6 pubmed publisher
    ..These findings suggest that HepG2 cells were more sensitive to the cytotoxicity of ginkgolic acid than primary rat hepatocytes, and CYP1A and CYP3A could metabolize ginkgolic acid to more toxic compounds. ..
  43. Boobis A, Kahn G, Whyte C, Brodie M, Davies D. Biphasic O-deethylation of phenacetin and 7-ethoxycoumarin by human and rat liver microsomal fractions. Biochem Pharmacol. 1981;30:2451-6 pubmed
  44. Holbik M, Krasteva S, Mayer N, Kählig H, Krenn L. Apparently no sedative benzoflavone moiety in passiflorae herba. Planta Med. 2010;76:662-4 pubmed publisher
  45. Lambrecht R, Sinclair P, Bement W, Sinclair J, Carpenter H, Buhler D, et al. Hepatic uroporphyrin accumulation and uroporphyrinogen decarboxylase activity in cultured chick-embryo hepatocytes and in Japanese quail (Coturnix coturnix japonica) and mice treated with polyhalogenated aromatic compounds. Biochem J. 1988;253:131-8 pubmed
  46. Jang J, Shin S, Choi B, Park D, Jeon J, Hwang S, et al. Antiteratogenic effects of alpha-naphthoflavone on 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) exposed mice in utero. Reprod Toxicol. 2007;24:303-9 pubmed
    ..These results suggest that AhR antagonists such as alpha-naphthoflavone could be promising candidates for reducing the incidence and severity of fetal malformations caused by TCDD exposure in utero. ..
  47. Frank D, Denisov I, Sligar S. Mixing apples and oranges: Analysis of heterotropic cooperativity in cytochrome P450 3A4. Arch Biochem Biophys. 2009;488:146-52 pubmed publisher
  48. Stolzenbach J, Larson R. BCNU-induced quantitative and qualitative changes in hepatic cytochrome P-450 can be correlated with cholestasis. Cancer Chemother Pharmacol. 1990;25:227-35 pubmed
    ..Thus, the delayed effects of BCNU on microsomal drug metabolism are probably secondary to its interference with bile formation. ..
  49. Malejka Giganti D, Magat W, Decker R. Sex hormone-mediated effects on the phase I and phase II metabolism of N-2-fluorenylacetamide. Modulation of 9-hydroxylation. Biochem Pharmacol. 1989;38:1075-82 pubmed
    ..Hence, in the presence of male hormones, relatively large amounts of 9-OH-2-FAA were formed and possibly retained in the liver. A role of this alcohol as a potential promoter in hepatocarcinogenesis by 2-FAA is suggested...
  50. Näslund B, Glaumann H, Warner M, Gustafsson J, Hansson T. Cytochrome P-450 b and c in the rat brain and pituitary gland. Mol Pharmacol. 1988;33:31-7 pubmed
    ..However, there was an induction of P-450 c in the olfactory bulbs since catalytic activity was inhibited with anti P-450c antibodies.(ABSTRACT TRUNCATED AT 400 WORDS) ..
  51. Tacchi Bedford A, Whyman G, McLean A. DNA alkylation by 1,2-dimethylhydrazine in the rat large intestine and liver: influence of diet and enzyme induction. Toxicology. 1988;50:181-91 pubmed
    ..As shown by our results, the nature of the diet would appear to be able to modulate the rate of metabolic activation of DMH and its binding to DNA in the target organ. ..
  52. Pacheco K, Tarkowski M, Sterritt C, Negri J, Rosenwasser L, Borish L. The influence of diesel exhaust particles on mononuclear phagocytic cell-derived cytokines: IL-10, TGF-beta and IL-1 beta. Clin Exp Immunol. 2001;126:374-83 pubmed
    ..Pro-inflammatory cytokines and factors rise when IL-10 is inhibited, and are suppressed when IL-10 is stimulated. These results are duplicated with benzo[a]pyrene, suggesting that the PAH portion of the DEP is the active agent. ..
  53. Seubert J, Darmon A, El Kadi A, D Souza S, Bend J. Apoptosis in murine hepatoma hepa 1c1c7 wild-type, C12, and C4 cells mediated by bilirubin. Mol Pharmacol. 2002;62:257-64 pubmed
    ..These results indicate that bilirubin, a potential AHR ligand, causes apoptosis in murine Hepa 1c1c7 WT cells by a mechanism(s) partially involving the AHR, disruption of membrane integrity, and increased intracellular ROS production. ..
  54. Hodson P, Qureshi K, Noble C, Akhtar P, Brown R. Inhibition of CYP1A enzymes by alpha-naphthoflavone causes both synergism and antagonism of retene toxicity to rainbow trout (Oncorhynchus mykiss). Aquat Toxicol. 2007;81:275-85 pubmed
    ..It demonstrates that effects on fish of different complex mixtures of hydrocarbons may not be easily predicted. ..
  55. Timme Laragy A, Van Tiem L, Linney E, Di Giulio R. Antioxidant responses and NRF2 in synergistic developmental toxicity of PAHs in zebrafish. Toxicol Sci. 2009;109:217-27 pubmed publisher
    ..Collectively, these findings demonstrate that antioxidant responses are a component of PAH synergistic developmental toxicity and that NRF2 is protective against prooxidant and PAH challenges during development. ..
  56. Aluru N, Renaud R, Leatherland J, Vijayan M. Ah Receptor-mediated impairment of interrenal steroidogenesis involves StAR protein and P450scc gene attenuation in rainbow trout. Toxicol Sci. 2005;84:260-9 pubmed
    ..Overall, endocrine disruption by xenobiotics acting via AhR includes impaired cortisol biosynthesis and abnormal cortisol target tissue GR responses in rainbow trout. ..
  57. Wang T, Milner M, Milner J, Kim Y. Estrogen receptor alpha as a target for indole-3-carbinol. J Nutr Biochem. 2006;17:659-64 pubmed
  58. de Waard P, Peijnenburg A, Baykus H, Aarts J, Hoogenboom R, Van Schooten F, et al. A human intervention study with foods containing natural Ah-receptor agonists does not significantly show AhR-mediated effects as measured in blood cells and urine. Chem Biol Interact. 2008;176:19-29 pubmed publisher
    ..We conclude that intake of NAhRAs from food may result in minor AhR-related effects measurable in human blood and urine. ..
  59. Moochhala S, Lee E, Hu G, Koh O, Becket G. Effects of bromocriptine on hepatic cytochrome P-450 monooxygenase system. Jpn J Pharmacol. 1989;49:285-91 pubmed
  60. Tsyrlov I, Goldfarb I, Gelboin H. Enzyme-kinetic and immunochemical characteristics of mouse cDNA-expressed, microsomal, and purified CYP1A1 and CYP1A2. Arch Biochem Biophys. 1993;307:259-66 pubmed
    ..8 times lower binding of Mab 1-7-1 to cDNA-expressed CYP1A2 than to CYP1A1. The results demonstrate the reliability of the vaccinia virus expression system for studies on the enzymology of mouse CYP1A1 and CYP1A2. ..
  61. Lake B, Charzat C, Tredger J, Renwick A, Beamand J, Price R. Induction of cytochrome P450 isoenzymes in cultured precision-cut rat and human liver slices. Xenobiotica. 1996;26:297-306 pubmed
    ..5. These results demonstrate that cultured liver slices may be used in evaluating the effect of xenobiotics on both rat and human CYP isoenzymes...
  62. Daniel W, Syrek M, Haduch A. The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazine neuroleptics. Eur Neuropsychopharmacol. 2002;12:371-7 pubmed
    ..The results obtained point to the drug structure and species differences in the contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazines. ..
  63. Zhao X, Zhong J, Liu X, Wang G. CYP3A4 mediated in vitro metabolism of vinflunine in human liver microsomes. Acta Pharmacol Sin. 2007;28:118-24 pubmed
    ..To study the metabolism of vinflunine and the effects of selective cytochrome P-450 (CYP450) inhibitors on the metabolism of vinflunine in human liver microsomes...
  64. Juvale K, Stefan K, Wiese M. Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2. Eur J Med Chem. 2013;67:115-26 pubmed publisher
    ..Inhibiting BCRP can be a solution to overcome MDR. We synthesized a series of flavones, 7,8-benzoflavones and 5,6-benzoflavones with varying substituents at positions 3, 3' and 4' of the (benzo)flavone structure...
  65. Yauk C, Buick J, Williams A, Swartz C, Recio L, Li H, et al. Application of the TGx-28.65 transcriptomic biomarker to classify genotoxic and non-genotoxic chemicals in human TK6 cells in the presence of rat liver S9. Environ Mol Mutagen. 2016;57:243-60 pubmed publisher
    ..65 is a sensitive biomarker of genotoxicity. A meta-analysis of datasets from 13 chemicals supports that different S9s can be used in TK6 cells, without impairing classification using the TGx-28.65 biomarker. ..
  66. Blaich G, Metzler M. The effects of pretreatment with 7,8-benzoflavone on drug-metabolizing enzymes and diethylstilboestrol metabolism in male hamster liver microsomal preparations. Xenobiotica. 1988;18:199-206 pubmed
    ..The possible implication of these data for the mechanism of liver tumour formation by the combined treatment of hamsters with 7,8-BF and DES is discussed. ..
  67. Gebremichael A, Tullis K, Denison M, Cheek J, Pinkerton K. Ah-receptor-dependent modulation of gene expression by aged and diluted sidestream cigarette smoke. Toxicol Appl Pharmacol. 1996;141:76-83 pubmed
  68. Goutman J, Waxemberg M, Doñate Oliver F, Pomata P, Calvo D. Flavonoid modulation of ionic currents mediated by GABA(A) and GABA(C) receptors. Eur J Pharmacol. 2003;461:79-87 pubmed
    ..Results indicate that mechanism/s underlying the modulation of ionotropic GABA receptors by some flavonoids differs from that described for classic benzodiazepine modulation. ..
  69. Flynn K, Maynard P, du Pasquier E, Lennard C, Stoilovic M, Roux C. Evaluation of iodine-benzoflavone and ruthenium tetroxide spray reagents for the detection of latent fingermarks at the crime scene. J Forensic Sci. 2004;49:707-15 pubmed
    ..Iodine-benzoflavone was the best technique on wallpaper, vinyl, brick, and raw wood. RTX was the best detection technique for fresh marks and marks aged up to one day on wallpaper and paint. ..
  70. Timme Laragy A, Cockman C, Matson C, Di Giulio R. Synergistic induction of AHR regulated genes in developmental toxicity from co-exposure to two model PAHs in zebrafish. Aquat Toxicol. 2007;85:241-50 pubmed
    ..This study furthers a mechanistic understanding of interactions underlying PAH synergistic toxicity. ..
  71. Goergens A, Frericks M, Esser C. The arylhydrocarbon receptor is only marginally involved in the antileukemic effects of its ligand curcumin. Anticancer Res. 2009;29:4657-64 pubmed
    ..Interestingly, transcriptional changes induced by curcumin and by anticarcinogenic 1,25-dihydroxy vitamin D3 overlapped by one third. We conclude that AhR is only marginally involved in the antileukemic effects of its ligand curcumin. ..
  72. Diaz G, Murcia H, Cepeda S. Bioactivation of aflatoxin B1 by turkey liver microsomes: responsible cytochrome P450 enzymes. Br Poult Sci. 2010;51:828-37 pubmed publisher
    ..5. This is the first study reporting the role of CYP2A6 in the bioactivation of AFB1 in an avian species and the role of CYP1A1 in any species. ..
  73. Reiners J, Cantu A, Pavone A, Smith S, Gardner C, Laskin D. Fluorescence assay for per-cell estimation of cytochrome P-450-dependent monooxygenase activities in keratinocyte suspensions and cultures. Anal Biochem. 1990;188:317-24 pubmed
    ..Constitutive per hepatocyte 7-ECD, 7-PRD, and 7-ERD activities were 357-, 96-, and 1926-fold greater, respectively, than the activities measured in suspensions of dorsal MEKs. ..
  74. Phillips I, Shephard E, Ashworth A, Rabin B. Cloning and sequence analysis of a rat liver cDNA coding for a phenobarbital-inducible microheterogenous cytochrome P-450 variant: regulation of its messenger level by xenobiotics. Gene. 1983;26:41-52 pubmed
    ..Solution hybridization analysis demonstrated that PB P-450 mRNA is increased 20-fold by phenobarbital treatment and decreased 3-fold by beta-naphthoflavone treatment. ..
  75. Watson D, Menard L, Stegeman J, Di Giulio R. Aminoanthracene is a mechanism-based inactivator of CYP1A in channel catfish hepatic tissue. Toxicol Appl Pharmacol. 1995;135:208-15 pubmed
    ..It is proposed that mechanism-based inactivation of CYP1A by AA accounts for the observed AA-dependent decrease in hepatic EROD activity in vitro and in vivo in channel catfish. ..
  76. Dhawan K, Sharma A. Restoration of chronic-Delta 9-THC-induced decline in sexuality in male rats by a novel benzoflavone moiety from Passiflora incarnata Linn. Br J Pharmacol. 2003;138:117-20 pubmed
    ..4 Upon discontinuation of THC, treatment with BZF (10 and 20 mg kg(-1) p.o.) also facilitated the early restoration chronic-THC-induced decline in libido, sperm count and sexual fertility within 7 days...
  77. Niermann T, Schmutz S, Erne P, Resink T. Aryl hydrocarbon receptor ligands repress T-cadherin expression in vascular smooth muscle cells. Biochem Biophys Res Commun. 2003;300:943-9 pubmed
    ..Regulation of adhesion proteins through the AHR pathway may represent a novel mechanism of action by atherogenic polycyclic aromatic hydrocarbons. ..
  78. Dhawan K, Kumar S, Sharma A. Nicotine reversal effects of the benzoflavone moiety from Passiflora incarnata Linneaus in mice. Addict Biol. 2002;7:435-41 pubmed
    ..These studies, although preliminary, suggest that the BZF may have value in treating nicotine addiction. ..
  79. van Vugt Lussenburg B, Damsten M, Maasdijk D, Vermeulen N, Commandeur J. Heterotropic and homotropic cooperativity by a drug-metabolising mutant of cytochrome P450 BM3. Biochem Biophys Res Commun. 2006;346:810-8 pubmed
    ..Second, this study shows that BM3 can be engineered to a drug-metabolising enzyme, making it a promising candidate to use as biocatalyst in drug discovery and synthesis. ..
  80. Bugiak B, Weber L. Hepatic and vascular mRNA expression in adult zebrafish (Danio rerio) following exposure to benzo-a-pyrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Aquat Toxicol. 2009;95:299-306 pubmed publisher
    ..The vascular-specific changes in gene expression will be linked to future studies examining alterations in cardiovascular function produced by acute AhR agonist exposure in adult fish. ..
  81. Beristain Castillo E, Martínez Vázquez M, Camacho Carranza R, Espinosa Aguirre J. CYP1A1 and Cnr nitroreductase bioactivated niclosamide in vitro. Mutagenesis. 2013;28:645-51 pubmed publisher
    ..Our findings indicated that a metabolite, derived from the action of CYP1A1 and a nitroreduction-reaction process, has a key role in the bioactivation of niclosamide. ..
  82. Locuson C, Williams P, Adcock J, Daniels J. Evaluation of tizanidine as a marker of canine CYP1A2 activity. J Vet Pharmacol Ther. 2016;39:122-30 pubmed publisher
    ..However, tizanidine may be a more selective CYP1A2 probe than phenacetin when conducting in vitro studies due to the presence of other phenacetin-metabolizing enzymes in dog liver microsomes. ..
  83. Rushmore T, King R, Paulson K, Pickett C. Regulation of glutathione S-transferase Ya subunit gene expression: identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds. Proc Natl Acad Sci U S A. 1990;87:3826-30 pubmed
    ..Our data suggest that regulation of gene expression by planar aromatic compounds can be mediated by a DNA sequence that is distinct from the XRE sequence. ..
  84. Ardies C, Lasker J, Lieber C. Characterization of the cytochrome P-450 monooxygenase system of hamster liver microsomes. Effects of prior treatment with ethanol and other xenobiotics. Biochem Pharmacol. 1987;36:3613-9 pubmed
  85. Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T. Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers--N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995;39:421-31 pubmed
    ..abstract truncated at 400 words) ..
  86. Donato M, Bassi A, Gomez Lechon M, Penco S, Herrero E, Adamo D, et al. Evaluation of the xenobiotic biotransformation capability of six rodent hepatoma cell lines in comparison with rat hepatocytes. In Vitro Cell Dev Biol Anim. 1994;30A:574-80 pubmed
    ..3-Methylcholanthrene and naphtoflavone treatment also resulted in a marked increase in 7-ethoxyresorufin O-deethylase activity in hepatocytes as well as in H4IIC3, McA-Rh7777, MH1C1, and Fao cells.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  87. Dhawan K, Sharma A. Prevention of chronic alcohol and nicotine-induced azospermia, sterility and decreased libido, by a novel tri-substituted benzoflavone moiety from Passiflora incarnata Linneaus in healthy male rats. Life Sci. 2002;71:3059-69 pubmed
    ..BZF, the strongest inhibitor of aromatase enzyme, when administered concurrently with substances like alcohol and nicotine restores sexual virility, libido and vigour in male rats by maintaining the blood-testosterone levels to be high. ..
  88. Cheshenko K, Brion F, Le Page Y, Hinfray N, Pakdel F, Kah O, et al. Expression of zebra fish aromatase cyp19a and cyp19b genes in response to the ligands of estrogen receptor and aryl hydrocarbon receptor. Toxicol Sci. 2007;96:255-67 pubmed
    ..The antiestrogenic effect of TCDD demonstrated raises further concerns about the neuroendocrine effects of AhR ligands. ..
  89. Singh B, Bhat N, Bhat H. Induction of NAD(P)H-quinone oxidoreductase 1 by antioxidants in female ACI rats is associated with decrease in oxidative DNA damage and inhibition of estrogen-induced breast cancer. Carcinogenesis. 2012;33:156-63 pubmed publisher
    ..In vitro studies using silencer RNA confirmed the role of NQO1 in prevention of oxidative DNA damage. Our studies further demonstrate that NQO1 upregulation by antioxidants is mediated through NRF2. ..
  90. Cheesman M, Baer B, Zheng Y, Gillam E, Rettie A. Rabbit CYP4B1 engineered for high-level expression in Escherichia coli: ligand stabilization and processing of the N-terminus and heme prosthetic group. Arch Biochem Biophys. 2003;416:17-24 pubmed
    ..These studies shed new light on the consequences of covalent heme processing in CYP4B1 and provide a facile system for future mechanistic and structural studies with the enzyme. ..
  91. Parente T, De Oliveira A, Beghini D, Chapeaurouge D, Perales J, Paumgartten F. Lack of constitutive and inducible ethoxyresorufin-O-deethylase activity in the liver of suckermouth armored catfish (Hypostomus affinis and Hypostomus auroguttatus, Loricariidae). Comp Biochem Physiol C Toxicol Pharmacol. 2009;150:252-60 pubmed publisher
    ..Our findings suggest that the CYP1A-like protein of locariid catfish recognizes DMBA, but not ethoxyresorufin, as a substrate. ..
  92. Wang A, Savas U, Stout C, Johnson E. Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1. J Biol Chem. 2011;286:5736-43 pubmed publisher
    ..The conservation of these P450 1B1 active site amino acid residues across vertebrate species suggests that these structural features are conserved. ..