Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name biphenyl
CAS 1,1′-biphenyl

Reference List

PubMed Abstract RScore(About this table)
18708084 Chan TS, Wilson JX, Selliah S, Bilodeau M, Zwingmann C, Poon R, O'Brien PJ: Organochlorines inhibit acetaminophen glucuronidation by redirecting UDP-glucuronic acid towards the D-glucuronate pathway. Toxicol Appl Pharmacol. 2008 Nov 1;232(3):456-62. Epub 2008 Jul 29.

A set of 6 arylated organochlorines, including 5 PCB (polychlorinated biphenyl) congeners, were assessed for their effects on APAP glucuronidation in isolated hepatocytes from male Sprague-Dawley rats.
BCPS-mediated inhibition of APAP glucuronidation in isolated hepatocytes had non-competitive characteristics and was insensitive to the inactivation of cytochrome P450.
1(0,0,0,1) Details
18640101 Dikalov S, Losik T, Arbiser JL: Honokiol is a potent scavenger of superoxide and peroxyl radicals. Biochem Pharmacol. 2008 Sep 1;76(5):589-96. Epub 2008 Jul 2.


Honokiol efficiently scavenged superoxide radicals in xanthine oxidase and cytochrome P-450 cell-free systems with the rate constant 3.2x10 (5) M (-1) s (-1), which is similar to reactivity of ascorbic acid but 20-times higher than reactivity of vitamin E analog trolox.
1(0,0,0,1) Details
19111380 Sood N, Lal B: Isolation of a novel yeast strain Candida digboiensis TERI ASN6 capable of degrading petroleum hydrocarbons in acidic conditions. J Environ Manage. 2009 Apr;90(5):1728-36. Epub 2008 Dec 25.

During the growth of TERI ASN6 in dibenzothiophene (DBT), DBT-sulfone and biphenyl-2-ol were detected.
An active cytochrome P450 system, implicated in hydrocarbon oxidation, was also detected in this yeast using degenerated primers based on its conserved regions.
1(0,0,0,1) Details
18672868 Pinto-Bazurco Mendieta MA, Negri M, Jagusch C, Muller-Vieira U, Lauterbach T, Hartmann RW: Synthesis, biological evaluation, and molecular modeling of abiraterone analogues: novel CYP17 inhibitors for the treatment of prostate cancer. J Med Chem. 2008 Aug 28;51(16):5009-18. Epub 2008 Aug 2.


Abiraterone, a steroidal cytochrome P450 17alpha-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer.
1(0,0,0,1) Details
19117374 Carlson EA, Roy NK, Wirgin II: Microarray Analysis of Polychlorinated Biphenyl Mixture-Induced Changes in Gene Expression among Atlantic Tomcod Populations Displaying Differential Sensitivity to Halogenated Aromatic Hydrocarbons. Environ Toxicol Chem. 2008 Dec 31:1.

First and second generation Atlantic tomcod Microgadus tomcod embryos derived from the Hudson River (HR; NY, USA) population are highly resistant to PCB -induced cytochrome P450 1A (CYP1A) expression and ELS toxicity when compared to embryos of Miramichi River (MR; NB, Canada) and Shinnecock Bay (SB; NY, USA) origin.
1(0,0,0,1) Details
19830680 Chan K, Lehmler HJ, Sivagnanam M, Feng CY, Robertson L, O'Brien PJ: Cytotoxic effects of polychlorinated biphenyl hydroquinone metabolites in rat hepatocytes. J Appl Toxicol. 2010 Mar;30(2):163-71.

The molecular mechanisms of PCB toxicity have been attributed to the toxicological properties of its metabolites, such as hydroquinones, formed by cytochrome-P-450 oxidation.
1(0,0,0,1) Details
19576179 Kasai N, Ikushiro S, Hirosue S, Arisawa A, Ichinose H, Wariishi H, Ohta M, Sakaki T: Enzymatic properties of cytochrome P450 catalyzing 3'-hydroxylation of naringenin from the white-rot fungus Phanerochaete chrysosporium. Biochem Biophys Res Commun. 2009 Sep 11;387(1):103-8. Epub 2009 Jul 1.

In addition, the recombinant S. cerevisiae cells expressing PcCYP65a2 metabolized such polyaromatic compounds as dibenzo-p-dioxin (DD), 2-monochloroDD, biphenyl, and naphthalene.
1(0,0,0,1) Details
19548353 Shimada T, Murajama N, Tanaka K, Takenaka S, Imai Y, Hopkins NE, Foroozesh MK, Alworth WL, Yamazaki H, Guengerich FP, Komori M: Interaction of polycyclic aromatic hydrocarbons with human cytochrome P450 1B1 in inhibiting catalytic activity. Chem Res Toxicol. 2008 Dec;21(12):2313-23.

Eleven polycyclic aromatic hydrocarbons (PAHs) and 14 acetylenic PAHs and biphenyls were used to analyze interactions with cytochrome P450 (P450) 1B1 in inhibiting catalytic activity, using 7-ethoxyresorufin O-deethylation (EROD) as a model reaction.
Most of the chemicals examined were direct inhibitors of P450 1B1 except for 4-(1-propynyl) biphenyl, a mechanism-based inhibitor.
1(0,0,0,1) Details
19563207 Shimada T, Tanaka K, Takenaka S, Foroozesh MK, Murayama N, Yamazaki H, Guengerich FP, Komori M: Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: a structure-function relationship study. Chem Res Toxicol. 2009 Jul;22(7):1325-33.

Fifty-one chemicals including derivatives of 16 flavonoids, three stilbenes, six pyrenes, seven naphthalenes, seven phenanthrenes, 10 biphenyls, 17beta-estradiol, and estrone were examined for their abilities to induce reverse type I binding spectra with human cytochrome P450 (P450) 1B1 and to inhibit 7-ethoxyresorufin O-deethylation (EROD) activities catalyzed by P450 1B1.
1(0,0,0,1) Details
18538762 Lu C, Su LY, Lee RM, Gao YJ: Superoxide anion mediates angiotensin II-induced potentiation of contractile response to sympathetic stimulation. Eur J Pharmacol. 2008 Jul 28;589(1-3):188-93. Epub 2008 May 5.


This potentiation was blunted by an angiotensin AT (1) receptor antagonist (2-ethoxy-1-[[2'-(1H-tetrazol-5-yl) biphenyl-4-yl] methyl]-1H-benzimidazole- 7-carboxylic acid, CV-11974), NAD (P) H oxidase inhibitor (apocynin), superoxide dismutase (SOD) and its mimetic tiron, but not affected by angiotensin AT (2) receptor antagonist and inhibitors of xanthine oxidase, cytochrome P450, and cyclooxygenase.
0(0,0,0,0) Details
19022331 Han X, O'Connor JC, Donner EM, Nabb DL, Mingoia RT, Snajdr SI, Clarke JJ, Kaplan AM: Non-coplanar 2,2',3,3',4,4',5,5',6,6'-decachlorobiphenyl (PCB 209) did not induce cytochrome P450 enzyme activities in primary cultured rat hepatocytes, was not genotoxic, and did not exhibit endocrine-modulating activities. Toxicology. 2009 Jan 31;255(3):177-86. Epub 2008 Oct 31.


2,2',3,3',4,4',5,5',6,6'-Decachlorobiphenyl (PCB 209) is a fully chlorinated, non-coplanar biphenyl.
0(0,0,0,0) Details
19969354 Lai I, Chai Y, Simmons D, Luthe G, Coleman MC, Spitz D, Haschek WM, Ludewig G, Robertson LW: Acute toxicity of 3,3',4,4',5-pentachlorobiphenyl (PCB 126) in male Sprague-Dawley rats: Effects on hepatic oxidative stress, glutathione and metals status. Environ Int. 2009 Dec 5.


Although polychlorinated biphenyl (PCBs) production, and new uses for PCBs, was halted in the 1970s in the United States, PCBs continue to be used in closed systems and persist in the environment, accumulating in fatty tissues.
0(0,0,0,0) Details
18788898 Verreault J, Maisonneuve F, Dietz R, Sonne C, Letcher RJ: Comparative hepatic activity of xenobiotic-metabolizing enzymes and concentrations of organohalogens and their hydroxylated analogues in captive Greenland sledge dogs (Canis familiaris). Environ Toxicol Chem. 2009 Jan;28(1):162-72.


When the exposed and control dogs were combined, the summed (sigma) plasma concentrations of OH-polychlorinated biphenyl (PCB) congeners were predicted by plasma sigmaPCB concentrations and EROD activity (p < or = 0.04), whereas testosterone hydroxylase, EH, and UDPGT activities were not significant predictors of these concentrations.
0(0,0,0,0) Details
19397311 Gay SC, Sun L, Maekawa K, Halpert JR, Stout CD: Crystal structures of cytochrome P450 2B4 in complex with the inhibitor 1-biphenyl-4-methyl-1H-imidazole: ligand-induced structural response through alpha-helical repositioning. Biochemistry. 2009 Jun 9;48(22):4762-71.
162(2,2,2,2) Details
19264347 Bonfanti P, Colombo A, Villa S, Comelli F, Costa B, Santagostino A: The effects of accumulation of an environmentally relevant polychlorinated biphenyl mixture on cytochrome P450 and P-glycoprotein expressions in fetuses and pregnant rats. Chemosphere. 2009 May;75(5):572-9. Epub 2009 Mar 4.
7(0,0,1,2) Details
18078376 Vega-Lopez A, Jimenez-Orozco FA, Ramon-Gallegos E, Garcia Latorre EA, Dominguez-Lopez ML: ESTROGENIC EFFECTS OF POLYCHLORINATED BIPHENYLS AND RELATION TO CYTOCHROME P4501A ACTIVITY IN THE ENDANGERED GOODEID FISH Ameca splendens. Environ Toxicol Chem. 2007 Dec 13:1.

The present study examines the relationships between cytochrome P450 1A (CYP1A) activity and vitellogenin (VTG) induction in Ameca splendens elicited by a polychlorinated biphenyl (PCB) mixture.
6(0,0,1,1) Details
18274624 Robertson LW, Berberian I, Borges T, Chen LC, Chow CK, Glauert HP, Filser JG, Thomas H: Suppression of Peroxisomal Enzyme Activities and Cytochrome P450 4A Isozyme Expression by Congeneric Polybrominated and Polychlorinated Biphenyls. PPAR Res. 2007;2007:15481.

None of the peroxisomal enzyme activities were significantly increased by any of the halogenated biphenyl congeners tested.
2(0,0,0,2) Details
18473165 Numata M, Fawcett JP, Saville DJ, Rosengren RJ: Hepatic cytochrome P450 activity and pollutant concentrations in paradise shelducks and southern black-backed gulls in the South Island of New Zealand. Ecotoxicology. 2008 Nov;17(8):697-708. Epub 2008 May 13.

Total polychlorinated biphenyl (PCB) concentrations (ranges: shelducks, 0.073-6.2; gulls, 8.2-330 ng/g wet weight) were high in landfill samples suggesting a link to EROD induction and, in landfill shelducks, EROD was independently associated with Hg and Pb concentration.
2(0,0,0,2) Details
19303460 Verreault J, Letcher RJ, Sonne C, Dietz R: In vitro metabolism of polychlorinated biphenyls and cytochrome P450 monooxygenase activities in dietary-exposed Greenland sledge dogs. Comp Biochem Physiol C Toxicol Pharmacol. 2009 Jul;150(1):91-100. Epub 2009 Mar 19.

The in vitro metabolism of a polychlorinated biphenyl (PCB) mixture was examined using hepatic microsomes of dietary-exposed Greenland sledge dogs (Canis familiaris) to an organohalogen-rich diet (Greenland minke whale blubber: EXP cohort) or a control diet (pork fat: CON cohort).
The associations between in vitro PCB metabolism, activity of oxidative hepatic microsomal cytochrome P450 (CYP) isoenzymes and concentrations of PCBs and hydroxylated metabolites were investigated.
1(0,0,0,1) Details
18414928 Braathen M, Mortensen AS, Sandvik M, Skare JU, Arukwe A: Estrogenic effects of selected hydroxy polychlorinated biphenyl congeners in primary culture of Atlantic Salmon (Salmo salar) hepatocytes. Arch Environ Contam Toxicol. 2009 Jan;56(1):111-22. Epub 2008 Apr 15.

Decreased mRNA transcription was observed for zona radiata protein (Zr-protein) and cytochrome P450 side-chain cleavage (P450scc) enzyme.
1(0,0,0,1) Details