Protein Information

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

Compound Information

Name naphthalene
CAS naphthalene

Reference List

PubMed Abstract RScore(About this table)
17910104 Saratale G, Kalme S, Bhosale S, Govindwar S: Biodegradation of kerosene by Aspergillus ochraceus NCIM-1146. J Basic Microbiol. 2007 Oct;47(5):400-5.

NADPH was the preferred cofactor for enzyme activity, which was inhibited by CO, indicating cytochrome P450 mediated reactions.
A significant increase in all the enzyme activities was observed when mycelium incubated for 18 h in mineral salts medium, containing cholesterol, camphor, naphthalene, 1,2-dimethoxybenzene, phenobarbital, n-hexane, kerosene or saffola oil as inducers.
1(0,0,0,1) Details
19798982 Li QY, Zu YG, Lu HY, Wang LM: [A new class of exciplex-formed probe detect of specific sequence DNA] . Guang Pu Xue Yu Guang Pu Fen Xi. 2009 Jul;29(7):1962-6.

A SNP-containing region of cytochrome P450 2C9 DNA systems was evaluated to define some of the structural and associated requirement of this new class of exciplex-formed probe, and a 24-base target was selected which contains single-nucleotide polymorphisms (SNP) in genes coding for cytochrome P450.
However the exciplex formed by the new pyrene derivative and naphthalene emitted strongly at -505 nm with large Stokes shifts (120-130 nm), and the monomer emission at 390 and 410 nm is nearly zero.
1(0,0,0,1) Details
17601809 Anh DH, Ullrich R, Benndorf D, Svatos A, Muck A, Hofrichter M: The coprophilous mushroom Coprinus radians secretes a haloperoxidase that catalyzes aromatic peroxygenation. Appl Environ Microbiol. 2007 Sep;73(17):5477-85. Epub 2007 Jun 29.

CrP brominated phenol to 2- and 4-bromophenols and selectively hydroxylated naphthalene to 1-naphthol.
The UV-visible spectrum of CrP II was highly similar to that of resting-state cytochrome P450 enzymes, with the Soret band at 422 nm and additional maxima at 359, 542, and 571 nm.
1(0,0,0,1) Details
17139609 Bhosale S, Saratale G, Govindwar S: Biotransformation enzymes in Cunninghamella blakesleeana (NCIM-687). J Basic Microbiol. 2006;46(6):444-8.

The enzyme activity preferred NADPH as a cofactor and showed inhibition with CO, indicating cytochrome P450 mediated reactions.
A significant increase in aniline hydroxylase enzyme activity was observed when mycelia incubated in incubation medium containing different inducers (viz. camphor, cholesterol, naphthalene, veratrole, phenobarbital, n -hexadecane and ethyl alcohol) when compared with mycelia incubated in same way but in absence of inducers.
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
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
19434406 Pecyna MJ, Ullrich R, Bittner B, Clemens A, Scheibner K, Schubert R, Hofrichter M: Molecular characterization of aromatic peroxygenase from Agrocybe aegerita. Appl Microbiol Biotechnol. 2009 Oct;84(5):885-97. Epub 2009 May 12.


Members of these extracellular biocatalysts produced by agaric basidiomycetes such as Agrocybe aegerita or Coprinellus radians catalyze reactions--for example, the peroxygenation of naphthalene, toluene, dibenzothiophene, or pyridine--which are actually attributed to cytochrome P450 monooxygenases.
0(0,0,0,0) Details
18160334 Platt KL, Aderhold S, Kulpe K, Fickler M: Unexpected DNA damage caused by polycyclic aromatic hydrocarbons under standard laboratory conditions. Mutat Res. 2008 Feb 29;650(2):96-103. Epub 2007 Nov 19.


Surprisingly, 11 PAHs, i.e., benzo [a] pyrene (BaP), benz [a] anthracene, 7,12-dimethylbenz [a] anthracene, 3-methylcholanthrene, fluoranthene, anthanthrene, 11H-benzo [b] fluorene, dibenz [a,h] anthracene, pyrene, benzo [ghi] perylene and benzo [e] pyrene caused DNA strand breaks even without external metabolic activation, while naphthalene, anthracene, phenanthrene and naphthacene were inactive.
0(0,0,0,0) Details
18054806 Hansen BH, Altin D, Vang SH, Nordtug T, Olsen AJ: Effects of naphthalene on gene transcription in Calanus finmarchicus (Crustacea: Copepoda). Aquat Toxicol. 2008 Jan 31;86(2):157-65. Epub 2007 Dec 4.

0(0,0,0,0) Details
20176620 Lanosa MJ, Willis DN, Jordt S, Morris JB: Role of Metabolic Activation and the TRPA1 Receptor in the Sensory Irritation Response to Styrene and Naphthalene. Toxicol Sci. 2010 Feb 22.

The current study was aimed at examining the role of cytochrome P450 (CYP450) activation and the electrophile-sensitive TRPA1 receptor in mediating the sensory irritation response to styrene and naphthalene.
93(0,3,3,3) Details
18447001 Cho TM, Rose RL, Hodgson E: The effect of chlorpyrifos-oxon and other xenobiotics on the human cytochrome P450-dependent metabolism of naphthalene and deet. Drug Metabol Drug Interact. 2007;22(4):235-62.
81(1,1,1,1) Details
19843705 Spiess PC, Morin D, Williams CR, Buckpitt AR: Protein Thiol Oxidation in Murine Airway Epithelial Cells in Response to Naphthalene or Diethyl Maleate. Am J Respir Cell Mol Biol. 2009 Oct 20.

Cytochrome P450-dependent metabolic activation to form reactive intermediates and loss of soluble cellular thiols (glutathione) are critical steps in naphthalene toxicity, but the precise mechanisms by which this chemical results in cellular injury remain unclear.
31(0,1,1,1) Details
18722660 Kilanowicz A, Skrzypinska-Gawrysiak M, Sapota A, Galoch A, Darago A: Subacute toxicity of polychlorinated naphthalenes and their effect on cytochrome P-450. Ecotoxicol Environ Saf. 2009 Feb;72(2):650-7. Epub 2008 Aug 22.

The aim of the study was to investigate the subacute toxicity of a polychlorinated naphthalene (PCN) mixture and its effect on cytochrome P-450 levels in rats.
8(0,0,1,3) Details
19399609 Brausch JM, Smith PN: Development of resistance to cyfluthrin and naphthalene among Daphnia magna. Ecotoxicology. 2009 Jul;18(5):600-9. Epub 2009 Apr 28.

When the cytochrome P450 inhibitor piperonyl butoxide was used in conjunction with cyfluthrin and naphthalene the sensitivity of resistant and control D. magna were equal, suggesting P450s were responsible for conveying resistance.
31(0,1,1,1) Details
18273912 Vijayavel K, Balasubramanian MP: DNA damage and cell necrosis induced by naphthalene due to the modulation of biotransformation enzymes in an estuarine crab Scylla serrata. J Biochem Mol Toxicol. 2008 Feb;22(1):1-7.

Biotransformation enzymes such as cytochrome P450, cytochrome b (5), NADPH cytochrome P450 reductase, aryl hydrocarbon hydroxylase, glutathione-S-transferase, and UDP-glucuronyl transferase were elevated in the hepatopancreas of naphthalene-exposed crabs in comparison with control.
6(0,0,1,1) Details
18385170 Yildirim AO, Veith M, Rausch T, Muller B, Kilb P, Van Winkle LS, Fehrenbach H: Keratinocyte growth factor protects against Clara cell injury induced by naphthalene. Eur Respir J. 2008 Sep;32(3):694-704. Epub 2008 Apr 2.

Cytochrome P (450) isoform 2F2, which converts NA into its toxic metabolite, was reduced by approximately 50%.
2(0,0,0,2) Details
16428131 Asikainen AH, Ruuskanen J, Tuppurainen KA: Alternative QSAR models for selected estradiol and cytochrome P450 ligands: comparison between classical, spectroscopic, CoMFA and GRID/GOLPE methods. SAR QSAR Environ Res. 2005 Dec;16(6):555-65.

2(0,0,0,2) Details
19648534 Morris JB, Buckpitt AR: Upper respiratory tract uptake of naphthalene. . Toxicol Sci. 2009 Oct;111(2):383-91. Epub 2009 Jul 31.

To assess the potential importance of nasal cytochrome P450 (CYP) metabolism, groups of rats were pretreated with the CYP inhibitor 5-phenyl-1-pentyne (PP) (100 mg/kg, ip).
1(0,0,0,1) Details
17669617 Letelier ME, Entrala P, Lopez-Alarcon C, Gonzalez-Lira V, Molina-Berrios A, Cortes-Troncoso J, Jara-Sandoval J, Santander P, Nunez-Vergara L: Nitroaryl-1,4-dihydropyridines as antioxidants against rat liver microsomes oxidation induced by iron/ascorbate, nitrofurantoin and naphthalene. Toxicol In Vitro. 2007 Dec;21(8):1610-8. Epub 2007 Jun 27.

These drugs are metabolized through cytochrome P (450) oxidative system, majority localized in the hepatic endoplasmic reticulum.
1(0,0,0,1) Details
17962375 Kartha JS, Yost GS: Mechanism-based inactivation of lung-selective cytochrome P450 CYP2F enzymes. Drug Metab Dispos. 2008 Jan;36(1):155-62. Epub 2007 Oct 25.

In conclusion, this study presents evidence that 3MI is a mechanism-based inhibitor of both CYP2F3 and CYP2F1, which are important enzymes in the bioactivation of pneumotoxicants such as 3MI or 1,1-dichloroethylene or carcinogens such as naphthalene, benzene, and styrene.
2(0,0,0,2) Details
19116287 Li Z, Okano S, Yoshinari K, Miyamoto T, Yamazoe Y, Shinya K, Ioku K, Kasai N: Soft-hydrothermal processing of red cedar bedding reduces its induction of cytochrome P450 in mouse liver. Lab Anim. 2009 Apr;43(2):205-11. Epub 2008 Dec 30.

In particular, several volatile sesquiterpenes, naphthalene-derived aromatics and 4,4-dimethyl-13alpha-androst-5-ene were decreased in the ST-cedar bedding, suggesting that these may be responsible for P450 induction.
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