Protein Information

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

Compound Information

Name atrazine
CAS

Reference List

PubMed Abstract RScore(About this table)
10647908 Hanioka N, Jinno H, Tanaka-Kagawa T, Nishimura T, Ando M: In vitro metabolism of simazine, atrazine and propazine by hepatic cytochrome P450 enzymes of rat, mouse and guinea pig, and oestrogenic activity of chlorotriazines and their main metabolites. Xenobiotica. 1999 Dec;29(12):1213-26.
32(0,1,1,2) Details
15234167 Londono DK, Siegfried BD, Lydy MJ: Atrazine induction of a family 4 cytochrome P450 gene in Chironomus tentans (Diptera: Chironomidae). Chemosphere. 2004 Aug;56(7):701-6.
19(0,0,3,4) Details
10665418 Miota F, Siegfried BD, Scharf ME, Lydy MJ: Atrazine induction of cytochrome P450 in Chironomus tentans larvae. Chemosphere. 2000 Feb;40(3):285-91.
15(0,0,2,5) Details
9711812 Hanioka N, Jinno H, Tanaka-Kagawa T, Nishimura T, Ando M: Changes in rat liver cytochrome P450 enzymes by atrazine and simazine treatment. Xenobiotica. 1998 Jul;28(7):683-98.
12(0,0,2,2) Details
9037261 Della Croce C, Morichetti E, Intorre L, Soldani G, Bertini S, Bronzetti G: Biochemical and genetic interactions of two commercial pesticides with the monooxygenase system and chlorophyllin. J Environ Pathol Toxicol Oncol. 1996;15(1):21-8.

Two commercial preparations of atrazine and zineb were tested on a diploid D7 strain of the yeast Saccharomyces cerevisiae using cells from logarithmic growth phase (with a high level of cytochrome P-450) and from stationary growth phase.
7(0,0,1,2) Details
19647285 Dong X, Zhu L, Wang J, Wang J, Xie H, Hou X, Jia W: Effects of atrazine on cytochrome P450 enzymes of zebrafish (Danio rerio). Chemosphere. 2009 Oct;77(3):404-12. Epub 2009 Jul 31.
7(0,0,1,2) Details
9920461 Hanioka N, Jinno H, Kitazawa K, Tanaka-Kagawa T, Nishimura T, Ando M, Ogawa K: In vitro biotransformation of atrazine by rat liver microsomal cytochrome P450 enzymes. Chem Biol Interact. 1998 Nov 27;116(3):181-98.
6(0,0,1,1) Details
8212068 Ugazio G, Burdino E, Dacasto M, Bosio A, van't Klooster G, Nebbia C: Induction of hepatic drug metabolizing enzymes and interaction with carbon tetrachloride in rats after a single oral exposure to atrazine. Toxicol Lett. 1993 Sep;69(3):279-88.

Results suggest that atrazine behaves like a relatively weak inducer of phenobarbital-inducible families of cytochrome P-450.
7(0,0,1,2) Details
8593046 Shao ZQ, Behki R: Characterization of the expression of the thcB gene, coding for a pesticide-degrading cytochrome P-450 in Rhodococcus strains. Appl Environ Microbiol. 1996 Feb;62(2):403-7.

Atrazine, simazine, or carbofuran, although metabolized by the system, had no effect on the thcB-lacZ expression.
3(0,0,0,3) Details
12174045 Coleman NV, Spain JC, Duxbury T: Evidence that RDX biodegradation by Rhodococcus strain DN22 is plasmid-borne and involves a cytochrome p-450. J Appl Microbiol. 2002;93(3):463-72.

Nitrite production from RDX was inhibited by metyrapone, menadione, piperonyl butoxide, n-octylamine and carbon monoxide and inducible by pyrrolidine, pyridine and atrazine.
2(0,0,0,2) Details
15178053 Keller JM, McClellan-Green P: Effects of organochlorine compounds on cytochrome P450 aromatase activity in an immortal sea turtle cell line. Mar Environ Res. 2004 Aug-Dec;58(2-5):347-51.

In addition, the GST-TS cells were exposed to 0.1-30 microM atrazine and 3-100 microM 4,4'-DDE.
2(0,0,0,2) Details
11697852 Menzel R, Bogaert T, Achazi R: A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible. Arch Biochem Biophys. 2001 Nov 15;395(2):158-68.

A few number of further CYP forms were found to be inducible by other xenobiotics like phenobarbital, atrazine, and clofibrate.
2(0,0,0,2) Details
10746939 Sanderson JT, Seinen W, Giesy JP, van den Berg M: 2-Chloro-s-triazine herbicides induce aromatase (CYP19) activity in H295R human adrenocortical carcinoma cells: a novel mechanism for estrogenicity?. Toxicol Sci. 2000 Mar;54(1):121-7.

Our laboratory is using the human H295R adrenocortical carcinoma cell line to examine chemicals for their potential to interfere with the activity and/or expression of several key cytochrome P450 (CYP) enzymes involved in the biosynthesis of steroid hormones.
In this report we demonstrated that the commonly used 2-chloro-s-triazine herbicides atrazine, simazine, and propazine dose-dependently (0-30 microM) induced aromatase (CYP19) activity to an apparent maximum of about 2.5-fold in H295R cells.
1(0,0,0,1) Details
15910738 Menzel R, Rodel M, Kulas J, Steinberg CE: CYP35: xenobiotically induced gene expression in the nematode Caenorhabditis elegans. Arch Biochem Biophys. 2005 Jun 1;438(1):93-102. Epub 2005 Apr 9.

Although over 80 cytochrome P450 (CYP) encoding genes have been identified in the genome of the nematode Caenorhabditis elegans very little is known about their involvement in biotransformation.
This paper demonstrates a concentration-dependent relationship of C. elegans CYP35A1, A2, A5, and C1 gene expression in response to four organic xenobiotics, namely atrazine, PCB52, fluoranthene, and lansoprazole.
1(0,0,0,1) Details
14961354 Downs CA, Fauth JE, Woodley CM: Assessing the health of grass shrimp (Palaeomonetes pugio) exposed to natural and anthropogenic stressors: a molecular biomarker system. Mar Biotechnol. 2001 Jul;3(4):380-97.

We developed a molecular biomarker system (MBS) to assess the physiological status of Palaomenetes pugio (grass shrimp) challenged with exposure to heat stress, cadmium, atrazine, and the water-accommodating fraction of either diesel fuel or bunker fuel No. 2.
The MBS assayed 9 specific cellular parameters of shrimp that are indicative of a nonstressed or stressed condition: heat-shock protein 60, heat-shock protein 70, alpha B-crystallin homologue, lipid peroxide, total glutathione level, ubiquitin, mitochondrial manganese superoxide dismutase, metallothionein, and cytochrome P-450 2E homologue.
1(0,0,0,1) Details
20183062 Abass K, Turpeinen M, Pelkonen O: An evaluation of the cytochrome P450 inhibition potential of selected pesticides in human hepatic microsomes. J Environ Sci Health B. 2009 Aug;44(6):553-63.

Some pesticides caused relatively potent inhibitions sporadically (carbendazim, CYP2D6, IC (50) = 12 micro M; atrazine, CYP3A4, IC (50) = 2.8 micro M; glyphosate, CYP2C9, IC (50) = 3.7 micro M; hexaflumuron, IC (50) = 6.0 micro M).
1(0,0,0,1) Details
11878473 Jin-Clark Y, Lydy MJ, Zhu KY: Effects of atrazine and cyanazine on chlorpyrifos toxicity in Chironomus tentans (Diptera: Chironomidae). Environ Toxicol Chem. 2002 Mar;21(3):598-603.

It is possible that these herbicides may affect cytochrome P450 enzymes to confer synergistic effects on the toxicity of chlorpyrifos.
1(0,0,0,1) Details
15210295 Kazeto Y, Place AR, Trant JM: Effects of endocrine disrupting chemicals on the expression of CYP19 genes in zebrafish (Danio rerio) juveniles. Aquat Toxicol. 2004 Jul 30;69(1):25-34.

Cytochrome P450 aromatase (CYP19) is the key steroidogenic enzyme responsible for conversion of androgens to estrogens which play a critical role in developmental sex differentiation and adult reproductive cycles in vertebrates.
The pharmaceutical, clofibrate, and the pesticide, atrazine, did not influence the expression of either CYP19 gene.
1(0,0,0,1) Details
18973769 Salaberria I, Hansen BH, Asensio V, Olsvik PA, Andersen RA, Jenssen BM: Effects of atrazine on hepatic metabolism and endocrine homeostasis in rainbow trout (Oncorhynchus mykiss). Toxicol Appl Pharmacol. 2009 Jan 1;234(1):98-106. Epub 2008 Oct 10.

Simultaneously we analyzed hepatic gene expression of cytochrome P450 (CYP) 1A and pi-class glutathione S-transferase (GST-P), and catalase (CAT) activity.
1(0,0,0,1) Details
19402758 Weil M, Scholz S, Zimmer M, Sacher F, Duis K: Gene expression analysis in zebrafish embryos: a potential approach to predict effect concentrations in the fish early life stage test. Environ Toxicol Chem. 2009 Sep;28(9):1970-8.

The effects of 14 substances on lethal and sublethal endpoints of the DarT and on expression of potential marker genes were investigated: the aryl hydrocarbon receptor 2, cytochrome P450 1A (cypla), heat shock protein 70, fizzy-related protein 1, the transcription factors v-maf musculoaponeurotic fibrosarcoma oncogene family protein g (avian) 1 and NF-E2-p45-related factor, and heme oxygenase 1 (hmox1).
For 10 (3,4- and 3,5-dichloroaniline, 1,4-dichlorobenzene, 2,4-dinitrophenol, atrazine, parathion-ethyl, chlorotoluron, genistein, 4-nitroquinoline-1-oxide, and cadmium) out of the 14 tested substances, LOEC values derived with the Gene-DarT differ by a factor of less than 10 from LOEC values of fish early life stage tests with zebrafish.
1(0,0,0,1) Details
8967773 Masaphy S, Henis Y, Levanon D: Manganese-enhanced biotransformation of atrazine by the white rot fungus Pleurotus pulmonarius and its correlation with oxidation activity. Appl Environ Microbiol. 1996 Oct;62(10):3587-93.

Lipid peroxidation, oxygenase and peroxidase activities, and the cytochrome P-450 concentration increased.
1(0,0,0,1) Details
16248553 Kawahigashi H, Hirose S, Ohkawa H, Ohkawa Y: Transgenic rice plants expressing human CYP1A1 remediate the triazine herbicides atrazine and simazine. J Agric Food Chem. 2005 Nov 2;53(22):8557-64.

The human cytochrome P450 CYP1A1 gene was introduced into rice plants (Oryza sativa cv.
1(0,0,0,1) Details
16608219 Kawahigashi H, Hirose S, Ohkawa H, Ohkawa Y: Phytoremediation of the herbicides atrazine and metolachlor by transgenic rice plants expressing human CYP1A1, CYP2B6, and CYP2C19. J Agric Food Chem. 2006 Apr 19;54(8):2985-91.

This study evaluated the expression of human cytochrome P450 genes CYP1A1, CYP2B6, and CYP2C19 in rice plants (Oryza sativa cv.
1(0,0,0,1) Details
17177535 Gotardo MC, Moraes LA, Assis MD: Metalloporphyrins as biomimetic models for cytochrome p-450 in the oxidation of atrazine. J Agric Food Chem. 2006 Dec 27;54(26):10011-8.
162(2,2,2,2) Details
10222312 Hanioka N, Jinno H, Tanaka-Kagawa T, Nishimura T, Ando M: In vitro metabolism of chlorotriazines: characterization of simazine, atrazine, and propazine metabolism using liver microsomes from rats treated with various cytochrome P450 inducers. Toxicol Appl Pharmacol. 1999 May 1;156(3):195-205.
82(1,1,1,2) Details
16527233 Ross MK, Filipov NM: Determination of atrazine and its metabolites in mouse urine and plasma by LC-MS analysis. Anal Biochem. 2006 Apr 15;351(2):161-73. Epub 2006 Feb 20.

We also used this methodology in a preliminary study of cytochrome P450-catalyzed metabolism of atrazine in vitro.
81(1,1,1,1) Details
7646049 Nagy I, Compernolle F, Ghys K, Vanderleyden J, De Mot R: A single cytochrome P-450 system is involved in degradation of the herbicides EPTC (S-ethyl dipropylthiocarbamate) and atrazine by Rhodococcus sp. strain NI86/21. Appl Environ Microbiol. 1995 May;61(5):2056-60.
82(1,1,1,2) Details
11129571 Shiota N, Kodama S, Inui H, Ohkawa H: Expression of human cytochromes P450 1A1 and P450 1A2 as fused enzymes with yeast NADPH-cytochrome P450 oxidoreductase in transgenic tobacco plants. Biosci Biotechnol Biochem. 2000 Oct;64(10):2025-33.

Among 11 isoforms of the human cytochrome P450 enzymes metabolizing xenobiotics, CYP 1A1 and CYP 1A2 were major P450 species in the metabolism of the herbicides chlortoluron and atrazine in a yeast expression system.
33(0,1,1,3) Details