methylcholanthrene

3-Methylcholanthrene
	Other names 20–Methylcholanthrene
Identifiers
Abbreviations	3-MC; 20-MC
CAS number	56-49-5
PubChem	299006
ChemSpider	264105
ChEMBL	CHEMBL40583
Jmol-3D images	Image 1
	SMILES c32cc1cccc5c1c(c2ccc4ccccc34)C(C)C5 ;
	InChI InChI=1S/C21H16/c1-13-11-15-6-4-7-16-12-19-17-8-3-2-5-14(17)9-10-18(19)20(13)21(15)16/h2-10,12-13H,11H2,1H3 ; Key: JVGJWHQKHATXLD-UHFFFAOYSA-N InChI=1/C21H16/c1-13-11-15-6-4-7-16-12-19-17-8-3-2-5-14(17)9-10-18(19)20(13)21(15)16/h2-10,12-13H,11H2,1H3; Key: JVGJWHQKHATXLD-UHFFFAOYAC ;
Properties
Molecular formula	C21H16
Molar mass	268.35 g/mol
Appearance	Yellow solid
Melting point	180 °C, 453 K, 356 °F
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

メチルコラントレン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/10/20 19:20:58」(JST)

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Methylcholanthrene (MCA) is a highly carcinogenic polycyclic aromatic hydrocarbon produced by burning organic compounds at very high temperatures^{[clarification needed]}. It is a yellow solid with a melting point around 180 °C. Methylcholanthrene is used in laboratory studies of chemical carcinogenesis. It is an alkylated derivative of benz[a]anthracene and has a similar UV spectrum. The most common isomer is 3-methylcholanthrene, although the methyl group can occur in other places.

3-Methylcholanthrene, a known carcinogen which builds up in the prostate due to cholesterol breakdown, is implicated in prostate cancer.^{[citation needed]} It "readily produces" primary sarcomas in mice.^[1]

References

^ Donald C. Malins, Katie M. Anderson, Naomi K. Gilman, Virginia M. Green, Edward A. Barker and Karl Erik Hellström (2004). "Development of a Cancer DNA Phenotype Prior to Tumor Formation". PNAS 101 (29): 10721–10725. doi:10.1073/pnas.0403888101. JSTOR 3372726. PMC 490001. PMID 15249662. //www.ncbi.nlm.nih.gov/pmc/articles/PMC490001/.

External links

National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet

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English Journal

Neutrophils are required for 3-methylcholanthrene-initiated, butylated hydroxytoluene-promoted lung carcinogenesis.

Vikis HG, Gelman AE, Franklin A, Stein L, Rymaszewski A, Zhu J, Liu P, Tichelaar JW, Krupnick AS, You M.SourceDepartment of Surgery, Washington University School of Medicine, St. Louis, Missouri; Alvin Siteman Cancer Center, Washington University School of Medicine, St. Louis, Missouri; Department of Pharmacology, Medical College of Wisconsin, Milwaukee, Wisconsin; MCW Cancer Center, Translational and Biomedical Research Center, Medical College of Wisconsin, Milwaukee, Wisconsin.
Molecular carcinogenesis.Mol Carcinog.2012 Dec;51(12):993-1002. doi: 10.1002/mc.20870. Epub 2011 Oct 17.
Multiple studies have shown a link between chronic inflammation and lung tumorigenesis. Inbred mouse strains vary in their susceptibility to methylcholanthrene (MCA)-initiated butylated hydroxytoluene (BHT)-promoted lung carcinogenesis. In the present study we investigated whether neutrophils play a
PMID 22006501

Basal and 3-methylcholanthrene-induced expression of cytochrome P450 1A, 1B and 1C genes in the Brazilian guppy, Poecilia vivipara.

Dorrington T, Zanette J, Zacchi FL, Stegeman JJ, Bainy AC.SourceBiochemistry Department, Universidade Federal de Santa Catarina, SC, 88034-257, Brazil. Electronic address: tarquindorrington@gmail.com.
Aquatic toxicology (Amsterdam, Netherlands).Aquat Toxicol.2012 Nov 15;124-125:106-13. doi: 10.1016/j.aquatox.2012.08.006. Epub 2012 Aug 14.
In fish there are four cytochrome P450 (CYP1) subfamilies: CYP1A, CYP1B, CYP1C, and CYP1D. Here we cloned Poecilia vivipara CYP1A, with an inferred amino acid sequence 91% identical to CYP1A from the killifish Fundulus heteroclitus, another member of the Cypriniformes, and an important model in ecot
PMID 22940225

Japanese Journal

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