Cyclochlorotine

Cyclochlorotine
Skeletal formula of cyclochlorotine
Ball-and-stick model of the cyclochlorotine molecule
Names
IUPAC name
1,2-Dichloro-15-ethyl-5,12-bis-hydroxymethyl-9-phenyl-dodecahydro-3a,6,10,13,16-pentaaza-cyclopentac yclohexadecene-4,7,11,14,17-pentaone
Other names
Cyclo[(R)-3-phenyl-β-alanyl-L-seryl-(2α,3α,4α)-3,4-dichloro-L-prolyl-L-2-aminobutanoyl-L-seryl]; Yellowed rice toxin
Identifiers
12663-46-6 YesY
ChemSpider 28426727 N
Jmol interactive 3D Image
KEGG C19379 YesY
PubChem 25565
Properties
C24H31Cl2N5O7
Molar mass 572.44 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Cyclochlorotine[1] (CC) is a mycotoxin produced by the fungus Penicillium islandicum[2] that causes liver damage and has carcinogenic properties.[3] It is listed as an IARC Group 3 carcinogen.

Chemically, it is a chlorinated cyclic peptide.[4]

References

  1. Zhou, ZH; Komiyama, M; Terao, K; Shimada, Y (1994). "Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro". Nat. Toxins 2 (6): 378–85. PMID 7704452.
  2. "Toxicology of Penicillium Islandicum". Nature 191 (4791): 864–865. 1961. Bibcode:1961Natur.191..864.. doi:10.1038/191864b0.
  3. Penicillium islandicum causes hepatic necrosis and has carcinogenic properties
  4. Kohei Mizutani, Yusuke Hirasawa, Yoshiko Sugita-Konishi, Naoki Mochizuki and Hiroshi Morita (2008). "Structural and Conformational Analysis of Hydroxycyclochlorotine and Cyclochlorotine, Chlorinated Cyclic Peptides from Penicillium islandicum". J. Nat. Prod. 71 (7): 1297–1300. doi:10.1021/np800150m. PMID 18558744.
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