Cyclochlorotine

Cyclochlorotine
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
CAS number	12663-46-6
PubChem	25565
KEGG	C19379 Y
Jmol-3D images	Image 1
SMILES O=C([C@H](CO)NC1=O)N[C@@H](C2=CC=CC=C2)CC(N[C@H](C(N3[C@H](C(N[C@H]1CC)=O)[C@H](Cl)[C@H](Cl)C3)=O)CO)=O
Properties
Molecular formula	C24H31Cl2N5O7
Molar mass	572.44 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cyclochlorotine^[1] (CC) is a secondary metabolite of the fungus Penicillium islandicum^[2] that causes hepatic necrosis and has carcinogenic properties.^[3] It is listed as an IARC Group 3 carcinogen.

Chemically, it is a chlorinated macrocyclic pentapeptide derived from the amino acids 3-phenyl-β-alanine, serine, dichloroproline, and aminobutyric acid^{[disambiguation needed ]}.^[4]

Although tributyltin (TBT) was recently found to induce apoptosis in different immune cells.^{[5][clarification needed]}

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. http://www.ihop-net.org/UniPub/iHOP/pm/193892.html?nr=3&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. 
5. ^ Lavastre, V; Girard, D (2002). "Tributyltin induces human neutrophil apoptosis and selective degradation of cytoskeletal proteins by caspases". J. Toxicol. Environ. Health Part A 65 (14): 1013–24. doi:10.1080/00984100290071270. PMID 12133234. http://www.ihop-net.org/UniPub/iHOP/pm/9516868.html?nr=6&pmid=12133234.