Cyclochlorotine

Cyclochlorotine
	File:Cyclochlorotine.png
	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
style="background: #F8EABA; text-align: center;" colspan="2" \| Identifiers
CAS number	12663-46-6
PubChem	25565
SMILES	Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" \| Properties
Molecular formula	C24H31Cl2N5O7
Molar mass	572.44 g mol−1
	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.

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

References

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↑ 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.
↑ "Toxicology of Penicillium Islandicum". Nature. 191 (4791): 864–865. 1961. doi:10.1038/191864b0.
↑ Penicillium islandicum causes hepatic necrosis and has carcinogenic properties
↑ 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.
↑ 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.

Cyclochlorotine
File:Cyclochlorotine.png
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
style="background: #F8EABA; text-align: center;" colspan="2" \| Identifiers
CAS number	12663-46-6
PubChem	25565
SMILES	Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" \| Properties
Molecular formula	C₂₄H₃₁Cl₂N₅O₇
Molar mass	572.44 g mol⁻¹
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references