Difference between revisions of "Cyclochlorotine"

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Cyclochlorotine
File:Cyclochlorotine.png
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
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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.

Chemically, it is a chlorinated macrocyclic pentapeptide derived from the amino acids 3-phenyl-β-alanine, serine, dichloroproline, and aminobutyric acid[disambiguation needed File:InterlanguageLinks-Asset-Pencil-Hover.gif].[4]

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

References

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  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. 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. 
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