Cyclochlorotine
File:Cyclochlorotine.png | |
Names | |
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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
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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
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3D model (JSmol)
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ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
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PubChem CID
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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). | |
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
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Overview
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]
References
- ↑ 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. Bibcode:1961Natur.191..864.. 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.
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