Cyclochlorotine: Difference between revisions

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Cyclochlorotine
	File:Cyclochlorotine.png
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
CAS Number	12663-46-6;
3D model (JSmol)	Interactive image;
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).
KEGG	C19379 ;
PubChem CID	25565;
	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
Chemical formula	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).
	verify (what is ?)
	Infobox references

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Revision as of 20:54, 16 July 2012

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

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.^[4]

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.

[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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@@ Line 32: / Line 32: @@
 '''Cyclochlorotine'''<ref>{{cite journal | title = Effects of cyclochlorotine on myofibrils in cardiomyocytes and on actin filament bundles in fibroblasts in vitro | journal = Nat. Toxins | year = 1994 | url = http://www.ihop-net.org/UniPub/iHOP/pm/193892.html?nr=3&pmid=7704452 | pmid = 7704452 | last1 = Zhou | first1 = ZH | last2 = Komiyama | first2 = M | last3 = Terao | first3 = K | last4 = Shimada | first4 = Y | volume = 2 | issue = 6 | pages = 378–85}}</ref> (CC) is a secondary metabolite of the fungus ''[[Penicillium islandicum]]''<ref>{{cite journal | title = Toxicology of Penicillium Islandicum | journal = Nature | volume = 191 | issue = 4791 | pages = 864–865 | year = 1961 | bibcode = 1961Natur.191..864. | doi = 10.1038/191864b0}}</ref> that causes hepatic necrosis and has carcinogenic properties.<ref>[http://medical-dictionary.thefreedictionary.com/Penicillium+islandicum Penicillium islandicum causes hepatic necrosis and has carcinogenic properties]</ref>  It is listed as an [[List of IARC Group 3 carcinogens|IARC Group 3 carcinogen]].
-Chemically, it is a [[chlorine|chlorinated]] [[macrocycle|macrocyclic]] [[pentapeptide]] derived from the amino acids [[3-phenyl-β-alanine]], [[serine]], [[dichloroproline]], and [[aminobutyric acid]]{{Disambiguation needed|date=June 2011}}.<ref>{{cite journal | title = Structural and Conformational Analysis of Hydroxycyclochlorotine and Cyclochlorotine, Chlorinated Cyclic Peptides from Penicillium islandicum | author = Kohei Mizutani, Yusuke Hirasawa, Yoshiko Sugita-Konishi, Naoki Mochizuki and Hiroshi Morita | journal = J. Nat. Prod. | year = 2008 | volume = 71 | issue = 7 | pages = 1297–1300 | doi = 10.1021/np800150m | pmid = 18558744}}</ref>
+Chemically, it is a [[chlorine|chlorinated]] [[macrocycle|macrocyclic]] [[pentapeptide]] derived from the amino acids [[3-phenyl-β-alanine]], [[serine]], [[dichloroproline]], and [[aminobutyric acid]].<ref>{{cite journal | title = Structural and Conformational Analysis of Hydroxycyclochlorotine and Cyclochlorotine, Chlorinated Cyclic Peptides from Penicillium islandicum | author = Kohei Mizutani, Yusuke Hirasawa, Yoshiko Sugita-Konishi, Naoki Mochizuki and Hiroshi Morita | journal = J. Nat. Prod. | year = 2008 | volume = 71 | issue = 7 | pages = 1297–1300 | doi = 10.1021/np800150m | pmid = 18558744}}</ref>
-Although [[tributyltin]] (TBT) was recently found to induce apoptosis  in different immune cells.<ref>{{cite journal | title = Tributyltin induces human neutrophil  apoptosis and selective degradation of cytoskeletal proteins by caspases | journal = J. Toxicol. Environ. Health Part A | year = 2002 | url = http://www.ihop-net.org/UniPub/iHOP/pm/9516868.html?nr=6&pmid=12133234 | pmid = 12133234 | last1 = Lavastre | first1 = V | last2 = Girard | first2 = D | volume = 65 | issue = 14 | pages = 1013–24 | doi = 10.1080/00984100290071270}}</ref>
 ==References==

Cyclochlorotine: Difference between revisions

Revision as of 20:54, 16 July 2012

Overview

References

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