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 20:53, 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^{[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.

[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.

[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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@@ Line 34: / Line 34: @@
 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>
-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>{{Clarify|date=March 2010}}
+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 20:53, 16 July 2012

Overview

References

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