Cyclochlorotine

Cyclochlorotine
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 Registry Number	12663-46-6^Y
ChemSpider	28426727^N
InChI InChI=1S/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1^N Key: PMBVHCCVEPYDSN-BADCMNFISA-N^N InChI=1/C24H31Cl2N5O7/c1-2-14-21(35)30-16(10-32)22(36)29-15(12-6-4-3-5-7-12)8-18(34)27-17(11-33)24(38)31-9-13(25)19(26)20(31)23(37)28-14/h3-7,13-17,19-20,32-33H,2,8-11H2,1H3,(H,27,34)(H,28,37)(H,29,36)(H,30,35)/t13-,14+,15-,16+,17+,19-,20+/m1/s1 Key: PMBVHCCVEPYDSN-BADCMNFIBI
Jmol-3D images	Image
KEGG	C19379^Y
PubChem	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
Molecular formula	C₂₄H₃₁Cl₂N₅O₇
Molar mass	572.44 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.^[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.