Cytochalasin F
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Mycotoxins |
| Catalog number | BBF-01759 |
| CAS | 36084-18-1 |
| Molecular Weight | 479.61 |
| Molecular Formula | C29H37NO5 |
Online Inquiry
Description
It is produced by the strain of Helminthosporium dematioideum, Coriolus vernicipes. It has many biological activities, such as inhibiting cytokinesis reversibly, inhibiting megasophil endocytosis and exocytosis.
Specification
| Synonyms | (7S,13E,16R,20R,21E)-6,7-Epoxy-20-hydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-13,21-diene-1,23-dione; 24-Oxa(14)cytochalasa-13,21-diene-1,23-dione,6,7-epoxy-20-hydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)- |
| IUPAC Name | (1S,4E,6R,10R,12E,14S,15S,17R,18S,19S,20S)-20-benzyl-6-hydroxy-10,17,18-trimethyl-2,16-dioxa-21-azatetracyclo[12.8.0.01,19.015,17]docosa-4,12-diene-3,22-dione |
| Canonical SMILES | CC1CCCC(C=CC(=O)OC23C(C=CC1)C4C(O4)(C(C2C(NC3=O)CC5=CC=CC=C5)C)C)O |
| InChI | InChI=1S/C29H37NO5/c1-18-9-7-13-21(31)15-16-24(32)34-29-22(14-8-10-18)26-28(3,35-26)19(2)25(29)23(30-27(29)33)17-20-11-5-4-6-12-20/h4-6,8,11-12,14-16,18-19,21-23,25-26,31H,7,9-10,13,17H2,1-3H3,(H,30,33)/b14-8+,16-15+/t18-,19+,21-,22+,23+,25+,26+,28-,29-/m1/s1 |
| InChI Key | CXWYFIYZAZBQGQ-QJMMVEIUSA-N |
Properties
| Boiling Point | 709.9 °C at 760 mmHg |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Corneal endothelial cytoskeletal changes in F-actin with aging, diabetes, and after cytochalasin exposure
E K Kim, D H Geroski, G P Holley, S I Urken, H F Edelhauser Am J Ophthalmol. 1992 Sep 15;114(3):329-35. doi: 10.1016/s0002-9394(14)71800-8.
We investigated the changes in endothelial cytoskeletal F-actin that occur with aging, diabetes, and exposure to cytochalasin D. Rabbit corneas, human donor corneas (with or without polymegethism), and corneas of diabetic individuals were studied. Endothelial F-actin was stained using nitrobenzoxadiazole-phallacidin. Results of these experiments demonstrated that F-actin of the rabbit and human corneal endothelium was arranged in linear circumferential strands that formed a hexagonal array. After in vitro perfusion of cytochalasin D to the corneal endothelium, the F-actin became randomly distributed throughout the cytoplasm, the hexagonal shape of the endothelial cell was disrupted, and endothelial permeability to carboxyfluorescein increased. Changes in F-actin were also observed in the endothelium of the human corneas with polymegethism, and in donor tissue having had previous posterior chamber intraocular lens implantation. The corneas of diabetic individuals also showed marked irregular F-actin fibers crossing the endothelial cell cytoplasm. These abnormal patterns of F-actin may contribute in part to the polymegethism observed in the corneal endothelial cells and may be the result of constant stress in cell volume regulation, particularly in the corneas of diabetic individuals.
2. Cytochalasin D acts as an inhibitor of the actin-cofilin interaction
Kazuyasu Shoji, Kazumasa Ohashi, Kaori Sampei, Masato Oikawa, Kensaku Mizuno Biochem Biophys Res Commun. 2012 Jul 20;424(1):52-7. doi: 10.1016/j.bbrc.2012.06.063. Epub 2012 Jun 20.
Cofilin, a key regulator of actin filament dynamics, binds to G- and F-actin and promotes actin filament turnover by stimulating depolymerization and severance of actin filaments. In this study, cytochalasin D (CytoD), a widely used inhibitor of actin dynamics, was found to act as an inhibitor of the G-actin-cofilin interaction by binding to G-actin. CytoD also inhibited the binding of cofilin to F-actin and decreased the rate of both actin polymerization and depolymerization in living cells. CytoD altered cellular F-actin organization but did not induce net actin polymerization or depolymerization. These results suggest that CytoD inhibits actin filament dynamics in cells via multiple mechanisms, including the well-known barbed-end capping mechanism and as shown in this study, the inhibition of G- and F-actin binding to cofilin.
3. Cytochalasin Derivatives from the Endozoic Curvularia verruculosa CS-129, a Fungus Isolated from the Deep-Sea Squat Lobster Shinkaia crosnieri Living in the Cold Seep Environment
Xue-Yi Hu, Chen-Yin Wang, Xiao-Ming Li, Sui-Qun Yang, Xin Li, Bin-Gui Wang, Shu-Yi Si, Ling-Hong Meng J Nat Prod. 2021 Dec 24;84(12):3122-3130. doi: 10.1021/acs.jnatprod.1c00907. Epub 2021 Nov 30.
A new cytochalasin dimer, verruculoid A (1), three new cytochalasin derivatives, including 12-nor-cytochalasin F (2), 22-methoxycytochalasin B6 (3), and 19-hydroxycytochalasin B (4), and 20-deoxycytochalasin B (5), a synthetic product obtained as a natural product for the first time, together with four known analogues (6-9), were isolated and identified from the culture extract of Curvularia verruculosa CS-129, an endozoic fungus obtained from the inner fresh tissue of the deep-sea squat lobster Shinkaia crosnieri, which was collected from the cold seep area of the South China Sea. Structurally, verruculoid A (1) represents the first cytochalasin homodimer containing a thioether bridge, while 12-nor-cytochalasin F (2) is the first 12-nor-cytochalasin derivative. Their structures were elucidated by detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis and ECD calculations confirmed their structures and absolute configurations. Compound 1 displayed activity against the human pathogenic bacterium Escherichia coli (MIC = 2 μg/mL), while compounds 4, 8, and 9 showed cytotoxicity against three tumor cell lines (HCT-116, HepG-2, and MCF-7) with IC50 values from 5.2 to 12 μM. The structure-activity relationship was briefly discussed.
Recommended Products
| BBF-03753 | Baicalin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
