C8273

Cytochalasin D

from Zygosporium mansonii, ≥98% (TLC and HPLC), powder

• Synonym(s): Lygosporin A, Zygosporin A
• Empirical Formula (Hill Notation): C₃₀H₃₇NO₆
• CAS Number: 22144-77-0
• Molecular Weight: 507.62
• Beilstein/REAXYS Number: 1632828
• EC Number: 244-804-1
• MDL number: MFCD00077706
• UNSPSC Code: 12352200
• PubChem Substance ID: 24893039
• NACRES: NA.77

Properties

• biological source: Zygosporium mansonii
• Quality Level: 300
• assay: ≥98% (TLC and HPLC)
• form: powder
• solubility: DMSO: soluble; ethanol: soluble
• antibiotic activity spectrum: fungi
• mode of action: DNA synthesis | interferes
• storage temp.: −20°C
• SMILES string: [H][C@@]12[C@H](C)C(=C)[C@@H](O)[C@@H]3\C=C\C[C@H](C)C(=O)[C@](C)(O)\C=C\[C@@H](OC(C)=O)[C@@]13C(=O)N[C@H]2Cc4ccccc4
• InChI: 1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1
• InChI key: SDZRWUKZFQQKKV-JHADDHBZSA-N

Description

General description

Cytochalasin D (CytoD) is commonly used to inhibit actin dynamics and study its role in cellular processes. This fungal-derived small organic compound acts as an inhibitor of the interaction between G-actin and cofilin by binding to G-actin. Additionally, CytoD inhibits the binding of cofilin to F-actin and reduces the rate of actin polymerization and depolymerization in living cells.

Cytochalasin D is a cell-permeable fungal toxin. It disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. Cytochalasin D inhibits smooth muscle contraction and insulin-stimulated but not basal transport of glucose.

Application

Cytochalasin D has been used:

• to treat H9c2 cells to study the relationship between cell stiffness and the F-actin cytoskeleton
• as inhibitor of receptor-mediated endocytosis to treat oligodendrocyte precursor cells (OPCs) to investigate the effect of inhibiting specific extracellular vesicle (EV) uptake pathways
• in in vitro embryo culture to artificially activate oocytes

Biochem/physiol Actions

Potent inhibitor of actin polymerization; disrupts actin microfilaments; activates the p53-dependent pathways; inhibits smooth muscle contraction; inhibits insulin-stimulated glucose transport.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges