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C8273

Sigma-Aldrich

Cytochalasin D

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

Synonym(s):

Lygosporin A, Zygosporin A

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About This Item

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

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

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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.

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Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hyperglycemia and hyperlipidemia can induce morphophysiological changes in rat cardiac cell line
Varela R, et al.
Biochemistry and Biophysics Reports (2021)
Extracellular vesicle-associated cholesterol supports the regenerative functions of macrophages in the brain
Vanherle S, et al.
Journal of Extracellular Vesicles (2023)
Cytochalasin D acts as an inhibitor of the actin-cofilin interaction
Shoji K, et al.
Biochemical and Biophysical Research Communications (2012)
Marie Olliver et al.
The Journal of infectious diseases, 208(9), 1474-1481 (2013-08-08)
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