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Merck
CN

C8273

Cytochalasin D

From Zygosporium mansonii, ≥98% (TLC and HPLC), actin polymerization inhibitor, 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
NACRES:
NA.77
PubChem Substance ID:
24893039
UNSPSC Code:
12352200
EC Number:
244-804-1
MDL number:
MFCD00077706
Beilstein/REAXYS Number:
1632828
Assay:
≥98% (TLC and HPLC)
Form:
powder
Quality level:
300

Key Documents

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Product Name

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

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

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

biological source

Zygosporium mansonii

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

Quality Level

300

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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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000486018
0000486018
0000493436
0000493436
0000439774

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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)
Advances of xenogeneic ovarian extracellular matrix hydrogels for in vitro follicle development and oocyte maturation
Frances-Herrero E, et al.
Biomaterials advances (2023)
Cytochalasin D acts as an inhibitor of the actin-cofilin interaction
Shoji K, et al.
Biochemical and Biophysical Research Communications (2012)
Extracellular vesicle-associated cholesterol supports the regenerative functions of macrophages in the brain
Vanherle S, et al.
Journal of Extracellular Vesicles (2023)
Marie Olliver et al.
The Journal of infectious diseases, 208(9), 1474-1481 (2013-08-08)
Streptococcus pneumoniae forms part of the normal nasopharyngeal flora but can also cause a broad spectrum of inflammatory diseases. Vitamin D has potent effects on human immunity, including induction of antimicrobial peptides and suppression of T-cell proliferation, but its ability
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