C8273

Cytochalasin D

Name: Cytochalasin D
Brand: SIGMA

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

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

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.

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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000486018

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)

Extracellular vesicle-associated cholesterol supports the regenerative functions of macrophages in the brain

Vanherle S, et al.

Journal of Extracellular Vesicles (2023)

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)

Immunomodulatory effects of vitamin D on innate and adaptive immune responses to Streptococcus pneumoniae.

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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