Cytochalasin C

Names

[ Name ]:
Cytochalasin C

[Synonym ]:
1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,6,6a,9,10,12,15-octahydro-6,12-dihydroxy-4,5,10,12-tetramethyl-3-(phenylmethyl)-, (7Z,13E)-
Acétate de (7Z,13E)-3-benzyl-6,12-dihydroxy-4,5,10,12-tétraméthyl-1,11-dioxo-2,3,3a,6,6a,9,10,11,12,15-décahydro-1H-cycloundéca[d]isoindol-15-yle
EINECS 244-803-6
(7Z,13E)-3-Benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1,11-dioxo-2,3,3a,6,6a,9,10,11,12,15-decahydro-1H-cycloundeca[d]isoindol-15-ylacetat
(7Z,13E)-3-Benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1,11-dioxo-2,3,3a,6,6a,9,10,11,12,15-decahydro-1H-cycloundeca[d]isoindol-15-yl acetate
Cytochalasin C from Metarrhizium anisopliae
MFCD00066080

Biological Activity

[Description]:

Cytochalasin C is a cell-permeable fungal toxin and induces the formation of nuclear rodlets. Cytochalasin C is 10 times less toxic in mice than is cytochalasin D[1][2][3].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Foissner I, et al. Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97.

[2]. Yahara I, et al. Correlation between effects of 24 different cytochalasins on cellular structures and cellular eventsand those on actin in vitro. J Cell Biol. 1982 Jan;92(1):69-78.

[3]. Trendowski M, et al. Tolerated doses in zebrafish of cytochalasins and jasplakinolide for comparison with tolerateddoses in mice in the evaluation of pre-clinical activity of microfilament-directed agents in tumormodel systems in vivo. In Vivo. 2014 Nov-Dec;28(6):1021-31.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
714.3±60.0 °C at 760 mmHg

[ Melting Point ]:
260-264ºC

[ Molecular Formula ]:
C₃₀H₃₇NO₆

[ Molecular Weight ]:
507.618

[ Flash Point ]:
385.8±32.9 °C

[ Exact Mass ]:
507.262085

[ PSA ]:
112.93000

[ LogP ]:
2.81

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
−20°C

[ Water Solubility ]:
methylene chloride: 5 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA5300500

CHEMICAL NAME :: (11)Cytochalasa-5,13,19-triene-1,17-dione, 21-(acetoxy)-7,18-dihydroxy-16,18-dimethyl- 10-phenyl-, (7S,13E,16S,18R,19E,21R)-

CAS REGISTRY NUMBER :: 22144-76-9

LAST UPDATED :: 199203

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 21,2268,1973

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310 + H330-H361

[ Precautionary Statements ]:
P260-P264-P280-P284-P301 + P310-P302 + P350

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;T: Toxic;

[ Risk Phrases ]:
26/27/28-63

[ Safety Phrases ]:
28-36/37-45

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
HA5300500

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Articles

Structure of cytochalasins and cytochalasin B binding sites in human erythrocyte membranes.

Biochemistry 19 , 679, (1980)

Twenty cytochalasins were tested for binding to and for inhibition of glucose transport in human erythrocyte membrane. In this membrane three cytochalasin B (CB) binding sites have been identified. Al...

Phenotype modulation in primary cultures of rat aortic smooth muscle cells. Effects of drugs that interfere with the functions of the vacuolar system and the cytoskeleton.

Virchows Arch.,. B, Cell Pathol. 59(1) , 1-10, (1990)

The transition of adult rat aortic smooth muscle cells from a contractile to a synthetic phenotype during the first week of primary culture on a substrate of fibronectin in serum-free medium was studi...

Cytoskeleton regulates expression of genes for transforming growth factor-beta 1 and extracellular matrix proteins in dermal fibroblasts.

J. Cell Physiol. 172(2) , 192-9, (1997)

Cytoskeleton not only controls cell morphology but also regulates cell growth, migration, differentiation, and gene expression, events which are fundamental to embryogenesis, carcinogenesis, and wound...