Cytochalasin E

Names

[ Name ]:
Cytochalasin E

[Synonym ]:
MFCD00005178
EINECS 252-835-7
(1Z)-14-Benzyl-6-hydroxy-4,6,15,15a-tetramethyl-3,13,14,14a,15,15a,16a,16b-octahydro[1,3]dioxacyclotridecino[4,5-d]oxireno[f]isoindole-5,10,12(4H,6H)-trione
[1,3]Dioxacyclotridecino[4,5-d]oxireno[f]isoindole-5,10,12(4H,6H)-trione, 3,13,14,14a,15,15a,16a,16b-octahydro-6-hydroxy-4,6,15,15a-tetramethyl-14-(phenylmethyl)-, (1Z)-
(1Z,7E)-14-Benzyl-6-hydroxy-4,6,15,15a-tetramethyl-3,13,14,14a,15,15a,16a,16b-octahydro[1,3]dioxacyclotridecino[4,5-d]oxireno[f]isoindole-5,10,12(4H,6H)-trione
[1,3]dioxacyclotridecino[4,5-d]oxireno[f]isoindole-5,10,12(4H,6H)-trione, 3,13,14,14a,15,15a,16a,16b-octahydro-6-hydroxy-4,6,15,15a-tetramethyl-14-(phenylmethyl)-, (1Z,7E)-
CYTOCHALACINE
CYTOCHALASIN 3
CYTOCHALICINE
CYTOCHALASIN E,ASPERGILLUS CLAVATUS
(7s,13e,16s,18r,19e)-18-dimethyl-10-phenyl

Biological Activity

[Description]:

Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth. Cytochalasin E is a potent actin depolymerization agent, and it binds and caps the barbed end of actin filaments to prevent actin elongation[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Autophagy >> Autophagy

[In Vitro]

Cytochalasin E prominently inhibits the growth of A549 cells in a dose-dependent manner[3]. Cytochalasin E could induce the up-regulation of autophagy-related protein (LC3-II) and SQSTM1/p62[3].

[References]

[1]. Udagawa T, et al. Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesisand tumor growth. J Pharmacol Exp Ther. 2000 Aug;294(2):421-7.

[2]. Lu QY, et al. Green tea extract modulates actin remodeling via Rho activity in an in vitro multistep carcinogenicmodel. Clin Cancer Res. 2005 Feb 15;11(4):1675-83.

[3]. Takanezawa Y, et al. Variation in the activity of distinct cytochalasins as autophagy inhibitiors in human lung A549 cells. Biochem Biophys Res Commun. 2017 Dec 16;494(3-4):641-647.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
705.1±60.0 °C at 760 mmHg

[ Melting Point ]:
206ºC

[ Molecular Formula ]:
C₂₈H₃₃NO₇

[ Molecular Weight ]:
495.564

[ Flash Point ]:
380.2±32.9 °C

[ Exact Mass ]:
495.225708

[ PSA ]:
114.46000

[ LogP ]:
1.92

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

[ Index of Refraction ]:
1.608

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA5360000

CHEMICAL NAME :: Cytochalasin E

CAS REGISTRY NUMBER :: 36011-19-5

LAST UPDATED :: 199203

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C28-H33-N-O7

MOLECULAR WEIGHT :: 495.62

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - coma Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 32,135,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2600 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - coma Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 32,135,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1300 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - coma Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 32,135,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2700 ug/kg

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

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 38,438,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - coma Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 32,135,1975 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 8100 ug/kg

SEX/DURATION :: female 7-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 38,438,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 3900 ug/kg

SEX/DURATION :: female 7-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 25,11,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 3600 ug/kg

SEX/DURATION :: female 7-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 25,11,1982

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+,T

[ Risk Phrases ]:
R26/27/28

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

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
HA5360000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
29349990

Articles

Excessive expression of the plant kinesin TBK5 converts cortical and perinuclear microtubules into a radial array emanating from a single focus.

Plant Cell Physiol. 48(5) , 753-61, (2007)

TBK5 is a plant-specific kinesin constantly expressed in tobacco BY-2 cells. An analysis of the distribution of green fluorescent protein-tagged TBK5 (GFP-TBK5) transiently expressed in BY-2 protoplas...

Cytochalasin E alters the cytoskeleton and decreases ENaC activity in Xenopus 2F3 cells.

Am. J. Physiol. Renal Physiol. 307(1) , F86-95, (2014)

Numerous reports have linked cytoskeleton-associated proteins with the regulation of epithelial Na(+) channel (ENaC) activity. The purpose of the present study was to determine the effect of actin cyt...

Biosynthesis: A carbonate architect emerges.

Nat. Chem. Biol. 10(7) , 486-7, (2014)