Lygosporin A

Names

[ Name ]:
Lygosporin A

[Synonym ]:
Methylmalonate
CYTOCHALACIND
Zygosporin A
Lygosporin A
CYTOCHALICIND
MFCD00077706
19-trien-17-one
Cytochalasin D,Zygosporin A
CYTOCHALASIN D
1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (7Z,13E)-
(7Z,13E)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylidene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1H-cycloundeca[d]isoindol-15-yl acetate
Cytohalasin d
EINECS 244-804-1
(7Z,13E)-3-Benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1H-cycloundeca[d]isoindol-15-yl acetate
7,18-Dihydroxy-10-phenyl-5,16,18-trimethyl-(11)cytochalas-21-acetoxy-6(12),13,19-trien-17-one
13C-Cytochalasin D

Biological Activity

[Description]:

Cytochalasin D (Zygosporin A; NSC 209835) is a potent and cell-permeable inhibitor of actin polymerization derived from fungus, inhibits the G-actin–cofilin interaction by binding to G-actin. Cytochalasin D (Zygosporin A; NSC 209835) also inhibits the binding of cofilin to F-actin and decreases the rate of both actin polymerization and depolymerization in living cells[1][2][3].

[Related Catalog]:

Signaling Pathways >> Cytoskeleton >> Arp2/3 Complex

Research Areas >> Others

[Target]

G-actin[1]

[References]

[1]. Shoji K, et al. Cytochalasin D acts as an inhibitor of the actin-cofilin interaction. Biochem Biophys Res Commun. 2012 Jul 20;424(1):52-7.

[2]. Flanagan MD, et al. Cytochalasins block actin filament elongation by binding to high affinity sites associated with F-actin. J Biol Chem. 1980 Feb 10;255(3):835-8.

[3]. May JA, et al. GPIIb-IIIa antagonists cause rapid disaggregation of platelets pre-treated with cytochalasin D. Evidence that the stability of platelet aggregates depends on normal cytoskeletal assembly. Platelets. 1998;9(3-4):227-32.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
712.1±60.0 °C at 760 mmHg

[ Melting Point ]:
255-260ºC

[ Molecular Formula ]:
C₃₀H₃₇NO₆

[ Molecular Weight ]:
507.618

[ Flash Point ]:
384.5±32.9 °C

[ Exact Mass ]:
507.262085

[ PSA ]:
112.93000

[ LogP ]:
2.64

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

[ Index of Refraction ]:
1.597

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GZ4850000

CHEMICAL NAME :: 1H-Cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3-alpha,4,5,6,6-alpha,9,10,12,15- decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-meth ylene-, 15-acetate

CAS REGISTRY NUMBER :: 22144-77-0

LAST UPDATED :: 199806

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C30-H37-N-O6

MOLECULAR WEIGHT :: 507.68

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 ug/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 36 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - excitement

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1850 ug/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 gm/kg

SEX/DURATION :: female 7-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1500 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1500 ug/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2100 ug/kg

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

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 900 ug/kg

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

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 4100 ug/kg

SEX/DURATION :: female 7-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 4700 ug/kg

SEX/DURATION :: female 7-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 600 ug/kg

REFERENCE :: JEZOAO Journal of Experimental Zoology. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1904- Volume(issue)/page/year: 250,339,1989

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H361

[ Precautionary Statements ]:
P264-P281-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45-S36-S37

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
GZ4850000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Preparation

Articles

Inhibition of autophagy suppresses sertraline-mediated primary ciliogenesis in retinal pigment epithelium cells.

PLoS ONE 10(2) , e0118190, (2015)

Primary cilia are conserved cellular organelles that regulate diverse signaling pathways. Autophagy is a complex process of cellular degradation and recycling of cytoplasmic proteins and organelles, a...

A new genetically encoded single-chain biosensor for Cdc42 based on FRET, useful for live-cell imaging.

PLoS ONE 9(5) , e96469, (2014)

Cdc42 is critical in a myriad of cellular morphogenic processes, requiring precisely regulated activation dynamics to affect specific cellular events. To facilitate direct observations of Cdc42 activa...

Cargoing P-gp inhibitors via nanoparticle sensitizes tumor cells against doxorubicin.

Int. J. Pharm. 478(2) , 745-52, (2015)

Inhibitors against multidrug resistance (MDR) efflux transporters have failed in most clinical settings due to unfavorable pharmacokinetic interactions with co-administered anti-cancer drug and their ...