CAS 3148-09-2|Verrucarin A

Introduction：Basic information about CAS 3148-09-2|Verrucarin A, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Verrucarin A BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Synonyms

Common Name	Verrucarin A
CAS Number	3148-09-2	Molecular Weight	488.52700
Density	1.32g/cm3	Boiling Point	747.4ºC at 760mmHg
Molecular Formula	C₂₆H₃₂O₉	Melting Point	>360ºC
MSDS	ChineseUSA	Flash Point	250.2ºC
Symbol	GHS06	Signal Word	Danger

Names

Name	verrucarin A
Synonym	More Synonyms

Verrucarin A BiologicalActivity

Description	Verrucarin A (Muconomycin A), a Type D macrocyclic mycotoxin derived from the pathogen fungus Myrothecium verrucaria, is an inhibitor of protein synthesis. Verrucarin A inhibits growth of leukemia cell lines and activates caspases and apoptosis and inflammatory signaling in macrophages. VA effectively increased the phosphorylation of p38 MAPK and diminished the phosphorylation of ERK/Akt. VA caused cell cycle deregulation through the induction of p21 and p53[1][2].
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>Cancer
In Vitro	Verrucarin A (0-0.6 μM/ml; 24-48 hours)-induces time- and dose-dependent growth inhibition in MCF-7 cells[1]. Verrucarin A increases the levels of reactive oxygen species (ROS), and subsequently induces mitochondrial membrane potential (Δψm) loss, leading to the increase of Bax/Bcl-2 ratio, cytochrome c release, caspase activation, PARP degradation, and apoptosis[1]. Cell Viability Assay[1] Cell Line: MCF-7 cells Concentration: 0-0.6 μM/ml Incubation Time: 24 and 48 hours Result: Growth of MCF-7 cells is significantly inhibited in a dose- and time-dependent manner, with the IC50s of 0.41 and 0.29 μM/ml for 24- and 48-h treatment periods, respectively.
References	[1]. Palanivel K, et al. Verrucarin A alters cell-cycle regulatory proteins and induces apoptosis through reactive oxygen species-dependent p38MAPK activation in the human breast cancer cell line MCF-7. Tumour Biol. 2014;35(10):10159-10167. [2]. Palanivel K, et al. Verrucarin A, a protein synthesis inhibitor, induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D. Biotechnol Lett. 2013;35(9):1395-1403.

Chemical & Physical Properties

Density	1.32g/cm3
Boiling Point	747.4ºC at 760mmHg
Melting Point	>360ºC
Molecular Formula	C₂₆H₃₂O₉
Molecular Weight	488.52700
Flash Point	250.2ºC
Exact Mass	488.20500
PSA	120.89000
LogP	1.78050
Index of Refraction	1.584
InChIKey	NLUGUZJQJYVUHS-IDXDZYHTSA-N
SMILES	CC1=CC2OC3CC4OC(=O)C=CC=CC(=O)OCCC(C)C(O)C(=O)OCC2(CC1)C4(C)C31CO1

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WH1314900

CHEMICAL NAME :: Spiro(16,18-methano-1H,3H,23H-(1,6,12)trioxacycloocta decino(3,4-d)(1)benzo pyran-17(18H),2'- oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-tr imethyl-, stereoisomer

CAS REGISTRY NUMBER :: 3148-09-2

LAST UPDATED :: 199209

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C27-H34-O9

MOLECULAR WEIGHT :: 502.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 870 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure) Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3900 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 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 :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 540 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 :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 14 mg/kg/8W-C

TOXIC EFFECTS :: Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 5 mg/kg/50D-C

TOXIC EFFECTS :: Blood - leukopenia Blood - changes in cell count (unspecified) Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 1 nmol/L

REFERENCE :: PLMEAA Planta Medica. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1953- Volume(issue)/page/year: 34,231,1978

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300 + H310 + H330
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;
Risk Phrases	26/27/28
RIDADR	UN 2811 6.1/PG 1
WGK Germany	3
RTECS	WH1314900
Packaging Group	I
Hazard Class	6.1(a)

Synonyms

Muconomycin A

Antibiotic 379Y

VER A

Verrucarin A

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