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3148-09-2

3148-09-2 structure
3148-09-2 structure
  • Name: Verrucarin A
  • Chemical Name: verrucarin A
  • CAS Number: 3148-09-2
  • Molecular Formula: C26H32O9
  • Molecular Weight: 488.52700
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-09-22 03:12:18
  • Modify Date: 2024-01-09 12:50:03
  • 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].
Name verrucarin A
Synonyms Muconomycin A
Antibiotic 379Y
VER A
Verrucarin A
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
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.
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

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
Symbol GHS06
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)
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