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Merck
CN

A2263

α-Amanitin

From Amanita phalloides, ≥85% (HPLC), RNA polymerase II and III inhibitor, powder

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About This Item

Empirical Formula (Hill Notation):
C39H54N10O14S
CAS Number:
Molecular Weight:
918.97
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
245-432-2
MDL number:
Beilstein/REAXYS Number:
1071138
Assay:
≥85% (HPLC)
Form:
powder
Quality level:
Technical Service
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Product Name

α-Amanitin, from Amanita phalloides, ≥85% (HPLC), powder

biological source

Amanita phalloides

Quality Level

assay

≥85% (HPLC)

form

powder

mol wt

918.97  g/mol

color

white to light yellow

mp

254-255 °C (lit.)

solubility

H2O: 1.0 mg/mL

ε (extinction coefficient)

13,500 at 310 nm in H2O at 1 M

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2

InChI

1S/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59)

InChI key

CIORWBWIBBPXCG-UHFFFAOYSA-N

Application

α-Amanitin has been used:
  • for inducing transcriptional arrest in NT2 cells prior to immunofluorescence assay
  • to induce nephrotoxicity in mice renal tissues
  • to induce and analyse genotoxicity in mice bone marrow cells by cell viability assay, comet assay and chromosomal aberration assay

Biochem/physiol Actions

Inhibits eukaryotic RNA polymerase II and III; does not inhibit RNA polymerase I or bacterial RNA polymerase; inhibits mammalian protein synthesis.
The major toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but does not inhibit RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.

Preparation Note

Store a 1 mg/ml aqueous stock solution frozen at -20°C. It does not degrade with repeated freeze-thaw cycles. Dilute into the appropriate buffer immediately prior to use. Product is destroyed by concentrated acid or base.

Disclaimer

When stored frozen in the dark, retained samples were found to be greater than 99% by HPLC after two years.


pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 1 Oral - STOT RE 2

target_organs

Kidney,Blood,Liver,Gastrointestinal tract,Respiratory Tract,Central nervous system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Prerna Sethi et al.
Neuroscience letters, 459(2), 100-104 (2009-05-02)
Micro-RNA (miRNA) mediated regulation of messenger RNA (mRNA) complexity in the central nervous system (CNS) is emerging as a critical factor in the control of CNS-specific gene expression during development, plasticity, aging and disease. In these studies, miRNA array and
Evaluation of the genotoxicity of alpha-amanitin in mice bone marrow cells
Marciniak B, et al.
Toxicon, 137, 1-6 (2017)
Alpha-amanitin poisoning, nephrotoxicity and oxidative stress: an experimental mouse model
Ergin M, et al.
Iranian Red Crescent Medical Journal, 17(8), e28068-e28068 (2015)



Global Trade Item Number

SKUGTIN
A2263-1MG04061833349946
A2263-100MG04061833228029