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Merck

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
UNSPSC Code:
12352202
NACRES:
NA.32
PubChem Substance ID:
EC Number:
245-432-2
MDL number:
Beilstein/REAXYS Number:
1071138

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Product Name

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

InChI key

CIORWBWIBBPXCG-UHFFFAOYSA-N

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)

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

biological source

Amanita phalloides

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

Quality Level

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1 of 4

This Item
A1304D4288L8511
form

powder

form

powder

form

powder

form

powder

assay

≥85% (HPLC)

assay

≥85% (HPLC)

assay

≥85% (HPLC)

assay

≥85% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

mol wt

918.97  g/mol

mol wt

-

mol wt

-

mol wt

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 1.0 mg/mL

solubility

-

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

solubility

H2O: 50 mg/mL

Application

α-Amanitin has been used:
  • for inducing transcriptional arrest in NT2 cells prior to immunofluorescence assay[1]
  • to induce nephrotoxicity in mice renal tissues[2]
  • to induce and analyse genotoxicity in mice bone marrow cells by cell viability assay, comet assay and chromosomal aberration assay[3]

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.

Disclaimer

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

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.

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

wgk

WGK 3

ppe

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


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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)
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
Davide Carnevali et al.
DNA research : an international journal for rapid publication of reports on genes and genomes, 24(1), 59-69 (2016-12-29)
With more than 500,000 copies, mammalian-wide interspersed repeats (MIRs), a sub-group of SINEs, represent ∼2.5% of the human genome and one of the most numerous family of potential targets for the RNA polymerase (Pol) III transcription machinery. Since MIR elements
Evaluation of the genotoxicity of alpha-amanitin in mice bone marrow cells
Marciniak B, et al.
Toxicon, 137, 1-6 (2017)
Emmanuelle Querido et al.
Journal of cell science, 124(Pt 10), 1703-1714 (2011-04-23)
Transcripts containing expanded CNG repeats, which are found in several neuromuscular diseases, are not exported from the nucleus and aggregate as ribonuclear inclusions by an unknown mechanism. Using the MS2-GFP system, which tethers fluorescent proteins to a specific mRNA, we

Questions

  1. Can we use this product (alpha amanitin: A2263) to block RNA PII for yeast cell (S. cerevisiae)?

    1 answer
    1. Yes, yeasts are eukaryotic organisms. α-Amanitin inhibits eukaryotic RNA polymerase II and III, but does not inhibit RNA polymerase I or bacterial RNA polymerase.

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