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A2263

Sigma-Aldrich

α-Amanitin

from Amanita phalloides, ≥85% (HPLC), powder

Empirical Formula (Hill Notation):
C39H54N10O14S
CAS Number:
Molecular Weight:
918.97
Beilstein:
1071138
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

biological source

Amanita phalloides

assay

≥85% (HPLC)

form

powder

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

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Amino Acid Sequence

Asn-Hyp-Hyi-Trp-Gly-Ile-Gly-Cys [Bridge: 4-8]

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

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.

Caution

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

Reconstitution

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Oral - STOT RE 2

Storage Class Code

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

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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)
Christian Vigneault et al.
Reproduction (Cambridge, England), 137(2), 245-257 (2008-11-07)
Bovine early embryos are transcriptionally inactive and subsist through the initial developmental stages by the consumption of the maternal supplies provided by the oocyte until its own genome activation. In bovine, the activation of transcription occurs during the 8- to...

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