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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

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Product Information Sheet

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