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A2263

Sigma-Aldrich

α-Amanitin

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

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Empirical Formula (Hill Notation):
C39H54N10O14S
CAS Number:
23109-05-9
Molecular Weight:
918.97
Beilstein:
1071138
EC Number:
245-432-2
MDL number:
MFCD00215842
PubChem Substance ID:
24890639
NACRES:
NA.32

biological source

Amanita phalloides

Quality Level

200

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
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 - H373

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

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Marie-Line Bortolin-Cavaillé et al.
Nucleic acids research, 37(10), 3464-3473 (2009-04-03)
MicroRNAs are tiny RNA molecules that play important regulatory roles in a broad range of developmental, physiological or pathological processes. Despite recent progress in our understanding of miRNA processing and biological functions, little is known about the regulatory mechanisms that
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)
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
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