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A2263

Sigma-Aldrich

α-Amanitin

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

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About This Item

Formule empirique (notation de Hill):
C39H54N10O14S
Numéro CAS:
23109-05-9
Poids moléculaire :
918.97
Numéro Beilstein :
1071138
Numéro CE :
245-432-2
Numéro MDL:
MFCD00215842
Code UNSPSC :
12352202
ID de substance PubChem :
24890639
Nomenclature NACRES :
NA.32

Source biologique

Amanita phalloides

Niveau de qualité

200

Pureté

≥85% (HPLC)

Forme

powder

Poids mol.

918.97  g/mol

Couleur

white to light yellow

Pf

254-255 °C (lit.)

Solubilité

H2O: 1.0 mg/mL

ε (coefficient d'extinction)

13,500 at 310 nm in H2O at 1 M

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

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

Actions biochimiques/physiologiques

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.

Attention

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H373

Classification des risques

Acute Tox. 1 Oral - STOT RE 2

Organes cibles

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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
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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