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Merck

A2263

α-Amanitin

From Amanita phalloides, ≥85% (HPLC), RNA polymerase II and III inhibitor, powder

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A propos de cet article

Formule empirique (notation de Hill) :
C39H54N10O14S
Numéro CAS:
Poids moléculaire :
918.97
UNSPSC Code:
12352202
NACRES:
NA.32
PubChem Substance ID:
EC Number:
245-432-2
MDL number:
Beilstein/REAXYS Number:
1071138
Assay:
≥85% (HPLC)
Form:
powder
Quality level:
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Nom du produit

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

biological source

Amanita phalloides

Quality Level

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

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

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

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.

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.

Disclaimer

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

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

Classe de stockage

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

ppe

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


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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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