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A2263 Sigma-Aldrich

α-Amanitin

from Amanita phalloides, ≥90% (HPLC), powder

  • CAS Number 23109-05-9

  • Empirical Formula (Hill Notation) C39H54N10O14S

  • Molecular Weight 918.97

  •  Beilstein/REAXYS Number 1071138

  •  EC Number 245-432-2

  •  MDL number MFCD00215842

  •  PubChem Substance ID 24890639

  •  NACRES NA.32

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Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, DNA-RNA Transcription Regulators, Gene Regulation and Expression, Mushroom,
Quality Level   200
biological source   Amanita phalloides
assay   ≥90% (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

Description

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
BD6195000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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