A2263

α-Amanitin

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

• 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

Properties

• Quality Level: 200
• 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

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 Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300 - H373
• Precautionary Statements: P260 - P264 - P270 - P301 + P310 - P314 - P405
• 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