CAS 23109-05-9

α-Amanitin

Description:

α-Amanitin is a cyclic peptide and a potent toxin primarily found in certain species of mushrooms, particularly the Amanita genus, such as the infamous Amanita phalloides, commonly known as the death cap mushroom. It is composed of eight amino acids and is known for its high toxicity, primarily affecting the liver and kidneys. The mechanism of action involves the inhibition of RNA polymerase II, an essential enzyme in the transcription process of eukaryotic cells, leading to a halt in mRNA synthesis and subsequent cellular apoptosis. α-Amanitin is characterized by its stability in acidic environments, which contributes to its toxicity when ingested. Symptoms of poisoning can include gastrointestinal distress, followed by a deceptive period of apparent recovery, after which severe liver and kidney damage may occur. Due to its high toxicity and potential for fatal outcomes, α-Amanitin is of significant interest in both toxicology and pharmacology, with ongoing research into its mechanisms and potential therapeutic applications.

Formula: C₃₉H₅₄N₁₀O₁₄S

InChI: InChI=1/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)/t16?,17?,19?,23-,24-,25-,26-,27-,31-,32-,64+/m0/s1

Synonyms:

• alpha-Amanitin
• Brn 1071138
• Cyclic(L-asparaginyl-4-hydroxy-L-prolyl-(R)-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl), cyclic (4-8)-sulfide, (R)-S-oxide
• Hsdb 3458
• alpha-Amanitine
• alpha-Amatoxin
• 9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8,9)(1,5,8,11,14)thiatetraazacyclooctadecino(18,17-b)indole, cyclic peptide deriv.
• 2-[29-(Butan-2-Yl)-21-(3,4-Dihydroxybutan-2-Yl)-2,14-Dihydroxy-11-Oxido-5,8,20,23,24,27,30,33-Octaoxo-1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23A-Octadecahydro-9,18-(Epiminoethanoiminoethanoiminoethanoiminomethano)Pyrrolo[1',2':8,9][1,5,8,11,14]Thiatetraazacyclooctadecino[18,17-B]Indol-6-Yl]Acetamide
• 2-[(2R,6S,9R,11R,18S,21S,23aS,29S)-29-[(2S)-butan-2-yl]-21-[(2R,3R)-3,4-dihydroxybutan-2-yl]-2,14-dihydroxy-11-oxido-5,8,20,23,24,27,30,33-octaoxo-1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23a-octadecahydro-9,18-(epiminoethanoiminoethanoiminoethanoiminomethano)pyrrolo[1',2':8,9][1,5,8,11,14]thiatetraazacyclooctadecino[18,17-b]indol-6-yl]acetamide

α-Amanitin, from Amanita Phalloides

CAS: 23109-05-9

α-Amanitin, from Amanita Phalloides

Formula: C₃₉H₅₄N₁₀O₁₄S

Purity: 93.6% (310nm) (Typical Value in Batch COA)

Color and Shape: Powder

Molecular weight: 918.96966g/mol

Ref: 54-BIA8415

α-Amanitine

CAS: 23109-05-9

Formula: C₃₉H₅₄N₁₀O₁₄S

Purity: (UV) ≥ 97.0%

Color and Shape: White to off-white solid

Molecular weight: 918.97

Ref: 7W-GE9202

α-Amanitin

CAS: 23109-05-9

alpha-Amanitin is the principal toxin of poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II.

Formula: C₃₉H₅₄N₁₀O₁₄S

Purity: 96.44% - ≥90%

Color and Shape: Solid

Molecular weight: 918.97

Ref: TM-T13540

α-Amanitin

CAS: 23109-05-9

a-Amanitin is a cyclic peptide that is found in mushrooms of the genus "Amanita", which can cause toxic effects if eaten. It has been shown to inhibit the growth of cancer cells by inhibiting mitochondrial membrane potential and reducing dna synthesis, as well as by triggering apoptosis. The structural analysis of a-amanitin has shown that it binds to surface glycoproteins on myeloma cells and triggers the activation of toll-like receptors (TLRs), which initiate an immune response against myeloma cells. This cyclic peptide also has been shown to reduce hepatic steatosis in mice by affecting mitochondrial membrane potential and inducing metabolic changes.
Indocyanine green, a fluorescent dye, has been shown to prevent α-amanitin toxicity in mice (Wang et al, 2023), and could be a possible antidote to poisoning by Amanita, such as death cap mushroom Amanita phalloides, which is the cause of over 90% of fatal mushroom poisoning.

Formula: C₃₉H₅₄N₁₀O₁₄S

Purity: Min. 95 Area-%

Color and Shape: White Powder

Molecular weight: 918.97 g/mol

Ref: 3D-FA57619