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alpha-amanitin

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Description

Alpha-Amanitin: A cyclic octapeptide with a thioether bridge between the cystine and tryptophan. It inhibits RNA POLYMERASE II. Poisoning may require LIVER TRANSPLANTATION. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

alpha-amanitin : A heterodetic cyclic peptide consisting of eight amino acid residues and containing a thioether bridge between a cysteine and a tryptophan residue. It is found in a number of poisonous mushrooms, including Amanita phalloides (the death cap), Galerina marginata, and and Conocybe filaris. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID20054823
SCHEMBL ID71812
MeSH IDM0000844

Synonyms (8)

Synonym
alpha-amanitine
alpha-amanitin
23109-05-9
2-[(6s,9r,11r,18s,21s,23as)-29-sec-butyl-21-[(2r)-2,3-dihydroxy-1-methylpropyl]-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)pyrrol
alpha-am
SCHEMBL71812
DTXSID1036709
2-[(1r,4s,10s,13s,16s,27r,34s)-34-butan-2-yl-13-[(3r)-3,4-dihydroxybutan-2-yl]-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-

Research Excerpts

Toxicity

The LD50 of alpha-amanitin was determined with intravenous and intraperitoneal injections. The cyclopeptide could reside in the two organs for a long last toxic effect.

ExcerptReferenceRelevance
" Administration of studied antidotes without alpha-AMA, was not associated with any adverse effects in hepatocytes."( Failure of benzylpenicillin, N-acetylcysteine and silibinin to reduce alpha-amanitin hepatotoxicity.
Dziegiel, P; Izykowska, I; Magdalan, J; Nowak, M; Ostrowska, A; Piotrowska, A; Szelag, A,
)
0.13
"The forward and reverse cDNA subtractive libraries before and after the toxic effect of alpha-amanitin were constructed by suppression subtractive hybridization and randomly selected clones from each subtractive library were screened by PCR and dot blot hybridization."( Study on genes with altered expression in alpha-amanitin poisoned mice and evaluation on antagonistic effects of traditional Chinese medicines against toxicity of alpha-amanitin.
Cao, M; Chen, Q; Hou, RT; Liu, J; Sun, Q; Xiang, WL; Yan, ZY; Yang, ZR; Zhang, J; Zhao, J, 2009
)
0.35
"To study the toxic effect of alpha-amanitin from Amanita fungi on mice in vivo."( [Toxicity of alpha-amanitin on mice in vivo].
Cao, M; Nie, YY; Yan, L; Yang, ZR; Zhao, J, 2009
)
0.35
"The LD50 of alpha-amanitin was determined with intravenous and intraperitoneal injections of alpha-amanitin."( [Toxicity of alpha-amanitin on mice in vivo].
Cao, M; Nie, YY; Yan, L; Yang, ZR; Zhao, J, 2009
)
0.35
" The cyclopeptide alpha-amanitin could reside in the two organs for a long last toxic effect."( [Toxicity of alpha-amanitin on mice in vivo].
Cao, M; Nie, YY; Yan, L; Yang, ZR; Zhao, J, 2009
)
0.35
" The results demonstrated that the toxin was not absorbed through the skin of the mice and that the percutaneous application of alpha amanitin did not have any toxic effects."( Dermal absorption and toxicity of alpha amanitin in mice.
Colakoglu, S; Erdem, H; Karahan, S; Kaya, E; Oktay, M; Surmen, MG; Turan, H; Yaykasli, KO, 2014
)
0.4
" Therefore, this study is aimed at comparing the toxic effects of alpha- and beta-amanitin on the MCF-7 cell line."( Evaluation and comparison of alpha- and beta-amanitin toxicity on MCF-7 cell line.
Bayram, R; Bayram, S; Gepdıremen, AA; Kaya, E; Yavuz, MZ; Yaykaşli, E; Yaykaşli, KO; Yilmaz, İ, 2014
)
0.4
"Amanita phalloides is one of the most toxic mushrooms worldwide, being responsible for the majority of human fatal cases of mushroom intoxications."( Antidotal effect of cyclosporine A against α-amanitin toxicity in CD-1 mice, at clinical relevant doses.
Bovolini, A; Carvalho, A; Carvalho, F; Costa, VM; das Neves, RP; Duarte, JA; Figueiredo, PR; Garcia, J; Malheiro, R; Rodrigues, DF, 2022
)
0.72
" Furthermore, we demonstrate that ICG is effective in blocking the toxic effect of α-amanitin in cells, liver organoids, and male mice, resulting in an overall increase in animal survival."( Identification of indocyanine green as a STT3B inhibitor against mushroom α-amanitin cytotoxicity.
Deng, Y; Luo, Y; Neely, GG; Shi, YC; Wan, AH; Wan, G; Wang, B; Wang, QP; Xu, Y; Xue, Y; Zhang, RX; Zhang, X; Zhao, BC; Zhao, XY, 2023
)
0.91

Pharmacokinetics

ExcerptReferenceRelevance
" We demonstrated the superior pharmacokinetic properties and therapeutic efficacy of the resulting Fc-SMDC over the SMDC in a prostate cancer xenograft mouse model."( Enhancing the Pharmacokinetics and Antitumor Activity of an α-Amanitin-Based Small-Molecule Drug Conjugate via Conjugation with an Fc Domain.
Avrutina, O; Gallo, F; Hechler, T; Kolmar, H; Korsak, B; Müller, C; Pahl, A; Yanakieva, D, 2021
)
0.62

Dosage Studied

ExcerptRelevanceReference
" Moreover, both in Drosophila and mammals, dosage compensation requires the contribution of specific non-coding RNAs."( RNA is an integral component of chromatin that contributes to its structural organization.
Azorín, F; Rodríguez-Campos, A, 2007
)
0.34
" The results demonstrated that simultaneous administration of α-AMA and each of tested antidotes (BPCN, CEFT, RIFSV) effectively protected human hepatocytes; however, in the group dosed with BPCN, the highest hepatocyte viability was observed."( Comparative antidotal efficacy of benzylpenicillin, ceftazidime and rifamycin in cultured human hepatocytes intoxicated with α-amanitin.
Dziędgiel, P; Gomułkiewicz, A; Magdalan, J; Ostrowska, A; Piotrowska, A; Szeląg, A, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (187)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (1.60)18.7374
1990's0 (0.00)18.2507
2000's32 (17.11)29.6817
2010's109 (58.29)24.3611
2020's43 (22.99)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (2.08%)6.00%
Case Studies6 (3.13%)4.05%
Observational0 (0.00%)0.25%
Other182 (94.79%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]