beta-Amanitin

Names

[ Name ]:
beta-Amanitin

[Synonym ]:
MFCD00151212
8,20,23,24,27,30,33-octaoxo--dihydroxy-1-methylpropyl)-11-oxide
EINECS 244-244-8
B-amanitin from amanita phalloides
B-Amanitine
,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-2,14-dihydroxy-21-(2,3

Biological Activity

[Description]:

β-Amanitin is a cyclic peptide toxin in the poisonous Amanita phalloides mushroom. β-Amanitin inhibits inhibits eukaryotic RNA polymerase II and III. β-Amanitin inhibits protein synthesis. β-Amanitin can be used as a cytotoxic component of antibody-drug conjugates (ADCs)[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin

[Target]

Traditional Cytotoxic Agents

[In Vitro]

β-Amanitin (0.01-100 µg/mL; 36 hours) shows toxicity in MCF-7 cells, and the rates of cell viability are calculated as 52%, 62%, 84%, 86%, and 91% at concentrations of 100, 10, 1, 0.1, and 0.01 µg/mL, respectively[2]. β-Amanitin shows a great inhibition of protein synthesis at both concentrations (10 µg/mL and 1 µg/mL) in MCF-7 cells for 24 hours[2]. Cell Viability Assay[2] Cell Line: MCF-7 cells Concentration: 0.01, 0.1, 1, 10, 100 µg/mL Incubation Time: 36 hours Result: Showed toxicity in MCF-7 cells.

[References]

[1]. Kaya E, et al. Evaluation and comparison of alpha- and beta-amanitin toxicity on MCF-7 cell line. Turk J Med Sci. 2014;44(5):728-32.

[2]. Lutz C, et al. Alpha- and Beta-Amanitin Total Synthesis. Angew Chem Int Ed Engl. 2020 Feb 24.

Chemical & Physical Properties

[ Molecular Formula ]:
C₃₉H₅₃N₉O₁₅S

[ Molecular Weight ]:
919.95400

[ Exact Mass ]:
919.33800

[ PSA ]:
394.30000

[ Index of Refraction ]:
1.695

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NJ8324000

CAS REGISTRY NUMBER :: 21150-22-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C39-H53-N9-O15-S

MOLECULAR WEIGHT :: 920.07

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 269,223,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,2142,1972

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H310-H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-P310

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
R26/27/28

[ Safety Phrases ]:
S7;S28;S45;S36/S37/S39

[ RIDADR ]:
UN 3462 6.1/PG 1

[ RTECS ]:
NJ8324000

[ Hazard Class ]:
6.1(a)

Articles

[Determination of amanitatoxins by HPLC].

Chudoku. Kenkyu. 16(4) , 441-5, (2003)

High-performance liquid chromatographic (HPLC) assay has been developed for the simultaneous determination of alpha-amanitin, beta-amanitin and phalloidin in serum. Three toxins were extracted by refl...

Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS) in toxicological analysis. Studies on the detection of clobenzorex and its metabolites within a systematic toxicological analysis procedure by GC-MS and by immunoassay and studies on the detection of alpha- and beta-amanitin in urine by atmospheric pressure ionization electrospray LC-MS.

J. Chromatogr. B. Biomed. Sci. Appl. 689(1) , 81-9, (1997)

GC-MS is the method of choice for toxicological analysis of toxicants volatile in GC while non-volatile and/or thermally labile toxicants need LC-MS for their determination. Studies are presented on t...

Validated electrospray liquid chromatographic-mass spectrometric assay for the determination of the mushroom toxins alpha- and beta-amanitin in urine after immunoaffinity extraction.

J. Chromatogr. B. Biomed. Sci. Appl. 748(1) , 125-35, (2000)

Specific detection of amanitins in body fluids is necessary for an early diagnosis of an intoxication with amanita mushrooms. In this paper, a liquid chromatographic-mass spectrometric assay after imm...