alpha-Amanitin

Modify Date: 2024-01-02 11:42:42

alpha-Amanitin Structure
alpha-Amanitin structure
Common Name alpha-Amanitin
CAS Number 23109-05-9 Molecular Weight 918.97000
Density 1.57 g/cm3 Boiling Point 1622.2ºC at 760 mmHg
Molecular Formula C39H54N10O14S Melting Point 254-255ºC(lit.)
MSDS Chinese USA Flash Point 934.9ºC
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger

 Use of alpha-Amanitin


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

 Names

Name α-amanitin
Synonym More Synonyms

 alpha-Amanitin Biological Activity

Description alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II.
Related Catalog
Target

ADCs cytotoxin, RNA-polymerase II[1]

In Vitro Alpha-Amanitin decreases TAF15 mRNA and TAF15 protein levels in MKN45 cells, and inhibits the RNAPII activity towards TAF15 mRNA[2]. alpha-Amanitin decreases cell viability by 14%, 21%, 41%, 44%, and 50% at concentrations of 100, 10, 1, 0.1, and 0.01 µg/mL, respectively. The LD50 of the alpha-Amanitin at 36 h is measured as 1 µg/mL. The total amount of protein within the cell at 24 h is significantly increased for the 1 µg/mL dose of alpha-Amanitin compared to the control[3]. Alpha-Amanitin dramatically decreases the expression of gap junctional genes (Gja1, Gja4 and Gjc1) and gonadotropin receptor genes (FSHr and LHr) in cumulus cells[4].
In Vivo The intravenous LD50 dose of alpha-Amanitin is 0.327 mg/kg body weight after intravenous injection into BALB/c mice. After 12 h of alpha-Amanitin injection in caudal vein, the levels of WBC, RBC and HGB decrease significantly, while those of BUN and Crea increase significantly in serum. alpha-Amanitin inhibits some genes (Hsp90b1, Irx4, etc.), whose encoded proteins regulate the RNA polymerase II activity. alpha-Amanitin down-regulates some proteins (Nmi, Trpc5, etc.) taking part in the transcription progress[1]. alpha-Amanitin has potent activity in DTC suppression. Mice injected with alpha-Amanitin (0.4 mg/kg, i.p.)-treated cells maintain their body weight, while those receiving a peritoneal injection of MKN45 cells show a constant decrease in body weight[2].
Cell Assay The MTT assay is used to evaluate the overall functional integrity and viability of the cultured cells. The MCF-7 cells are put into 96-well plates (2×104 for each well), which are incubated for 24 h. The specific concentrations of alpha-Amanitin and β-Amanitin are added to the cell culture medium, and plates are incubated for an additional 36 h. MTT solution (1:10 ratio) and dimethyl sulfoxide (DMSO) (100 µL) are then added to the cell culture medium and plates are incubated overnight. The absorbance is measured at 570 nm on a plate reader. This experiment is repeated 3 times. The absorbance data are calculated as percentages according to the control group.
Animal Admin For tumorigenicity tests, six colonies (untreated) and DTCs derived from MKN45 cells are individually injected subcutaneously into the left and right side of the backs of six 6-week-old female nude mice (BALB/cAjcl-nu/nu). These mice are monitored for 49 days after the inoculation or until tumors reach 10 mm in the largest diameter, and are then euthanized. For the PC model, 1.0×106 MKN45 cells are injected intraperitoneally into six 6-week-old female nude mice (BALB/cAjcl-nu/nu). Mice are then treated with CIS (4.0 mg/kg, intraperitoneal administration) or a combination of CIS and alpha-Amanitin (0.4 mg/kg, intraperitoneal administration). For the combination treatment, alpha-Amanitin is given 24 hours before CIS. Body weight is monitored for 28 days after the treatment.
References

[1]. Zhao J, et al. Pathological effects of the mushroom toxin alpha-amanitin on BALB/c mice. Peptides. 2006 Dec;27(12):3047-3052.

[2]. Kume K, et al. α-Amanitin Restrains Cancer Relapse from Drug-Tolerant Cell Subpopulations via TAF15. Sci Rep. 2016 May 16;6:25895

[3]. 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

[4]. Park MW, et al. RNA Polymerase II Inhibitor, α-Amanitin, Affects Gene Expression for Gap Junctions and Metabolic Capabilities of Cumulus Cells, but Not Oocyte, during in vitro Mouse Oocyte Maturation. Dev Reprod. 2013 Mar;17(1):63-72

 Chemical & Physical Properties

Density 1.57 g/cm3
Boiling Point 1622.2ºC at 760 mmHg
Melting Point 254-255ºC(lit.)
Molecular Formula C39H54N10O14S
Molecular Weight 918.97000
Flash Point 934.9ºC
Exact Mass 918.35400
PSA 400.09000
Index of Refraction 1.694

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BD6195000
CHEMICAL NAME :
alpha-Amanitine
CAS REGISTRY NUMBER :
23109-05-9
LAST UPDATED :
199612
DATA ITEMS CITED :
23
MOLECULAR FORMULA :
C39-H54-N10-O14-S
MOLECULAR WEIGHT :
919.09
WISWESSER LINE NOTATION :
T C6 B5 R5-18--18-/MP& A K L 2BJ P& IM KS NVM QVN WVM C&VM F&VM I&VM L&VM O&VM&&TTTJ FQ KO P1

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 :
100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Mammal - cattle Liver
DOSE/DURATION :
3 mg/L
REFERENCE :
CBINA8 Chemico-Biological Interactions. (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1969- Volume(issue)/page/year: 56,289,1985

 Safety Information

Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H300-H310-H330-H373
Precautionary Statements P260-P264-P280-P284-P301 + P310-P302 + P350
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T+: Very toxic;
Risk Phrases R26/27/28
Safety Phrases 36/37/39-45-36/37-28
RIDADR UN 3462 6
WGK Germany 3
RTECS BD6195000
Packaging Group I
Hazard Class 6.1(a)

 Preparation


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 Synonyms

α-Amanitin,cyclo[L-Asparaginyl-4-hydroxy-L-proly-(R-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl]cyclic(4-8)-sulfide(R)-S-oxide
alpha-amanitin
MFCD00215842
EINECS 245-432-2
A-AMANITIN
AMANITIN,A
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