CAS 23109-05-9|alpha-Amanitin
Introduction：Basic information about CAS 23109-05-9|alpha-Amanitin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | ChineseUSA | Flash Point | 934.9ºC |
| Symbol | GHS06, GHS08 | Signal Word | Danger |
Names
| Name | α-amanitin |
|---|---|
| Synonym | More Synonyms |
alpha-Amanitin BiologicalActivity
| Description | alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II. |
|---|---|
| Related Catalog | Signaling Pathways >>Antibody-drug Conjugate >>ADC CytotoxinSignaling Pathways >>Cell Cycle/DNA Damage >>DNA/RNA SynthesisResearch Areas >>Cancer |
| 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 |
| InChIKey | CIORWBWIBBPXCG-NUCBJAHASA-N |
| SMILES | 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)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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
- 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 |
|---|---|
| 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
Articles13
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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 |
