Amicoumacin A
Amicoumacin A is an orally active antibiotic. Amicoumacin A targets bacterial ribosomes and inhibits bacterial translation by stabilizing the interaction between mRNA and ribosomes. Amicoumacin A induces cancer cell death by targeting eukaryotic ribosomes. Amicoumacin A exhibits anti-inflammatory and anti-ulcer activities, inhibits carrageenan-induced paw edema, and prevents stress-induced gastric ulcers. Amicoumacin A inhibits the growth of Gram-positive bacteria, Salmonella spp., Shigella spp., Helicobacter pylori, and methicillin-resistant Staphylococcus aureus. Amicoumacin A can be used in the research of lung cancer, breast cancer, bacterial infections, inflammatory edema and gastric ulcers[2].
For research use only. We do not sell to patients.
- CAS No.: 78654-44-1
- Formula: C20H29N3O7
- Molecular Weight:423.46
-
Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Biological Activity
-
Chemical Information
- Purity & Documentation
- References
-
Help & FAQs
All Antibiotic Isoforms
More
Biological Activity
Amicoumacin A (0-5 μM; 25-120 min) inhibits both scanning-dependent and IRES-dependent mRNA translation in HEK293T cells, Krebs-2 cell-free systems, and S. cerevisiae cell-free extracts[1].
Amicoumacin A (100 μM; 5 min pre-incubation + 10 min mRNA incubation) inhibits mammalian translation elongation in rabbit reticulocyte lysates by stalling 80S ribosomes along mRNA[1].
Amicoumacin A (50 nM-100 μM; 72 h) exhibits 2- to 4-fold greater cytotoxicity against human cancer cell lines (A549, MCF-7) than against non-cancerous cell lines (HEK293T, VA13), with IC50 values ranging from 0.2 μM to 1.2 μM[1].
Amicoumacin A (30 μM; 10 min) reduces the production level of tripeptides in E. coli ribosomes and impairs the ability of most ribosomes to complete multiple rounds of elongation cycles[3].
Amicoumacin A (30 min at 37 °C) potently inhibits protein synthesis in E. coli S30 cell extracts with an IC50 of 0.45 μM, and inhibits protein synthesis in the PURE system composed of purified translation components with an IC50 of 0.20 μM[4].
Amicoumacin A (0-1000 μM; 30 sec at 37 °C) inhibits ribosomal translocation in a concentration-dependent manner in vitro, with nearly complete inhibition observed at 1000 μM[4].
Amicoumacin A (2 μM; 30 min at 37 °C) inhibits the synthesis of firefly luciferase in E. coli S30 cell extracts[4].
Amicoumacin A exhibits inhibitory activity against Gram-positive bacteria[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Cell Line:A549 cells, MCF-7 cells, HEK293T cells, VA13 cells
-
Concentration:50 nM to 100 μM
-
Incubation Time:72 h
-
Result:Achieved an IC50 of 0.2 μM for A549 lung cancer cells.
Achieved an IC50 of 0.3 μM for MCF-7 breast cancer cells.
Achieved an IC50 of 0.55 μM for HEK293T non-cancerous embryonic kidney cells.
Achieved an IC50 of 1.2 μM for VA13 non-cancerous lung fibroblast cells.
Amicoumacin-A (10-25 mg/kg; p.o.; single dose) dose-dependently prevents stress-induced gastric ulcers in male Sprague-Dawley rats[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Animal Model:Wistar rats (male)[5]
-
Dosage:10 mg/kg; 25 mg/kg; 50 mg/kg
-
Administration:p.o.，single dose
-
Result:Reduced paw edema swelling to 66.7% (7.6% inhibition) at 10 mg/kg.
Reduced paw edema swelling to 61.0% (15.5% inhibition) at 25 mg/kg.
Reduced paw edema swelling to 49.4% (31.6% inhibition) at 50 mg/kg.
-
Animal Model:Sprague-Dawley rats (male)[5]
-
Dosage:10 mg/kg; 25 mg/kg
-
Administration:p.o.， single dose
-
Result:Reduced the mean ulcer index to 2.80 (34.1% preventive ratio) at 10 mg/kg.
Reduced the mean ulcer index to 1.20 (71.8% preventive ratio) at 25 mg/kg.
Chemical Information
-
CAS No. 78654-44-1
-
Molecular Weight 423.46
-
Formula C20H29N3O7
-
SMILES
O=C1C2=C(O)C=CC=C2C[C@@](O1)([H])[C@H](CC(C)C)NC([C@@H](O)[C@@H](O)[C@@H](N)CC(N)=O)=O
-
Structure Classification
-
Initial Source
Bacillus pumilus
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Prokhorova IV, et al. Amicoumacin A induces cancer cell death by targeting the eukaryotic ribosome. Sci Rep. 2016;6:27720. Published 2016 Jun 14. [Content Brief]
[3]. Maksimova EM, et al. Multifaceted Mechanism of Amicoumacin A Inhibition of Bacterial Translation. Front Microbiol. 2021;12:618857. Published 2021 Feb 12. [Content Brief]
[4]. Polikanov YS, et al. Amicoumacin a inhibits translation by stabilizing mRNA interaction with the ribosome. Mol Cell. 2014;56(4):531-540. [Content Brief]
[5]. Itoh J, et al. Amicoumacin-A, a new antibiotic with strong antiinflammatory and antiulcer activity. J Antibiot (Tokyo). 1981 May;34(5):611-3. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Amicoumacin A Related Classifications
HY-127072 Related Classifications
Powered by Bioz