X-206
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| Category | Antibiotics |
| Catalog number | BBF-01901 |
| CAS | 36505-48-3 |
| Molecular Weight | 871.1 |
| Molecular Formula | C47H82O14 |
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Description
X-206 is an ionophore antibiotic produced by Streptomyces sp. X 206. It acts as a potent and selective inhibitor of SARS-CoV-2.
Specification
| Synonyms | Antibiotic X-206 |
| IUPAC Name | (2R)-2-[(2S,3S,6R)-6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(R)-[(2S,5S)-5-[(2R,3R,5S)-5-[(2R,5R,6S)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxy-3,5-dimethyloxolan-2-yl]-5-methyloxolan-2-yl]-hydroxymethyl]-6-hydroxy-3,5-dimethyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2-hydroxybutyl]-3-methyloxan-2-yl]propanoic acid |
| Canonical SMILES | CCC1C(CCC(O1)C2(CC(C(O2)(C3(CCC(O3)C(C4(C(CC(C(O4)CC5(C(CCC(O5)C(C)C(CC6CCC(C(O6)C(C)C(=O)O)C)O)C)O)C)C)O)O)C)O)C)C)(C)O |
| InChI | InChI=1S/C47H82O14/c1-12-37-42(9,52)19-18-38(57-37)43(10)23-29(6)47(55,61-43)44(11)20-17-35(58-44)40(49)46(54)28(5)21-26(3)36(60-46)24-45(53)27(4)14-16-34(59-45)30(7)33(48)22-32-15-13-25(2)39(56-32)31(8)41(50)51/h25-40,48-49,52-55H,12-24H2,1-11H3,(H,50,51)/t25-,26-,27-,28+,29+,30-,31+,32+,33+,34+,35-,36+,37-,38+,39-,40+,42+,43-,44-,45+,46+,47+/m0/s1 |
| InChI Key | XSBSGLXIQBCTKN-SARHNJKISA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | viruses |
| Melting Point | 133-145°C |
Reference Reading
1. Potent antimalarial activities of polyether antibiotic, X-206
K Otoguro, A Kohana, C Manabe, A Ishiyama, H Ui, K Shiomi, H Yamada, S Omura J Antibiot (Tokyo). 2001 Aug;54(8):658-63. doi: 10.7164/antibiotics.54.658.
In the course of our screening program to discover antimalarial antibiotics, which are active against drug resistant Plasmodium falciparum in vitro and rodents infected with P. berghei in vivo, from the culture broth of microorganisms, we found a selective and potent active substance produced by an actinomycete strain K99-0413. It was identified as a known polyether antibiotic, X-206. We also compared the in vitro antimalarial activities and cytotoxicities of 12 known polyethers with X-206. Among them, X-206 showed the most selective and potent inhibitory effect against both drug resistant and sensitive strains of P. falciparum. Comparison of biological activities and ion-affinities of the above antibiotics suggests that monovalent cations play an important biological role for the intracellular growth of P. falciparum in parasitized erythrocytes. Moreover, X-206 showed potent in vivo antimalarial activity on the rodent model, though the therapeutic window was narrow compared with its selective toxicity in vitro. These observations are the first report of antimalarial activity of X-206.
2. Ionophore antibiotic X-206 is a potent inhibitor of SARS-CoV-2 infection in vitro
Esben B Svenningsen, Jacob Thyrsted, Julia Blay-Cadanet, Han Liu, Shaoquan Lin, Jaime Moyano-Villameriel, David Olagnier, Manja Idorn, Søren R Paludan, Christian K Holm, Thomas B Poulsen Antiviral Res. 2021 Jan;185:104988. doi: 10.1016/j.antiviral.2020.104988. Epub 2020 Nov 25.
Pandemic spread of emerging human pathogenic viruses, such as the current SARS-CoV-2, poses both an immediate and future challenge to human health and society. Currently, effective treatment of infection with SARS-CoV-2 is limited and broad spectrum antiviral therapies to meet other emerging pandemics are absent leaving the World population largely unprotected. Here, we have identified distinct members of the family of polyether ionophore antibiotics with potent ability to inhibit SARS-CoV-2 replication and cytopathogenicity in cells. Several compounds from this class displayed more than 100-fold selectivity between viral-induced cytopathogenicity and inhibition of cell viability, however the compound X-206 displayed >500-fold selectivity and was furthermore able to inhibit viral replication even at sub-nM levels. The antiviral mechanism of the polyether ionophores is currently not understood in detail. We demonstrate, e.g. through unbiased bioactivity profiling, that their effects on the host cells differ from those of cationic amphiphiles such as hydroxychloroquine. Collectively, our data suggest that polyether ionophore antibiotics should be subject to further investigations as potential broad-spectrum antiviral agents.
3. High-resolution three-dimensional MR angiography of rodent tumors: morphologic characterization of intratumoral vasculature
Christian Fink, Fabian Kiessling, Michael Bock, Matthias Philipp Lichy, Bernd Misselwitz, Peter Peschke, Norbert E Fusenig, Rainer Grobholz, Stefan Delorme J Magn Reson Imaging. 2003 Jul;18(1):59-65. doi: 10.1002/jmri.10318.
Purpose: To evaluate high-resolution three-dimensional MR angiography (MRA) for the visualization and morphologic characterization of intratumoral vasculature. Materials and methods: Two subcutaneous rodent tumor models (human skin carcinoma HaCaT-ras-A-5RT3 grown in nude mice and rat prostate carcinoma R3327-AT1 grown in Copenhagen rats) were examined with a clinical 1.5 T MR-system. For MRA a dedicated high-resolution three-dimensional gradient echo pulse sequence with a voxel size of 166 x 206 x 320 microm(3) was performed after injection of Gadomer-17. The image analysis included a correlation of intratumoral vessels with histology. Signal intensity measurements were performed in the vena cava, the tumor underlying muscle, and in various regions of the tumor. Signal-to-noise-ratios (SNR) and contrast-to-noise-ratios (CNR) were calculated from this measurement. Results: High-resolution MRA allowed a clear distinction of intratumoral blood vessels. The mouse tumor model tended to be strongly vascularized with several intratumoral blood vessels clearly displayed by MRA. When correlated with histology, these intratumoral blood vessels had a size in the range of 300 to 400 microm. In contrast, rat tumors had only sparse capillary intratumoral blood vessels that could only be demonstrated by histology. In both tumor models, dilated blood vessels were observed in the subcutaneous tissue near the tumor. In general, areas with a strong contrast enhancement correlated with viable, well vascularized tumor regions, whereas non-enhancing tumor areas correlated with tumor necrosis or hypoxic areas. Conclusion: High-resolution three-dimensional MRA allows the visualization of intratumoral vasculature in rodent models. With minimal hardware and software modifications, high-resolution MRA could be performed on a clinical 1.5 T MRI scanner. Morphologic characterization of intratumoral blood vessels could add important insights into the process of tumor angiogenesis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
