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BioViotica
Aureothin
265
CHF
CHF 265.00
In stock
BVT-0303-M0011 mgCHF 265.00
BVT-0303-M0055 mgCHF 830.00
| Product Details | |
|---|---|
| Synonyms | Mycolutein; Distacin; JA 2814K; Antibiotic 74A; BRN 0058476 |
| Product Type | Chemical |
| Properties | |
| Formula |
C22H23NO6 |
| MW | 397.4 |
| Merck Index | 10:879 |
| CAS | 2825-00-5 |
| RTECS | UQ0800000 |
| Source/Host Chemicals | Isolated from Streptomyces thioluteus. |
| Purity Chemicals | ≥96% (HPLC) |
| Appearance | Yellow solid. |
| Solubility | Soluble in 100% ethanol, methanol, DMSO, dimethylformamide, dicholormethane or acetone. |
| Identity | Determined by 1H-NMR and UV. |
| Declaration | Manufactured by BioViotica. |
| InChi Key | GQKXCBCSVYJUMI-RCGCBBHSSA-N |
| Smiles | COC1=C(C)C(=O)C(C)=C(O1)C1C\C(CO1)=C\C(\C)=C\C1=CC=C(C=C1)[N+]([O-])=O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light when in solution. |
| Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- NADH dehydrogenase (NADH-Coenzyme Q oxidoreductase; Complex I) inhibitor. Inhibits mitochondrial respiration and oxidative phosphorylation (OXPHOS).
- Antitrypanosomal, antibacterial, antifungal, insecticidal and pesticidal.
- Antitumor compound.
- Potent anti-HIV agent.
Product References
- The structure of aureothin, a nitro compound obtained from Streptomyces thioluteus: Y. Hirata, et al.; Tetrahedron 14, 252 (1961)
- Identification of mycolutein and pulvomycin as aureothin and labilomycin respectively: J.L. Schwartz, et al.; J. Antibiot. 29, 236 (1976)
- Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase: T. Friedrich, et al.; Eur. J. Biochem. 219, 691 (1994)
- Absolute configuration of (+)-aureothin: A toxic Metabolite posessing gamma-pyrone unit: Y. Ishibashi, et al.; Bull. Chem. Soc. Jpn. 68, 3643 (1995)
- Gamma-pyrone compounds with selective and potent anti-Helicobacter pylori activity: M. Taniguchi, et al.; J. Antibiot. 53, 844 (2000)
- Dissection of the late steps in aureothin biosynthesis: M. Müller, et al.; ChemBioChem 7, 37 (2006)
- New aureothin derivative, alloaureothin, from Streptomyces sp. MM23: J.Y. Ueda, et al.; J. Antibiot. 60, 321 (2007)
- Chemoenzymatic total synthesis of the antiproliferative polyketide (+)-(R)-aureothin: M. Werneburg & C. Hertweck; Chembiochem 9, 2064 (2008)
- Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites: K. Otoguro, et al.; J. Antibiot. 61, 372 (2008)
- Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies: M. Höllerhagen, et al.; Exp. Neurol. 220, 133 (2009)
- Evolution of metabolic diversity in polyketide-derived pyrones: using the non-colinear Aureothin assembly line as a model system: B. Busch, et al.; Phytochemistry 70, 1833 (2009)
- Exploiting enzymatic promiscuity to engineer a focused library of highly selective antifungal and antiproliferative Aureothin analogues: M. Werneburg, et al.; J. Am. Chem. Soc. 132, 10407 (2010)
- Potent inhibition of HIV replication in primary human cells by novel synthetic polyketides inspired by Aureothin: A. Herrmann, et al.; Sci. Rep. 10, 1326 (2020)
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