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BioViotica
Tropodithietic acid
115
CHF
CHF 115.00
In stock
BVT-0152-M0011 mgCHF 115.00
BVT-0152-M0055 mgCHF 430.00
| Product Details | |
|---|---|
| Synonyms | TDA |
| Product Type | Chemical |
| Properties | |
| Formula |
C8H4O3S2 |
| MW | 212.3 |
| CAS | 750590-18-2 |
| Source/Host Chemicals | Isolated from Roseobacter gallaeciensis. |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | Orange solid. |
| Solubility | Soluble in DMSO, methanol or acetone. |
| Identity | Determined by 1H-NMR and UV. |
| Declaration | Manufactured by BioViotica. |
| InChi Key | BLFCMITWMARUSM-UHFFFAOYSA-N |
| Smiles | OC(=O)C1=C2SSC2=CC=CC1=O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Antibiotic. Isomeric to thiotropocin.
- Antibacterial. Active against Gram-positive and Gram-negative bacteria.
- Antifungal and anti-nematodical.
- Shows antitumor activity.
- Cytotoxic against selected mammalian neuronal cell lines.
- Bacterial signal substance.
- Acts as potent membrane antiporter for protons in exchange for cytoplasmic cations (e. g., K+). TDA collapses the cellular proton motive force (PMF) by affecting the transmembrane proton gradient but not the membrane potential.
Product References
- Thiotropocin, a new sulfur-containing 7-membered-ring antibiotic produced by a Pseudomonas sp.: K. Kintaka, et al.; J. Antibiot. 37, 1294 (1984)
- Thiotropocin biosynthesis. Shikimate origin of a sulfur-containing tropolone derivative: D.E. Cane, et al.; JACS 114, 8479 (1992)
- Investigation of secondary metabolites of North Sea bacteria: fermentation, isolation, structure elucidation and bioactivity: L. Liang; Dissertation Univ. Goettingen page 1-136 (2003) [TDA isolation, spectral data, cryst. Structure]
- Antibiotic production by a Roseobacter clade-affiliated species from the German Wadden Sea and its anta-gonistic effects on indigenous isolates: T. Brinkhoff, et al.; Appl. Environ. Microbiol. 70, 2560 (2004)
- Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism: E.M. Greer, et al.; J. Org. Chem. 73, 280 (2008)
- Genetic dissection of tropodithietic acid biosynthesis by marine Roseobacters: H. Geng, et al.; Appl. Environ. Microbiol. 74, 1535 (2008)
- Expression of tropodithietic acid biosynthesis is controlled by a novel autoinducer: H. Geng & R. Belas; J. Bacteriol. 192, 4377 (2010)
- Resistance and tolerance to tropodithietic acid, an antimicrobial in aquaculture, is hard to select: C. H. Porsby, et al.; Antimicrob. Agents Chemother. 55, 1332 (2011)
- A novel inducer of Roseobacter motility is also a disruptor of algal symbiosis: P. Sule & R. Belas; J. Bacteriol. 195, 637 (2013)
- Characterisation of non-autoinducing tropodithietic acid (TDA) production from marine sponge Pseudovibrio species: C. Harrington, et al.; Mar. Drugs 12, 5960 (2014)
- Biosynthesis of the antibiotic tropodithieticacid by the marine bacterium Phaeobacter inhibens: N.L. Brock, et al.; Chem. Comm. 50, 5487 (2014)
- Phaeobacter inhibens from the Roseobacter clade has an environmental niche as a surface colonizer in harbors: L. Gram, et al.; System. Appl. Microbiol. 38, 483 (2015)
- Cytotoxic effects of tropodithietic acid on mammalian clonal cell lines of neuronal and glial origin: H. Wichmann, et al.; Mar. Drugs 13, 7113 (2015)
- Influence of iron on production of the antibacterial compound tropodithietic acid and its noninhibitory analog in Phaeobacter inhibens: P. W. D`Alvise, et al.; Appl. Environ. Microbiol. 82, 502 (2016)
- Mode of action and resistance studies unveil new roles for tropodithietic acid as an anticancer agent and the γ glutamyl cycle as a proton sink: M. Wilson, et al.; PNAS 113, 1630 (2016)
- Dual function of tropodithietic acid as antibiotic and signaling molecule in global gene regulation of the probiotic bacterium Phaeobacter inhibens: P.G. Beyersmann, et al.; Sci. Rep. 7, 730 (2017)
- Diversity and antimicrobial activity of hydrobionts associated microorganisms from the sea of Japan with the occurrence of tropodithietic acid producing bacteria: L. A. Romanenko, et al.; Microbiol. Res. J. Int. 20, MRJI.34949/1 (2017)
- Antimicrobial and antibiofilm molecules produced by marine bacteria: F. Desriac, et al.; Blue Biotechnol. J. 2, 789 (2018)
- Tropodithietic acid induces oxidative stress response, cell envelope biogenesis and iron uptake in Vibrio vulnificus: K.K. Dittmann, et al.; Environ. Microbiol. Rep. 11, 581 (2019)
- Bacterial tropone natural products and derivatives: overview of their biosynthesis, bioactivities, ecological role and biotechnological potential: Y. Duan, et al.; ChemBioChem 21, 1 (2020)
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