Tropodithietic acid

CHF 110.00
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BVT-0152-M0011 mgCHF 110.00
BVT-0152-M0055 mgCHF 440.00
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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
  • 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
  1. Thiotropocin, a new sulfur-containing 7-membered-ring antibiotic produced by a Pseudomonas sp.: K. Kintaka, et al.; J. Antibiot. 37, 1294 (1984)
  2. Thiotropocin biosynthesis. Shikimate origin of a sulfur-containing tropolone derivative: D.E. Cane, et al.; JACS 114, 8479 (1992)
  3. 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]
  4. 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)
  5. 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)
  6. Genetic dissection of tropodithietic acid biosynthesis by marine Roseobacters: H. Geng, et al.; Appl. Environ. Microbiol. 74, 1535 (2008)
  7. Expression of tropodithietic acid biosynthesis is controlled by a novel autoinducer: H. Geng & R. Belas; J. Bacteriol. 192, 4377 (2010)
  8. 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)
  9. A novel inducer of Roseobacter motility is also a disruptor of algal symbiosis: P. Sule & R. Belas; J. Bacteriol. 195, 637 (2013)
  10. Characterisation of non-autoinducing tropodithietic acid (TDA) production from marine sponge Pseudovibrio species: C. Harrington, et al.; Mar. Drugs 12, 5960 (2014)
  11. Biosynthesis of the antibiotic tropodithieticacid by the marine bacterium Phaeobacter inhibens: N.L. Brock, et al.; Chem. Comm. 50, 5487 (2014)
  12. 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)
  13. Cytotoxic effects of tropodithietic acid on mammalian clonal cell lines of neuronal and glial origin: H. Wichmann, et al.; Mar. Drugs 13, 7113 (2015)
  14. 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)
  15. 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)
  16. 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)
  17. 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)
  18. Antimicrobial and antibiofilm molecules produced by marine bacteria: F. Desriac, et al.; Blue Biotechnol. J. 2, 789 (2018)
  19. 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) 
  20. 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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