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Tropodithietic acid

BVT-0152-M001 1 mg $170.00
BVT-0152-M005 5 mg $595.00
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Additional Information

Product Data
Synonyms TDA
Properties
Formula C8H4O3S2
MW 212.3
CAS 750590-18-2
Source/Host Chemicals Isolated from Roseobacter gallaeciensis.
Purity ≥98% (HPLC)
Appearance Orange solid.
Solubility Soluble in DMSO, methanol or acetone.
Identity Determined by 1H-NMR and UV.
Origin Manufactured by BioViotica.
InChi Key BLFCMITWMARUSM-UHFFFAOYSA-N
Product Type Chemical
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.
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Product 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.

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. Tropodithietic acid production in Phaeobacter gallaeciensis is regulated by N-acyl homoserine lactone-mediated quorum sensing: M. Berger, et al.; J. Bacteriol. 193, 6576 (2011)
  10. Genetic analysis of the upper phenylacetate catabolic pathway in the production of tropodithietic acid by Phaeobacter gallaeciensis: M. Berger, et al.; Appl. Environ. Microbiol. 78, 3539 (2012)
  11. A novel inducer of Roseobacter motility is also a disruptor of algal symbiosis: P. Sule & R. Belas; J. Bacteriol. 195, 637 (2013)
  12. Characterisation of non-autoinducing tropodithietic acid (TDA) production from marine sponge Pseudovibrio species: C. Harrington, et al.; Mar. Drugs 12, 5960 (2014)
  13. Biofilm formation and antibiotic production in Ruegeria mobilis are influenced by intracellular concentrations of cyclic dimeric guanosinmonophosphate: P.W. D'Alvise, et al.; Appl. Environ. Microbiol. 16, 1252 (2014)
  14. Biosynthesis of the antibiotic tropodithieticacid by the marine bacterium Phaeobacter inhibens: N.L. Brock, et al.; Chem. Comm. 50, 5487 (2014)
  15. 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)
  16. Cytotoxic effects of tropodithietic acid on mammalian clonal cell lines of neuronal and glial origin: H. Wichmann, et al.; Mar. Drugs 13, 7113 (2015)
  17. 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)
  18. 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)
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