Tropodithietic acid [TDA]

Bioviotica
Product Code: BVT-0152
Supplier: Bioviotica

CodeSizePrice
BVT-0152-M0011 mg£110.00
Quantity:
BVT-0152-M0055 mg£395.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
TDA
Appearance:
Orange solid.
CAS:
750590-18-2
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Hazards:
H302, H319
InChi:
InChI=1S/C8H4O3S2/c9-4-2-1-3-5-7(13-12-5)6(4)8(10)11/h1-3H,(H,10,11)
InChiKey:
BLFCMITWMARUSM-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 750590-18-2. Formula: C8H4O3S2. MW: 212.3. Isolated from Roseobacter gallaeciensis. 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.
MDL:
MFCD24485342
Molecular Formula:
C8H4O3S2
Molecular Weight:
212.3
Package Type:
Plastic Vial
Precautions:
P280, P301, P312, P305, P351, P338, P337, P313
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. 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.
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
OC(=O)C1=C2SSC2=CC=CC1=O
Solubility Chemicals:
Soluble in DMSO, methanol or acetone.
Source / Host:
Isolated from Roseobacter gallaeciensis.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.

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 gamma 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)