Tropodithietic acid
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| Category | Antibiotics |
| Catalog number | BBF-04524 |
| CAS | 750590-18-2 |
| Molecular Weight | 212.25 |
| Molecular Formula | C8H4O3S2 |
| Purity | ≥98% |
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Description
Tropodithietic acid (TDA) is a broad-spectrum antibiotic produced by the marine bacterium Roseobacter gallaeciensis. It is effective against a variety of Gram-negative α-proteobacteria, γ-proteobacteria, and flavobacteria as well as Gram-positive actinobacteria strains in a disc assay.
Specification
| Synonyms | TDA |
| Storage | Store at -20°C |
| IUPAC Name | 3-oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid |
| Canonical SMILES | C1=CC(=O)C(=C2C(=C1)SS2)C(=O)O |
| InChI | InChI=1S/C8H4O3S2/c9-4-2-1-3-5-7(13-12-5)6(4)8(10)11/h1-3H,(H,10,11) |
| InChI Key | BLFCMITWMARUSM-UHFFFAOYSA-N |
Properties
| Appearance | Faint Yellow to Dark Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 435.6±55.0°C at 760 mmHg |
| Density | 1.7±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Dual function of tropodithietic acid as antibiotic and signaling molecule in global gene regulation of the probiotic bacterium Phaeobacter inhibens
Jürgen Tomasch, Paul G Beyersmann, Kwangmin Son, Roman Stocker, Irene Wagner-Döbler, Meinhard Simon, Markus Göker, Thorsten Brinkhoff Sci Rep . 2017 Apr 7;7(1):730. doi: 10.1038/s41598-017-00784-7.
Antibiotics are typically regarded as microbial weapons, but whereas their function at concentrations lethal for bacteria is often well characterized, the role of antibiotics at much lower concentrations as possibly found under natural conditions remains poorly understood. By using whole-transcriptome analyses and phenotypic screenings of the marine bacterium Phaeobacter inhibens we found that the broad-spectrum antibiotic tropodithietic acid (TDA) causes the same regulatory effects in quorum sensing (QS) as the common signaling molecule N-acyl-homoserine lactone (AHL) at concentrations 100-fold lower than the minimal inhibitory concentration against bacteria. Our results show that TDA has a significant impact on the expression of ~10% of the total genes of P. inhibens, in the same manner as the AHL. Furthermore, TDA needs the AHL associated LuxR-type transcriptional regulator, just as the AHL molecule. Low concentrations of antibiotics can obviously have a strong influence on the global gene expression of the bacterium that produces it and drastically change the metabolism and behaviour of the bacterium. For P. inhibens this includes motility, biofilm formation and antibiotic production, all important for settlement on new host-associated surfaces. Our results demonstrate that bacteria can produce antibiotics not only to antagonise other bacteria, but also to mediate QS like endogenous AHL molecules.
2. Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens
Alexander Nikolay, Nelson L Brock, Jeroen S Dickschat Chem Commun (Camb) . 2014 May 28;50(41):5487-9. doi: 10.1039/c4cc01924e.
The biosynthesis of tropodithietic acid was investigated using a combinatorial approach of feeding experiments, gene knockouts and bioinformatic analyses. The mechanism of sulfur introduction is distinct from known mechanisms in holomycin, thiomarinol A and gliotoxin biosynthesis.
3. Contributions of tropodithietic acid and biofilm formation to the probiotic activity of Phaeobacter inhibens
Marta Gomez-Chiarri, David R Nelson, Wenjing Zhao, David Rowley, Murni Karim, Christine Dao BMC Microbiol . 2016 Jan 5;16:1. doi: 10.1186/s12866-015-0617-z.
Background:The probiotic bacterium Phaeobacter inhibens strain S4Sm, isolated from the inner shell surface of a healthy oyster, secretes the antibiotic tropodithietic acid (TDA), is an excellent biofilm former, and increases oyster larvae survival when challenged with bacterial pathogens. In this study, we investigated the specific roles of TDA secretion and biofilm formation in the probiotic activity of S4Sm.Results:Mutations in clpX (ATP-dependent ATPase) and exoP (an exopolysaccharide biosynthesis gene) were created by insertional mutagenesis using homologous recombination. Mutation of clpX resulted in the loss of TDA production, no decline in biofilm formation, and loss of the ability to inhibit the growth of Vibrio tubiashii and Vibrio anguillarum in co-colonization experiments. Mutation of exoP resulted in a ~60% decline in biofilm formation, no decline in TDA production, and delayed inhibitory activity towards Vibrio pathogens in co-colonization experiments. Both clpX and exoP mutants exhibited reduced ability to protect oyster larvae from death when challenged by Vibrio tubiashii. Complementation of the clpX and exoP mutations restored the wild type phenotype. We also found that pre-colonization of surfaces by S4Sm was critical for this bacterium to inhibit pathogen colonization and growth.Conclusions:Our observations demonstrate that probiotic activity by P. inhibens S4Sm involves contributions from both biofilm formation and the production of the antibiotic TDA. Further, probiotic activity also requires colonization of surfaces by S4Sm prior to the introduction of the pathogen.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
