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MedKoo Cat#: 329846 | Name: Tropodithietic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tropodithietic acid is a broad spectrum tropolone antibiotic with activity against both Gram-negative and Gram-positive bacteria.

Chemical Structure

Tropodithietic acid
Tropodithietic acid
CAS#750590-18-2

Theoretical Analysis

MedKoo Cat#: 329846

Name: Tropodithietic acid

CAS#: 750590-18-2

Chemical Formula: C8H4O3S2

Exact Mass: 211.9602

Molecular Weight: 212.24

Elemental Analysis: C, 45.27; H, 1.90; O, 22.61; S, 30.21

Price and Availability

Size Price Availability Quantity
1mg USD 525.00 2 Weeks
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Related CAS #
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Synonym
Tropodithietic acid, TDA
IUPAC/Chemical Name
3-Oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid
InChi Key
BLFCMITWMARUSM-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H4O3S2/c9-4-2-1-3-5-7(13-12-5)6(4)8(10)11/h1-3H,(H,10,11)
SMILES Code
O=C(C1=C2SSC2=CC=CC1=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The marine metabolite tropodithietic acid (TDA), produced by several Roseobacter clade bacteria, is known for its broad antimicrobial activity. TDA is of interest not only as a probiotic in aquaculture, but also because it might be of use as an antibacterial agent in non-marine or non-aquatic environments, and thus the potentially cytotoxic influences on eukaryotic cells

Preparing Stock Solutions

The following data is based on the product molecular weight 212.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Cui H, Lu J, Ding W, Zhang W. Genomic Features and Antimicrobial Activity of Phaeobacter inhibens Strains from Marine Biofilms. Mar Drugs. 2024 Oct 31;22(11):492. doi: 10.3390/md22110492. PMID: 39590772; PMCID: PMC11595833. 2: Loh AAR, Hu D, Law JMYJ, Xiong ELW, Deignan LK, Summers S, Pereyra JPA, Case RJ. Draft genome of a Pseudovibrio sp. isolated from the skeleton of Pachyseris speciosa from a Singaporean reef. Microbiol Resour Announc. 2024 Nov 12;13(11):e0076324. doi: 10.1128/mra.00763-24. Epub 2024 Sep 30. PMID: 39345107; PMCID: PMC11556074. 3: Svendsen PB, Henriksen NNSE, Jarmusch SA, Andersen AJC, Smith K, Selsmark MW, Zhang S-D, Schostag MD, Gram L. Co-existence of two antibiotic-producing marine bacteria: Pseudoalteromonas piscicida reduce gene expression and production of the antibacterial compound, tropodithietic acid, in Phaeobacter sp. Appl Environ Microbiol. 2024 Sep 18;90(9):e0058824. doi: 10.1128/aem.00588-24. Epub 2024 Aug 13. PMID: 39136490; PMCID: PMC11409694. 4: Alghamdi AK, Parween S, Hirt H, Saad MM. Unraveling the genomic secrets of Tritonibacter mobilis AK171: a plant growth-promoting bacterium isolated from Avicennia marina. BMC Genomics. 2024 Jul 5;25(1):672. doi: 10.1186/s12864-024-10555-0. PMID: 38969999; PMCID: PMC11225332. 5: Höing L, Sowa ST, Toplak M, Reinhardt JK, Jakob R, Maier T, Lill MA, Teufel R. Biosynthesis of the bacterial antibiotic 3,7-dihydroxytropolone through enzymatic salvaging of catabolic shunt products. Chem Sci. 2024 Apr 24;15(20):7749-7756. doi: 10.1039/d4sc01715c. PMID: 38784727; PMCID: PMC11110157. 6: Roager L, Athena-Vasileiadi D, Gram L, Sonnenschein EC. Antagonistic activity of Phaeobacter piscinae against the emerging fish pathogen Vibrio crassostreae in aquaculture feed algae. Appl Environ Microbiol. 2024 Mar 20;90(3):e0143923. doi: 10.1128/aem.01439-23. Epub 2024 Feb 13. PMID: 38349149; PMCID: PMC10952492. 7: Droumpali A, Liu Y, Ferrer-Florensa X, Sternberg C, Dimaki M, Andersen AJC, Strube ML, Kempen PJ, Gram L, Taboryski R. Biosynthesis enhancement of tropodithietic acid (TDA) antibacterial compound through biofilm formation by marine bacteria Phaeobacter inhibens on micro-structured polymer surfaces. RSC Adv. 2023 Nov 9;13(47):33159-33166. doi: 10.1039/d3ra05407a. PMID: 37964901; PMCID: PMC10641763. 8: Henriksen NNSE, Schostag MD, Balder SR, Bech PK, Strube ML, Sonnenschein EC, Gram L. The ability of Phaeobacter inhibens to produce tropodithietic acid influences the community dynamics of a microalgal microbiome. ISME Commun. 2022 Nov 3;2(1):109. doi: 10.1038/s43705-022-00193-6. PMID: 37938341; PMCID: PMC9723703. 9: Bech PK, Zhang SD, Henriksen NNSE, Bentzon-Tilia M, Strube ML, Gram L. The potential to produce tropodithietic acid by Phaeobacter inhibens affects the assembly of microbial biofilm communities in natural seawater. NPJ Biofilms Microbiomes. 2023 Mar 23;9(1):12. doi: 10.1038/s41522-023-00379-3. PMID: 36959215; PMCID: PMC10036634. 10: Lindqvist LL, Jarmusch SA, Sonnenschein EC, Strube ML, Kim J, Nielsen MW, Kempen PJ, Schoof EM, Zhang SD, Gram L. Tropodithietic Acid, a Multifunctional Antimicrobial, Facilitates Adaption and Colonization of the Producer, Phaeobacter piscinae. mSphere. 2023 Feb 21;8(1):e0051722. doi: 10.1128/msphere.00517-22. Epub 2023 Jan 9. PMID: 36622251; PMCID: PMC9942592. 11: Srinivas S, Berger M, Brinkhoff T, Niggemann J. Impact of Quorum Sensing and Tropodithietic Acid Production on the Exometabolome of Phaeobacter inhibens. Front Microbiol. 2022 Jun 21;13:917969. doi: 10.3389/fmicb.2022.917969. PMID: 35801100; PMCID: PMC9253639. 12: Morris MM, Kimbrel JA, Geng H, Tran-Gyamfi MB, Yu ET, Sale KL, Lane TW, Mayali X. Bacterial Community Assembly, Succession, and Metabolic Function during Outdoor Cultivation of Microchloropsis salina. mSphere. 2022 Aug 31;7(4):e0023122. doi: 10.1128/msphere.00231-22. Epub 2022 Jun 22. PMID: 35730934; PMCID: PMC9429889. 13: Henriksen NNSE, Lindqvist LL, Wibowo M, Sonnenschein EC, Bentzon-Tilia M, Gram L. Role is in the eye of the beholder-the multiple functions of the antibacterial compound tropodithietic acid produced by marine Rhodobacteraceae. FEMS Microbiol Rev. 2022 May 6;46(3):fuac007. doi: 10.1093/femsre/fuac007. PMID: 35099011; PMCID: PMC9075582. 14: Tesdorpf JE, Geers AU, Strube ML, Gram L, Bentzon-Tilia M. Roseobacter Group Probiotics Exhibit Differential Killing of Fish Pathogenic Tenacibaculum Species. Appl Environ Microbiol. 2022 Mar 22;88(6):e0241821. doi: 10.1128/aem.02418-21. Epub 2022 Jan 26. PMID: 35080904; PMCID: PMC8939348. 15: Toplak M, Teufel R. Three Rings to Rule Them All: How Versatile Flavoenzymes Orchestrate the Structural Diversification of Natural Products. Biochemistry. 2022 Jan 18;61(2):47-56. doi: 10.1021/acs.biochem.1c00763. Epub 2021 Dec 28. PMID: 34962769; PMCID: PMC8772269. 16: Belikov SI, Petrushin IS, Chernogor LI. Genome Analysis of the Janthinobacterium sp. Strain SLB01 from the Diseased Sponge of the Lubomirskia baicalensis. Curr Issues Mol Biol. 2021 Dec 11;43(3):2220-2237. doi: 10.3390/cimb43030156. PMID: 34940130; PMCID: PMC8929069. 17: Majzoub ME, McElroy K, Maczka M, Schulz S, Thomas T, Egan S. Genomic Evolution of the Marine Bacterium Phaeobacter inhibens during Biofilm Growth. Appl Environ Microbiol. 2021 Sep 10;87(19):e0076921. doi: 10.1128/AEM.00769-21. Epub 2021 Sep 10. PMID: 34288701; PMCID: PMC8432577. 18: Duan Y, Toplak M, Hou A, Brock NL, Dickschat JS, Teufel R. A Flavoprotein Dioxygenase Steers Bacterial Tropone Biosynthesis via Coenzyme A-Ester Oxygenolysis and Ring Epoxidation. J Am Chem Soc. 2021 Jul 14;143(27):10413-10421. doi: 10.1021/jacs.1c04996. Epub 2021 Jul 1. PMID: 34196542; PMCID: PMC8283759. 19: Koblitz J, Will SE, Riemer SA, Ulas T, Neumann-Schaal M, Schomburg D. The Metano Modeling Toolbox MMTB: An Intuitive, Web-Based Toolbox Introduced by Two Use Cases. Metabolites. 2021 Feb 17;11(2):113. doi: 10.3390/metabo11020113. PMID: 33671140; PMCID: PMC7923039. 20: Wolter LA, Wietz M, Ziesche L, Breider S, Leinberger J, Poehlein A, Daniel R, Schulz S, Brinkhoff T. Pseudooceanicola algae sp. nov., isolated from the marine macroalga Fucus spiralis, shows genomic and physiological adaptations for an algae-associated lifestyle. Syst Appl Microbiol. 2021 Jan;44(1):126166. doi: 10.1016/j.syapm.2020.126166. Epub 2020 Nov 27. PMID: 33310406.