MedKoo Biosciences

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

MedKoo CAT#: 329846

CAS#: 750590-18-2

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

Chemical Structure

Tropodithietic acid

CAS# 750590-18-2

Instruction

Theoretical Analysis

MedKoo Cat#: 329846
Name: Tropodithietic acid
CAS#: 750590-18-2
Chemical Formula: C8H4O3S2
Exact Mass: 211.96
Molecular Weight: 212.237
Elemental Analysis: C, 45.27; H, 1.90; O, 22.61; S, 30.21

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Product Data:

Product Data

Instruction:

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Preparing Stock Solutions

The following data is based on the product molecular weight 212.237000000000000000000000000000 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.

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

Molarity Calculator

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Reconstitution Calculator

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1: Brock NL, Nikolay A, Dickschat JS. Biosynthesis of the antibiotic tropodithietic acid by the marine bacterium Phaeobacter inhibens. Chem Commun (Camb). 2014 May 28;50(41):5487-9. doi: 10.1039/c4cc01924e. PubMed PMID: 24723119. 2: Harrington C, Reen FJ, Mooij MJ, Stewart FA, Chabot JB, Guerra AF, Glöckner FO, Nielsen KF, Gram L, Dobson AD, Adams C, O'Gara F. Characterisation of non-autoinducing tropodithietic Acid (TDA) production from marine sponge Pseudovibrio species. Mar Drugs. 2014 Dec 10;12(12):5960-78. doi: 10.3390/md12125960. PubMed PMID: 25513851; PubMed Central PMCID: PMC4278212. 3: Geng H, Belas R. TdaA regulates Tropodithietic acid synthesis by binding to the tdaC promoter region. J Bacteriol. 2011 Aug;193(15):4002-5. doi: 10.1128/JB.00323-11. Epub 2011 May 27. PubMed PMID: 21622742; PubMed Central PMCID: PMC3147533. 4: Wichmann H, Vocke F, Brinkhoff T, Simon M, Richter-Landsberg C. Cytotoxic Effects of Tropodithietic Acid on Mammalian Clonal Cell Lines of Neuronal and Glial Origin. Mar Drugs. 2015 Nov 27;13(12):7113-23. doi: 10.3390/md13127058. PubMed PMID: 26633426; PubMed Central PMCID: PMC4699232. 5: Rabe P, Klapschinski TA, Brock NL, Citron CA, D'Alvise P, Gram L, Dickschat JS. Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid. Beilstein J Org Chem. 2014 Aug 6;10:1796-801. doi: 10.3762/bjoc.10.188. eCollection 2014. PubMed PMID: 25161739; PubMed Central PMCID: PMC4142847. 6: D'Alvise PW, Phippen CB, Nielsen KF, Gram L. Influence of Iron on Production of the Antibacterial Compound Tropodithietic Acid and Its Noninhibitory Analog in Phaeobacter inhibens. Appl Environ Microbiol. 2015 Oct 30;82(2):502-9. doi: 10.1128/AEM.02992-15. PubMed PMID: 26519388; PubMed Central PMCID: PMC4711134. 7: Prol García MJ, D'Alvise PW, Rygaard AM, Gram L. Biofilm formation is not a prerequisite for production of the antibacterial compound tropodithietic acid in Phaeobacter inhibens DSM17395. J Appl Microbiol. 2014 Dec;117(6):1592-600. doi: 10.1111/jam.12659. Epub 2014 Oct 30. PubMed PMID: 25284322. 8: Berger M, Neumann A, Schulz S, Simon M, Brinkhoff T. Tropodithietic acid production in Phaeobacter gallaeciensis is regulated by N-acyl homoserine lactone-mediated quorum sensing. J Bacteriol. 2011 Dec;193(23):6576-85. doi: 10.1128/JB.05818-11. Epub 2011 Sep 23. PubMed PMID: 21949069; PubMed Central PMCID: PMC3232910. 9: Porsby CH, Webber MA, Nielsen KF, Piddock LJ, Gram L. Resistance and tolerance to tropodithietic acid, an antimicrobial in aquaculture, is hard to select. Antimicrob Agents Chemother. 2011 Apr;55(4):1332-7. doi: 10.1128/AAC.01222-10. Epub 2011 Jan 24. PubMed PMID: 21263047; PubMed Central PMCID: PMC3067165. 10: Zhao W, Dao C, Karim M, Gomez-Chiarri M, Rowley D, Nelson DR. Contributions of tropodithietic acid and biofilm formation to the probiotic activity of Phaeobacter inhibens. BMC Microbiol. 2016 Jan 5;16:1. doi: 10.1186/s12866-015-0617-z. PubMed PMID: 26728027; PubMed Central PMCID: PMC4700733. 11: Berger M, Brock NL, Liesegang H, Dogs M, Preuth I, Simon M, Dickschat JS, Brinkhoff T. Genetic analysis of the upper phenylacetate catabolic pathway in the production of tropodithietic acid by Phaeobacter gallaeciensis. Appl Environ Microbiol. 2012 May;78(10):3539-51. doi: 10.1128/AEM.07657-11. Epub 2012 Mar 9. PubMed PMID: 22407685; PubMed Central PMCID: PMC3346364. 12: Wilson MZ, Wang R, Gitai Z, Seyedsayamdost MR. 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. Proc Natl Acad Sci U S A. 2016 Feb 9;113(6):1630-5. doi: 10.1073/pnas.1518034113. Epub 2016 Jan 22. PubMed PMID: 26802120; PubMed Central PMCID: PMC4760781. 13: Rasmussen BB, Grotkjær T, D'Alvise PW, Yin G, Zhang F, Bunk B, Spröer C, Bentzon-Tilia M, Gram L. Vibrio anguillarum Is Genetically and Phenotypically Unaffected by Long-Term Continuous Exposure to the Antibacterial Compound Tropodithietic Acid. Appl Environ Microbiol. 2016 Jul 15;82(15):4802-10. doi: 10.1128/AEM.01047-16. Print 2016 Aug 1. PubMed PMID: 27235441; PubMed Central PMCID: PMC4984299. 14: Geng H, Belas R. Expression of tropodithietic acid biosynthesis is controlled by a novel autoinducer. J Bacteriol. 2010 Sep;192(17):4377-87. doi: 10.1128/JB.00410-10. Epub 2010 Jul 2. PubMed PMID: 20601479; PubMed Central PMCID: PMC2937372. 15: Wichmann H, Brinkhoff T, Simon M, Richter-Landsberg C. Dimethylsulfoniopropionate Promotes Process Outgrowth in Neural Cells and Exerts Protective Effects against Tropodithietic Acid. Mar Drugs. 2016 May 6;14(5). pii: E89. doi: 10.3390/md14050089. PubMed PMID: 27164116; PubMed Central PMCID: PMC4882563. 16: Greer EM, Aebisher D, Greer A, Bentley R. Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism. J Org Chem. 2008 Jan 4;73(1):280-3. Epub 2007 Dec 7. PubMed PMID: 18062698. 17: Geng H, Bruhn JB, Nielsen KF, Gram L, Belas R. Genetic dissection of tropodithietic acid biosynthesis by marine roseobacters. Appl Environ Microbiol. 2008 Mar;74(5):1535-45. doi: 10.1128/AEM.02339-07. Epub 2008 Jan 11. PubMed PMID: 18192410; PubMed Central PMCID: PMC2258615. 18: Mitra S, Sana B, Mukherjee J. Ecological roles and biotechnological applications of marine and intertidal microbial biofilms. Adv Biochem Eng Biotechnol. 2014;146:163-205. doi: 10.1007/10_2014_271. Review. PubMed PMID: 24817086. 19: Gram L, Rasmussen BB, Wemheuer B, Bernbom N, Ng YY, Porsby CH, Breider S, Brinkhoff T. Phaeobacter inhibens from the Roseobacter clade has an environmental niche as a surface colonizer in harbors. Syst Appl Microbiol. 2015 Oct;38(7):483-93. doi: 10.1016/j.syapm.2015.07.006. Epub 2015 Aug 14. PubMed PMID: 26343311. 20: Porsby CH, Gram L. Phaeobacter inhibens as biocontrol agent against Vibrio vulnificus in oyster models. Food Microbiol. 2016 Aug;57:63-70. doi: 10.1016/j.fm.2016.01.005. Epub 2016 Jan 21. PubMed PMID: 27052703.

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Tropodithietic acid featured