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MedKoo Cat#: 527875 | Name: LED209
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Description:

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

LED209 is a novel non-toxic inhibitor of the binding signals to QseC, preventing its autophosphorylation and consequently inhibiting QseC-mediated activation of virulence gene expression.

Chemical Structure

LED209
LED209
CAS#245342-14-7

Theoretical Analysis

MedKoo Cat#: 527875

Name: LED209

CAS#: 245342-14-7

Chemical Formula: C19H17N3O2S2

Exact Mass: 383.0762

Molecular Weight: 383.48

Elemental Analysis: C, 59.51; H, 4.47; N, 10.96; O, 8.34; S, 16.72

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
LED 209; LED-209; LED209
IUPAC/Chemical Name
1-Phenyl-3-[4-(phenylsulfamoyl)phenyl]thiourea
InChi Key
HNDRSTUKPCLQLT-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H17N3O2S2/c23-26(24,22-17-9-5-2-6-10-17)18-13-11-16(12-14-18)21-19(25)20-15-7-3-1-4-8-15/h1-14,22H,(H2,20,21,25)
SMILES Code
S=C(NC1=CC=C(S(=O)(NC2=CC=CC=C2)=O)C=C1)NC3=CC=CC=C3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
LED209 is a potent small molecule inhibitor of bacterial receptor QseC, is a potent prodrug that is highly selective for QseC.
In vitro activity:
This study examined the effect of adrenergic compounds on L. pneumophila, and discovered that the adrenergic receptor antagonists benoxathian, naftopidil, propranolol and labetalol, as well as the QseC sensor kinase inhibitor LED209, reduced the growth of L. pneumophila in broth or amoebae, while replication in macrophages was enhanced. Reference: Microbiology (Reading). 2015 Jul;161(7):1392-406. https://pubmed.ncbi.nlm.nih.gov/25873585/
In vivo activity:
To determine if a more rigorous dosing regimen would increase protection against S. Typhimurium infection, LED209 (20 mg/kg) was administered at 3 h before, at the time of, and 3, 6, 9, and 12 h after intraperitoneal injection of a lethal dose of S. Typhimurium. At 48 h, only 14% of the untreated mice remained alive, with none surviving beyond 72 h postinfection, whereas 43% of the LED209-treated mice remained alive and survived up to 8 days after infection, when these animals were sacrificed (Fig. 5B). Reference: mBio. 2014 Nov 11;5(6):e02165. https://pubmed.ncbi.nlm.nih.gov/25389178/
Solvent mg/mL mM
Solubility
DMF 25.0 65.23
DMSO 135.0 352.04
Ethanol 0.2 0.39
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 383.48 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
Formulation protocol:
1. Zhou Z, Dong Z, Wang L, Song R, Mei N, Chen T, Luo L, Ding Q, Wang X, Tang S. Cellulose membrane modified with LED209 as an antibacterial and anti-adhesion material. Carbohydr Polym. 2021 Jan 15;252:117138. doi: 10.1016/j.carbpol.2020.117138. Epub 2020 Sep 28. PMID: 33183597. 2. Harrison CF, Kicka S, Kranjc A, Finsel I, Chiriano G, Ouertatani-Sakouhi H, Soldati T, Scapozza L, Hilbi H. Adrenergic antagonists restrict replication of Legionella. Microbiology (Reading). 2015 Jul;161(7):1392-406. doi: 10.1099/mic.0.000094. Epub 2015 Apr 14. PMID: 25873585. 3. Yang Q, Zou P, Cao Z, Wang Q, Fu S, Xie G, Huang J. QseC Inhibition as a Novel Antivirulence Strategy for the Prevention of Acute Hepatopancreatic Necrosis Disease (AHPND)-Causing Vibrio parahaemolyticus. Front Cell Infect Microbiol. 2021 Jan 21;10:594652. doi: 10.3389/fcimb.2020.594652. PMID: 33553003; PMCID: PMC7859628. 4. Curtis MM, Russell R, Moreira CG, Adebesin AM, Wang C, Williams NS, Taussig R, Stewart D, Zimmern P, Lu B, Prasad RN, Zhu C, Rasko DA, Huntley JF, Falck JR, Sperandio V. QseC inhibitors as an antivirulence approach for Gram-negative pathogens. mBio. 2014 Nov 11;5(6):e02165. doi: 10.1128/mBio.02165-14. PMID: 25389178; PMCID: PMC4235214.
In vitro protocol:
1. Zhou Z, Dong Z, Wang L, Song R, Mei N, Chen T, Luo L, Ding Q, Wang X, Tang S. Cellulose membrane modified with LED209 as an antibacterial and anti-adhesion material. Carbohydr Polym. 2021 Jan 15;252:117138. doi: 10.1016/j.carbpol.2020.117138. Epub 2020 Sep 28. PMID: 33183597. 2. Harrison CF, Kicka S, Kranjc A, Finsel I, Chiriano G, Ouertatani-Sakouhi H, Soldati T, Scapozza L, Hilbi H. Adrenergic antagonists restrict replication of Legionella. Microbiology (Reading). 2015 Jul;161(7):1392-406. doi: 10.1099/mic.0.000094. Epub 2015 Apr 14. PMID: 25873585.
In vivo protocol:
1. Yang Q, Zou P, Cao Z, Wang Q, Fu S, Xie G, Huang J. QseC Inhibition as a Novel Antivirulence Strategy for the Prevention of Acute Hepatopancreatic Necrosis Disease (AHPND)-Causing Vibrio parahaemolyticus. Front Cell Infect Microbiol. 2021 Jan 21;10:594652. doi: 10.3389/fcimb.2020.594652. PMID: 33553003; PMCID: PMC7859628. 2. Curtis MM, Russell R, Moreira CG, Adebesin AM, Wang C, Williams NS, Taussig R, Stewart D, Zimmern P, Lu B, Prasad RN, Zhu C, Rasko DA, Huntley JF, Falck JR, Sperandio V. QseC inhibitors as an antivirulence approach for Gram-negative pathogens. mBio. 2014 Nov 11;5(6):e02165. doi: 10.1128/mBio.02165-14. PMID: 25389178; PMCID: PMC4235214.
1: Han Y, Wang Y, Yu Y, Chen H, Shen Y, Du L. Indole-Induced Reversion of Intrinsic Multiantibiotic Resistance in Lysobacter enzymogenes. Appl Environ Microbiol. 2017 Aug 17;83(17). pii: e00995-17. doi: 10.1128/AEM.00995-17. Print 2017 Sep 1. PubMed PMID: 28625984; PubMed Central PMCID: PMC5561299. 2: Johnson BK, Abramovitch RB. Small Molecules That Sabotage Bacterial Virulence. Trends Pharmacol Sci. 2017 Apr;38(4):339-362. doi: 10.1016/j.tips.2017.01.004. Epub 2017 Feb 14. Review. PubMed PMID: 28209403; PubMed Central PMCID: PMC5679398. 3: Rooks MG, Veiga P, Reeves AZ, Lavoie S, Yasuda K, Asano Y, Yoshihara K, Michaud M, Wardwell-Scott L, Gallini CA, Glickman JN, Sudo N, Huttenhower C, Lesser CF, Garrett WS. QseC inhibition as an antivirulence approach for colitis-associated bacteria. Proc Natl Acad Sci U S A. 2017 Jan 3;114(1):142-147. doi: 10.1073/pnas.1612836114. Epub 2016 Dec 15. PubMed PMID: 27980034; PubMed Central PMCID: PMC5224399. 4: Li Z, Zheng Q, Xue X, Shi X, Zhou Y, Da F, Qu D, Hou Z, Luo X. Pyroptosis of Salmonella Typhimurium-infected macrophages was suppressed and elimination of intracellular bacteria from macrophages was promoted by blocking QseC. Sci Rep. 2016 Nov 17;6:37447. doi: 10.1038/srep37447. PubMed PMID: 27853287; PubMed Central PMCID: PMC5112599. 5: Harrison CF, Kicka S, Kranjc A, Finsel I, Chiriano G, Ouertatani-Sakouhi H, Soldati T, Scapozza L, Hilbi H. Adrenergic antagonists restrict replication of Legionella. Microbiology. 2015 Jul;161(7):1392-406. doi: 10.1099/mic.0.000094. Epub 2015 Apr 14. PubMed PMID: 25873585. 6: Xue XY, Mao XG, Li Z, Chen Z, Zhou Y, Hou Z, Li MK, Meng JR, Luo XX. A potent and selective antimicrobial poly(amidoamine) dendrimer conjugate with LED209 targeting QseC receptor to inhibit the virulence genes of gram negative bacteria. Nanomedicine. 2015 Feb;11(2):329-39. doi: 10.1016/j.nano.2014.09.016. Epub 2014 Nov 15. PubMed PMID: 25461286. 7: Yang Q, Anh ND, Bossier P, Defoirdt T. Norepinephrine and dopamine increase motility, biofilm formation, and virulence of Vibrio harveyi. Front Microbiol. 2014 Nov 6;5:584. doi: 10.3389/fmicb.2014.00584. eCollection 2014. PubMed PMID: 25414697; PubMed Central PMCID: PMC4222227. 8: Curtis MM, Russell R, Moreira CG, Adebesin AM, Wang C, Williams NS, Taussig R, Stewart D, Zimmern P, Lu B, Prasad RN, Zhu C, Rasko DA, Huntley JF, Falck JR, Sperandio V. QseC inhibitors as an antivirulence approach for Gram-negative pathogens. MBio. 2014 Nov 11;5(6):e02165. doi: 10.1128/mBio.02165-14. PubMed PMID: 25389178; PubMed Central PMCID: PMC4235214. 9: Spencer H, Karavolos MH, Bulmer DM, Aldridge P, Chhabra SR, Winzer K, Williams P, Khan CM. Genome-wide transposon mutagenesis identifies a role for host neuroendocrine stress hormones in regulating the expression of virulence genes in Salmonella. J Bacteriol. 2010 Feb;192(3):714-24. doi: 10.1128/JB.01329-09. Epub 2009 Nov 20. PubMed PMID: 19933366; PubMed Central PMCID: PMC2812446. 10: Disarming, not destroying: targeting QseC. Future Microbiol. 2008 Oct;3(5):485-7. doi: 10.2217/17460913.3.5.485. PubMed PMID: 18811230. 11: Payne DJ. Microbiology. Desperately seeking new antibiotics. Science. 2008 Sep 19;321(5896):1644-5. doi: 10.1126/science.1164586. PubMed PMID: 18801989. 12: Rasko DA, Moreira CG, Li de R, Reading NC, Ritchie JM, Waldor MK, Williams N, Taussig R, Wei S, Roth M, Hughes DT, Huntley JF, Fina MW, Falck JR, Sperandio V. Targeting QseC signaling and virulence for antibiotic development. Science. 2008 Aug 22;321(5892):1078-80. doi: 10.1126/science.1160354. PubMed PMID: 18719281; PubMed Central PMCID: PMC2605406.