245342-14-7

Basic information

• Product Name: N-PHENYL-4-[[(PHENYLAMINO)THIOXOMETHYL]AMINO]-BENZENESULFONAMIDE
• Synonyms: LED209;N-PHENYL-4-[[(PHENYLAMINO)THIOXOMETHYL]AMINO]-BENZENESULFONAMIDE;N-Phenyl-4-(3-phenylthioureido)benzenesulfonamide;N-Phenyl-4-(3-phenylthioureido)benzenesulfonamide LED209;LED209 hydrate;N-phenyl-4-[[(phenylamino)thioxomethyl]amino]benzenesulfonamide hydrate
• CAS NO: 245342-14-7
• Molecular Formula: C₁₉H₁₇N₃O₂S₂
• Molecular Weight: 383.48718
• Product Categories: Inhibitors
• Mol File: 245342-14-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 549.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.437±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: insoluble in EtOH; insoluble in H2O; insoluble in DMSO
• PKA: 8.77±0.10(Predicted)
• CAS DataBase Reference: N-PHENYL-4-[[(PHENYLAMINO)THIOXOMETHYL]AMINO]-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENYL-4-[[(PHENYLAMINO)THIOXOMETHYL]AMINO]-BENZENESULFONAMIDE(245342-14-7)
• EPA Substance Registry System: N-PHENYL-4-[[(PHENYLAMINO)THIOXOMETHYL]AMINO]-BENZENESULFONAMIDE(245342-14-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 245342-14-7(Hazardous Substances Data)

Usage

Biological Activity

many bacterial pathogens rely on a conserved membrane histidine sensor kinase, qsec, to respond to host adrenergic signaling molecules and bacterial signals in order to promote the expression of virulence factors. led209 is a potent prodrug that is highly selective for qsec.

in vitro

led209-mediated inhibition of virulence gene expression inhibited the secretion of espa and espb, two proteins encoded within the locus of enterocyte effacement that are required for escherichia coli (ehec) to translocate bacterial proteins into host cells and cause attaching-effacing (ae) lesions. at 5 pm, led209 abolished ehec ae lesion formation on cultured epithelial cells. unlike conventional antibiotics, led209 does not kill or hinder ehec growth or trigger the ehec sos response [1].

in vivo

led209 [20 mg per kilogram of body weight (mg/kg)] was given orally to mice 3 hours before and 3 hours after intraperitoneal injection of a lethal dose of s. typhimurium. twenty-four hours after infection, only 30% of untreated mice remained alive, whereas 80% of the led209-treated mice were still alive. all the s. typhimurium– infected mice died within 72 hours of infection, and 20% of led209-treated mice survived up to 12 days [1].

IC 50

<10 μm

references

[1] 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.

Upstream product

• 127-77-5 p-aminobenzenesulphonanilide 
• 103-72-0 phenyl isothiocyanate 
• 2080-33-3 N-[4-(phenylsulfamoyl)phenyl]acetamide 
• 62-53-3 aniline 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Relevant articles and documents

METHODS OF INHIBITING BACTERIAL VIRULENCE AND COMPOUNDS RELATING THERETO

The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.