18226-47-6

Upstream product

• 18226-43-2 1,3,5-benzenetriethanol 
• 80935-59-7 2,2',2''-(benzene-1,3,5-triyl)triacetonitrile 
• 4435-67-0 1,3,5-benzenetriacetic acid 
• 18226-42-1 1,3,5-Tris(bromomethyl)benzene 
• 859032-83-0 benzene-1,3,5-triyl-tri-acetic acid triethyl ester 

Downstream Products

• 61582-68-1 1,3,5-tris(mercaptoethyl)benzene 
• 374607-03-1 1,3,5-tris[(2'-diphenylphosphanyl)ethyl]benzene 
• 85294-17-3 4-[3,5-Bis-(3-chlorocarbonyl-propyl)-phenyl]-butyryl chloride 
• 23639-68-1 4-[3,5-Bis-(3-carboxy-propyl)-phenyl]-butyric acid 
• 85294-27-5 5,10,15-(1,3,5-tris(benzenetributyryl)tris(α,α,α-o-aminophenyl))-20-(α-o-pivalamidophenyl)porphyrin 

Relevant academic research and scientific papers

Antibiotic Conjugates with an Artificial MECAM-Based Siderophore Are Potent Agents against Gram-Positive and Gram-Negative Bacterial Pathogens

The development of novel drugs against Gram-negative bacteria represents an urgent medical need. To overcome their outer cell membrane, we synthesized conjugates of antibiotics and artificial siderophores based on the MECAM core, which are imported by bacterial iron uptake systems. Structures, spin states, and iron binding properties were predicted in silico using density functional theory. The capability of MECAM to function as an effective artificial siderophore in Escherichia coli was proven in microbiological growth recovery and bioanalytical assays. Following a linker optimization focused on transport efficiency, five β-lactam and one daptomycin conjugates were prepared. The most potent conjugate 27 showed growth inhibition of Gram-positive and Gram-negative multidrug-resistant pathogens at nanomolar concentrations. The uptake pathway of MECAMs was deciphered by knockout mutants and highlighted the relevance of FepA, CirA, and Fiu. Resistance against 27 was mediated by a mutation in the gene encoding ExbB, which is involved in siderophore transport.