ArticleAntibiotics (Basel, Switzerland)2021
Triphenilphosphonium Analogs of Chloramphenicol as Dual-Acting Antimicrobial and Antiproliferating Agents.
Article in Antibiotics (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 36 citations in OpenAlex.
- Toward Mitochondrial Targeting of Resistant Triple-Negative Breast Cancer Using Triphenylphosphonium-Conjugated Antimicrobial Peptides.ACS pharmacology & translational science · 2025Article
- Antimicrobial activity of triphenylphosphonium (TPP) conjugates of alkynyl-substituted nucleic bases and their analogues.The Journal of antibiotics · 2025Article
- Alkyltriphenylphosphonium-Functionalized Hyperbranched Polyethyleneimine Nanoparticles for Safe and Efficient Bacterial Eradication: A Structure-Property Relationship Study.International journal of molecular sciences · 2025Article
- Rhodamine 19 Alkyl Esters as Effective Antibacterial Agents.International journal of molecular sciences · 2024Article
- Triphenylphosphonium Analogs of Short Peptide Related to Bactenecin 7 and Oncocin 112 as Antimicrobial Agents.Pharmaceutics · 2024Article
- Penetration of Triphenylphosphonium Derivatives through the Cell Envelope of Bacteria ofPharmaceuticals (Basel, Switzerland) · 2023Article
- Observation of Cytotoxicity of Phosphonium Derivatives Is Explained: Metabolism Inhibition and Adhesion Alteration.Antibiotics (Basel, Switzerland) · 2023Article
- Conjugates of Chloramphenicol Amine and Berberine as Antimicrobial Agents.Antibiotics (Basel, Switzerland) · 2022Article
- MDR Pumps as Crossroads of Resistance: Antibiotics and Bacteriophages.Antibiotics (Basel, Switzerland) · 2022Review
- Rational Design 2-Hydroxypropylphosphonium Salts as Cancer Cell Mitochondria-Targeted Vectors: Synthesis, Structure, and Biological Properties.Molecules (Basel, Switzerland) · 2021Article
- Binding and Action of Triphenylphosphonium Analog of Chloramphenicol upon the Bacterial Ribosome.Antibiotics (Basel, Switzerland) · 2021Article
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Authors and funding
18 authors at 9 institutions in 3 countries.
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Abstract
In the current work, in continuation of our recent research, we synthesized and studied new chimeric compounds, including the ribosome-targeting antibiotic chloramphenicol (CHL) and the membrane-penetrating cation triphenylphosphonium (TPP), which are linked by alkyl groups of different lengths. Using various biochemical assays, we showed that these CAM-Cn-TPP compounds bind to the bacterial ribosome, inhibit protein synthesis in vitro and in vivo in a way similar to that of the parent CHL, and significantly reduce membrane potential. Similar to CAM-C4-TPP, the mode of action of CAM-C10-TPP and CAM-C14-TPP in bacterial ribosomes differs from that of CHL. By simulating the dynamics of CAM-Cn-TPP complexes with bacterial ribosomes, we proposed a possible explanation for the specificity of the action of these analogs in the translation process. CAM-C10-TPP and CAM-C14-TPP more strongly inhibit the growth of the Gram-positive bacteria, as compared to CHL, and suppress some CHL-resistant bacterial strains. Thus, we have shown that TPP derivatives of CHL are dual-acting compounds targeting both the ribosomes and cellular membranes of bacteria. The TPP fragment of CAM-Cn-TPP compounds has an inhibitory effect on bacteria. Moreover, since the mitochondria of eukaryotic cells possess qualities similar to those of their prokaryotic ancestors, we demonstrate the possibility of targeting chemoresistant cancer cells with these compounds.
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