ArticleACS infectious diseases2019
Modification at the 2'-Position of the 4,5-Series of 2-Deoxystreptamine Aminoglycoside Antibiotics To Resist Aminoglycoside Modifying Enzymes and Increase Ribosomal Target Selectivity.
Article in ACS infectious diseases, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 35 citations in OpenAlex.
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- Antimicrobial activity of metal-based nanoparticles: a mini-review.Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine · 2024Review
- Mechanistic plasticity in ApmA enables aminoglycoside promiscuity for resistance.Nature chemical biology · 2024Article
- Facile Synthesis of 5-Bromo-Infection and drug resistance · 2024Article
- Success stories of natural product-derived compounds from plants as multidrug resistance modulators in microorganisms.RSC advances · 2023Review
- Importance of Co-operative Hydrogen Bonding in the Apramycin-Ribosomal Decoding A-Site Interaction.ChemMedChem · 2023Article
- Design, Synthesis, and Bioassay of 2'-Modified Kanamycin A.Molecules (Basel, Switzerland) · 2022Article
- Structure-Activity Relationships for 5'' Modifications of 4,5-Aminoglycoside Antibiotics.ChemMedChem · 2022Article
- Structural basis for plazomicin antibiotic action and resistance.Communications biology · 2021Article
- Article
- Synthesis of a Pseudodisaccharide Suitable for Synthesis of Ring I Modified 4,5-2-Deoxystreptamine Type Aminoglycoside Antibiotics.The Journal of organic chemistry · 2020Article
- Synthesis of Gentamicin Minor Components: Gentamicin B1 and Gentamicin X2.Organic letters · 2020Article
- Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells.Antibiotics (Basel, Switzerland) · 2020Article
- Aminoglycosides: Time for the Resurrection of a Neglected Class of Antibacterials?ACS infectious diseases · 2020Article
- Apralogs: Apramycin 5-Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
A series of derivatives of the 4,5-disubstituted class of 2-deoxystreptamine aminoglycoside antibiotics neomycin, paromomycin, and ribostamycin was prepared and assayed for (i) their ability to inhibit protein synthesis by bacterial ribosomes and by engineered bacterial ribosomes carrying eukaryotic decoding A sites, (ii) antibacterial activity against wild type Gram negative and positive pathogens, and (iii) overcoming resistance due to the presence of aminoacyl transferases acting at the 2'-position. The presence of five suitably positioned residual basic amino groups was found to be necessary for activity to be retained upon removal or alkylation of the 2'-position amine. As alkylation of the 2'-amino group overcomes the action of resistance determinants acting at that position and in addition results in increased selectivity for the prokaryotic over eukaryotic ribosomes, it constitutes an attractive modification for introduction into next generation aminoglycosides. In the neomycin series, the installation of small (formamide) or basic (glycinamide) amido groups on the 2'-amino group is tolerated.
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