ArticleThe Journal of antibiotics2015
Tackling vancomycin-resistant bacteria with 'lipophilic-vancomycin-carbohydrate conjugates'.
Article in The Journal of antibiotics, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
18 citing papers in PubMed, 70 citations in OpenAlex.
- Strategic re-engineering of antibiotics.Nature reviews bioengineering · 2025Article
- New Conjugates of Vancomycin with Cell-Penetrating Peptides-Synthesis, Antimicrobial Activity, Cytotoxicity, and BBB Permeability Studies.Molecules (Basel, Switzerland) · 2024Article
- Surface-mediated self-assembly of click-reactive cello-oligosaccharides for fabricating functional nonwoven fabrics.Science and technology of advanced materials · 2024Article
- Thioglycosides Act as Metabolic Inhibitors of Bacterial Glycan Biosynthesis.ACS infectious diseases · 2023Article
- Vibrational Optical Activity Study of Four Antibiotic (Lipo)glycopeptides: Vancomycin, Oritavancin, Dalbavancin, and Teicoplanin.ACS omega · 2022Article
- A Modified Vancomycin Molecule Confers Potent Inhibitory Efficacy against Resistant Bacteria Mediated by Metallo-β-Lactamases.Molecules (Basel, Switzerland) · 2022Article
- Recent Advances in the Development of Semisynthetic Glycopeptide Antibiotics: 2014-2022.ACS infectious diseases · 2022Review
- Thiol- and Disulfide-Containing Vancomycin Derivatives Against Bacterial Resistance and Biofilm Formation.ACS medicinal chemistry letters · 2021Article
- Regulation of Resistance in Vancomycin-Resistant Enterococci: The VanRS Two-Component System.Microorganisms · 2021Review
- Dismantling the bacterial glycocalyx: Chemical tools to probe, perturb, and image bacterial glycans.Bioorganic & medicinal chemistry · 2021Review
- Maxamycins: Durable Antibiotics Derived by Rational Redesign of Vancomycin.Accounts of chemical research · 2020Article
- Vancomycin C-Terminus Guanidine Modifications and Further Insights into an Added Mechanism of Action Imparted by a Peripheral Structural Modification.ACS infectious diseases · 2020Article
- Transportan 10 improves the pharmacokinetics and pharmacodynamics of vancomycin.Scientific reports · 2019Article
- Developments in Glycopeptide Antibiotics.ACS infectious diseases · 2018Article
- Oversized galactosides as a probe for conformational dynamics in LacY.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Novel vancomycin-peptide conjugate as potent antibacterial agent against vancomycin-resistantInfection and drug resistance · 2018Article
- A review on cell wall synthesis inhibitors with an emphasis on glycopeptide antibiotics.MedChemComm · 2017Review
- Review of vancomycin-induced renal toxicity: an update.Therapeutic advances in endocrinology and metabolism · 2016Review
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Vancomycin, a glycopeptide antibiotic, has long been a drug of choice for life-threatening Gram-positive bacterial infections. Vancomycin confers its antibacterial activity by inhibiting bacterial cell wall biosynthesis. However, over the time, vancomycin has also been rendered ineffective by vancomycin-resistant bacteria (VRB). These bacteria developed resistance to it by alteration of cell wall precursor from D-Ala-D-Ala to D-Ala-D-Lac (vancomycin-resistant Enterococci, VRE), which leads to manifold reduction in the binding constant and results in the loss of antibacterial activity. Herein, we report various vancomycin-sugar analogs, based on a simple design rationale, which exhibit increased binding affinity to VRB, thereby resensitizing VRB to vancomycin. Optimized vancomycin-sugar conjugate exhibited 150-fold increase in affinity for N,N'-diacetyl-Lys-D-Ala-D-Lac compared with vancomycin. This improved binding affinity was also reflected in its antibacterial activity, wherein the MIC value was brought down from 750 to 36 μM against VRE (VanA phenotype). To further sensitize against VRE, we appended lipophilic alkyl chain to optimized vancomycin-sugar conjugate. This lipophilic-vancomycin-sugar conjugate was >1000-fold (MIC=0.7 μM) and 250-fold (MIC=1 μM) more effective against VanA and VanB strains of VRE, respectively, compared with vancomycin. Therefore, this synthetically simple approach could lead to the development of new generation of glycopeptide antibiotics, which can be clinically used to tackle VRB infections.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.