ArticleACS infectious diseases2020
Vancomycin C-Terminus Guanidine Modifications and Further Insights into an Added Mechanism of Action Imparted by a Peripheral Structural Modification.
Article in ACS infectious diseases, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 41 citations in OpenAlex.
- Vancomycin resistance in gram-positive infections: evolutionary strategies of survival.Archives of microbiology · 2026Review
- Guanidiniocarbonyl-Pyrrole (GCP) C- and N-Terminus Modifications of Vancomycin.The Journal of organic chemistry · 2025Article
- Strategic re-engineering of antibiotics.Nature reviews bioengineering · 2025Article
- Vancomycin-Teixobactin Conjugates.Journal of the American Chemical Society · 2025Article
- Tetrachloromaxamycins: Divergent Total Synthesis and Initial Assessments.The Journal of organic chemistry · 2024Article
- Biguanide-Vancomycin Conjugates are Effective Broad-Spectrum Antibiotics against Actively Growing and Biofilm-Associated Gram-Positive and Gram-Negative ESKAPE Pathogens and Mycobacteria.Journal of the American Chemical Society · 2024Article
- Vancomycin-Polyguanidino Dendrimer Conjugates Inhibit Growth of Antibiotic-Resistant Gram-Positive and Gram-Negative Bacteria and Eradicate Biofilm-AssociatedACS infectious diseases · 2024Article
- Tetrachlorovancomycin: Total Synthesis of a Designed Glycopeptide Antibiotic of Reduced Synthetic Complexity.Journal of the American Chemical Society · 2023Article
- Detection of intact vancomycin-arginine as the active antibacterial conjugate inRSC medicinal chemistry · 2023Article
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- Divergent Total Synthesis and Characterization of Maxamycins.Journal of the American Chemical Society · 2023Article
- Synthesis and Characterization of DOTAM-Based Sideromycins for Bacterial Imaging and Antimicrobial Therapy.ACS infectious diseases · 2023Article
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- Peptidoglycan-Directed Chemical Ligation for Selective Inhibition on Gram-Positive Bacteria.ACS omega · 2023Article
- Current Promising Strategies against Antibiotic-Resistant Bacterial Infections.Antibiotics (Basel, Switzerland) · 2022Review
- Synthesis and Structure-Activity Studies of β-Barrel Assembly Machine Complex Inhibitor MRL-494.ACS infectious diseases · 2022Article
- Natural products and drug discovery.National science review · 2022Review
- Recent Advances in the Development of Semisynthetic Glycopeptide Antibiotics: 2014-2022.ACS infectious diseases · 2022Review
- Evaluation of Toxic Properties of New Glycopeptide Flavancin on Rats.Pharmaceuticals (Basel, Switzerland) · 2022Article
- Old and modern antibiotic structures with potential for today's infections.ADMET & DMPK · 2022Review
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A series of vancomycin C-terminus guanidine modifications is disclosed that improves antimicrobial activity, enhances the durability of antimicrobial action against selection or induction of resistance, and introduces a synergistic mechanism of action independent of d-Ala-d-Ala binding and inhibition of cell wall biosynthesis. The added mechanism of action results in induced bacterial cell permeability, which we show may involve interaction with cell envelope teichoic acid. Significantly, the compounds examined that contain two combined peripheral modifications, a (4-chlorobiphenyl)methyl (CBP) and C-terminus guanidinium modification, offer opportunities for new treatments against not only vancomycin-sensitive but especially vancomycin-resistant bacteria where they act by two synergistic and now durable mechanisms of action independent of d-Ala-d-Ala/d-Lac binding and display superb antimicrobial potencies (MIC 0.6-0.15 μg/mL, VanA VRE). For the first time, we demonstrate that the synergistic behavior of the peripheral modifications examined requires the presence of both the CBP and guanidine modifications in a single molecule versus their combined use as an equimolar mixture of singly modified compounds. Finally, we show that a prototypical member of the series, G3-CBP-vancomycin (
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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.