ArticleACS infectious diseases2018
N-Terminus Alkylation of Vancomycin: Ligand Binding Affinity, Antimicrobial Activity, and Site-Specific Nature of Quaternary Trimethylammonium Salt Modification.
Article in ACS infectious diseases, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
20 citing papers in PubMed, 36 citations in OpenAlex.
- Assessing Vancomycin-Formyl Peptide Conjugate Binding to the Surface of Resistant Staphylococcus aureus via Flow Cytometry.Chembiochem : a European journal of chemical biology · 2026Article
- Antibacterial activity and mechanism of optimized THPA conjugated dipeptides against methicillin-resistant Staphylococcus aureus.The Journal of antibiotics · 2026Article
- 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
- 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
- Advances in the Synthesis of Biologically Active Quaternary Ammonium Compounds.International journal of molecular sciences · 2024Review
- Deriving Novel Quaternary Ammonium Compound Disinfectant Scaffolds from a Natural Product: Mechanistic Insights of the Quaternization of Ianthelliformisamine C.ChemMedChem · 2023Article
- Synthesis and Antibacterial Evaluation of Novel Vancomycin Derivatives Containing Quaternary Ammonium Moieties.ACS omega · 2023Article
- Shapeshifting bullvalene-linked vancomycin dimers as effective antibiotics against multidrug-resistant gram-positive bacteria.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Bioorthogonal Functionalization of Material Surfaces with Bioactive Molecules.ACS applied materials & interfaces · 2023Article
- 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
- Maxamycins: Durable Antibiotics Derived by Rational Redesign of Vancomycin.Accounts of chemical research · 2020Article
- Attenuating the Selection of Vancomycin Resistance AmongACS infectious diseases · 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
- Instructive Advances in Chemical Microbiology Inspired by Nature's Diverse Inventory of Molecules.ACS infectious diseases · 2020Review
- C1-CBP-vancomycin: Impact of a Vancomycin C-Terminus Trimethylammonium Cation on Pharmacological Properties and Insights into Its Newly Introduced Mechanism of Action.The Journal of organic chemistry · 2020Article
- More QACs, more questions: Recent advances in structure activity relationships and hurdles in understanding resistance mechanisms.Tetrahedron letters · 2019Article
- Exploration of the site-specific nature and generalizability of a trimethylammonium salt modification on vancomycin: A-ring derivatives.Tetrahedron · 2019Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A series of vancomycin derivatives alkylated at the N-terminus amine were synthesized, including those that contain quaternary trimethylammonium salts either directly at the terminal amine site or with an intervening three-carbon spacer. The examination of their properties provides important comparisons with a C-terminus trimethylammonium salt modification that we recently found to improve the antimicrobial potency of vancomycin analogues through an added mechanism of action. The N-terminus modifications disclosed herein were well-tolerated, minimally altering model ligand binding affinities (d-Ala-d-Ala) and antimicrobial activity, but did not induce membrane permeabilization that was observed with a similar C-terminus modification. The results indicate that our earlier observations with the C-terminus modification are sensitive to the site as well as structure of the trimethylammonium salt modification and are not simply the result of nonspecific effects derived from introduction of a cationic charge.
Indexed as
Identifiers
What OpenQuestion holds
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.