Synthesis of Human Milk Oligosaccharides-Fluoroquinolone Conjugates and Investigation of Their Antimicrobial Activity.
- 1Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, StavangerNO-4036, Norway.
- 2Department of Chemistry, University of Bergen, BergenNO-5020, Norway.
Abstract
The copper-catalyzed azide-alkyne cycloaddition reaction was applied to conjugate four human milk oligosaccharides (HMOs) with antimicrobial fluoroquinolones (FQs) (ciprofloxacin and sparfloxacin) to obtain a total of 12 per-O-acetylated and unprotected HMO-FQ conjugates. These compounds underwent antimicrobial testing against Gram-positive (Streptococcus agalactiae, Enterococcus faecalis, and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. The HMO-FQ conjugates exhibited the most significant antimicrobial activity against E. coli and S. aureus reaching minimum inhibitory concentration as low as 1.56 μM and 3.13 μM, respectively. A general trend was that per-O-acetylated HMO-FQ conjugates exhibited higher antimicrobial activity than their unprotected counterparts. The antimicrobial activity of the tested HMO-FQ conjugates is expected to arise from the ciprofloxacin and sparfloxacin moieties because per-O-acetylated and unprotected HMOs did not exhibit any antimicrobial activity. Additionally, the HMO-FQ conjugates displayed no cytotoxicity as evident from test on two cell lines (HepG2 and MRC5).
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BibTeX
@article{sang2026synthesis,
title = {{Synthesis of Human Milk Oligosaccharides-Fluoroquinolone Conjugates and Investigation of Their Antimicrobial Activity.}},
author = {Liza Nguyen Van Sang and Emil Lindbäck and Magne O Sydnes},
journal = {Bioconjugate chemistry},
year = {2026},
month = sep,
doi = {10.1021/acs.bioconjchem.6c00334},
url = {https://europepmc.org/article/MED/42915460},
note = {CC BY},
}
RIS
TY - JOUR
TI - Synthesis of Human Milk Oligosaccharides-Fluoroquinolone Conjugates and Investigation of Their Antimicrobial Activity.
AU - Liza Nguyen Van Sang
AU - Emil Lindbäck
AU - Magne O Sydnes
PY - 2026
DA - 2026/09/01
JO - Bioconjugate chemistry
DO - 10.1021/acs.bioconjchem.6c00334
UR - https://europepmc.org/article/MED/42915460
AB - The copper-catalyzed azide-alkyne cycloaddition reaction was applied to conjugate four human milk oligosaccharides (HMOs) with antimicrobial fluoroquinolones (FQs) (ciprofloxacin and sparfloxacin) to obtain a total of 12 per-O-acetylated and unprotected HMO-FQ conjugates. These compounds underwent antimicrobial testing against Gram-positive (Streptococcus agalactiae, Enterococcus faecalis, and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. The HMO-FQ conjugates exhibited the most significant antimicrobial activity against E. coli and S. aureus reaching minimum inhibitory concentration as low as 1.56 μM and 3.13 μM, respectively. A general trend was that per-O-acetylated HMO-FQ conjugates exhibited higher antimicrobial activity than their unprotected counterparts. The antimicrobial activity of the tested HMO-FQ conjugates is expected to arise from the ciprofloxacin and sparfloxacin moieties because per-O-acetylated and unprotected HMOs did not exhibit any antimicrobial activity. Additionally, the HMO-FQ conjugates displayed no cytotoxicity as evident from test on two cell lines (HepG2 and MRC5).
SN - 1043-1802
SN - 1520-4812
ER -