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A rapid synthesis of low-nanomolar divalent LecA inhibitors in four linear steps from d-galactose pentaacetate.
Chem Commun (Camb). 2020 Aug 04; 56(62):8822-8825.CC

Abstract

Chronic infections with Pseudomonas aeruginosa are associated with the formation of bacterial biofilms. The tetrameric P. aeruginosa lectin LecA is a virulence factor and an anti-biofilm drug target. Increasing the overall binding affinity by multivalent presentation of binding epitopes can enhance the weak carbohydrate-ligand interactions. Low-nanomolar divalent LecA ligands/inhibitors with up to 260-fold valency-normalized potency boost and excellent selectivity over human galectin-1 were synthesized from d-galactose pentaacetate and benzaldehyde-based linkers in four linear steps.

Authors+Show Affiliations

Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany. alexander.titz@helmholtz-hzi.de and Deutsches Zentrum für Infektionsforschung (DZIF), Standort Hannover-Braunschweig, 38124 Braunschweig, Germany and Department of Pharmacy, Saarland University, 66123 Saarbrücken, Germany.Université Grenoble Alpes, CNRS, CERMAV, 38000 Grenoble, France.Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany. alexander.titz@helmholtz-hzi.de.Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany. alexander.titz@helmholtz-hzi.de.Université Grenoble Alpes, CNRS, CERMAV, 38000 Grenoble, France.Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany. alexander.titz@helmholtz-hzi.de.Deutsches Zentrum für Infektionsforschung (DZIF), Standort Hannover-Braunschweig, 38124 Braunschweig, Germany and Department of Pharmacy, Saarland University, 66123 Saarbrücken, Germany and Drug Design and Optimization, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany.Université Grenoble Alpes, CNRS, CERMAV, 38000 Grenoble, France.Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland, Helmholtz Centre for Infection Research, 66123 Saarbrücken, Germany. alexander.titz@helmholtz-hzi.de and Deutsches Zentrum für Infektionsforschung (DZIF), Standort Hannover-Braunschweig, 38124 Braunschweig, Germany and Department of Pharmacy, Saarland University, 66123 Saarbrücken, Germany.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32628229

Citation

Zahorska, Eva, et al. "A Rapid Synthesis of Low-nanomolar Divalent LecA Inhibitors in Four Linear Steps From D-galactose Pentaacetate." Chemical Communications (Cambridge, England), vol. 56, no. 62, 2020, pp. 8822-8825.
Zahorska E, Kuhaudomlarp S, Minervini S, et al. A rapid synthesis of low-nanomolar divalent LecA inhibitors in four linear steps from d-galactose pentaacetate. Chem Commun (Camb). 2020;56(62):8822-8825.
Zahorska, E., Kuhaudomlarp, S., Minervini, S., Yousaf, S., Lepsik, M., Kinsinger, T., Hirsch, A. K. H., Imberty, A., & Titz, A. (2020). A rapid synthesis of low-nanomolar divalent LecA inhibitors in four linear steps from d-galactose pentaacetate. Chemical Communications (Cambridge, England), 56(62), 8822-8825. https://doi.org/10.1039/d0cc03490h
Zahorska E, et al. A Rapid Synthesis of Low-nanomolar Divalent LecA Inhibitors in Four Linear Steps From D-galactose Pentaacetate. Chem Commun (Camb). 2020 Aug 4;56(62):8822-8825. PubMed PMID: 32628229.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A rapid synthesis of low-nanomolar divalent LecA inhibitors in four linear steps from d-galactose pentaacetate. AU - Zahorska,Eva, AU - Kuhaudomlarp,Sakonwan, AU - Minervini,Saverio, AU - Yousaf,Sultaan, AU - Lepsik,Martin, AU - Kinsinger,Thorsten, AU - Hirsch,Anna K H, AU - Imberty,Anne, AU - Titz,Alexander, PY - 2020/7/7/pubmed PY - 2020/7/7/medline PY - 2020/7/7/entrez SP - 8822 EP - 8825 JF - Chemical communications (Cambridge, England) JO - Chem. Commun. (Camb.) VL - 56 IS - 62 N2 - Chronic infections with Pseudomonas aeruginosa are associated with the formation of bacterial biofilms. The tetrameric P. aeruginosa lectin LecA is a virulence factor and an anti-biofilm drug target. Increasing the overall binding affinity by multivalent presentation of binding epitopes can enhance the weak carbohydrate-ligand interactions. Low-nanomolar divalent LecA ligands/inhibitors with up to 260-fold valency-normalized potency boost and excellent selectivity over human galectin-1 were synthesized from d-galactose pentaacetate and benzaldehyde-based linkers in four linear steps. SN - 1364-548X UR - https://www.unboundmedicine.com/medline/citation/32628229/A_rapid_synthesis_of_low-nanomolar_divalent_LecA_inhibitors_in_four_linear_steps_from_d-galactose_pentaacetate L2 - https://doi.org/10.1039/d0cc03490h DB - PRIME DP - Unbound Medicine ER -
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