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β-Mannosyl Triazoles as Mimics of Galactosyl Galectin-3 and Galectin-9 N-Terminal Domain Inhibitors

Sjövall, Fredrik LU orcid and Nilsson, Ulf J. LU orcid (2026) In ChemBioChem 27(7).
Abstract

Mannosyl β-C-1 amidotriazoles have previously been reported to have higher selectivity for galectin-9N (N-terminal domain) than the corresponding galactoside C3 amidotriazoles have, which were more selective for galectin-3. This study further investigated this by synthesis of mono- and bis-aryltriazolyl mannoside analogues to known high-affinity galectin-3 galactosyl-derived inhibitors. Following synthesis, affinity measurements using competititve fluorescence polarization assays were performed which indicated low affinity of the bis-aryltriazolyl mannosyls, while the mono-aryltriazolyl mannosyls analogs possessed improved affinity, albeit with lower and selectivity. From conformational calculations it was implied that the weak-binding... (More)

Mannosyl β-C-1 amidotriazoles have previously been reported to have higher selectivity for galectin-9N (N-terminal domain) than the corresponding galactoside C3 amidotriazoles have, which were more selective for galectin-3. This study further investigated this by synthesis of mono- and bis-aryltriazolyl mannoside analogues to known high-affinity galectin-3 galactosyl-derived inhibitors. Following synthesis, affinity measurements using competititve fluorescence polarization assays were performed which indicated low affinity of the bis-aryltriazolyl mannosyls, while the mono-aryltriazolyl mannosyls analogs possessed improved affinity, albeit with lower and selectivity. From conformational calculations it was implied that the weak-binding bis-aryltriazolyl mannosyl analogues do not find the same conformation and binding pose as the parent galactoside compounds.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Galectins/antagonists & inhibitors, Triazoles/chemistry, Galectin 3/antagonists & inhibitors, Humans, Blood Proteins, Galactosides/chemistry, Protein Domains/drug effects
in
ChemBioChem
volume
27
issue
7
article number
e70319
pages
10 pages
publisher
John Wiley & Sons Inc.
external identifiers
  • pmid:41969275
  • scopus:105035571273
  • pmid:41969275
ISSN
1439-4227
DOI
10.1002/cbic.70319
language
English
LU publication?
yes
additional info
© 2026 The Author(s). ChemBioChem published by Wiley‐VCH GmbH.
id
e93baecc-bbdf-4006-b58a-5d6a47a59259
date added to LUP
2026-04-16 21:48:53
date last changed
2026-05-13 15:36:13
@article{e93baecc-bbdf-4006-b58a-5d6a47a59259,
  abstract     = {{<p>Mannosyl β-C-1 amidotriazoles have previously been reported to have higher selectivity for galectin-9N (N-terminal domain) than the corresponding galactoside C3 amidotriazoles have, which were more selective for galectin-3. This study further investigated this by synthesis of mono- and bis-aryltriazolyl mannoside analogues to known high-affinity galectin-3 galactosyl-derived inhibitors. Following synthesis, affinity measurements using competititve fluorescence polarization assays were performed which indicated low affinity of the bis-aryltriazolyl mannosyls, while the mono-aryltriazolyl mannosyls analogs possessed improved affinity, albeit with lower and selectivity. From conformational calculations it was implied that the weak-binding bis-aryltriazolyl mannosyl analogues do not find the same conformation and binding pose as the parent galactoside compounds.</p>}},
  author       = {{Sjövall, Fredrik and Nilsson, Ulf J.}},
  issn         = {{1439-4227}},
  keywords     = {{Galectins/antagonists & inhibitors; Triazoles/chemistry; Galectin 3/antagonists & inhibitors; Humans; Blood Proteins; Galactosides/chemistry; Protein Domains/drug effects}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{7}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{ChemBioChem}},
  title        = {{β-Mannosyl Triazoles as Mimics of Galactosyl Galectin-3 and Galectin-9 N-Terminal Domain Inhibitors}},
  url          = {{http://dx.doi.org/10.1002/cbic.70319}},
  doi          = {{10.1002/cbic.70319}},
  volume       = {{27}},
  year         = {{2026}},
}