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Design and synthesis of novel 3-triazolyl-1-thiogalactosides as galectin-1, -3 and -8 inhibitors

van Klaveren, Sjors LU ; Dernovšek, Jaka ; Jakopin, Žiga ; Anderluh, Marko ; Leffler, Hakon LU ; Nilsson, Ulf J. LU and Tomašič, Tihomir (2022) In RSC Advances 12(29). p.18973-18984
Abstract

Galectins are galactoside-binding proteins that play a role in various pathophysiological conditions, making them attractive targets in drug discovery. We have designed and synthesised a focused library of aromatic 3-triazolyl-1-thiogalactosides targeting their core site for binding of galactose and a subsite on its non-reducing side. Evaluation of their binding affinities for galectin-1, -3, and -8N identified acetamide-based compound 36 as a suitable compound for further affinity enhancement by adding groups at the reducing side of the galactose. Synthesis of its dichlorothiophenyl analogue 59 and the thiodigalactoside analogue 62 yielded promising pan-galectin inhibitors.

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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
RSC Advances
volume
12
issue
29
pages
12 pages
publisher
Royal Society of Chemistry
external identifiers
  • pmid:35873334
  • scopus:85134351063
ISSN
2046-2069
DOI
10.1039/d2ra03163a
language
English
LU publication?
yes
id
48838ddf-693a-4235-93f2-91c7f382ebec
date added to LUP
2022-09-22 15:46:22
date last changed
2024-11-15 12:35:24
@article{48838ddf-693a-4235-93f2-91c7f382ebec,
  abstract     = {{<p>Galectins are galactoside-binding proteins that play a role in various pathophysiological conditions, making them attractive targets in drug discovery. We have designed and synthesised a focused library of aromatic 3-triazolyl-1-thiogalactosides targeting their core site for binding of galactose and a subsite on its non-reducing side. Evaluation of their binding affinities for galectin-1, -3, and -8N identified acetamide-based compound 36 as a suitable compound for further affinity enhancement by adding groups at the reducing side of the galactose. Synthesis of its dichlorothiophenyl analogue 59 and the thiodigalactoside analogue 62 yielded promising pan-galectin inhibitors.</p>}},
  author       = {{van Klaveren, Sjors and Dernovšek, Jaka and Jakopin, Žiga and Anderluh, Marko and Leffler, Hakon and Nilsson, Ulf J. and Tomašič, Tihomir}},
  issn         = {{2046-2069}},
  language     = {{eng}},
  month        = {{06}},
  number       = {{29}},
  pages        = {{18973--18984}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{RSC Advances}},
  title        = {{Design and synthesis of novel 3-triazolyl-1-thiogalactosides as galectin-1, -3 and -8 inhibitors}},
  url          = {{http://dx.doi.org/10.1039/d2ra03163a}},
  doi          = {{10.1039/d2ra03163a}},
  volume       = {{12}},
  year         = {{2022}},
}