Scaffold diversity for enhanced activity of glycosylated inhibitors of fungal adhesion

Martin, Harlei, Somers, Tara, Dwyer, Mathew, Robson, Ryan, Pfeffer, Frederick M., Bjornsson, Ragnar, Krämer, Tobias, Kavanagh, Kevin and Velasco-Torrijos, Trinidad 2020, Scaffold diversity for enhanced activity of glycosylated inhibitors of fungal adhesion, RSC Medicinal Chemistry, vol. 11, no. 12, December 2020, pp. 1386-1401, doi: 10.1039/d0md00224k.

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Title Scaffold diversity for enhanced activity of glycosylated inhibitors of fungal adhesion
Author(s) Martin, Harlei
Somers, Tara
Dwyer, Mathew
Robson, Ryan
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M.
Bjornsson, Ragnar
Krämer, Tobias
Kavanagh, Kevin
Velasco-Torrijos, Trinidad
Journal name RSC Medicinal Chemistry
Volume number 11
Issue number 12
Season December 2020
Start page 1386
End page 1401
Total pages 17
Publisher Royal Society of Chemistry (RSC)
Place of publication Cambridge, Eng.
Publication date 2020-08-17
ISSN 2632-8682
Keyword(s) Science & Technology
Life Sciences & Biomedicine
Biochemistry & Molecular Biology
Chemistry, Medicinal
Pharmacology & Pharmacy
Summary Candida albicans is one of the most prevalent fungal pathogens involved in hospital acquired infections. It binds to glycans at the surface of epithelial cells and initiates infection. This process can be blocked by synthetic carbohydrates that mimic the structure of cell surface glycans. Herein we report the evaluation of a series of divalent glycosides featuring aromatic (benzene, squaramide) and bicyclic aliphatic (norbornene) scaffolds, with the latter being the first examples of their kind as small molecule anti-adhesion glycoconjugates. Galactosides 1 and 6, built on an aromatic core, were most efficient inhibitors of adhesion of C. albicans to buccal epithelial cells, displacing up to 36% and 48%, respectively, of yeast already attached to epithelial cells at 138 μM. Remarkably, cis-endo-norbornene 21 performed comparably to benzene-core derivatives. Conformational analysis reveals a preference for compounds 1 and 21 to adopt folded conformations. These results highlight the potential of norbornenes as a new class of aliphatic scaffolds for the synthesis of anti-adhesion compounds.
Language eng
DOI 10.1039/d0md00224k
Indigenous content off
Field of Research 0601 Biochemistry and Cell Biology
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2020, Royal Society of Chemistry
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