2. Academic Validation
  3. Synthetic development of sugar amino acid oligomers towards novel podophyllotoxin analogues

Synthetic development of sugar amino acid oligomers towards novel podophyllotoxin analogues

  • Bioorg Med Chem. 2021 Dec 15:52:116501. doi: 10.1016/j.bmc.2021.116501.
Megan Bouchard 1,  Thomas Tremblay 1,  Marie-Pier Paré-Lacroix 1,  Mathieu Gagné-Boulet 2,  Sébastien Fortin 2,  Denis Giguère 3
Affiliations

Affiliations

  • 1 Département de Chimie, 1045 av. De la Médecine, Université Laval, Québec City, QC G1V 0A6, Canada.
  • 2 Centre de recherche du CHU de Québec-Université Laval, Axe oncologie, Hôpital Saint-François d'Assise, 10 rue de l'Espinay, Quebec City, QC G1L 3L5, Canada; Faculté de Pharmacie, 1050 avenue de la Médecine, Université Laval, Quebec City, QC G1V 0A6, Canada.
  • 3 Département de Chimie, 1045 av. De la Médecine, Université Laval, Québec City, QC G1V 0A6, Canada. Electronic address: denis.giguere@chm.ulaval.ca.
PMID: 34837817 DOI: 10.1016/j.bmc.2021.116501
Abstract

In this work, we have developed an approach for the synthesis of sugar amino acid oligomers based on the glucosamine scaffold. We found that the solid-phase approach was unsuccessful for the preparation of sugar amino acid oligomers and the limitation of the liquid-phase approach revolved around the low solubility of larger oligomers. Nevertheless, this strategy allowed the coupling of alkynylated carbohydrate Amino acids with podophyllotoxin-bearing an azide functional group yielding novel podophyllotoxin analogues. Due to their low solubility, the antiproliferative study revealed no Anticancer activity of these newly synthesized analogues.

Keywords

Antiproliferative compounds; Etoposide; Glycomimetics; Podophyllotoxin analogues; Sugar amino acids.

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