Synthesis and Preliminary Biological Evaluation of Fluorescent Glycofused Tricyclic Derivatives of Amyloid β-Peptide Ligands

Giuseppe D'Orazio, Laura Colombo, Mario Salmona, Barbara La Ferla

Research output: Contribution to journalArticlepeer-review

Abstract

Fluorescent glycofused tricyclic compounds were synthesized through the domino conjugate oxa-Michael addition/aldol condensation of 2-hydroxybenzaldehydes with protected 3-oxoglucal by exploiting activation with an organocatalyst. Stereoselectivity was obtained by using (R)-(+)-α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether as the catalyst. All synthesized compounds presented good optical properties. All compounds were able to bind to synthetic amyloid β 1-42 peptide aggregates and to label amyloid plaques from brain sections of transgenic mice affected with Alzheimer's disease with staining properties comparable to thioflavin T.

Original languageEnglish
Pages (from-to)1660-1664
JournalEuropean Journal of Organic Chemistry
Volume2016
DOIs
Publication statusPublished - 2016

Keywords

  • Amyloid beta-peptides
  • Diagnostic agents
  • Domino reactions
  • Fluorescence
  • Medicinal chemistry
  • Organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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