New Route to Glycosylated Porphyrins via Aromatic Nucleophilic Substitution (SNAr)-Synthesis and Cellular Uptake Studies

Int J Mol Sci. 2022 Sep 26;23(19):11321. doi: 10.3390/ijms231911321.

Abstract

Glycoporphyrins are group of compounds of high value for the purpose of photodynamic therapy and other biomedical applications. Despite great progress in the field, new diversity-oriented syntheses of carbohydrate-porphyrin hybrids are increasingly desired. Herein, we present efficient, mild, and metal-free conditions for synthesis of glycoporphyrins. The versatile nature of the SNAr procedure is presented in 16 examples. Preliminary biological studies have been conducted on the cytotoxicity and cellular uptake of the final molecules.

Keywords: SNAr; carbohydrates; cellular uptake; glycoporphyrins; nucleophilic aromatic substitution; photodynamic therapy; photosensitisers; porphyrins.

MeSH terms

  • Carbohydrates
  • Glycosylation
  • Photochemotherapy* / methods
  • Porphyrins*

Substances

  • Carbohydrates
  • Porphyrins