Glycosidase activated release of fluorescent 1,8-naphthalimide probes for tumor cell imaging from glycosylated 'pro-probes'

Chem Commun (Camb). 2016 Nov 18;52(89):13086-13089. doi: 10.1039/c6cc06451e. Epub 2016 Sep 27.

Abstract

Glycosylated 4-amino-1,8-naphthalimide derivatives possess a native glycosidic linkage that can be selectively hydrolysed in situ by glycosidase enzymes to release the naphthalimide as a fluorescent imaging or therapeutic agent. In vitro studies using a variety of cancer cell lines demonstrated that the naphthalimides only get taken up into cells upon enzymatic cleavage from the glycan unit; a mechanism that offers a novel approach for the targeted delivery of probes/drugs.

MeSH terms

  • 1-Naphthylamine / analogs & derivatives*
  • 1-Naphthylamine / chemistry
  • 1-Naphthylamine / metabolism
  • Cell Line, Tumor
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism*
  • Glycoside Hydrolases / metabolism*
  • Glycosylation
  • HeLa Cells
  • Humans
  • Molecular Imaging / methods*
  • Naphthalimides / chemistry*
  • Naphthalimides / metabolism*
  • Quinolones / chemistry*
  • Quinolones / metabolism*

Substances

  • Fluorescent Dyes
  • Naphthalimides
  • Quinolones
  • 4-amino-1,8-naphthalimide
  • 1-Naphthylamine
  • Glycoside Hydrolases