Linker Hydrophilicity Modulates the Anticancer Activity of RGD-Cryptophycin Conjugates

Chemistry. 2021 Jan 13;27(3):1015-1022. doi: 10.1002/chem.202003471. Epub 2020 Dec 8.

Abstract

Most anticancer agents are hydrophobic and can easily penetrate the tumor cell membrane by passive diffusion. This may impede the development of highly effective and tumor-selective treatment options. A hydrophilic β-glucuronidase-cleavable linker was used to connect the highly potent antimitotic agent cryptophycin-55 glycinate with the αv β3 integrin ligand c(RGDfK). Incorporation of the self-immolative linker containing glucuronic acid results in lower cytotoxicity than that of the free payload, suggesting that hydrophilic sugar linkers can preclude passive cellular uptake. In vitro drug-release studies and cytotoxicity assays demonstrated the potential of this small molecule-drug conjugate, providing guidance for the development of therapeutics containing hydrophobic anticancer drugs.

Keywords: antitumor agents; beta-glucuronidase; drug delivery; integrin; small molecule drug conjugates.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Depsipeptides / chemistry*
  • Depsipeptides / pharmacology*
  • Drug Liberation
  • Humans
  • Hydrophobic and Hydrophilic Interactions*
  • Oligopeptides / chemistry*

Substances

  • Antineoplastic Agents
  • Depsipeptides
  • Oligopeptides
  • arginyl-glycyl-aspartic acid