Design and synthesis of zinc protoporphyrin IX-adamantane/cyclodextrin/cellulose nanocrystals complexes for anticancer photodynamic therapy

Bioorg Med Chem Lett. 2021 Jun 1:41:128024. doi: 10.1016/j.bmcl.2021.128024. Epub 2021 Apr 9.

Abstract

Two protoporphyrin IX (PpIX) adamantane derivatives were synthesized and then metallated with zinc. The Zn-PpIX derivatives, exhibiting a high singlet oxygen quantum yield, were tested for their photodynamic activity against the HT-29 cell line. In order to enhance their water-solubility and their cellular bioavailability, these photosensitizers were encapsulated into the hydrophobic cavity of cyclodextrins (CD) previously attached to cellulose nanocrystals (CNCs) via electrostatic interactions. Under illumination, the encapsulated adamantanyl-porphyrins exerted an enhanced in vitro cytotoxicity, as compared with the corresponding free photosensitizers.

Keywords: Cellulose nanocrystals; Colorectal cancer; Nanoparticles; Photodynamic therapy; Porphyrins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / chemistry
  • Adamantane / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cellulose / chemistry
  • Cellulose / pharmacology*
  • Cyclodextrins / chemistry
  • Cyclodextrins / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Molecular Structure
  • Nanoparticles / chemistry
  • Photochemotherapy*
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology*
  • Protoporphyrins / chemistry
  • Protoporphyrins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Cyclodextrins
  • Photosensitizing Agents
  • Protoporphyrins
  • zinc protoporphyrin
  • Cellulose
  • Adamantane