Mechanism toward Turn-on of Polysaccharide-Porphyrin Complexes for Fluorescence Probes and Photosensitizers in Photodynamic Therapy in Living Cells

ChemMedChem. 2021 Mar 3;16(5):793-803. doi: 10.1002/cmdc.202000656. Epub 2020 Oct 29.

Abstract

β-(1,3-1,6)-D-Glucan, λ-carrageenan, tamarind gum, and pullulan can dissolve various porphyrin derivatives via the formation of complexes in water using a high-speed vibration milling method. The aqueous solutions of the resulting complexes exhibit long-term stability. Despite the adverse effects of the self-quenching process, notable fluorescence and improved photodynamic activity of the polysaccharide-complexed porphyrin derivatives were observed in the presence of liposomes, micelles, cyclodextrins, and HeLa cells. It was noted that the type of porphyrins was more important than the type of polysaccharides present in the complex. Porphyrin self-aggregates were monodispersed in the lipid membranes of the liposomes and lysosomes. The polysaccharide-complexed porphyrin derivatives showed increased photodynamic activity toward HeLa cells under photoirradiation between 610 and 740 nm.

Keywords: aggregation; fluorescent probes; host-guest systems; polysaccharide; porphyrinoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Photochemotherapy*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology*
  • Polysaccharides / chemistry
  • Polysaccharides / pharmacology*
  • Porphyrins / chemistry
  • Porphyrins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Fluorescent Dyes
  • Photosensitizing Agents
  • Polysaccharides
  • Porphyrins