Internal heavy atom effect of Au(III) and Pt(IV) on hypocrellin A for enhanced in vitro photodynamic therapy of cancer

Bioorg Med Chem Lett. 2013 Oct 1;23(19):5317-24. doi: 10.1016/j.bmcl.2013.07.064. Epub 2013 Aug 6.

Abstract

Hypocrellin A (HA), an a natural perylene quinine photosensitizers (PSs), can chelate with heavy metal ions, including Au(III) and Pt(IV), to form a 1:2 complex, which exhibits enhanced (1)O2 generation quantum yield through the increased intersystem crossing efficiency mediated by internal heavy atom effect. Besides, the chelate process greatly improved the water solubility of HA. Comparative studies with HA and complexes have demonstrated that the heavy-atom effect on HA molecules enhances the efficiency of in vitro photodynamic (PDT) efficacy.

Keywords: Anticancer activity; Complex; Hypocrellin A; Internal heavy atom effect; Intersystem crossing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / therapeutic use
  • Gold / chemistry*
  • Gold / pharmacology
  • HeLa Cells
  • Humans
  • Metals, Heavy / chemistry
  • Microscopy, Fluorescence
  • Models, Biological
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Perylene / analogs & derivatives*
  • Perylene / chemistry
  • Perylene / pharmacology
  • Perylene / therapeutic use
  • Phenol
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology*
  • Photosensitizing Agents / therapeutic use
  • Platinum / chemistry*
  • Platinum / pharmacology
  • Quinones / chemistry*
  • Quinones / pharmacology*
  • Quinones / therapeutic use
  • Solubility
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Coordination Complexes
  • Metals, Heavy
  • Photosensitizing Agents
  • Quinones
  • Phenol
  • Platinum
  • Perylene
  • Gold
  • hypocrellin A