New long-wavelength perylenequinones: synthesis and phototoxicity of hypocrellin B derivatives

Biochim Biophys Acta. 2000 Sep 1;1523(1):6-12. doi: 10.1016/s0304-4165(00)00081-7.

Abstract

Five new derivatives of hypocrellin B were obtained from the reactions of hypocrellin B with ammonia and ethanolamine. Their photophysical and photochemical properties were investigated. The phototoxicity of one compound on AH cells irradiated with red light (lambda = 600-700 nm) was also studied. Their significantly enhanced red absorptivities at wavelengths longer than 600 nm and singlet oxygen-generating function qualify them as promising photodynamic therapy agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonia / chemistry
  • Animals
  • Cell Survival / drug effects
  • Ethanolamine / chemistry
  • Liver Neoplasms, Experimental
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Oxygen
  • Perylene / analogs & derivatives*
  • Perylene / chemistry
  • Perylene / toxicity
  • Photochemistry
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / toxicity
  • Quinones / chemical synthesis*
  • Quinones / chemistry*
  • Quinones / toxicity
  • Singlet Oxygen
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Photosensitizing Agents
  • Quinones
  • Singlet Oxygen
  • Ethanolamine
  • Perylene
  • Ammonia
  • Oxygen
  • hypocrellin B