Butylamino-demethoxy-hypocrellins and photodynamic therapy decreases human cancer in vitro and in vivo

Biochim Biophys Acta. 2001 Nov 29;1537(3):222-32. doi: 10.1016/s0925-4439(01)00074-6.

Abstract

2-Butylamino-2-demethoxy-hypocrellin A (BAHA) and B (BAHB) are new photosensitizers synthesized by a mild reaction of hypocrellins and butylamine. In BAHA and BAHB, the peri-hydroxylated perylenequinone structure of the parent hypocrellins is preserved and the red absorption is enhanced distinctly. Electron paramagnetic resonance spin trapping measurements and 9,10-diphenylanthracene bleaching studies were used to investigate the photodynamic action of BAHA and BAHB in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2(*-)) produced by illuminating BAHA and BAHB in aerobic solution have been observed. Compared with hypocrellin A and B, BAHA and BAHB primarily remained able to generate 1O2 and enhanced distinctly the O2(*-)-generating abilities. The photodynamic action of BAHA and BAHB in the therapy of cancer was investigated in vitro and in vivo. Both in vitro and in vivo results revealed a significant decrease in cancer cell growth. Laser or dye alone had no effect, indicating that intratumor BAHA and laser therapy may prove useful in unresectable cancer.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line / drug effects
  • Cell Survival
  • Humans
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Neoplasm Transplantation
  • Pancreatic Neoplasms / drug therapy*
  • Perylene / analogs & derivatives*
  • Perylene / chemical synthesis
  • Perylene / therapeutic use*
  • Perylene / toxicity
  • Photochemotherapy
  • Photosensitizing Agents / therapeutic use*
  • Quinones / chemical synthesis
  • Quinones / therapeutic use*
  • Quinones / toxicity

Substances

  • 2-butylamino-2-demethoxy-hypocrellin A
  • 2-butylamino-2-demethoxy-hypocrellin B
  • Photosensitizing Agents
  • Quinones
  • Perylene