Methyl pyropheophorbide-a analogues: potential fluorescent probes for the peripheral-type benzodiazepine receptor. Effect of central metal in photosensitizing efficacy

J Med Chem. 2005 Jun 2;48(11):3692-5. doi: 10.1021/jm050039k.

Abstract

Pyropheophorbides and their metal complexes were synthesized to investigate their applications as nonradioactive peripheral benzodiazepine receptor (PBR) binding probes and photosensitizers for use in photodynamic therapy. They were found to be localized in mitochondria and showed significant binding to PBR. In some cases, the PBR binding values were similar to that for 17 (PK11195, 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)isoquinoline-3-carboxamide). However, no direct correlation between 17 displacement ability and photosensitizing efficacy of photosensitizers was observed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Indium*
  • Isoquinolines / pharmacology
  • Ligands
  • Mice
  • Mitochondria / metabolism
  • Nickel*
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Porphyrins / pharmacology
  • Receptors, GABA-A / metabolism*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • Xenograft Model Antitumor Assays
  • Zinc*

Substances

  • Isoquinolines
  • Ligands
  • Organometallic Compounds
  • Photosensitizing Agents
  • Porphyrins
  • Receptors, GABA-A
  • pyropheophorbide-a methylester
  • Indium
  • Nickel
  • Zinc
  • PK 11195