Preparation and in vitro photodynamic activities of novel axially substituted silicon (IV) phthalocyanines and their bovine serum albumin conjugates

Bioorg Med Chem Lett. 2006 May 1;16(9):2450-3. doi: 10.1016/j.bmcl.2006.01.075. Epub 2006 Feb 7.

Abstract

Two novel axially substituted phthalocyanines, namely bis(4-(4-acetylpiperazine)phenoxy)phthalocyaninatosilicon (IV) (1) and its N-methylated derivative 2, have been synthesized. The dicationic phthalocyanine 2 is non-aggregated in water and exhibits good photophysical properties. The non-covalent BSA conjugates of these compounds have also been prepared. Compound 2 and the conjugate 2-BSA show extremely high photodynamic activities toward B16 melanoma cancer cell lines. The corresponding 50% growth-inhibitory (IC50) ratios are 33 and 38 nM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cattle
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • In Vitro Techniques
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Mice
  • Molecular Structure
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry
  • Organosilicon Compounds / pharmacology*
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology*
  • Serum Albumin, Bovine / chemistry*
  • Stereoisomerism

Substances

  • Indoles
  • Organosilicon Compounds
  • Photosensitizing Agents
  • bis(4-(4-acetylpiperazine)phenoxy)phthalocyaninatosilicon
  • silicon phthalocyanine
  • Serum Albumin, Bovine