DNA-binding, enzyme inhibition, and photochemical properties of chalcone-containing metallophthalocyanine compounds

Bioorg Chem. 2018 Dec:81:71-78. doi: 10.1016/j.bioorg.2018.08.002. Epub 2018 Aug 4.

Abstract

In this study, two novel phthalocyanine complexes were synthesized using their corresponding metal salts and 4-(4-(3-(2,4,5-trimethoxyphenyl)acryloyl)phenoxy)phthalo-nitrile as chalcone ligand (4), which was prepared from the reaction of 4-nitrophthalonitrile with 4-hydroxyphenyl-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (3). These metallophthalocyanines showed good solubility in organic solvents such as CDCl3, DCM, THF, DMF, and DMSO. The novel phthalocyanine compounds 4a (Pc-Zn) and 4b (Pc-Co) were characterized using their UV-vis, FT-IR, 1H NMR, 13C NMR, and MALDI-TOF mass spectra and elemental analysis. Then the DNA-binding and xanthine oxidase and carbonic anhydrase-I inhibition properties of compounds 4a and 4b were investigated. Photochemical properties (such as singlet oxygen generation and photodegradation) of this novel chalcone phthalocyanine (4a) were determined in dimethyl sulfoxide (DMSO).

Keywords: Chalcone; DNA-binding; Enzyme inhibition; Photochemical; Phthalocyanine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites / drug effects
  • Cattle
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • DNA / drug effects*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Isoindoles
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Photochemical Processes
  • Spectrometry, Fluorescence
  • Structure-Activity Relationship
  • Xanthine Oxidase / antagonists & inhibitors*
  • Xanthine Oxidase / metabolism

Substances

  • Enzyme Inhibitors
  • Indoles
  • Isoindoles
  • Ligands
  • Organometallic Compounds
  • Chalcone
  • DNA
  • calf thymus DNA
  • Xanthine Oxidase
  • phthalocyanine