DNA cleavage properties and synthesis of metallophthalocyanines with 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-oxy substituents

ABSTRACT

The aim of the present study is to perform synthesis of novel metallophthalocyanines (pcs) with high solubility. The synthesis and characterization of 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted zinc, magnesium, and cobalt pcs are reported. These compounds have been characterized using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectra. The aggregation investigations carried out in different concentrations indicate that 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted pc complexes do not have any aggregation behavior for the concentration range of 1 × 10⁻⁵−1 × 10⁻⁶ M in THF. DPPH radical scavenging activity, metal chelating activity, and reducing power of the compounds were evaluated. The DNA gel electrophoresis studies revealed that new phthalonitrile and its metallophthalocyanine compounds cleavaged plasmid DNA (pBR322). Additionally, the ground-state geometries of the complexes were optimized using density functional theory methods at B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structure.

KEYWORDS:

• Phthalocyanine
• synthesis
• electronic structure
• aggregation
• DNA cleavage

Funding

This study was supported by the Research Fund of Yuzuncu Yıl University.