Phthalocyanine and azaphthalocyanines containing eugenol: synthesis, DNA interaction and comparison of lipase inhibition properties

Abstract

Novel eugenol-substituted zinc(II) azaphthalocyanines (ZnAzaPcs) were synthesised and their lipase inhibition and DNA binding properties compared with phthalocyanines (Pcs) containing eugenol. This is the first study on lipase inhibition and DNA binding of Pcs and AzaPcs containing a pharmacophore group, such as eugenol. the novel ZnAzaPcs were characterised using a combination of FT-IR, (HNMR)-H-1, (CNMR)-C-13, UV-Vis, MS and elemental analysis. the crystal structures of two pyrazine compounds were also determined by the single crystal diffraction technique. This study showed that two phthalocyanines compounds (3a and 4a) could be potential lipase inhibitor agents due to greater hydrophobicity than other azaphtalocyanines. Compound 4a displayed lowest IC50 value. Non-intercalative binding to DNA was identified only for compound 2a.