Journal of Chemical Sciences

, Volume 129, Issue 8, pp 1247–1256 | Cite as

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

  • Günay Kaya Kantar
  • Özlem Faiz
  • Onur Şahin
  • Selami Şaşmaz
Regular Article
  • 119 Downloads

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, \(^{1}\hbox {H}\) NMR, \(^{13}\hbox {C}\) NMR, 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 \(\hbox {IC}_{50}\) value. Non-intercalative binding to DNA was identified only for compound 2a.

Graphical Abstract:

SYNOPSIS 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.
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Keywords

Azaphthalocyanine eugenoe lipase inhibition phthalocyanine DNA interaction 

Supplementary material

12039_2017_1320_MOESM1_ESM.docx (649 kb)
Supplementary material 1 (docx 648 KB)

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Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  • Günay Kaya Kantar
    • 1
  • Özlem Faiz
    • 1
  • Onur Şahin
    • 2
  • Selami Şaşmaz
    • 1
  1. 1.Department of Chemistry, Science and Art FacultyRecep Tayyip Erdogan UniversityRizeTurkey
  2. 2.Scientific and Technological Research Application and Research CenterSinop UniversitySinopTurkey

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