Synthesis, characterization, DNA interaction, molecular docking, and α‐glucosidase inhibition studies of 3‐(pyrimidin‐2‐ylthio) groups substituted water soluble zinc (II) phthalocyanine

Abstract

In this work, 3‐(pyrimidin‐2‐ylthio)phthalonitrile (n‐MP1), non‐peripherally 3‐(pyrimidin‐2‐ylthio) groups substituted Zn (II) phthalocyanine (n‐MP2), and its water soluble derivative (n‐MP3) have been firstly synthesized and characterized with spectral data. The interaction of the n‐MP3 complex with DNA was examined in vitro using UV–visible titrimetric and thermal denaturation assays and in silico by performing molecular docking studies. In addition, the antidiabetic activity of n‐MP3 was revealed spectroscopically by studying α‐glucosidase inhibition activities. The spectroscopic results indicated that n‐MP3 effectively binds to CT‐DNA with a Kb value of 2.0 × 105 M−1 and interacts with CT‐DNA via noncovalent binding mode. Besides, docking studies divulged that n‐MP3 exhibits a stronger binding tendency (BE: −10.64 kcal/mol) with DNA than the control compounds, (7.78 kcal/mol for ethidium bromide and −6.21 kcal/mol for cisplatin). Consequently, due to its strong DNA binding activity, n‐MP3 may be suitable for antimicrobial and anticancer applications after further toxicological test systems. Also, n‐MP3 complex inhibited the activity of α‐glucosidase with the IC50 value of 1.44 ± 0.08 μM, whereas IC50 value of acarbose was 237.24 ± 1.80 μM. Therefore, it can be said that n‐MP3 is a very effective α‐glucosidase inhibitor.