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.