New imino-methoxy derivatives: design, synthesis, characterization, antimicrobial activity, DNA interaction and molecular docking studies

Abstract

Four new diarylmethylamine imine compounds (5a-5d) were prepared in order to examine their DNA binding properties, antimicrobial activity and molecular docking. The compounds were characterized by the common spectroscopic and analytic methods. Furthermore, solid-state structure of compounds 5a and 5c were determined by single-crystal X-ray diffraction studies. The compounds were then investigated for their DNA binding properties employing UV absorption, fluorescence spectroscopy under the physiological pH condition Tris-HCl buffer at pH 7.4. The compounds 5a-5d showed moderate binding constants with Kb values of 3.56 ± 0.3 × 10⁴, 2.18 ± 0.2 × 10⁵, 1.44 ± 0.3 × 10⁵ and 2.56 ± 0.3 × 10⁴ M⁻¹, respectively. The molecular dockings were performed to investigate the ligand-DNA interactions. The in-silico DNA-compound interaction studies showed that the compounds interact with DNA in groove binding mode. Antimicrobial activity studies of imine compounds were tested against E. coli as bacteria, S. typhimurium, S. aureus, B. cereus, B. subtilis, and C. albicans as fungi. While all compounds show moderate activity against bacteria, no activity against fungi has been investigated.

Communicated by Ramaswamy H. Sarma

Keywords:

• Imino-methoxy
• diarylmethylamine
• X-ray structure
• DNA binding
• molecular docking

Acknowledgements

The authors are thankful to the Scientific Research Projects Unit of Kahramanmaraş Sütcü Imam University (Project code: BAP-2017/6-34 M), (Turkey). Furthermore, we would like to thank the Research Council of the Turkish Council of Higher Education (YÖK 100/2000) for awarding a postgraduate scholarship (to SO).

Disclosure statement

The authors declare no conflicts of interest.

Credit authorship contribution statement

Sultan Onur: Investigation. Mustafa Çeşme: Data curation, Software, Writing—review & editing Investigation. Muhammet Köse: Data curation, Software, Writing—review & editing. Ferhan Tümer: Supervision, Project administration, Writing—Original draft.