Synthesis, characterization, biological activity and theoretical studies of a 2-amino-6-methoxybenzothiazole-based fluorescent Schiff base


ALPASLAN G., BOYACIOĞLU B., DEMİR N., TÜMER Y., Yapar G., YILDIRIM N., ...More

JOURNAL OF MOLECULAR STRUCTURE, vol.1180, pp.170-178, 2019 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1180
  • Publication Date: 2019
  • Doi Number: 10.1016/j.molstruc.2018.11.065
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.170-178
  • Keywords: 2-amino-6-methoxybenzothiazole, Molecular modeling, Biological activities, DNA binding, Sensors, CRYSTAL-STRUCTURE, COLORIMETRIC SENSORS, ANION RECOGNITION, DNA-BINDING, DFT, EQUILIBRIUM, ANTIOXIDANT, RECEPTORS, COMPLEXES, RAMAN

Abstract

A new Schiff base, (E)-3,5-dimethoxy-2-((6-methoxybenzo[d]thiazol-2-ylimino)methyl)- phenol, was prepared from the reaction of 2-amino-6-methoxybenzothiazole and 2-hydroxy-4,6-dimethoxybenzaldehyde and characterized with elemental analysis, FTIR, UV-VIS, NMR and single crystal X-ray diffraction techniques. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. The interactions of the compound with DNA were studied with the ultraviolet-visible (UV-VIS) spectra and gel electrophoresis method. The experimental results indicated that the 2-amino-6-methoxybenzothiazole-based Schiff base could bind to DNA via an intercalative mode and showed that it cleaved DNA without the need for external agents. Additionally, the Schiff base showed colorimetric sensor properties for fluoride and cyanide anions in dimethyl sulfoxide.