ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

An efficient 2-aminothiazolesalicylaldehyde fluorescent chemosensor for Fe²⁺ ion detection and a potential inhibitor of NUDT5 signaling hormone for breast cancer cell and molecular keypad lock application

Summaya Banu Basha, Immanuel David Charles, Nandhakumar Raju, Sakthivel Manokaran, and Hemalatha Kuzhandaivel

Department of Chemistry, Coimbatore Institute of Technology, Anna University, Coimbatore, India

E-mail: nandhakumar@karunya.edu

Received: 25 February 2022  Accepted: 12 July 2022

Abstract:

A novel thiazole phenol conjugate, 2-aminothiazolesalicylaldehyde (receptor1) was designed and synthesized for the first time through a single step process via Schiff base condensation reaction. The formation of receptor1 was confirmed by FTIR, ¹³C NMR, and ¹H NMR. The IR spectra confirmed the presence of the aldimine formation. It is further supported by the proton NMR, showing the disappearance of aldehyde peaks and the formation of a new imine peak. This is further corroborated by the ¹³C NMR. The receptor1 complexing with various metal ions were studied through fluorescence spectroscopy showed its selectivity toward Fe²⁺ ion following a reverse photoinduced electron transfer (PET) process compared to all other potentially competing ions. The receptor1 was applied as a sensor to sense Fe²⁺ ion in water samples. The detection limit for Fe²⁺ ion in drinking water was substantially lower (0.003 µM) than the EPA (environmental protection agency) recommendation (5.37 M). The capability of receptor1 in recovering Fe²⁺ ion in bore water, tap water, and drinking water was up to 99.5%. The receptor1 was also used as a chelating ligand (receptor1) in molecular docking and it was assessed as a potential inhibitor of NUDT5, a silence hormone signaling for breast cancer. The test compound (PDB: 5NWH) showed good affinity toward the target receptor1 with the binding energy of – 5.23 kcal mol⁻¹. Furthermore, the receptor1 showed excellent reversibility property on adding EDTA solution. Due to the marvelous reversible property, a molecular-scale sequential information processing circuit is designed for the multi-task behavior such as ‘Writing-Reading-Erasing-Reading’ in the form of binary logic gate. The consecutive addition of Fe²⁺ ion and EDTA solution to receptor1 paves a way for the construction of INHIBIT logic gate. Additionally, the receptor1 showed the mimicking behavior of molecular keypad lock.

Keywords: Salicylaldehyde; Reverse PET; Fluorescent quenching; Molecular docking; NUDT5

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02373-z

Chemical Papers 76 (11) 7061–7073 (2022)