Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

Sharmin Akther Rupa; Md Abdul Majed Patwary; William Emmanuel Ghann; Adams Abdullahi; A K M Royhan Uddin; Md Mayez Mahmud; Md Aminul Haque; Jamal Uddin; Mohsin Kazi

doi:10.1039/d3ra04364a

Synthesis of a novel hydrazone-based compound applied as a fluorescence turn-on chemosensor for iron(iii) and a colorimetric sensor for copper(ii) with antimicrobial, DFT and molecular docking studies

RSC Adv. 2023 Aug 9;13(34):23819-23828. doi: 10.1039/d3ra04364a. eCollection 2023 Aug 4.

Authors

Sharmin Akther Rupa¹, Md Abdul Majed Patwary¹, William Emmanuel Ghann², Adams Abdullahi², A K M Royhan Uddin¹, Md Mayez Mahmud³, Md Aminul Haque⁴, Jamal Uddin², Mohsin Kazi⁵

Affiliations

¹ Department of Chemistry, Comilla University Cumilla-3506 Bangladesh mamajedp@gmail.com.
² Center for Nanotechnology, Department of Natural Sciences, Coppin State University Baltimore USA.
³ Tokushima University, Faculty of Pharmaceutical Science Tokushima Shi 770-0026 Japan.
⁴ Department of Chemistry, Jagannath University Dhaka-1100 Bangladesh.
⁵ Department of Pharmaceutics, College of Pharmacy, King Saud University P.O. Box 2457 Riyadh 11451 Saudi Arabia.

Abstract

Hydrazone-hydrazide-based linkers perform a crucial role in environmental as well as biological fields. Such linkers are employed to detect exact metal ions at a minute level; hence, numerous probes are available. Even though thiophene-based molecules have a unique position in the medicinal arena, only very few chemosensors are reported based on such a moiety. In this current work, a novel hydrazide-hydrazone-based fluorogenic molecule 5-bromo-2-hydroxy-N'-[(1E)-1-(thiophen-2-yl)ethylidene]benzohydrazide (L) has been successfully designed and synthesized. The sensing studies of L demonstrated a ratio metric as well as turn-on-enhanced fluorescence and colorimetric response toward Fe³⁺ and Cu²⁺ ions, respectively and it was observed to be insensitive toward various metal ions. The Job plots revealed that the binding stoichiometry of L and metal ions is 2 : 1. In addition, density functional theory (DFT) results strongly suggested that L can be used as a powerful colorimetric sensor for the detection of Cu²⁺ ions. In vitro antimicrobial activities of L were evaluated by disk diffusion and results revealed good antibacterial activities against E. coli. Further, molecular docking was executed with DNA gyrase (PDB ID: 1KZN) of E. coli and the calculated interaction energy value was found to be -7.7 kcal mol^-1. Finally, molecular docking, fluorescence, colorimetry and the HOMO-LUMO energy gap of the compound can provide new insights into developing drugs and detecting metals in biomolecules.