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

DFT Analyses of arsylsemicarbazone group as functional compound for application as excellent fluorescent probes and medicament: study on virtual screening through molecular docking

Debosreeta Bose, Akash Sil, Parna Chakraborty, Saumya Dasgupta, Jayanta Mukhopadhyay, and Madhumita Mukhopadhyay

Department of Chemistry, Amity Institute of Applied Sciences, Amity University, Kolkata, India

E-mail: dbose@kol.amity.edu

Received: 20 December 2023  Accepted: 15 May 2024

Abstract:

The present invention reports two novel functional compounds, 2-hydroxy-3-naphthaldehyde thiosemicarbazone (2H3NTS) and 2-hydroxy-3-naphthaldehyde semicarbazone (2H3NS), as plausible fluorescent probes possessing excited state intramolecular proton transfer property, and they are not yet reported to be synthesized by any research group. The DFT study reveals significantly higher Stokes shift (31,476 cm⁻¹) for 2H3NS indicating swift relaxation from initial to the emissive state and reduces self-quenching from self-molecular absorption which favours its practical application. Consequently, successive in vitro activity of 2H3NTS and 2H3NS is studied in silico using molecular docking towards the inhibition capacity of target kinase protein like CDK, primarily responsible for cell growth. As expected, 2H3NS is capable of binding with both competitive ATP binding SITE I and non-competitive SITE II which lies below the T-loop, thereby inhibiting the cell growth and differentiation. However, 2H3NTS with polarizable sulphur is incapable of binding at SITE I with selective inhibition posing the ATP site to be well conserved.

Graphical Abstract

2-Hydroxy-3-naphthaldehyde thiosemicarbazone (2H3NTS) and 2-hydroxy-3-naphthaldehyde semicarbazone (2H3NS) are theoretically established to be fluorescent possessing excited state intramolecular proton transfer (ESIPT) property. The DFT study reveals significantly higher Stokes shift (31,746 cm⁻¹) for 2H3NS indicating swift relaxation which favours its practical application. 2H3NS is capable of binding both competitive ATP binding SITE I and non-competitive SITE II, thereby inhibiting the cell growth and differentiation. However, 2H3NTS with polarizable sulphur is incapable of binding at SITE I with selective inhibition posing the ATP site to be well conserved.

Keywords: Density Functional Theory; 2-Hydroxy-3-naphthaldehyde thiosemicarbazone; 2-Hydroxy-3-naphthaldehyde semicarbazone; Molecular Docking; Intramolecular Proton Transfer

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03526-y

Chemical Papers 78 (10) 6069–6082 (2024)