A quinoline-based fluorescent labelling for zinc detection and DFT calculations

Nur Syamimi Mohamad, and Ling, Ling Tan and Goh, Choo Ta and Lee, Yook Heng and Nadhratun Naiim Mobarak, and Azwan Mat Lazim, and Suhaila Sapari, and Fazira Ilyana Abdul Razak, and Nurul Izzaty Hassan, (2022) A quinoline-based fluorescent labelling for zinc detection and DFT calculations. Sains Malaysiana, 51 (12). pp. 3949-3966. ISSN 0126-6039


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8-carboxamidoquinoline derivatives were gradually investigated as zinc’s label in resolving weak water solubility, poor membrane permeability, and difficulty measuring free Zn2+ ion in cells quantitatively. The potential of 2-oxo-2-(quinolin-8-ylamino)acid (OQAA) as zinc’s label was prepared and characterized spectroscopically. Theoretical and experimental data of OQAA were compared and discussed. The optimized molecular structure, molecular orbital of HOMO-LUMO, energy band gaps, and molecular electrostatic potential (MEP) of OQAA were carried out using the DFT method with Becke-3-Parameter-Lee-Yang-Parr (B3LYP) and 6-31G(d,p) basis set. The intermolecular interaction energy of OQAA-Zn is calculated by using the hybrid method of GEN with a basis set of LANL2DZ for Zn2+ ion and DFT/6-31G(d,p) for OQAA ligand. OQAA exhibited remarkable and excellent fluorescence enhancement selective and qualitatively only for Zn2+ than other metal cations tested (Fe2+, Cu2+, Co2+, Ni2+, Hg2+, Cd2+) under a long wavelength. Job’s plot and 1H NMR titrations indicate OQAA-Zn2+ has a binding ratio at 1:1 stoichiometry (M1L1). Substantial shifting of amide N-H proton to higher chemical shift and intensity of the proton peak of N-H amide decrease abruptly implies that Zn2+ is binding to an amide. These changes confirmed interactions among the ligand OQAA and metal Zn2+ ion. As a result of the benefits discussed, OQAA could effectively and selectively optimize and fabricate for Zn2+ sensors.

Item Type:Article
Keywords:Density functional theory; Fluorescent sensor; Metal cation; Zinc label, 8-carboxamidoquinoline
Journal:Sains Malaysiana
ID Code:21194
Deposited By: Siti Zarenah Jasin
Deposited On:22 Feb 2023 02:08
Last Modified:27 Feb 2023 06:39

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