Sains Malaysiana 51(12)(2022): 3949-3966

http://doi.org/10.17576/jsm-2022-5112-07

A Quinoline-Based Fluorescent Labelling for Zinc Detection and DFT Calculations

(Pelabelan Pendarfluor Berasaskan Kuinolina untuk Pengesanan Zink dan Pengiraan DFT)

NUR SYAMIMI MOHAMAD¹, LING LING TAN¹, GOH CHOO TA¹, LEE YOOK HENG², NADHRATUN NAIIM MOBARAK², AZWAN MAT LAZIM², SUHAILA SAPARI³, FAZIRA ILYANA ABDUL RAZAK³ & NURUL IZZATY HASSAN^2,*

¹Southeast Asia Disaster Prevention Research Initiative (SEADPRI-UKM), Institute for Environment and Development (LESTARI), Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

²Department of Chemical Sciences, Faculty of Science & Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

³Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81300 Skudai, Johor Bahru, Johor Darul Takzim, Malaysia

Received: 8 June 2022/Accepted: 1 September 2022

Abstract

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.

Keywords: Density functional theory; fluorescent sensor; metal cation; zinc label; 8-carboxamidoquinoline

Abstrak

Bahan terbitan 8-karboksamidokuinolina semakin mendapat perhatian sebagai label zink dalam menyelesaikan masalah keterlarutan air yang lemah, kebolehtelapan membran yang lemah, dan kesukaran mengukur ion Zn²⁺ bebas dalam sel secara kuantitatif. Sebatian asid 2-okso-2-(kuinolina-8-ylamino) (OQAA) yang berpotensi sebagai label zink telah disintesiskan dan dicirikan secara spektroskopi. Data teori dan uji kaji OQAA dibandingkan dan dibincangkan. Struktur molekul yang dioptimumkan, orbital molekul HOMO-LUMO, jurang jalur tenaga dan potensi elektrostatik molekul (MEP) OQAA telah dijalankan menggunakan kaedah DFT dengan Becke-3-Parameter-Lee-Yang-Parr (B3LYP) dan set asas 6-31G(d,p). Seterusnya, tenaga interaksi antara molekul OQAA-Zn dihitung menggunakan kaedah hibrid GEN dengan set asas LANL2DZ untuk ion Zn²⁺ dan DFT/6-31G(d,p) untuk ligan OQAA. OQAA menunjukkan peningkatan pendarfluor yang luar biasa dan cemerlang secara selektif dan kualitatif hanya untuk Zn²⁺ berbanding kation logam lain yang diuji (Fe²⁺, Cu²⁺, Co²⁺, Ni²⁺, Hg²⁺, Cd²⁺) di bawah lampu UV gelombang panjang. Plot Job dan titrasi ¹H NMR menunjukkan OQAA-Zn²⁺ mempunyai nisbah pengikatan pada stoikiometri 1:1 (M₁L₁). Peralihan besar amida N-H proton kepada anjakan kimia yang lebih tinggi dan keamatan puncak proton amida N-H menurun secara mendadak memberi gambaran bahawa Zn²⁺ terikat pada amida. Perubahan ini mengesahkan terdapat interaksi antara ligan OQAA dan ion logam Zn²⁺. Kesimpulannya, hasil kajian yang dibincangkan ini membuktikan sebatian OQAA ini boleh dilanjutkan dengan pengoptimuman dan fabrikasi sensor Zn²⁺ yang berkesan dan selektif. 

Kata kunci: Kation logam; label zink; sensor pendarfluor; 8-karboksamidokuinolina; teori kefungsian ketumpatan

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^*Pengarang untuk surat-menyurat; email: drizz@ukm.edu.my