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

REFERENCES

Al-Khalqi, E.M., Hamid, M.A.A., Shamsudin, R., Al-Hardan, N.H., Jalar, A. & Keng, L.K. 2021. Zinc oxide nanorod electrolyte-insulator- Semiconductor sensor for enhanced 2-Methoxyethanol selectivity. IEEE Sensors Journal 21(5): 6234-6240.

Atalay, Y.B., Di Toro, D.M. & Carbonaro, R.F. 2013. Estimation of stability constants for metal-ligand complexes containing neutral nitrogen donor atoms with applications to natural organic matter. Geochimica et Cosmochimica Acta 122: 464-477.

Awual, M.R., Kobayashi, T., Miyazaki, Y., Motokawa, R., Shiwaku, H., Suzuki, S., Okamoto, Y. & Yaita, T. 2013. Selective lanthanide sorption and mechanism using novel hybrid Lewis base (N-Methyl-N-phenyl-1,10-phenanthroline-2-carboxamide) ligand modified adsorbent. Journal of Hazardous Materials 252-253: 313-320.

Bányai, I. 2018. Dynamic NMR for coordination chemistry. The Royal Society of Chemistry 42: 7569-7581.

Basabe-Desmonts, L., Müller, T.J.J. & Crego-Calama, M. 2007. Design of fluorescent materials for chemical sensing. Chemical Society Reviews 36(6): 993-1017.

Bozym, R.A., Thompson, R.B. & Fierke, C.A. 2006. Importance of measuring free zinc in cells. In Reviews in Fluorescence 2006, edited by Geddes, C.D. & Lakowicz, J.R. Boston: Springer. pp. 399-419.

Bukheet Hassan, H. 2014. Density function theory B3LYP/6-31G**calculation of geometry optimization and energies of donor-bridge-acceptor molecular system. Research Article International Journal of Current Engineering and Technology 4(4): 2342-2345.

Chandrakumar, K.R.S. & Pal, S. 2002. A systematic study on the reactivity of Lewis acid-base complexes through the local hard-soft acid-base principle. Journal of Physical Chemistry A 106(48): 11775-11781.

Chen, Y., Han, K.Y. & Liu, Y. 2007. Effective switch-on fluorescence sensing of zinc (II) ion by 8-Aminoquinolino-β-Cyclodextrin/Adamantaneacetic acid system in water. Bioorganic and Medicinal Chemistry 15(13): 4537-4542.

Czaplinska, B., Spaczynska, E. & Musiol, R. 2018. Quinoline fluorescent probes for zinc - from diagnostic to therapeutic molecules in treating neurodegenerative diseases. Medicinal Chemistry 14(1): 19-33.

Dong, Y., Fan, R., Chen, W., Wang, P. & Yang, Y. 2017. A simple quinolone schiff-base containing CHEF based fluorescence' turn-on' chemosensor for distinguishing Zn²⁺ and Hg²⁺ with high sensitivity, selectivity and reversibility. Dalton Transactions 46(20): 6769-6775.

Dong, Z., Le, X., Zhou, P., Dong, C. & Ma, J. 2014. An 'off-on-off' fluorescent probe for the sequential detection of Zn²⁺ and hydrogen sulfide in aqueous solution. New Journal of Chemistry 38(4): 1802-1808.

Fu, H., Liu, H., Zhao, L., Xiao, B., Fan, T. & Jiang, Y. 2019. A quinoline-based selective 'turn on' chemosensor for zinc (II) via Quad-core complex, and its application in live cell imaging. Tetrahedron 75(49): 130710.

Galano, A. & Alvarez-Idaboy, J.R. 2006. A new approach to counterpoise correction to BSSE. Journal of Computational Chemistry 27(11): 1203-1210.

Gupta, V.K., Jain, A.K. & Maheshwari, G. 2006. A new Zn^2+-selective potentiometric sensor based on dithizone - PVC membrane. Chemia Analityczna 51(6): 889-898.

Hashmi, M.A., Khan, A., Ayub, K. & Farooq, U. 2014. Spectroscopic and density functional theory studies of 5, 7, 3’, 5’-Tetrahydroxyflavanone from the leaves of Olea ferruginea. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 128: 225-230.

Hudson, G.A., Cheng, L., Yu, J., Yan, Y., Dyer, D.J., McCarroll, M.E. & Wang, L. 2010. Computational studies on response and binding selectivity of fluorescence sensors. J. Phys. Chem. B 114(2): 870-876.

Jensen, F. 2010. An atomic counterpoise method for estimating inter- and intramolecular basis set superposition errors. Journal of Chemical Theory and Computation 6(1): 100-106.

Kadir, M.A., Abdul Razak, F.I. & Haris, N.S.H. 2020. Experimental and DFT data of p-Chlorocalix[4]arene as drugs receptor. Data in Brief 32: 106263.

Siti Shafura, A.Karim, Chang-Fu Dee, Burhanuddin Yeop Majlis & Mohd Ambri Mohamed. 2019. Recent progress on fabrication of zinc oxide nanorod-based field effect transistor biosensors. Sains Malaysiana 48(6): 1301-1310.

Kaur, H., Chhibber, M. & Mittal, S. 2017. Acyclic arylamine-based ionophores as potentiometric sensors for Zn²⁺ and Ni²⁺ ions. Journal of Carbon Research 3(4): 34.

Kerru, N., Gummidi, L., Bhaskaruni, S.V.H.S., Maddila, S.N., Singh, P. & Jonnalagadda, S.B. 2019. A comparison between observed and DFT calculations on structure of 5-(4-chlorophenyl)-2-amino-1,3,4-thiadiazole. Scientific Reports 9(1): 1-17.

Khairul, Wan M., Mohd Faizuddin Abu Hasan, Adibah Izzati Daud, Hafiza Mohamed Zuki, Ku Halim Ku Bulat & Maisara Abdul Kadir. 2016. Theoretical and experimental investigation of pyridyl-thiourea derivatives as ionophores for Cu (II) ion detection. Malaysian Journal of Analytical Sciences 20(1): 73-84.

Li, Q.F., Wang, J.T., Wu, S., Ge, G.W., Huang, J., Wang, Z., Yang, P. & Lin, J. 2018. A water-soluble fluorescent chemosensor having a high affinity and sensitivity for Zn²⁺ and its biological application. Sensors and Actuators, B: Chemical 259: 484-491.

Lopes, J.F., Rocha, W.R., dos Santos, H.F. & de Almeida. W.B. 2010. An investigation of the BSSE effect on the evaluation of ab initio interaction energies for cisplatin-water complexes. Journal of the Brazilian Chemical Society 21(5): 887-896.

Ma, Q.J., Zhang, X.B., Han, Z.X., Huang, B., Jiang, Q., Shen, G.L. & Yu, R.Q. 2011. A ratiometric fluorescent probe for zinc ions based on the quinoline fluorophore. International Journal of Environmental Analytical Chemistry 91(1): 74-86.

Mancin, F. & Tecilla, P. 2007. Zinc(II) complexes as hydrolytic catalysts of phosphate diester cleavage: From model substrates to nucleic acids. New Journal of Chemistry 31(6): 800-817.

Mehdi, H., Gong, W., Guo, H., Watkinson, M., Ma, H., Wajahat, A. & Ning, G. 2017. Aggregation-Induced emission (AIE) fluorophore exhibits a highly ratiometric fluorescent response to Zn²⁺ in vitro and in human liver cancer cells. Chemistry - A European Journal 23(53): 13067-13075.

Mohamad, N.S., Zakaria, N.H., Daud, N., Tan, L.L., Goh, C.T., Lee, Y.H. & Hassan, N.I. 2021. The role of 8-amidoquinoline derivatives as fluorescent probes for zinc ion determination. Sensors 21(1): 311.

Mortier, K.A., Zhang, G.F., van Peteghem, C.H. & Lambert, W.E. 2004. Adduct formation in quantitative bioanalysis: Effect of ionization conditions on paclitaxel. Journal of the American Society for Mass Spectrometry 15(4): 585-592.

Nandiyanto, A.B.D., Oktiani, R. & Ragadhita, R. 2019. How to read and interpret FTIR spectroscope of organic material. Indonesian Journal of Science and Technology 4(1): 97-118.

Nitsche, C. & Otting, G. 2018. NMR studies of ligand binding. Current Opinion in Structural Biology 48: 16-22.

Oturak, H., Kaya Kinaytürk, N. & Sahin, G. 2015. Structure and vibrational studies of ±1-(1H-benzoimidazol-2-YL) ethanol, using DFT method. Acta Physica Polonica A 128(2): 417-421.

Ozel, A.E., Celik, S. & Akyuz, S. 2009. Vibrational spectroscopic investigation of free and coordinated 5-aminoquinoline: The IR, Raman and DFT studies. Journal of Molecular Structure 924-926: 523-530.

Park, G.J., Kim, H., Lee, J.J., Kim, Y.S., Lee, S.Y., Lee, S., Noh, I. & Kim, C. 2015. A highly selective turn-on chemosensor capable of monitoring Zn²⁺ concentrations in living cells and aqueous solution. Sensors and Actuators, B: Chemical 215: 568-576.

Petyunin, G.P. & Sysun, V.N. 1974. Preparation of aminoacridine salts. Pharmaceutical Chemistry Journal 9(7): 444-447.

Ponnuvel, K. & Padmini, V. 2016. Turn-on fluorescence chemosensor for fluoride ions and its applicability in imaging of living cells. Journal of Luminescence 169: 289-294.

Prabavathi, N., Nilufer, A. & Krishnakumar, V. 2014. FT-IR, FT-Raman and DFT quantum chemical study on the molecular conformation, vibrational and electronic transitions of 1-(m-(Trifluoromethyl)phenyl) piperazine. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 121: 483-493.

Sahudin, M.A., Su’ait, M.S., Tan, L.L., Lee, Y.H. & Abd Karim. N.H. 2019. Zinc (II) salphen complex-based fluorescence optical sensor for biogenic amine detection. Analytical and Bioanalytical Chemistry 411(24): 6449-6461.

Salim, A.S., Girgis, A.S., Basta, A.H., El-Saied, H., Mohamed, M.A. & Bedair, A.H. 2018. Comparative DFT computational studies with experimental investigations for novel synthesized fluorescent pyrazoline derivatives. Journal of Fluorescence 28(4): 913-931.

Sethupathi, M., Jayamani, A., Muthusankar, G., Sakthivel, P., Sekar, K., Gandhi, S., Sengottuvelan, N., Gopu, G. & Selvaraju, C. 2020. Colorimetric and fluorescence sensing of Zn²⁺ ion and its bio-imaging applications based on macrocyclic “tet a” derivative. Journal of Photochemistry and Photobiology B: Biology 207: 111854.

Shamsipur, M., Yousefi, M., Hosseini, M., Ganjali, M.R., Sharghi, H. & Naeimi, H. 2001. A Schiff base complex of Zn (II) as a neutral carrier for highly selective PVC membrane sensors for the sulfate ion. Analytical Chemistry 73(13): 2869-2874.

Shi, D., Zhou, X. & Zheng, T. 2014. Recognition and fluorescent sensing of zinc ions using organic fluorophores-based sensor molecules. Journal of the Iranian Chemical Society 12(2): 293-308.

Shyamal, M., Mazumdar, P., Maity, S., Samanta, S., Sahoo, G.P. & Misra, A. 2016. Highly selective turn-on fluorogenic chemosensor for robust quantification of Zn (II) based on aggregation induced emission enhancement feature. ACS Sensors 1(6): 739-747.

Song, H. & Zhang, Z. 2019. A quinoline-based ratiometric fluorescent probe for discriminative detection of Zn ²⁺ and Cd ²⁺ with different binding modes, and its Zn ²⁺ complex for relay sensing of pyrophosphate and adenosine triphosphate. Dyes and Pigments 165: 172-181.

Szabó, L., Chiş, V., Pîrnǎu, A., Leopold, N., Cozar, O. & Orosz, Sz. 2009. Spectroscopic and theoretical study of amlodipine besylate. Journal of Molecular Structure 924: 385-392.

Tharmaraj, V. & Pitchumani, K. 2013. A highly selective ratiometric fluorescent chemosensor for Cu(II) based on dansyl-functionalized thiol stabilized silver nanoparticles. Journal of Materials Chemistry B 1(14): 1962-1967.

Tian, X., Guo, X., Yu, F. & Jia, L. 2016. An oxalamidoquinoline-based fluorescent sensor for selective detection of Zn2+ in solution and living cells and its logic gate behavior. Sensors and Actuators, B: Chemical 232: 181-187.

Urano, Y., Kamiya, M., Kanda, K., Ueno, T., Hirose, K. & Nagano, T. 2005. Evolution of fluorescein as a platform for finely tunable fluorescence probes. Journal of the American Chemical Society 127(13): 4888-4894.

Williams, D. & Fleming, I. 2007. Spectroscopic Methods in Organic Chemistry. 6th ed. London: McGraw-Hill Education.

Ying, K.S., Awang Ngah, F.A., Sapari, S., Lee, Y.H. & Hasbullah, S.A. 2019. Complexation study of bis-thiourea compound with aluminium ion as ionophore for development of potentiometric ion sensor. Sains Malaysiana 48(12): 2649-2661.

You, Q.H., Chan, P.S., Chan, W.H., Hau, S.C.K., Lee, A.W.M., Mak, N.K., Mak, T.C.W. & Wong, R.N.S. 2012. A quinolinyl antipyrine based fluorescence sensor for Zn²⁺ and its application in bioimaging. RSC Advances 2(29): 11078-11083.

Yue, Y., Dong, Q., Zhang, Y., Sun, Y. & Gong, Y. 2015. A highly selective 'turn-on' fluorescent chemosensor based on 8-aminoquinoline for detection of Zn²⁺. Analytical Methods 7(13): 5661-5666.

Zhang, Y., Guo, X., Si, W., Jia, L. & Qian, X. 2008. Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. Organic Letters 10(3): 473-476.

^*Corresponding author; email: drizz@ukm.edu.my