Difluoroboron Curcumin Complex: A Study on Determination of Acidity Constants and Quantitative Analysis of Arsenic(III)

https://doi.org/10.22146/ijc.66990

Nguyen Quoc Thang(1), Tran Nguyen Minh An(2), Le Thi Thanh Tran(3), Do Tam Nhan(4), Mai Ngoc Tan(5), Le Van Tan(6*)

(1) Faculty of Chemical Engineering, Industrial University of Ho Chi Minh City, Ho Chi Minh City, Vietnam
(2) Faculty of Chemical Engineering, Industrial University of Ho Chi Minh City, Ho Chi Minh City, Vietnam
(3) Chemical and Environmental Science Department, Dalat University, Lam Dong Province, Vietnam
(4) Nuclear Research Institute, Lam Dong Province, Vietnam
(5) Faculty of Retraining and Continuing Education, Dak Nong Community College, Dak Nong Province, Vietnam
(6) Faculty of Chemical Engineering, Industrial University of Ho Chi Minh City, Ho Chi Minh City, Vietnam
(*) Corresponding Author

Abstract


In this study, the complex of difluoroboron, curcumin (BF2-Cur), has been synthesized and characterized via the combination of Boron trifluoride-diethyl etherate ((C2H5)2OBF3) and curcumin. However, the new dissociation constants, pKa1 and pKa2 of the BF2-Cur complex, have been indicted by the values of 8.44 ± 0.16 and 9.76 ± 0.13, respectively. On the other hand, the reagent was also used to determine As(III) in aqueous solutions by UV–Vis spectrophotometry. As a result, the method was validated for accuracy, precision, linearity, and sensitivity, and the linear range was from 1.0 to 25.0 µmol/L, with the linear regression, A = 0.0027 C + 0.0106, correlation coefficient R2 = 0.9969. Besides, the limit of detection (LOD) and limit of quantification (LOQ) were determined as 0.83 and 2.10 µmol/L, respectively. Thus, the developed method is successfully used for quantitative analysis of total arsenic in wastewater by reducing As(V) to As(III), then determining As(III) with high accuracy results.


Keywords


BF2-Cur; total arsenic; UV-Vis spectrophotometry; the conformation of complex; UFF

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References

[1] Saxena, G., and Bharagava, R.N., 2017, “Organic and Inorganic Pollutants in Industrial Wastes, Their Ecotoxicological Effects” in Environmental Pollutants and Their Bioremediation Approaches, 1st Ed., Eds. Bharagave, R.N., CRC Press, Boca Raton, Florida, US, 23–56.

[2] Li, H., Zhang, Q., Jiang, W., Collier, S., Sun, Y., and Zhang, Q., 2021, Characteristics and sources of water-soluble organic aerosol in a heavily polluted environment in Northern China, Sci. Total Environ., 758, 143970.

[3] Hanif, N.M., Adnan, S.N.N., Latif, M.T., Zakaria, Z., Abdullahand, M.P., and Othman, M.R., 2012, The composition of surfactants in river water and its influence to the amount of surfactants in drinking water, World Appl. Sci. J., 17 (8), 970–975.

[4] Lellis, B., Fávaro-Polonio, C.Z., Pamphile, J.A., and Polonio, J.C., 2019, Effects of textile dyes on health and the environment and bioremediation potential of living organisms, Biotechnol. Res. Innovation, 3 (2), 275–290.

[5] Ali, M.M., Ali, M.L., Islam, M.S., and Rahman, M.Z., 2016, Preliminary assessment of heavy metals in water and sediment of Karnaphuli River, Bangladesh, Environ. Nanotechnol. Monit. Manage., 5, 27–35.

[6] Shankar, S., Shanker, U., and Shikha, 2014, Arsenic Contamination of groundwater: A review of sources, prevalence, health risks, and strategies for mitigation, Sci. World J., 2014, 304524.

[7] Flora, S.J.S., 2015, Handbook of Arsenic Toxicology, Academic Press, Oxford, UK.

[8] Mähler, J., Persson, I., and Herbert, R.B., 2013, Hydration of arsenic oxyacid species, Dalton Trans., 42 (5), 1364–1377.

[9] Uddin, A.H., Khalid, R.S., Khan, U.A., and Abbas, S.A., 2013, Determination of arsenic content of available traditional medicines in Malaysia using hydride generation atomic absorption spectrometry, Trop. J. Pharm. Res., 12 (6), 1053–1056.

[10] Paula, J.F.R., Froes-Silva, R.E.S., and Ciminelli, V.S.T., 2012, Arsenic determination in complex mining residues by ICP OES after ultrasonic extraction, Microchem. J., 104, 12–16.

[11] Shahlaei, M., and Pourhossein, A., 2014, Determination of arsenic in drinking water samples by electrothermal atomic absorption spectrometry after preconcentration using the biomass of Aspergillus niger loaded on activated charcoal, J. Chem., 2014, 912619.

[12] Musil, S., Matoušek, T., Currier, J.M., Stýblo, M., and Dědina, J., 2014, Speciation analysis of arsenic by selective hydride generation-cryotrapping-atomic fluorescence spectrometry with flame-in-gas-shield atomizer: Achieving extremely low detection limits with inexpensive instrumentation, Anal. Chem., 86 (20), 10422–10428.

[13] Mutic, J.J., Manojlovic, D.D., Stankovic, D., and Lolic, A.D., 2011, Development of inductively coupled plasma atomic emission spectrometry for arsenic determination in wine, Pol. J. Environ. Stud., 20 (1), 133–139.

[14] Paul, R.L., 2011, Evaluation of radiochemical neutron activation analysis methods for determination of arsenic in biological materials, Anal. Chem., 83 (1), 152–156.

[15] Babar, N.U.A., Joya, K.S., Tayyab, M.A., Ashiq, M.N., and Sohail, M., 2019, Highly sensitive and selective detection of arsenic using electrogenerated nanotextured gold assemblage, ACS Omega, 4, 13645−13657.

[16] Gamboa, J.C.M., Cornejo, L., Acarapi, J., and Squella, J.A., 2013, Determination of arsenic (III) by differential pulse polarography in the waters of Camarones area, Chile, J. Chil. Chem. Soc., 58 (4), 2031−2034.

[17] Ferrari, E., Asti, M., Benassi, R., Pignedoli, F., and Saladini, M., 2013, Metal binding ability of curcumin derivatives: a theoretical vs. experimental approach, Dalton Trans., 42 (15), 5304–5313.

[18] Jiang T., Zhi, X.L., Zhang, Y.H., Pan, L.F., and Zhou, P., 2012, Inhibitory effect of curcumin on the Al(III)-induced Aβ42 aggregation and neurotoxicity in vitro, Biochim. Biophys. Acta, Mol. Basis Dis., 1822 (8), 1207–1215.

[19] Pucci, D., Bellini, T., Crispini, A., D'Agnano, I., Liguori, P.F., Garcia-Orduña, P., Pirillo, S., Valentini, A., and Zanchetta, G., 2012, DNA binding and cytotoxicity of fluorescent curcumin-based Zn(II) complexes, Med. Chem. Commun., 3 (4), 462–468.

[20] Meza-Morales, W., Estévez-Carmona, M.M., Alvarez-Ricardo, Y., Obregón-Mendoza, M.A., Cassani, J., Ramírez-Apan, M.T., Escobedo-Martínez, C., Soriano-García, M., Reynolds, W.F., and Enríquez, R.G., 2019, Full structural characterization of homoleptic complexes of diacetylcurcumin with Mg, Zn, Cu, and Mn: Cisplatin-level cytotoxicity in vitro with minimal acute toxicity in vivo, Molecules, 24 (8), 1598.

[21] Choodum, A., Jirapattanasophon, V., Boonkanon, C., Taweekarn, T., and Wongniramalkul, W., 2020, Difluoroboron-curcumin doped starch film and digital image colorimetry for semi-quantitative analysis of arsenic, Anal. Sci., 36 (5), 577–582.

[22] Sirawatcharin, S., Saithongdee, A., Chaicham, A., Tomapatanaget, B., Imyim, A., and Praphairaksit, N., 2014, Naked-eye and colorimetric detection of arsenic(III) using difluoroboron-curcumin in aqueous and resin bead support systems, Anal. Sci., 30 (12), 1129–1134.

[23] Chaicham, A., Kulchat, S., Tumcharern, G., Tuntulani, T., and Tomapatanaget, B., 2010, Synthesis, photophysical properties, and cyanide detection in aqueous solution of BF2-curcumin dyes, Tetrahedron, 66 (32), 6217–6223.

[24] Zhang, Y., Tu, L., Lu, L., Li, Y., Song, L., Qi, Q., Song, H., Li, Z., and Huang, W., 2020, Screening and application of boron difluoride complexes of curcumin as colorimetric and ratiometric fluorescent probes for bisulfite, Anal. Methods, 12 (11), 1514–1521.

[25] Ran, C., Xu, X., Raymond, S.B., Ferrara, B.J., Neal, K., Bacskai, B.J., Medarova, Z., and Moore, A., 2009, Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of Amyloid-β deposits, J. Am. Chem. Soc., 131 (42), 15257–15261.

[26] Bernabé-Pineda, M., Ramírez-Silva, M.T., Romero-Romo, M., González-Vergara, E., and Rojas-Hernández, A., 2004, Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition, Spectrochim. Acta, Part A, 60 (5), 1091–1097.

[27] Baum, L., and Ng, A., 2004, Curcumin interaction with copper and iron suggests one possible mechanism of action in Alzheimer's disease animal models, J. Alzheimer's Dis., 6 (4), 367–377.

[28] Behari, J.R., and Prakas, R., 2006, Determination of total arsenic content in water by atomic absorption spectroscopy (AAS) using vapour generation assembly (VGA), Chemosphere, 63 (1), 17–21.

[29] Klotz, E., Doyle, R., Gross, E., and Mattson, B., 2011, The Equilibrium Constant for Bromothymol Blue: A General Chemistry Laboratory Experiment Using Spectroscopy, J. Chem. Educ., 88 (5), 637–639.

[30] Zabihi, F., Kiani, F., Yaghobi, M., Shahidi, S.A., and Koohyar, F., 2020, The theoretical calculations and experimental measurements of acid dissociation constant and thermodynamic properties of glycyl-aspartic acid in aqueous solution at different temperatures, J. Chil. Chem. Soc., 65 (2), 4759–4768.

[31] Laali, K.K., Greves, W.J., Correa-Smits, S.J., Zwarycz, A.T., Bunge, S.D., Borosky, G.L., Manna, A., Paulus, A., and Chanan-Khan, A., 2018, Novel fluorinated curcuminoids and their pyrazole and isoxazole derivatives: Synthesis, structural studies, computational/docking and in-vitro bioassay, J. Fluorine Chem., 206, 82–98.

[32] Dubbeldam, D., Vreede, J., Vlugt, T.J.H., and Calero, S., 2019, Highlights of (bio-)chemical tools and visualization software for computational science, Curr. Opin. Chem. Eng., 23, 1–13.



DOI: https://doi.org/10.22146/ijc.66990

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