An Undergraduate Experiment Using Cyclodextrin – Assisted Sensitive Fluorescence Detection and Quantitation of Dapsone Drug in Wastewater Samples

Mohammed A. Meetani^1, , Ahmad Alhalabi², Mohammed K. Al-tabaji¹, Noor I Albadawi¹, Nada Elmari¹, Soleiman Hisaindee¹, Abdullah Al-Hemyari¹ and Munjed Maraqa²

¹Chemistry Department, College of Science, United Arab Emirates University, P.O. Box 15551 Al-Ain, UAE

²Civil and Environmental Engineering Department, United Arab Emirates University, P.O. Box 15551 Al-Ain, UAE

Cite this paper

Mohammed A. Meetani, Ahmad Alhalabi, Mohammed K. Al-tabaji, Noor I Albadawi, Nada Elmari, Soleiman Hisaindee, Abdullah Al-Hemyari and Munjed Maraqa. An Undergraduate Experiment Using Cyclodextrin – Assisted Sensitive Fluorescence Detection and Quantitation of Dapsone Drug in Wastewater Samples. World Journal of Chemical Education. 2019; 7(4):242-247. doi: 10.12691/WJCE-7-4-2

Abstract

The guest-host interaction between Dapsone drug and β-cyclodextrin (β-CD) was investigated using fluorescence spectroscopy, ¹H-NMR, and liquid chromatography with fluorescence detection. The optimized conditions for the interaction were investigated by spectrofluorometry and were found to be at 0.2 mg/mL (0.176 mM) of β-CD and pH 8.8. For these conditions, very low concentration of Dapsone drug of 2.4 ng/mL (12.97 nM) can be detected. The standard addition method was utilized to detect Dapsone in influent and effluent wastewater samples in the sub parts per billion concentration range by HPLC-FLD using β-CD as an additive in the mobile phase.

Keywords

dapsone, β-cyclodextrin, fluorescence, guest-host interaction, wastewater

Copyright

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References

[1]	Zhu YI, Stiller MJ. Dapsone and sulfones in dermatology: overview and update. Journal of the American Academy of Dermatology, 45(3),420-434, 2001.
[2]	Wozel G, Blasum C. Dapsone in dermatology and beyond. Archives of dermatological research,306(2), 103-124, 2014.
[3]	Zampeli E, Moutsopoulos HM. Dapsone: an old drug effective for subacute cutaneous lupus erythematosus.Rheumatology (Oxford) 58(5), 920-921, May 2019.
[4]	do Amaral LH, do Carmo FA, Amaro MI, de Sousa VP, da Silva L, de Almeida GS, et al. Development and Characterization of Dapsone Cocrystal Prepared by Scalable Production Methods. AAPS PharmSciTech. , 19(6), 2687-2699, 2018.
[5]	van de Steeg E, Schuren FHJ, Obach RS, van Woudenbergh C, Walker GS, Heerikhuisen M, et al. An Ex Vivo Fermentation Screening Platform to Study Drug Metabolism by Human Gut Microbiota. Drug Metabolism and Disposition, 46(11), 1596-1607, Nov, 2018;
[6]	Braun DE, Griesser UJ. Supramolecular Organization of Nonstoichiometric Drug Hydrates: Dapsone. Frontiers in Chemistry, 6, 31, Feb 2018.
[7]	Essousi H, Barhoumi H. Electroanalytical application of molecular imprinted polyaniline matrix for dapsone determination in real pharmaceutical samples. Journal of Electroanalytical Chemistry, 818. 131-139, 2018.
[8]	Moncrieff J. Determination of dapsone in serum and saliva using reversed-phase high-performance liquid chromatography with ultraviolet or electrochemical detection. Journal of Chromatography B: Biomedical Sciences and Applications, 654(1), 103-110, 1994.
[9]	Farthing CA, Farthing DE, Koka S, Larus T, Fakhry I, Xi L, et al. A simple and sensitive HPLC fluorescence method for determination of tadalafil in mouse plasma. Journal of chromatography B, Analytical technologies in the biomedical and life sciences, 878(28), 2891-2895, 2010.
[10]	Rocha DG, Santos FA, Gomes AA, Faria AF. Validation of a LC-MS/MS Multiresidue Methodology Based on a QuEChERS Approach for the Determination of Fluoroquinolones, Sulfonamides and Trimethoprim in Poultry and Porcine Kidney According to the Normative Instruction 24/2009-MAPA %J Journal of the Brazilian Chemical Society,28, 76-86, 2017.
[11]	Meyer AG, Easton CJ, Lincoln SF, Simpson GW. β-Cyclodextrin as a Scaffold for Supramolecular Chemistry, To Reverse the Regioselectivity of Nitrile Oxide Cycloadditions. The Journal of Organic Chemistry, 63(24), 9069-9075, 1998.
[12]	Dong N, Cheng L-n, Wang X-l, Li Q, Dai C-y, Tao Z. Significant fluorescence enhancement by supramolecular complex formation between berberine chloride and cucurbit(n = 7)uril and its analytical application. Talanta, 84(3), 684-689, 2011.
[13]	Baglole KN, Boland PG, Wagner BD. Fluorescence enhancement of curcumin upon inclusion into parent and modified cyclodextrins. Journal of Photochemistry and Photobiology A: Chemistry, 173(3), 230-237, 2005.
[14]	Ma L, Tang B, Chu C. Spectrofluorimetric study of the β-cyclodextrin–dapsone–linear alcohol supramolecular system and determination of dapsone. Analytica Chimica Acta, 469(2), 273-283, 2002.
[15]	Skiba M, Wouessidjewe D, Puisieux F, Duchêne D, Gulik A. Characterization of amphiphilic β-cyclodextrin nanospheres. International Journal of Pharmaceutics, 142(1), 121-124, 1996.
[16]	Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. Journal of Pharmaceutical Science. , 85(10), 1017-1025, 1996.
[17]	Stella VJ, Rajewski RA. Cyclodextrins: their future in drug formulation and delivery. Pharmacuetical Research, 14(5), 556-567, 1997.
[18]	Cui X, Zhang P, Yang X, Yang M, Zhou W, Zhang S, et al. beta-CD/ATP composite materials for use in dispersive solid-phase extraction to measure (fluoro)quinolone antibiotics in honey samples. Analytica Chimica Acta 878, 131-139, 2015.
[19]	Kopperi M, Riekkola ML. Non-targeted evaluation of selectivity of water-compatible class selective adsorbents for the analysis of steroids in wastewater. Analytica Chimica Acta. 920, 47-53, 2016.
[20]	Wu X, Yang M, Zeng H, Xi X, Zhang S, Lu R, et al. Effervescence-assisted dispersive solid-phase extraction using ionic-liquid-modified magnetic beta-cyclodextrin/attapulgite coupled with high-performance liquid chromatography for fungicide detection in honey and juice. Journal of seperation Science, 39(22), 4422-4428, 2016.
[21]	Kongsted J, Osted A, Mikkelsen KV, Astrand PO, Christiansen O. Solvent effects on the n-->pi* electronic transition in formaldehyde: a combined coupled cluster/molecular dynamics study. Journal of Chemical Physics. 121(17), 8435-8345, 2004.
[22]	Thordarson P. Determining association constants from titration experiments in supramolecular chemistry. Chemical Society reviews. 40(3):1, 305-233. 2011