Selective Separation and Preconcentration of Caffeine from Natural and Pharmaceutical Products using New Polyurethane Foams

Authors

  • Samah Ali Chemistry Department, College of Science, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia; The National Organization for Drug Control and Research, Al-Agouzah, Giza, Egypt
  • Samy M. Abdel Azeem Chemistry Department, Faculty of Science, Fayoum University, Fayoum City, Egypt; Chemistry Department, Al-Quwaiyiah College of Science and Humanities, Shaqra University, Saudi Arabia
  • Arshi Naqv Chemistry Department, College of Science, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia
  • Mohamed F. El-Shahat Chemistry Department, Faculty of Science, Ain-Shams University, Cairo, Egypt
  • Amr M Addeck Chemistry Department, College of Science, Taibah University, Al-Madinah Al-Munawarah, Saudi Arabia; The Higher Institute of Optics Technology (HIOT), Heliopolis, Cairo, Egypt https://orcid.org/0000-0003-2505-1325

DOI:

https://doi.org/10.1590/s2175-97902022e20175%20%20

Keywords:

Polyurethane foam (PUF), Alizarin yellow G, Caffeine separation, Adsorption isotherms, in silico screening

Abstract

Two polyurethane foam-based sorbents (PUF) were synthesized by imprinting and grafting techniques and examined for selective separation and preconcentration of caffeine (CAF) in some pharmaceutical products and in black tea. Molecularly imprinted PUF was synthesized based on hydrogen-bonding interactions between CAF and alizarin yellow G (AYG) and subsequent polymerization into PUF. The static experiments indicated optimum sorption conditions at pH=6.5 and 5.5 for imprinted PUF (AY-IPUF) and grafted PUF (AY-GPUF), respectively. In the online experiments, the suitable preconcentration time was found to be 40 and 20s for (AY-IPUF) and (AY-GPUF), respectively, at a flow rate of 1.75 mL.min-1. Desorption of CAF has been affected by passing 500 μL of 0.05, 0.01 mol.L−1 HCl eluent onto (AY-IPUF) and (AY-GPUF), respectively. The online methods have provided satisfactory enrichment factors of 8.4 and 10.5 for (AY-IPUF) and (AY-GPUF), respectively. The time consumed for preconcentartion, elution and determination steps was 1.48 and 1.05 min, thus, the throughput was 42 and 57 h-1, for (AY-IPUF) and (AY-GPUF), respectively. The developed sorbents were studied for the determination of CAF in pharmaceutical samples which will be helpful to minimize caffeinism. Finally, in silico bioactivity, ADMET and drug-likeness predictive computational studies of caffeine were also carried out.

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References

Ababneh AN, Abu-Dalo MA, Horn C, Hernandez MT. Polarographic determination of benzotriazoles and their sorption behavior on granular activated carbon. Int J Environ Sci Technol. 2019;16(2):833-42.

Abdel Azeem SM, Mohamed Attaf SM, El-Shahat MF. Acetylacetone phenylhydrazone functionalized polyurethane foam: Determination of copper, zinc and manganese in environmental samples and pharmaceutics using flame atomic absorption spectrometry. React Funct Polym. 2013;73(1):182-91.

Ahmad Bhawani S, Fong SS, Mohamad Ibrahim MN. Spectrophotometric Analysis of Caffeine. Int J Analyt Chem. 2015;2015:7.

Al-blewi F, Rezki N, Naqvi A, Qutb Uddin H, Al-Sodies S, Messali M, et al. A Profile of the In Vitro Anti-Tumor Activity and In Silico ADME Predictions of Novel Benzothiazole Amide-Functionalized Imidazolium Ionic Liquids. Int J Mol Sci. 2019;20(12):2865.

Altun ML, Ceyhan T, Kartal M, Atay T, Özdemir N, Cevheroğlu Ş. LC method for the analysis of acetylsalicylic acid, caffeine and codeine phosphate in pharmaceutical preparations. J Pharm Biomed Anal. 2001;25(1):93-101.

Amini T, Hashemi P. Preconcentration and GC-MS determination of caffeine in tea and coffee using homogeneous liquid-liquid microextraction based on solvents volume ratio alteration. J Chromatogr B. 2018;1092:252-7.

Andreeva E, Dmitrienko S, Zolotov Y. Sorption of caffeine and theophylline on hypercrosslinked polystyrene. Moscow Univ Chem Bull. 2010;65:38-41.

Anthemidis AN, Ioannou K-IG. Evaluation of polychlorotrifluoroethylene as sorbent material for on-line solid phase extraction systems: Determination of copper and lead by flame atomic absorption spectrometry in water samples. Anal Chim Acta. 2006;575(1):126-32.

Avila MAS. Experiment and modelling of the competitive sorption and transport of chlorinated ethenes in porous media: Cuvillier Verlag; 2005.

Azeem SMA, Ali S, El-Shahat MF. Sorption characteristics of caffeine onto untreated polyurethane foam: application to its determination in human plasma. Anal Sci. 2011;27(11):1133.

Banerjee S, Chattopadhyaya MC. Adsorption characteristics for the removal of a toxic dye, tartrazine from aqueous solutions by a low cost agricultural by-product. Arabian J Chem. 2017;10(Supplement 2):S1629-S38.

Bhatia I, Ullah MR. Polyphenols of tea. IV. - Qualitative and quantitative study of the polyphenols of different organs and some cultivated varieties of tea plant. J Sci Food Agric. 1968;19(9):535-42.

Bojdi MK, Behbahani M, Sahragard A, Amin BG, Fakhari A, Bagheri A. A palladium imprinted polymer for highly selective and sensitive electrochemical determination of ultra-trace of palladium ions. Electrochim Acta. 2014;149(Supplement C):108-16.

Boonkerd S, Lauwers M, Detaevernier MR, Michotte Y. Separation and simultaneous determination of the components in an analgesic tablet formulation by micellar electrokinetic chromatography. J Chromatogr A. 1995;695(1):97-102.

Burham N, Abdel-Azeem SM, El-Shahat F. Determination of lead and cadmium in tap water and apple leaves after preconcentration on a new acetylacetone bonded polyurethane foam sorbent. Int J Environ Anal Chem. 2008;88(11):775-89.

Camel V. Solid phase extraction of trace elements. Spectrochim Acta Part B. 2003;58(7):1177-233.

Corciova A, Ivanescu B. Determination of caffeine content from different pharmaceutical and natural products. Eur Chem Bull. 2016;5(4):138-41.

Cristea AN. Tratat de farmacologie. Editura Medicală, București. 2012.

de Almeida GN, de Sousa LM, Pereira Netto AD, Cassella RJ. Characterization of solid-phase extraction of Fe(III) by unloaded polyurethane foam as thiocyanate complex. Journal J Colloid and Interface Sci. 2007;315(1):63-9.

De Boer JH. The Dynamical Character of Adsorption, 2nd ed. London Oxford University Press; 1968.

Egan WJ, Lauri G. Prediction of intestinal permeability. Adv Drug Delivery Rev. 2002;54(3):273-89.

El-Shahat MF, Burham N, Abdel Azeem SM. Flow injection analysis-solid phase extraction (FIA-SPE) method for preconcentration and determination of trace amounts of penicillins using methylene blue grafted polyurethane foam. J Hazard Mater. 2010;177(1):1054-60.

Ferreira SLC, Andrade HMC, dos Santos HC. Characterization and determination of the thermodynamic and kinetic properties of the adsorption of the molybdenum(VI)- calmagite complex onto active carbon. J Colloid Interface Sci. 2004;270(2):276-80.

Forrest GI, Bendall DS. The distribution of polyphenols in the tea plant (Camellia sinensis L.). Biochem J. 1969;113(5):741-55.

Franeta J, Agbaba D, Eric S, Pavkov S, Aleksic M, Vladimirov S. HPLC assay of acetylsalicylic acid, paracetamol, caffeine and phenobarbital in tablets. Farmaco. 2002;57(9):709-13.

Gawargious Y, Abbas E, Hassan H. Determination of Traces Of Bismuth in Water with Polyurethane Foak Thin-Layer Spectrophotometry. Anal Lett. 1988;21(8):1477-86.

Ge L, Wang S, Yu J, Li N, Ge S, Yan M. Molecularly imprinted polymer grafted porous au-paper electrode for an microfluidic electro-analytical origami device. Adv Funct Mater. 2013;23(24):3115-23.

Ghose AK, Viswanadhan VN, Wendoloski JJ. Prediction of hydrophobic (lipophilic) properties of small organic molecules using fragmental methods: an analysis of ALOGP and CLOGP methods. J Phys Chem A. 1998;102(21):3762-72.

Hameed BH, Din ATM, Ahmad AL. Adsorption of methylene blue onto bamboo-based activated carbon: Kinetics and equilibrium studies. J Hazard Mater . 2007;141(3):819-25.

Hashimoto F, Nonaka G-i, Nishioka I. Tannins and Related Compounds. LXXVII.: Novel Chalcan-flavan Dimers, Assamicains A, B and C, and a New Flavan-3-ol and Proanthocyanidins from the Fresh Leaves of Camella sinensis L. var. assamica KITAMURA. Chem Pharm Bull. 1989;37(1):77-85.

Horie H, Nesumi A, Ujihara T, Kohata K. Rapid determination of caffeine in tea leaves. J Chromatogr A . 2002;942(1):271-3.

Huo Q, Li J, Liu G, Qi X, Zhang X, Ning Y, et al. Adsorption desulfurization performances of Zn/Co porous carbons derived from bimetal-organic frameworks. Chem Eng J. 2019;362:287-97.

Ivanescu B, Vlase L, Lungu C, Corciova A. HPLC analysis of phenolic compounds from artemisia species. Eur Chem Bull . 2016;5(4):119-23.

Kumar PS, Ramalingam S, Sathyaselvabala V, Kirupha SD, Murugesan A, Sivanesan S. Removal of cadmium (II) from aqueous solution by agricultural waste cashew nut shell. Korean J Chem Eng. 2012;29(6):756-68.

Li J-M, Meng X-G, Hu C-W, Du J. Adsorption of phenol, p-chlorophenol and p-nitrophenol onto functional chitosan. Bioresour Technol. 2009;100(3):1168-73.

Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2001;46(1-3):3-26.

Marchisio P, Sales A, Cerutti S, Marchevski E, Martinez L. On-line preconcentration/determination of lead in Ilex paraguariensis samples (mate tea) using polyurethane foam as filter and USN-ICP-OES. J Hazard Mater . 2005;124(1):113-8.

Muegge I, Heald SL, Brittelli D. Simple selection criteria for drug-like chemical matter. J Med Chem. 2001;44(12):1841-6.

Ogah CO, Obebe OT. Caffeine content of cocoa and coffee beverages in Lagos, Nigeria. J Innovative Res Eng Sci. 2016;3(1):404-11.

Poole CF. New trends in solid-phase extraction. Trends Anal Chem. 2003;22(6):362-73.

Pragathiswaran C, Sibi S, Sivanesan P. Comparison studies of various adsorption isotherms for aloe vera adsorbent. Int J Res Pharm Chem. 2013;3(4):886-9.

Ramos-Martos N, Aguirre-Gómez F, Molina-Díaz A, Capitán-Vallvey LF. Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations. J AOAC Int. 2001;84(3):676-83.

Ruxton C. The impact of caffeine on mood, cognitive function, performance and hydration: a review of benefits and risks. Nutr Bull. 2008;33(1):15-25.

Salam SMAAA. Chemically modified polyurethane foam for pre-concentration and separation of inorganic and organic species: Duisburg, Essen, 2008; 2008.

Santos C, Costa J, Santos J, Vaz-Carneiro A, Lunet N. Caffeine intake and dementia: systematic review and meta-analysis. J Alzheimer’s Dis. 2010;20(s1):S187-S204.

Sena MM, Poppi RJ. N-way PLS applied to simultaneous spectrophotometric determination of acetylsalicylic acid, paracetamol and caffeine. J Pharm Biomed Anal . 2004;34(1):27-34.

Talio MC, Acosta MG, Alesso M, Luconi MO, Fernández LP. Quantification of caffeine in dietary supplements and energy drinks by solid-surface fluorescence using a pre-concentration step on multi-walled carbon nanotubes and Rhodamine B. Food Addit Contam Part A. 2014;31(8):1367-74.

Thomsen V, Schatzlein D, Mercuro D. Limits of detection in spectroscopy. Spectroscopy. 2003;18(12):112-4.

Turnbull D, Rodricks JV, Mariano GF. Neurobehavioral hazard identification and characterization for caffeine. Regul Toxicol Pharmacol. 2016;74:81-92.

Veber DF, Johnson SR, Cheng H-Y, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem . 2002;45(12):2615-23.

Wang S, Li H, Xu L. Application of zeolite MCM-22 for basic dye removal from wastewater. J Colloid Interface Sci . 2006;295(1):71-8.

Wanyika HN, Gatebe EG, Gitu LM, Ngumba EK, Maritim CW. Determination of caffeine content of tea and instant coffee brands found in the Kenyan market. African J Food Sci. 2010;4(6):353-8.

Wells MJ. Principles of extraction and the extraction of semivolatile organics from liquids. Sample Preparation Tech Anal Chem.

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Published

2022-12-23

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Original Article

How to Cite

Selective Separation and Preconcentration of Caffeine from Natural and Pharmaceutical Products using New Polyurethane Foams. (2022). Brazilian Journal of Pharmaceutical Sciences, 58. https://doi.org/10.1590/s2175-97902022e20175