UTILIZATION OF EOSIN DYE AS AN ION PAIRING AGENT FOR DETERMINATION OF PHARMACEUTICALS: A BRIEF REVIEW


Habibur Rahman

Abstract


Globally, dyes are widely used in the pharmaceutical, food, textile, cosmetics, plastics, leather, paint, ink and paper industries. Eosin is an acidic orange-pink dye and has very strong staining properties. Haematoxylin and eosin Y (H&E) combination is the most common staining and primary diagnostic technique in histo-pathological laboratories. This review mainly discussed the utility of eosin dye in quality control laboratories as an ion pairing agent for drug analysis. Eosin Y is one the most common ion pairing agent and its mono and di anionic forms of eosin Y are capable of interacting with many drug molecules to form colored/fluorescent binary or ternary complexes that can be analyzed with or without extraction by spectrofluorimetry and/or spectrophotometry. Quenching fluorescence and advantages of spectrofluorimetry over spectrophotometry were also discussed. Fluorescence detection greatly enhances the sensitivity and providing a sensitive and relatively inexpensive instrumental method of analysis using eosin Y for various important drugs in pure, commercial dosage forms and biological fluids


Keywords


Eosin Y, Ion pairing agent, Spectrofluorimetry, commercial dosage forms

| PDF | HTML |

References


Hunger K. Industrial dyes: chemistry, properties, applications. Wiley-VCH, Verlag GmbH and Co. KGa A, Weinhiem; 2003.

Seema A, Babulal R. Fluorescence spectrometric study of eosin yellow dye–surfactant interactions. Arab J Chem 2009;2:7-12.

Vanzin D, Freitas CF, Pellosi DS, Batistela AR, Machado AEH, Pontes RM. et al. Experimental and computational studies of protolytic and tautomeric equilibria of erythrosin B and eosin Y in water/DMSO. RSC Adv 2016;6:110312-28.

Nikitina NA, Reshetnyak EA, Svetlova NV, Petrossyan NOM. Protolytic properties of dyes embedded in gelatin films. J Braz Chem Soc 2011;22:857-66.

Sabnis RW. Handbook of biological dyes and stains: synthesis and Industrial Applications, John Wiley and Sons, Inc, Hoboken, NJ; 2010. p. 173.

Espada J, Valverde P, Stockert JC. Selective fluorescence of eosinophilic structures in grasshopper and mammalian testis stained with haematoxylin-eosin. Histochemistry 1993;99:385-90.

Raj G. Photochemistry: In. Photochemical reactions and their kinetics. 5th ed. Meerut: India, Goel publishing house; 2008. p. 125-6.

Srivastava V, Singh PP. Eosin Y catalyzed photoredox synthesis: a review. RSC Adv 2017;7:31377-92.

Hari DP, Koning B. Synthetic applications of eosin Y in photoredox catalysis. Chem Commun 2014;50:6688-99.

Hari DP. Eosin Y catalyzed visible light oxidative C–C and C–P bond formation. Org Lett 2011;13:3852-5.

Atul KS, Ruchi C, Lal Dhar SY. Eosin Y catalyzed visible light mediated aerobic photo-oxidative cleavage of the C–C double bond of styrenes. Tetrahedron Lett 2015;56:653-6.

Waheed AA, Rao KS, Gupta PD. Mechanism of dye binding in the protein assay using eosin dyes. Anal Biochem 2000;287:73-9.

Waheed AA, Gupta PD. Application of an eosin B dye method for estimating a wide range of proteins. J Biochem Biophys Methods 1996;33:187-96.

Waheed AA, Gupta PD. Estimation of protein using eosin B dye. Anal Biochem 1996;233:249-52.

Kristen MM, Michael TM, Lanxuan TD, Chloe EA, Stephan G, Worachart S. et al. Eosin B as a novel antimalarial agent for drug-resistant Plasmodium falciparum. Antimicrob Agents Chemother 2006;50:3132-41.

Piergallini R, Loupis N. Teeth whitening composition comprising activating agents, such as Eosin B and erythrosine B. U. S. Pat Appl Publ US 2007128132. Chem Abstr 2007;147:38007.

Brumley WC, Farley JW. Determining eosin as a groundwater migration tracer by capillary electrophoresis/laser-induced fluorescence using a multi wavelength laser. Electrophoresis 2003;24:2335-9.

Chen PL, Liu SP, Liu ZF, Hu XL. Study on the ternary ion-association complex nanoparticles of palladium (II)-famotidine and halogen-fluorescein dyes by the resonance rayleigh scattering and their application. Sci Sin Chim 2011;41:1059-71.

Junbo L, Xiaoli Y, Jinxiang Y, Lina L. Resonance rayleigh scattering and resonance nonlinear scattering methods for the determination of nicardipine hydrochloride using eosin Y as a probe. RSC Adv 2016;6:25887-93.

Jiahong H, Ri Q, Wenpo L, Shaohua X, Zhongrong S, Qiang L, et al. Voltammetric sensor based on eosin Y film modified glassy carbon electrode for simultaneous determination of hydroquinone and catechol. Anal Meth 2014;6:6494-503.

Pratim DP, Anurag R, Sumita D, Devi PS. Enhanced stability of Zn2SnO4 with N719, N3 and eosin Y dye molecules for DSSC application. Phys Chem Chem Phys 2016;18:1429-38.

Arad A, Mimouni D, Ben-Amitai D, Zeharia A, Mimouni M. Efficacy of topical application of eosin compared with zinc oxide paste and corticosteroid cream for diaper dermatitis. Dermatology 1999;199:319-22.

Teresinha L, Philippe D, Alexandre H, Pierre EW. Topical application of eosin to burns produces interference in measurement of serum vancomycin by fluorescence polarization immunoassay. Clin Chem 1997;43:1238-40.

Nail A, Ramazan G, Mehmet T. A new atomic absorption-based method development for indirect determination of histamine in fish samples, dairy products, and alcoholic beverages by flame AAS. Anal Meth 2016;25:5142-51.

Gao Y, Li Y, Yao L, Li S, Liu J, Zhang H. Catalyst-free activation of peroxides under visible LED light irradiation through photoexcitation pathway. J Hazard Mat 2017;329:272-9.

Pan Z, Peng J, Zang X, Lei G, He Y, Liu D. Study on the interaction between three benzimidazole anthelmintics and eosin Y by high performance liquid chromatography associating with resonance light scattering and its application. Anal Bioanal Chem 2016;408:5247-59.

Wen T, Li NB, Lu HQ. A turn-on fluorescent sensor for sensitive and selective detection of sodium dodecyl sulfate based on the eosin Y/Polyethyleneimine system. Anal Chem 2013;85:10863-8.

Sidney U, Bernard H, Nathan OK, Julius M. Principle of Fluorescence. Fluorescence assay in biology and medicine, A volume in Molecular Biology: An International series of Monographs and text book; 1969. p. 1-41.

Pesez M, Bartos J. Colorimetric and fluorimetric analysis of organic compounds and drugs (clinical and biochemical analysis), New York, Marcel Dekker Inc; 1974. p. 803-4.

Yoshikazu F, Itsuo M, Kinuko F, Yoshihiro N, Takeshi T. Determination of chlorpromazine, thiamine, lincomycin, ofloxacin and theophylline by ternary complex formation with eosin and palladium (II). Chem Pharm Bull 1987;35:5004-9.

Kaur A, Gupta U. Simultaneous spectrophotometric determination of eosin and erythrosine with Cr (VI) reagent in micellar media using mean centering of ratio spectra. Chem Sci Trans 2012;1:424-30.

Chakraborty M, Panda AK. Spectral behaviour of eosin Y in different solvents and aqueous surfactant media. Spectrochim Acta Part A 2011;81:458-65.

Kibblewhite J, Drummond GG, Grieser F, Thistlethwaite PJ. Lipoidaleos in and fluorescein derivatives as probes of the electrostatic characteristics of self-assembled surfactant/water interfaces. J Phys Chem 1989;93:7464-73.

Lakowicz JR. Principles of fluorescence spectroscopy. In: Lakowicz JR. editors. Quenching of fluorescence. 3rd ed. Springer, Boston, MA; 2006. p. 277-330.

Phillips SR, Wilson LJ, Borkman RF. Acrylamide and iodide fluorescence quenching as a structural probe of tryptophan microenvironment in bovine lens crystallins. Curr Eye Res 1986;5:611-9.

Punyiczki M, Norman JA, Rosenberg A. Interaction of acrylamide with proteins in the concentration range used for fluorescence quenching studies. Biophys Chem 1993;47:9-19.

Lange R, Anzenbacher P, Müller S, Maurin L, Balny C. Interaction of tryptophan residues of cytochrome P45scc with a highly specific fluorescence quencher, a substrate analogue, compared to acrylamide and iodide. Eur J Biochem 1994;226:963-70.

Geddes CG. Optical thin film polymeric sensors for the determination of aqueous chloride, bromide and iodide ions at high pH, based on the quenching of fluorescence of two acridinium dyes. Dyes Pigments 2000;45:243-51.

Willard DM, Carillo LL, Jung J, Orden AV. CdSe-ZnS quantum dots as resonance energy transfer donors in a model protein-protein binding assay. Nano Lett 2001;1:469-74.

Haas E, Wilchek M, Katzir EK, Steinberg IZ. Distribution of end-to-end distances of oligopeptides in solution as estimated by energy transfer. Proc Natl Acad Sci USA 1975;72:1807-11.

Lakowicz JR, Gryczynski I, Wiczk W, Laczko G, Franklyn CP, Johnson ML. Conformational distributions of melittin in water/methanol mixtures from frequency-domain measurements of nonradiative energy transfer. Biophys Chem 1990;36:99-115.

Chapman ER, Alexander K, Vorherr T, Carafoil E, Storm DR. Fluorescence energy transfer analysis of calmodulin. cntdot. peptide complexes. Biochemistry 1992;31:12819-25.

Heyduk T. Measuring protein conformational changes by FRET/lRET. Curr Opin Biotechnol 2002;13:292-6.

Hink MA, Bisseling T, Visser AJWG. Imaging protein-protein interactions in living cells. Plant Mol Biol 2002;50:871-83.

Parsons M, Vojnovic B, Beg SA. Imaging protein–protein interactions in cell motility using fluorescence resonance energy transfer (FRET). Biochem Soc Trans 2004;32:431-3.

El-Rabbat N, Askal HF, Khashaba PY, Attia NN. A validated spectrofluorometric assay for the determination of certain macrolide antibiotics in pharmaceutical formulations and spiked biological fluids. J AOAC Int 2006;89:1276-87.

Gillis V, Kubic TA. Spectrofluorometric analysis of illicit drug samples, employing a corrected excitation spectrofluorometer. ISA Trans 1975;14:261-9.

Nahata A, Dixit VK. Spectrofluorimetric estimation of scopoletin in Evolvulus alsinoides Linn. and Convolvulus pluricaulis Choisy. Indian J Pharm Sci 2008;70:834-7.

Sethiya NK, Nahata A, Dixit VK. Simultaneous spectrofluorimetric determination of scopoletin and mangiferin in a methanolic extract of Canscora decussates Chult. Asian J Trad Med 2008;3:224-9.

Gupta NK, Nahata A, Dixit VK. Development of spectrofluorimetric method for the determination of curcumin. Asian J Trad Med 2010;5:12-8.

Nahata A, Gupta NK, Dixit VK. A simple and rapid spectrofluorimetric method for the determination of testosterone in biological fluids. Oriental Pharm Exp Med 2011;11:147-51.

Belal F, El-Brashy A, El-Enany N, El-Bahay N. Spectrofluorometric determination of olanzapine and fluphenazine hydrochloride in pharmaceutical preparations and human plasma using eosin: application to stability studies. J AOAC Int 2008;91:1309-17.

Attia KAM, Mohamad AA, Emara MS. A fluorescence quenching based method for the determination of risperidone in bulk and tablets. Eur J Biomed Pharm Sci 2015;2:17-27.

Rahman N, Siddiqui S, Azmi SNH. Spectrofluorimetric method for the determination of doxepin hydrochloride in commercial dosage forms. AAPS PharmSciTech 2009;10:1381-7.

Derayea SM, Omar MA, Abdel-Lateef MA, Hassan AI. Development and validation of a new spectrofluorimetric method for the determination of some beta-blockers through fluorescence quenching of eosin Y. Application to content uniformity test. Open Chem 2016;14:258-66.

Rahman N, Haque SM. Spectrofluorimetric determination of labetalol hydrochloride in pharmaceutical preparations and urine samples. Int J Biomed Sci 2008;4:140-6.

Ibrahim FA, Belal F, El-Brashy A. Fluorometric determination of some aminoquinoline antimalarials using eosin. Microchem J 1989;39:65-70.

Wahba MK, El-Enany N, Belal F. Application of the stern–volmer equation for studying the spectrofluorimetric quenching reaction of eosin with clindamycin hydrochloride in its pure form and pharmaceutical preparations. Anal Methods 2015;7:10445-51.

Hammad MA, Omar MA, Eltoukhi WE. Validation of rapid and sensitive spectrofluorimetric assay for determination of four triptans in pure and dosage forms; application to human plasma and content uniformity testing. Pharm Anal Acta 2016;7:1-8.

Omar AM, Abdel-Mageed HO, Abdel-Gaber AA, Abdel-Megied MA. Spectrophotometric and spectrofluorimetric determination of certain angiotensin receptor blockers through complex formation. J Pharm Sci Res 2011;3:1499-510.

Kaur K, Malik AK. Study on the fluorescence quenching reaction of Amitriptyline and clomipramine hydrochlorides with eosin Y and its analytical application. J Fluoresc 2013;23:533-42.

Azmi SNH, Al-Fazari A, Al-Badaei M, Al-Mahrazi R. Utility of eosin Y as a complexing reagent for the determination of citalopram hydrobromide in commercial dosage forms by fluorescence spectrophotometry. Luminescence 2015;30:1352-9.

Derayea S, Omar M, Mohammed B, Ali R. Sensitive spectrofluorimetric protocol for the determination of fluoxetine and paroxetine through binary complex formation with eosin Y. Anal Chem Lett 2016;6:508-17.

Walash MI, El-Brashy AM, Metwally MES, Abdelal AA. Fluorimetric determination of ethionamide in pharmaceutical preparations and biological fluids. J Chin Chem Soc 2004;51:1059-64.

Attia TZ, Omar MA. Spectrofluorimetric determination of thioridazine and flupentixol in dosage forms; application to content uniformity test. Luminescence 2016;31:1091-7.

Arici M, Kilinci E. Validated spectroflurometric method for the determination of sunitinib malate, dye complexation approach for a novel anticancer drug. Acta Pahrm Sci 2010;52:469-85.

Ibrahim F, El-Din MKS, Eid MI, Wahba MEK. Validated stability-indicating spectrofluorimetric methods for the determination of ebastine in pharmaceutical preparations. Chem Cent J 2011;5:1-14.

Zakhari NA, Rizk M, Walash MI, Ibrahim F. Fluorimetric determination of certain phenothiazine derivatives using eosin. Anal Lett 1985;18:1405-17.

Raghubabu K, Mohan N, Kalyanaramu B, Ramdas C, Rao MN. Development of new visible spectrophotometric determination of tiaprofenic acid in bulk and formulations. Asian J Pharm Clin Res 2013;6:77-9.

Sreeja U, Gurupadayya B, Chandan R. Novel spectrophotometric methods for the quantification of desvenlafaxinein pure and pharmaceutical dosage form. Asian J Pharm Clin Res 2015;8:267-70.

Lotfy HM, Saleh SS. Recent development in ultraviolet spectrophotometry through the last decade (2006-2016): a review. Int J Pharm Pharm Sci 2016;8:40-56.

Walash MI, Belal FF, Eid MI, Mohamed SAE. Spectrophotometric determination of tizanidine and orphenadrine via ion pair complex formation using eosin Y. Chem Cent J 2011;5:1-9.

Abd El-Hay SS, El-Mammli MY, Shalaby AA. Determination of clemastine hydrogen fumarate, desloratadine, losartan potassium and mexopril HCl through binary complex formation with eosin. Arab J Chem 2016;9:S541-7.

Derayea SM, Askal HF, Abdelmageed OH, El Hamd MA. Spectrophotometric determination of amlodipine and nicardipine in pharmaceutical formulations via binary complex formation with eosin Y. J Appl Pharm Sci 2012;2:84-9.

Dhamra MY, Al-Sabha TN, Al-Ghabsha TS. Spectrophotometric determination of terbutaline sulphate and tetracycline hydrochloride via ion pair complex formation using Eosin Y. Pak J Anal Environ Chem 2014;15:84-92.

Walash MI, Rizk MS, Eid MI, Fathy ME. Spectrophotometric determination of four macrolide antibiotics in pharmaceutical formulations and biological fluids via binary complex formation with eosin and spectrophotometry. J AOAC Int 2007;90:1579-87.

Abdellatef HE, Ayad MM, Taha EA. Spectrophotometric and atomic absorption spectrometric determination of ramipril and perindopril through ternary complex formation with eosin and Cu (II). J Pharm Biomed Anal 1999;18:1021-7.

Ayad MM, Al Shalaby AA, Abdellatef HE. Spectrophotometric and AAS determination of ramipril and enalapril through ternary complex formation. J Pharm Biomed Anal 2002;28:311-21.

Gouda AAE, El-Sheikh R, Amin AS. Spectrophotometric determination of some fluoroquinolones antibacterial drugs in pure form and in pharmaceuticals formulations. Anal Chem An Indian J 2008;7:676-83.

Belal TS, Mahrou MS, Daabees HG, Abdel Khalek M, Khami MM. Validated spectrophotometric methods for the determination of memantine hydrochloride in tablets using eosin and 2,4 dinitrofluorobenzene reagents. Res J Pharm Biol Chem Sci 2014;4:1481-93.

Rahman N, Rahman H. Quantitative analysis of perindopril erbumine in pharmaceutical preparations by spectrophotometry via ternary complex formation with Zn (II) and eosin and charge transfer complexation with iodine. Spectroscopy 2011;25:123-36.

El-Enany N. Spectrophotometric determination of gliclazide in pharmaceuticals and biological fluids through ternary complex formation with eosin and palladium (II). Farmaco 2004;59:63-9.

El-Brashy AM, El-Sayed MM, El-Sepai FA. Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes. Il Farmaco 2004;59:809-17.

Deepakumari HN, Revanasiddappa HD. Sensitive spectrophotometric method for the determination of olanzapine and orphenadrine in pure and dosage forms by ternary complex formation with eosin and lead (II). Chem Sci J 2012;70:1-8.

Almasri IM, Al-Laham MK. Development and validation of spectrophotometric method for determination of cefixime and glimepiride by ternary complex formation with eosin and Cu (II). Indo Am J Pharm Res 2014;4:5670-7.

El-Didamony AM. Spectrophotometric determination of sparfloxacin in pharmaceutical preparations by ternary complex formation with Pd (II) and eosin. Anal Lett 2007;40:2708-20.

Mori I, Fujita Y, Kawabe H, Fujita K, Tanaka T, Kishimoto A. Application of xanthene derivatives in analytical chemistry. Part LVII. Spectrophtometric determination of minocycline using gallium and eosin. Analyst 1986;111:1409-12.

Bkhaitan MM, Mirza AZ. Spectrophotometric method for determination of meclizine in pure and dosage forms via ion pair complex formation using eosin Y. Curr Pharm Anal 2016;12:1-6.

Belal WF, El-Enany N, Elmansi H. Determination of tolterodine tartrate in pharmaceutical preparations using eosin, application to stability study. Int J Pharma Sci Res 2011;2:2849-55.

Zhebentyaev AL, Zhernosek AK. Extraction-spectrophotometric determination of berberine sulphate in tablets using eosin as a reagent. Pharmazie 1996;51:252-5.

Burla SVS, Peruri VVS, Chandra BS. Development and validation of spectrophotometric methods for the quantification of solifenacin succinate: application to tablet dosage forms. Int Lett Chem Phys Astron 2013;10:167-82.

Naggar AH, Elnasr TAS, Sayed AAS, Kotb A, El Sayed AAY. Determination of metoclopramide hydrochloride in pharmaceutical formulations using three different spectrophotometric methods. Pharm Anal Acta 2017;8:1-9.

Ramadan AA, Mandil H. Spectrophotometric determination of carbinoxamine maleate in pharmaceutical formulations by ternary complex formation with Cu (II) and eosin. Anal Biochem 2006;353:133-7.

Walash MI, Belal F, El-Enany N, Elmansi H. Spectrophotometric and spectrofluorimetric methods for the determination of dothiepin hydrochloride in its pure and dosage forms using eosin. Int J Biomed Sci 2010;6:327-34.

Omar MA. Spectrophotometric and spectrofluorimetric determination of certain diuretics through ternary complex formation with eosin and lead (II). J Fluorescence 2010;20:275-81.

El-Walily AFM, Belal F, Bakry RS. Spectrophotometric and spectrofluorimetric determination of ciprofloxacin and norfloxacin by ternary complex formation with eosin and palladium (II). J Pharm Biomed Anal 1996;14:561-9.

Souri E, Torabad M, Tehrani MB. Spectrophotometric and spectrofluorimetric methods for the determination of ropinirole content in pharmaceutical dosage forms. J Chin Pharm Sci 2016;25:876-81.

Deraeya SMS. An application of eosin Y for the selective spectrophotometric and spectrofluorimetric determination of mebeverine hydrochloride. Anal Meth 2014;6:2270-5.

Ammar RA, El-Brashy AM, Al-Sahly TN. Spectrophotometric and spectrofluorometric determination of doxazosin mesylate in tablets via eosin Y. Asian J Chem 2014;26:57-62.

Kelania K, Bebawyb LI, Abdel-Fattah L. Determination of astemizole, terfenadine and flunarizine hydrochloride by ternary complex formation with eosin and lead (II). J Pharm Biomed Anal 1999;18:985-92.

El-Din MS, Ibrahim F, Shalan S, El-Aziz H. New validated spectrofluorimetric and spectrophotometric methods for the determination of clopidogrel in pharmaceutical preparations using eosin. Int J Pharm 2016;6:53-63.

Elokely KM, Eldawy MA, Elkersh MA, El-Moselhy TF. Fluorescence spectrometric determination of drugs containing α-methylene sulfone/sulfonamide functional groups using N1-methylnicotinamide chloride as a fluorogenic agent. Int J Anal Chem 2011;1-9. http://dx.doi.org/ 10.1155/2011/840178

Darwish IA, Khedr AS, Askal HF, Mahmoud RM. Simple fluorimetric method for determination of certain antiviral drugs via their oxidation with cerium (IV). Il Farmaco 2005;60:555-62.

Mazzarino L, Bellettini IC, Minatti E, Lemos-Senna E. Development and validation of a fluorimetric method to determine curcumin in lipid and polymeric nanocapsule suspensions. Braz J Pharm Sci 2010;46:219-26.

El-Shaboury SR, Hussein SA, Mohamed NA, El-Sutohy MM. Spectrofluorimetric method for determination of some angiotensin II receptor antagonists. J Pharm Anal 2012;2:12-8.

Gouda AA, El-Sayed MIK, Amin AS, El Sheikh R. Spectrophotometric and spectrofluorometric methods for the determination of non-steroidal anti-inflammatory drugs: a review. Arab J Chem 2013;6:145-63.

Omar MA, Abdelmageed OH, Derayea SM, Uno T, Atia TZ. Spectrofluorimetric determination of certain antidepressant drugs in human plasma. J Anal Sci Tech 2013;4:1-10.

Bonfilio R. Recent applications of analytical techniques for quantitative pharmaceutical analysis: a review. Wseas Transactions Bio Biomed 2010;7:316-38.

Kaur K, Singh B, Malik AK. Chemiluminescence and spectrofluorimetric methods for determination of fluoroquinolones: a review. Anal Lett 2011;44:1602-39.




About this article

Title

UTILIZATION OF EOSIN DYE AS AN ION PAIRING AGENT FOR DETERMINATION OF PHARMACEUTICALS: A BRIEF REVIEW

Keywords

Eosin Y, Ion pairing agent, Spectrofluorimetry, commercial dosage forms

DOI

10.22159/ijpps.2017v9i12.21220

Date

01-12-2017

Additional Links

Manuscript Submission

Journal

International Journal of Pharmacy and Pharmaceutical Sciences
Vol 9, Issue 12, 2017 Page: 1-9

Online ISSN

0975-1491

Statistics

78 Views | 17 Downloads

Authors & Affiliations

Habibur Rahman
Department of General Studies, Jubail Industrial College, P.O. Box 10099, Jubail Industrial City 31961, Saudi Arabia
Saudi Arabia


Article Tools



Refbacks

  • There are currently no refbacks.