Fluorimetric Investigation of Host-Guest Complexation of Nizatidine with β-Cyclodextrin and its Analytical Application

Abstract

The supramolecular interaction of nizatidine (NIZ) and β-cyclodextrin (β-CD) has been studied by spectrofluorimetry. The results showed that β-CD reacted with NIZ to form an inclusion complex.The NIZ-β-CDcomplex formed a host-guest complex in 1:1 stoichiometryand inclusion constant (K = 3.15×102 L mol-1) and wasascertained by the typical double reciprocal plots. Furthermore, the thermodynamic parameters (ΔH°, ΔS° and ΔG°)associated with the inclusion process were also determined. Based on the significant enhancement of the fluorescence intensity of NIZ produced through complex formation, a simple, accurate, rapid and highly sensitive spectrofluorometric method for the determination of NIZ in aqueous solution in the presence of β-CD wasdeveloped. The measurement of relative fluorescence intensity was carried with excitation at 314 nm.The factors affecting the inclusion complex formation were studied and optimized. Under the optimum reactionconditions, linear relationships with good correlation coefficients (0.999) were in the concentration range of 0.04-0.1μg mL–1for spectrofluorimetry. The limit of detection (LOD) was found to be1.2710-3 μgmL-1.The proposedmethod was successfully applied to the analysis of NIZ pharmaceutical dosage formulations with good accuracy; therecovery percentages ranged from 95.4–106.85%.

Keywords

• Nizatidine
• inclusion complex
• β-cyclodextrin
• Spectrophotometry
• Spectrofluorimetry

References

1. [1] Mosinger J, Tomankova V, Nemcova I, Zyka J. Cyclodextrins in analytical chemistry. Anal Lett., 2001;34:1979–2004.
2. [2] Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem Rev 1998;98: 1743–53.
3. [3] Szejtli J, Osa T (Eds.) (1996). Comprehensive Supramolecular Chemistry, vol. 3, Pergamon, Oxford.
4. [4] Manzoori JL, Amjadi M. Spctrofluorometric study of host– guest complexation of ibuprofen with β-cyclodextrin and its analytical application.Spectrochim. Acta, Part A 2003;59:909–16.
5. [5] Manzoori JL, Amjadi M.Spectrofluorimetric and cyclodextrin enhanced spectrofluorimetric methods for the determination of naphazoline in nasal and eye drops. Indian J Chem 2003; 42:2988–92.
6. [6] BerzasNevado JJ, Murillo Pulgarín JA, Gómez Laguna MA.Spectrofluorimetric study of the β-cyclodextrin: vitamin K3 complex and determination of vitamin K3. Talanta2001; 53:951–9.
7. [7] Tang B, Ma L, Ma C.Spectrofluorimetric study of the β- cyclodextrin rubidate complex and determination of rubidate by β-CD-enhanced fluorimetry.Talanta2002;L58:841–8
8. [8] Archontaki HA, Vertzoni MV, Athanassiou-Malaki MH.Study on the inclusion complexes of bromazepam with β- and β-hydroxypropylcyclodextrins. J Pharm Biomed Anal2002;28:761–9.

9. [9] Xiliang G, Yu Y, Guoyan Z, Guomei Z, Jianbin C, Shaomin S. Study on inclusion interaction of piroxicamwith β-cyclodextrin derivatives.Spectrochim.Acta, Part A2003;59:3379–86.
10. [10] Elbashir AA, Suliman FEO, Saad B, Aboul-Enein H.Y.Capillary electrophoretic separation and computational modeling of inclusion complexes of β- cyclodextrin and 18-crown-6 ether with primaquine and quinocide.BiomedChromatogr.,2010;24:393-8.
11. [11] Elbashir AA, Suliman FO. Computational modeling of capillary electrophoretic behavior of primary amines using dual system of 18-crown-6 and β-cyclodextrin.) J.Chromatogr. A2011;1218:5344-51.
12. [12] Elbashir AA, Saad B, Ali ASM, Saleh MI, Aboul-Enein HY.Enantioselective analysis of primaquine and its impurity quinocide by capillary electrophoresis. BiomedChromatogr.,2009;23:295-301.
13. [13] Marquez JC, Hernandez M, Garcia Sanchez F. Enhanced Spectrofluorimetric Determination of the Pesticide Warfarin by Means of the Inclusion Complex With β- Cyclodextrin. Analyst, 1990;115:1003-5.
14. [14] Elbashir AA, Dsugi NFA, Mohmed TOM, Aboul-Enein HY. Spectrofluorometric analytical applications of cyclodextrins, DOI 10.1002/bio.2504, Luminescence, 2013.
15. [15] Monson PL, Mueller RA, Breese GR. Principles of Pharmacology, Chapman and Hall, l064.(1995).
16. [16] Klotz U, Dammann HG, Gottlieb WR, Walter TA,Keohane P. Nizatidine (300 mg nocte) does not interfere with diazepam pharmacokinetics in man.Brit J, ClinPharmacol1987; 23:105-6.
17. [17] Klotz U, Gottieb WR, Keohane PP, Dammann HG.Nocturnal doses of ranitidine and nizatidine do not affect the disposition of diazepam.J. ClinPharmacol.,1987 ;27: 210-2.
18. [18] El-Yazbi FA, Gazy AA, Mahgoub H, El-Sayed MA, Youssef RM.Spectrophotometric and titrimetric determination of nizatidine in capsules, J. Pharm. Biomed. Anal.2003; 31:1027–34.
19. [19] Hassan EM, and Belal F. Kinetic spectrophotometric determination of nizatidine and ranitidine in pharmaceutical preparations, J. Pharm. Biomed.Anal.2002;27:31–8.
20. [20] El-Gendy AE, El-Bardicy MG, Loutfy HM, El-Tarras MF.Stability indicating method for the determination of nizatidine using 3-methyl-2-benzothiazolinone hydrazone, Spectrosc.Lett.2001;34:221– 34.
21. [21] Darwish IA, Hussein SA, Mahmoud AM, Hassan AI. A sensitive spectrophotometric method for the determination of H 2-receptor antagonists by means of Nbromosuccinimide and p-aminophenol. Acta Pharmaceutica, 2008;58:87-97.
22. [22] Nikolic K, Bogavac M, Stankovic B. J. Coulometric determination of nizatidine.J.Pharm Biomed Anal.,1995;13:683-5.
23. [23] Tracqui A, Kintz P, Mangin P.Determination of nizatidine and two of its main metabolites in human serum using high-performance liquid chromatography J. Chromatogr. Biomed. Appl. 1990;94: 369-76.
24. [24] Carlucci G. High-performance liquid chromatographic assay for nizatidine, a new H2 blocker, in human plasma and urine using disposable solid-phase extraction columns .J. Chromatogr.Biomed.Appl. 1990; 90: 490-494.
25. [25] Tracqui A, Kintz P, Kreissig P, Mangin P, Lugnier AA, Chaumont A. J.HPLC-BESTIMMUNG VON NIZATIDIN IN SERUM UND URIN | [HPLC determinationofnizatidine in serumandurine].Fresenius Z. Antal. Chem. 1988; 332: 468-9.
26. [26] Ho C, Huang H.-M, Hsu S.-Y., Shaw C.-Y, Chang B.- L.Simultaneous high-performance liquid chromatographic analysis for famotidine, ranitidine HCl, cimetidine, and nizatidine in commercial products, Drug Dev. Ind. Pharm. 1999; 25: 379–85.
27. [27] Imre S, Vlase L, Leucuţa SE.HPLC method for quantification of nizatidine and its N-desmethylmetabolite in human plasma. Revue Roumaine de Chimie2007;52:261- 6.
28. [28] Youssef RM.Validated stability-indicating methods for the determination of nizatidine in the presence of its sulfoxide derivative. J. AOACInt 2008; 91:73-82.
29. [29] Koricanac Z, Jovanovic T, Stankovic B.Determination of nizatidine in pharmaceutical formulations by potentiometric titration.Pharmazie 1995;50: 151-2
30. [30] Kapetanovic V, Milovanovic L, Vhadmirov S.Differential pulse polarographic determination of nizatidine in pharmaceutical formulations. Farmaco II1994;49: 377-9.
31. [31] Tang B, Jia BX, Shi SF.Flow injection spectrofluorimetric study of the supramolecular interaction between β- cyclodextrin and dequalinium chloride and its analytical application.Spectrochim.Acta, Part A2005;61:2203–09.
32. [32] Maafi M, Laassis B, Aaron J.-J., Mahedero MC, De La Peña AM, Salinas, F.Photochemically induced fluorescence investigation of a β-cyclodextrin: Azure A inclusion complex and determination of analytical parametersJ. Incl. Phenom. 1995;22:235-47.
33. [33] Connors KA.Binding Constants: The Measurement of Molecular Complex Stability, Wiley, New York, 1987.
34. [34] Catena GC, Bright FV.Thermodynamic study on the effects of beta-cyclodextrin inclusion with anilinonaphthalenesulfonates, Anal.Chem.1989;61:905–9.
35. [35] Rekharsky MV, Inoue Y. Complexation Thermodynamics of Cyclodextrins. Chem Rev1998;98:1875–1918.
36. [36] Inoue Y, Hakushi T, Liu Y, Tong LH, Shen BJ, Jin DS.Thermodynamics of molecular recognition by cyclodextrins. 1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with. alpha-, beta-, and gamma-cyclodextrins: enthalpy–entropy compensation.J Am ChemSoc1993;115:475–81.
37. [37] Zhang Q, Jiang Z, Guo Y, Li R.Complexation study of brilliant cresyl blue with β-cyclodextrin and its derivatives by UV-vis and fluorospectrometry.Spectrochim.Acta, Part A 2008;69:65–70.
38. [38] Validation of analytical procedure: Text and Methodology. International Conference on Harmonization Q2(R1), 2005:1450. Accessed at: http://www.bioforum.org.il/Uploads/Editor/karen/q2_r1_st ep4.pdf