Abstract
The formation of a host-guest inclusion complex of the antiparasitic drug nitazoxanide (NTZ) with β-cyclodextrin (β-CD) in aqueous solution has been characterized by electrochemical methods, cyclic and differential pulse voltammetry, and UV-Vis absorption spectroscopy. The nature of the host-guest inclusion complex between NTZ and β-CD has been elucidated. The experimental results confirmed the existence of 1:1 inclusion complex of NTZ with β-CD. The binding constants describing the extent of formation of the complexes have been determined, using Benesi-Hildebrand plots, using voltammetry and UV-Vis spectroscopy. NTZ exhibits an affinity for β-CD. A special configuration of the complex has been proposed.
Graphical abstract
.
Similar content being viewed by others
References
Anderson VR, Curran MP (2007) Drugs 67:1947
Davila-Gutierrez CE, Vasquez C, Trujillo-Hernandez B, Huerta M (2002) Am J Trop Med Hyg 66:251
Rossignol JF, Cavier R (1976) 2-Benzamido 5-nitrothiazoles. US Patent 3,950,351, 13 April 1976 (1975) Chem Abstr 83:28216n
Cohen SA (2005) Curr Med Res Opin 21:999
Fox LM, Saravolatz LD (2005) Clin Infect Dis 40:1173
Chan-Bacab MJ, Hernández-Núñez E, Navarrete-Vázquez G (2009) J Antimicrob Chemother 63:1292
Guttner Y, Windsor HM, Viiala CH, Dusci L, Marshall BJ (2003) Antimicrob Agents Chemother 47:3780
Keeffe EB, Rossignol JF (2009) World J Gastroenterol 15:1805
Gilles HM, Hoffman PS (2002) Trends Parasitol 18:95
Hemphill A, Müller N, Müller J (2007) Anti-Infect Agents Med Chem 6:273
Rasheed A, Kumar CKA, Sravanthi VVNSS (2008) Sci Pharm 76:567
Irie T, Uekama K (1997) J Pharm Sci 86:147
Castro-Hermida JA, Freire-Santos F, Oteiza-López ÁM, Ares-Mazás E (2000) J Parasitol 86:1118
Dang XJ, Nie MY, Tong J, Li HL (1998) J Electroanal Chem 448:61
Ferreira FDR, Da Silva EG, De Leo LPM, Calvo EJ, Bento EDS, Goulart MOF, De Abreu FC (2010) Electrochim Acta 56:797
Radi AEM, Eissa SH (2011) Coll Czech Chem Commun 76:13
Yáñez C, Salazar R, Núñez-Vergara LJ, Squella JA (2004) J Pharm Biomed Anal 35:51
Valero M, Costa SMB, Ascenso JR, Velázquez MM, Rodríguez LJ (1999) J Inclusion Phenom 35:663
El-Kemary M, Organero JA, Santos L, Douhal A (2006) J Phys Chem B 110:14128
Muthu Prabhu AA, Venkatesh G, Rajendiran N (2010) J Solution Chem 39:1061
Sankaranarayanan RK, Siva S, Venkatesh G, Muthu Prabhu AA, Rajendiran N (2011) J Mol Liq 161:107
Maupas B, Letellier S, Guyon F (1996) J Inclusion Phenom Mol Recognit Chem 23:259
Jain R, Yadav RK, Rather JA (2013) J Pharm Anal. doi:10.1016/j.jpha.2013.07.005
El-Desoky HS, Ghoneim MM, Abdel-Galeil MM (2010) J Braz Chem Soc 21:669
Radi AE, El-Ghany NA, Wahdan T (2012) Monatsh Chem 143:697
Bard AJ (1984) Encyclopedia of electrochemistry of elements. Marcel Dekker, New York
Garrido E, Lima J, Delerue-Matos C, Borges F, Silva A, Piedade J, Oliveira Brett A (2003) J Agric Food Chem 51:876
Garrido E, Lima J, Delerue-Matos C, Borges F, Silva A, Brett A (2001) Anal Chim Acta 434:35
Ikenoya S, Masui M, Ohmori H, Sayo H (1974) J Chem Soc Perkin Trans 2:571
Bard AJ, Faulkner LR (1980) Electrochemical methods: fundamentals and applications. ??Wiley & Sons, New York
Strelets V, Mamedjarova I, Nefedova M, Pysnograeva N, Sokolov V, Pospisil L, Hanzlik J (1991) J Electroanal Chem 310:179
Basan H, Göer NG, Ertaş N, Orbey MT (2001) J Pharm Biomed Anal 26:171
Xiang TX, Anderson BD (1990) Int J Pharm 59:45
Bekers O, Beijnen JH, Otagiri M, Bult A, Underberg WJM (1990) J Pharm Biomed Anal 8:671
Arias-Blanco MJ, Moyano JR, Perez-Martinez JI, Gines JM (1998) J Pharm Biomed Anal 18:275
Hoffman PS, Sisson G, Croxen MA, Welch K, Harman WD, Cremades N, Morash MG (2007) Antimicrob Agents Chemother 51:868
Benesi HA, Hildebrand JH (1949) J Am Chem Soc 71:2703
Snor W, Liedl E, Weiss-Greiler P, Viernstein H, Wolschann P (2009) Int J Pharm 381:146
Nakai Y, Yamamoto K, Terada K, Kajiyama A, Sasaki I (1986) Chem Pharm Bull 34:2178
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Radi, AE., Nassef, H.M. & El-Naggar, AE. Electrochemical and spectral characterization of the host-guest inclusion complex of the antiparasitic drug nitazoxanide with β-cyclodextrin. Monatsh Chem 145, 421–426 (2014). https://doi.org/10.1007/s00706-013-1109-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-013-1109-1