Physico-chemical characterization of an amphiphilic cyclodextrin/genistein complex

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 5, 2010, Pages 1064-1068

  Cannava C ^a   Crupi, V ^a   Ficarra, P ^a   Guardo, M ^a   Majolino, D ^a   Mazzaglia, A ^b   Stancanelli, R ^a   Venuti, V ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b CNR   (Italy)

Author keywords

Amphiphilic cyclodextrin; FTIR ATR spectroscopy; Genistein; Inclusion complexes; UV vis spectroscopy

Indexed keywords

2 OLIGO(ETHYLENEOXIDE) 6 HEXYLTHIO BETA CYCLODEXTRIN; CYCLODEXTRIN; GENISTEIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; COMPLEX FORMATION; DRUG MIXTURE; DRUG STABILITY; DRUG STRUCTURE; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

BETA-CYCLODEXTRINS; CHEMISTRY, PHARMACEUTICAL; CIRCULAR DICHROISM; DRUG CARRIERS; DRUG COMPOUNDING; DRUG STABILITY; GENISTEIN; HYDROGEN BONDING; NANOSTRUCTURES; POLYETHYLENE GLYCOLS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE;

EID: 73049099257     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.11.025     Document Type: Article

References (26)

1. Thompson D., and Chaubal M.V. Cyclodextrins (CDs)-excipients by definition, drug delivery systems by function (part I: injectable applications). Drug Deliv. Technol. 2 (2000) 34-38
2. Zhang G., Shuang S., Dong Z., Dong C., and Pan J. Investigation on the inclusion behavior of neutral red with β-cyclodextrin, hydroxypropyl-β-cyclodextrin and sulfobutylether-β-cyclodextrin. Anal. Chim. Acta 474 (2002) 189-195
3. Tang B., Ma L., Wang H.Y., and Zhang G.Y. Study on the supramolecular interaction of curcumin and β-cyclodextrin by spectrophotometry and its analytical application. J. Agric. Food Chem. 50 (2002) 1355-1361
4. Li S., and Purdy W.C. Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 92 (1992) 1457-1470
5. Daruhazi A.E., Szente L., Balogh B., Matyus P., Beni S., Takacs M., Gergely A., Horvath P., Szoke E., and Lemberkovics E. Utility of cyclodextrins in the formulation of genistein. Part 1. Preparation and physicochemical properties of genistein complexes with native cyclodextrins. J. Pharm. Biomed. Anal. 48 (2008) 636-640
6. Figueiras A., Ribeiro L., Vieira M.T., and Veiga F. Preparation and physicochemical characterization of omeprazole:methyl-beta-cyclodextrin inclusion complex in solid state. J. Incl. Phenom. Macrocycl. Chem. 57 (2007) 173-177
7. Saenger W., and Steiner T. Cyclodextrin inclusion complexes: host-guest interactions and hydrogen-bonding networks. Acta Crystrallogr. A 54 (1998) 798-805
8. Makedonopoulou S., and Mavridis I. Structure of the inclusion complex of β-cyclodextrin with 1,12-dodecanedioic acid using synchrotron radiation data; a detailed dimeric β-cyclodextrin structure. Acta Crystrallogr. B 56 (2000) 322-331
9. Rafati A.A., Bagheri A., Iloukhani H., and Zarinehzad M. Study of inclusion complex formation between a homologous series of n-alkyltrimethylammonium bromides and β-cyclodextrin, using conductometric technique. J. Mol. Liq. 116 (2005) 37-41
10. Stancanelli R., Ficarra R., Cannavà C., Guardo M., Calabrò M.L., Ficarra P., Ottanà R., Maccari R., Crupi V., Majolino D., and Venuti V. UV-vis and FTIR-ATR characterization of 9-fluorenon-2-carboxyester/(2-hydroxypropyl)-β-cyclodextrin inclusion complex. J. Pharm. Biomed. Anal. 47 (2008) 704-709
11. Crupi V., Ficarra R., Guardo M., Majolino D., Stancanelli R., and Venuti V. UV-vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins. J. Pharm. Biomed. Anal. 44 (2007) 110-117
12. Rossi B., Verrocchio P., Viliani G., Scarduelli G., Guella G., and Mancini I. Vibrational properties of inclusion complexes: the case of indomethacin-cyclodextrin. J. Chem. Phys. 125 (2006) 044511-1-044511-7
13. Bratu I., Hernanz A., Gavira J.M., and Bora G.H. FT-IR spectroscopy of inclusion complexes of beta-cyclodextrin with fenbufen and ibuprofen. Rom. J. Phys. 50 (2005) 1063-1069
14. Garcia-Zubiri I.X., Gonzales-Gaitano G., Sanchez M., and Isasi J.R. FTIR study of dibenzofuran-2-carboxylic acid and its complexes with β-cyclodextrin. Vib. Spectrosc. 33 (2003) 205-213
15. Sortino S., Petralia S., Darcy R., Donohue R., and Mazzaglia A. Photochemical outcome modification of diflunisal by a novel cationic amphiphilic cyclodextrin. New J. Chem. 27 (2003) 602-608
16. Quaglia F., Ostacolo L., Mazzaglia A., Villari V., Zaccaria D., and Sciortino M.T. The intracellular effects of non-ionic amphiphilic cyclodextrin nanoparticles in the delivery of anticancer drugs. Biomaterials 30 (2009) 374-382
17. McNicholas S., Rencurosi A., Lay L., Mazzaglia A., Sturiale L., Perez M., and Darcy R. Amphiphilic N-glycosyl-thiocarbamoyl cyclodextrins: synthesis, selfassembly and fluorimetry of recognition by Lens culinaris lectin. Biomacromolecules 8 (2007) 1851-1857
18. Fournier E., Dufresne M.H., Smith D.C., Ranger M., and Leroux J.C. A novel one-step drug-loading procedure for water-soluble amphiphilic nanocarriers. Pharm. Res. 21 (2004) 962-968
19. Raffoul J.J., Wang Y., Kucuk O., Forman J.D., Sarkar S.H., and Hillman G.G. Genistein inhibits radiation-induced activation of NF-kappaB in prostate cancer cells promoting apoptosis and G2/M cell cycle arrest. BMC Cancer 6 (2006) 107
20. Suh K.S., Koh G., Park C.Y., Woo J.T., Kim S.W., Kim J.W., Park I.K., and Kim Y.S. Soybean isoflavones inhibit tumor necrosis factor-alpha-induced apoptosis and the production of interleukin-6 and prostaglandin E2 in osteoblastic cells. Phytochemistry 63 (2003) 209-215
21. R. Stancanelli, M. Guardo, C. Cannavà, G. Guglielmo, P. Ficarra, V. Villari, N. Micali, A. Mazzaglia, Amphiphilic cyclodextrins as nanocarriers of genistein: a spectroscopic investigation pointing out the structural properties of the host/drug complex system, J. Pharm. Sci., in press.
22. Mazzaglia A., Donohue R., Ravoo B.J., and Darcy R. Novel amphiphilic cyclodextrins: graft-synthesis of heptakis (6-deoxy-6alkylthio) beta-cyclodextrin 2-oligo(ethylene-glycol) conjugates and their w-halo derivatives. Eur. J. Org. Chem. (2001) 1715-1721
23. Crupi V., Longo F., Majolino D., and Venuti V. T dependence of vibrational dynamics of water in ion-exchanged zeolites A: a detailed Fourier transform infrared attenuated total reflection study. J. Chem. Phys. 123 (2005) Art. 154702
24. Usha S., Johnson I.M., and Malathi R. Interaction of resveratrol and genistein with nucleic acids. J. Biochem. Mol. Biol. 38 (2005) 198-205
25. Silvestrin R.M., and Wabster F.X. Spectrometric Identification of Organic Compounds (1997), John Wiley and Sons, New York pp. 95-180
26. Motlekar N., Khan M.A., and Youan B.C. Preparation and characterization of genistein containing poly(ethylene glycol) microparticles. J. Appl. Polym. Sci. 101 (2006) 2070-2078