Complexation of sulfonamides with β-cyclodextrin studied by experimental and theoretical methods

Journal of Pharmaceutical Sciences

Volumn 99, Issue 7, 2010, Pages 3166-3176

  Zoppi, Ariana ^a   Quevedo, Mario A ^a   Delrivo, Alicia ^a   Longhi, Marcela R ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

Complexation; Cyclodextrins; Molecular modeling; NMR spectroscopy; Phase solubility studies; Solubility; Sulfonamides

Indexed keywords

BETA CYCLODEXTRIN; SULFADIAZINE; SULFADIMIDINE; SULFAMERAZINE;

ARTICLE; COMPLEX FORMATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; HYDROPHOBICITY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 77953297417     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22062     Document Type: Article

References (26)

1. Connor EE. 1998. Sulfonamide antibiotics. Primary Care Update Ob/Gyns 5:32-35.
2. Supuran CT, Casini A, Scozzafava A. 2003. Protease inhibitors of the sulfonamide type: Anticancer, antiinflammatory, and antiviral agents. Med Res Rev 23:535-558. (Pubitemid 37034144)
3. Golzar Hossaina GM, Amoroso AJ, Banua A, Malika KMA. 2007. Syntheses and characterisation of mercury complexes of sulfadiazine, sulfamerazine and sulfamethazine. Polyhedron 26:967-974.
4. Sanchez Pena M, Acedo MJ, Salinas F, Mahedero MC, Aaron JJ. 1995. Analysis of sulfamethazine in the presence of sulfamerazine or sulfadiazine by first-derivative photochemically induced fluorescence. J Pharm Biomed Anal 13:1107-1112.
5. Garcia-Alvarez-Coque MC, Simo-Alfonso EF, Ramis-Ramos G, Esteve-Romero JS. 1995. High-performance micellar liquid chromatography determination of sulphonamides in pharmaceuticals after azodye precolumn derivatization. J Pharm Biomed Anal 13:237-245.
6. Fromming KH, Szejtli J. 1994. Cyclodextrins in pharmacy. Dordrecht, The Netherlands: Kluwer Academic Publishers.
7. Brewster ME, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59:645-666.
8. De Araújo MVG, Vieira EKB, Silva Lázaro G, Conegero LS, Almeida LE, Barreto LS, da Costa NB Jr, Gimenez IF. 2008. Sulfadiazine/ hydroxypropyl-β-cyclodextrin host-guest system: Characterization, phase-solubility and molecular modeling. Bioorg Med Chem 16:5788-5794. (Pubitemid 351699276)
9. Granero GE, Maitre MM, Garnero C, Longhi MR. 2008. Synthesis, characterization and in vitro release studies of a new acetazolamide-HP-β- CD-TEA inclusion complex. Eur J Med Chem 43:464-470. (Pubitemid 351323986)
10. Granero GE, Garnero C, Longhi MR. 2003. The effect of a basic substance and pH on cyclodextrin complexation of sulfisoxazole. Eur J Pharm Sci 20:285-293.
11. Pose-Vilarnovo B, Perdomo-López I, Echezarreta-López M, Schroth-Pardo P, Estrada E, Torres-Labandeira JJ. 2001. Improvement of water solubility of sulfamethizole through its complexation with β-and hydroxypropyl-β-cyclodextrin - Characterization of the interaction in solution and in solid state. Eur J Pharm Sci 13:325-331. (Pubitemid 32522585)
12. Higuchi T, Connors K. 1965. Phase solubility techniques. In: Reilly C, editor. Advances in analytical chemistry and instrumentation. New York: Wiley Interscience. pp. 117-212.
13. Ganza-Gonzalez A, Vila-Jato JL, Anguiano-Igea S, Otero-Espinar FJ, Blanco-Mendez JJ. 1994. A proton nuclear magnetic resonance study of the inclusion complex of naproxen with β-cyclodextrin. Int J Pharm 106:179-185. (Pubitemid 24133694)
14. Allouche AR. Gabedit is a free Graphical User Interface for computational chemistry packages. It is available from http://gabedit.sourceforge.net/.
15. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Jr., Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko AP, Piskorz I, Komaromi R, Gomperts RL, Fox Martin DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. 1998. Software: GAUSSIAN 98. Pittsburgh, PA, USA: Gaussian, Inc. www.gaussian.com.
16. Schaftenaar G, Noordik JH. 2000. Molden: A pre- and post-processing program for molecular and electronic structures. J Comput Aided Mol Design 14:123-134. (Pubitemid 30110670)
17. Case DA, Cheatham TE, Darden T, Gohlke H, Luo R, Merz KM, Onufriev A, Jr., Simmerling C, Wang B, Woods RJ. 2005. The Amber biomolecular simulation programs. Comput Chem 26:1668-1688.
18. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662. (Pubitemid 128590223)
19. Kuhn B, Gerber P, Schulz-Gasch T, Stahl MJ. 2005. Validation and use of the MM-PBSA approach for drug discovery. Med Chem 48:4040-4048. (Pubitemid 40800612)
20. Humphrey W, Dalke A, Schulten K. 1996. VMD: Visual molecular dynamics. J Mol Graph 14:33-38.
21. Ventura CA, Giannone I, Paolino D, Pistara V, Corsaro A, Puglisi G. 2005. Preparation of celecoxib-dimethyl-β-cyclodextrin inclusion complex: Characterization and in vitro permeation study. Eur J Med Chem 40:624-631.
22. Ventura CA, Giannone I, Musumeci T, Pignatello R, Ragni L, Landolfi C, Milanese C, Paolino D, Puglisi G. 2006. Physicochemical characterization of disoxaril-dimethyl-β-cyclodextrin inclusion complex and in vitro permeation studies. Eur J Med Chem 41:233-240.
23. Mele A, Mendichi R, Selva A. 1998. Non-covalent associations of cyclomaltooligosaccharides (cyclodextrins) with trans-β-carotene in water: Evidence for the formation of large aggregates by light scattering and NMR spectroscopy. Carbohydr Res 310:261-267. (Pubitemid 28461903)
24. Loftsson T, Másson M, Brewster ME. 2004. Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci 93:1091-1099.
25. Ogruc-Ildiz G, Akyuz S, Ozel AE. 2009. Experimental, ab initio and density functional theory studies on sulfadiazine. J Mol Struct 924-926:514-522.
26. Zoppi A, Quevedo MA, Longhi MR. 2008. Specific binding capacity of β-cyclodextrin with cis and trans enalapril: Physicochemical characterization and structural studies by molecular modeling. Bioorg Med Chem 16:8403-8412.