title: Ternary cyclodextrin polyurethanes containing phosphate groups: Synthesis and complexation of ciprofloxacin.
abstract: Synthesis of ternary polyurethanes (PUs) from hexamethylenediisocyanate, β-cyclodextrin and β-glycerophosphate (acid and calcium salt) was studies varying synthesis parameters such as monomer proportion, heating method (reflux and microwave), and catalyst amount. Favorable conditions were provided by microwave irradiation and use of β-glycerophosphoric acid although the results suggest that it is possible to obtain ternary PUs with the calcium salt. FTIR data indicated the existence of secondary urea linkages. After characterization of ternary PUs by FTIR spectroscopy, XRD and thermal analysis, as well as evidences that the cyclodextrin cavities remained active toward inclusion of guest molecules, the possibility of inclusion of the antibiotic ciprofloxacin was evaluated. Absence of ciprofloxacin melting peak in DSC curves indicated that it is molecularly dispersed within the polymer, possibly included in the cyclodextrin. In vitro release experiments suggested additional non-inclusion interactions, showing also that the use of dialysis membranes may mask the actual release profile.
authors.affiliation: Programa da Pós-graduação em Ciência e Engenharia de Materiais, Av. Marechal Rondon s/n, Cidade Universitária "Prof. José Aloísio de Campos", CEP 491000-000, São Cristóvão, SE, Brazil.
authors.forename: Mirna Pereira
authors.initials: MP
authors.lastname: Moreira
authors.affiliation: Programa da Pós-graduação em Ciência e Engenharia de Materiais, Av. Marechal Rondon s/n, Cidade Universitária "Prof. José Aloísio de Campos", CEP 491000-000, São Cristóvão, SE, Brazil.
authors.forename: George Ricardo Santana
authors.initials: GRS
authors.lastname: Andrade
authors.affiliation: CARBOPOL, Laboratório de Síntese de Polímeros Derivados de Carboidratos, Faculdade Pio Décimo, Av. Presidente Tancredo Neves, 5655, Jabotiana, Aracaju, SE, 49095000, Brazil.
authors.forename: Marcia Valeria Gaspar
authors.initials: MVG
authors.lastname: de Araujo
authors.affiliation: CARBOPOL, Laboratório de Síntese de Polímeros Derivados de Carboidratos, Faculdade Pio Décimo, Av. Presidente Tancredo Neves, 5655, Jabotiana, Aracaju, SE, 49095000, Brazil.
authors.forename: Tatiana
authors.initials: T
authors.lastname: Kubota
authors.affiliation: Programa da Pós-graduação em Ciência e Engenharia de Materiais, Av. Marechal Rondon s/n, Cidade Universitária "Prof. José Aloísio de Campos", CEP 491000-000, São Cristóvão, SE, Brazil; Programa de Pós-graduação em Química, Av. Marechal Rondon s/n, Cidade Universitária "Prof. José Aloísio de Campos", CEP 491000-000, São Cristóvão, SE, Brazil. Electronic address: gimenez@ufs.br.
authors.forename: Iara F
authors.initials: IF
authors.lastname: Gimenez
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002152:Calorimetry, Differential Scanning; D002939:Ciprofloxacin / Q000737:chemistry*; D065546:Drug Liberation; D005994:Glycerophosphates / Q000737:chemistry*; D011140:Polyurethanes / Q000138:chemical synthesis* / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D014961:X-Ray Diffraction; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D005994:Glycerophosphates; D011140:Polyurethanes; D047392:beta-Cyclodextrins; D002939:Ciprofloxacin; C031215:betadex; C031463:beta-glycerophosphoric acid
keywords: Ciprofloxacin; Drug delivery; Inclusion complex; Ternary polyurethane; β-Cyclodextrin; β-Glycerophosphate