title: Promising applications in drug delivery systems of a novel β-cyclodextrin derivative obtained by green synthesis.
abstract: An efficient and green method has been developed for the synthesis of succinyl-β-cyclodextrin in aqueous media obtaining very good yield. Acidic groups have been introduced in the synthesized carrier molecule to improve the guest-host affinity. To evaluate the suitability of the novel excipient focused to develop oral dosage forms, albendazole, a BSC class II compound, was chosen as a model drug. The β-cyclodextrin derivative and the inclusion complex were thoroughly characterized in solution and solid state by phase solubility studies, FT-IR spectroscopy, SEM, XRD, ESI-MS, DSC, 1D (1)H NMR, 1D (13)C NMR, selective 1D TOCSY, 2D COSY, 2D HSQC, 2D HMBC and ROESY NMR spectroscopy. Phase solubility studies indicated that both of them β-cyclodextrin and succinyl-β-cyclodextrin formed 1:1 inclusion complexes with albendazole, and the stability constants were 68M(-1) (β-cyclodextrin), 437M(-1) (succinyl-β-cyclodextrin), respectively. Water solubility and dissolution rate of albendazole were significantly improved in complex forms. Thus, the succinyl-β-cyclodextrin derivative could be a promising excipient to design oral dosage forms.
authors.affiliation: IQUIR-CONICET, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina; Área Técnica Farmacéutica, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina.
authors.forename: Agustina
authors.initials: A
authors.lastname: García
authors.affiliation: IQUIR-CONICET, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina; Área Técnica Farmacéutica, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina. Electronic address: leonardi@iquir-conicet.gov.ar.
authors.forename: Darío
authors.initials: D
authors.lastname: Leonardi
authors.affiliation: IQUIR-CONICET, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina; Área Técnica Farmacéutica, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Santa Fe, Argentina. Electronic address: lamas@iquir-conicet.gov.ar.
authors.forename: María C
authors.initials: MC
authors.lastname: Lamas
mesh_terms: D015766:Albendazole / Q000008:administration & dosage* / Q000737:chemistry; D000871:Anthelmintics / Q000008:administration & dosage* / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D004337:Drug Carriers / Q000138:chemical synthesis / Q000737:chemistry*; D055772:Green Chemistry Technology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization; D019802:Succinic Acid / Q000138:chemical synthesis / Q000737:chemistry*; D014961:X-Ray Diffraction; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000871:Anthelmintics; D004337:Drug Carriers; D047392:beta-Cyclodextrins; D019802:Succinic Acid; D015766:Albendazole; C031215:betadex
keywords: Cyclodextrin derivatives; Green synthesis; Inclusion complex