title: Preparation and characterization of soluble branched ionic β-cyclodextrins and their inclusion complexes with triclosan.
abstract: This study aims to synthesize, characterize and investigate the water solubility and cytotoxicity of branched anionic/cationic β-cyclodextrins (bβCDs) obtained by reaction with epichlorohydrin and chloroacetic acid or choline chloride, respectively, by a single step polycondensation reaction. Obtained ionic bβCDs were investigated as an attempt to comparatively study anionic and cationic bβCDs. Water solubility of both ionic derivatives was similar (400 mg/mL) at neutral and basic pHs and remarkably higher than that of their neutral homologues. Additionally, a pH-dependent solubility of anionic bβCDs was observed. Cytotoxicity of ionic bβCDs was evaluated on Human colon carcinoma Caco-2 cells and high cell viability (>99%) was observed in the range of 0-100 mg/mL for anionic and cationic samples, in the same range of that of neutral and parent β-CDs. Additionally, complexes formation capacity with triclosan, a poor water soluble antimicrobial agent, was confirmed by several techniques observing a complexation limit around 4 mg/mL for both systems and higher stability constant for anionic bβCDs than cationic derivatives.
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain.
authors.forename: Flor
authors.initials: F
authors.lastname: Gómez-Galván
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain; BCMaterials, Building 500-1st Floor, Bizkaia Science and Technology Park, 48160 Derio, Spain. Electronic address: leyre.perez@ehu.es.
authors.forename: Leyre
authors.initials: L
authors.lastname: Pérez-Álvarez
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain.
authors.forename: Janire
authors.initials: J
authors.lastname: Matas
authors.affiliation: Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal; iBET, Instituto de Biologia Experimental e Tecnológica, Apartado 12, 2780-901 Oeiras, Portugal.
authors.forename: Arturo
authors.initials: A
authors.lastname: Álvarez-Bautista
authors.affiliation: Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal; iBET, Instituto de Biologia Experimental e Tecnológica, Apartado 12, 2780-901 Oeiras, Portugal.
authors.forename: Joana
authors.initials: J
authors.lastname: Poejo
authors.affiliation: Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal; iBET, Instituto de Biologia Experimental e Tecnológica, Apartado 12, 2780-901 Oeiras, Portugal.
authors.forename: Catarina M
authors.initials: CM
authors.lastname: Duarte
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain.
authors.forename: Leire
authors.initials: L
authors.lastname: Ruiz-Rubio
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain.
authors.forename: Jose Luis
authors.initials: JL
authors.lastname: Vila-Vilela
authors.affiliation: Departamento de Química Física (Laboratorio de Química Macromolecular), Universidad del País Vasco (UPV/EHU), B° Sarriena s/n, 48940 Leioa, Vizcaya, Spain; BCMaterials, Building 500-1st Floor, Bizkaia Science and Technology Park, 48160 Derio, Spain.
authors.forename: Luis M
authors.initials: LM
authors.lastname: León
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry; D000891:Anti-Infective Agents, Local / Q000008:administration & dosage* / Q000737:chemistry; D018938:Caco-2 Cells; D002470:Cell Survival / Q000187:drug effects; D004337:Drug Carriers / Q000009:adverse effects / Q000138:chemical synthesis / Q000737:chemistry*; D004811:Epichlorohydrin / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D007477:Ions / Q000009:adverse effects / Q000138:chemical synthesis / Q000737:chemistry; D012995:Solubility; D014260:Triclosan / Q000008:administration & dosage* / Q000737:chemistry; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000009:adverse effects / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000085:Acetates; D000891:Anti-Infective Agents, Local; D004337:Drug Carriers; D007477:Ions; D047392:beta-Cyclodextrins; D014867:Water; D004811:Epichlorohydrin; D014260:Triclosan; C006972:chloroacetic acid
keywords: Branched ionic cyclodextrins; Cytotoxicity; Epichlorohydrin; Water solubility