title: Sulfadiazine/hydroxypropyl-beta-cyclodextrin host-guest system: Characterization, phase-solubility and molecular modeling.
abstract: In this work we prepared and characterized an inclusion complex of the dihydropteroate synthase inhibitor sulfadiazine (SDZ) in 2-hydroxypropyl-beta-cyclodextrin (HPBCD). From the phase-solubility diagram we observed an increase in the water solubility of the drug, calculating a binding constant of 1879M(-1). The inclusion mode involves a NH(2)-in orientation of the drug in the HPBCD cavity, according to the 2D NMR (ROESY) data and confirmed by molecular modeling using the semiempirical PM6 and RM1 methods.
authors.affiliation: Departamento de Química, Universidade Federal de Sergipe (UFS), Av. Marechal Rondon s/n, Campus Universitário Prof. José Aloísio de Campos, CEP 491000-000, São Cristóvão, SE, Brazil.
authors.forename: Márcia Valéria Gaspar
authors.initials: MV
authors.lastname: de Araújo
authors.forename: Elze Kelly Barbosa
authors.initials: EK
authors.lastname: Vieira
authors.forename: Gilderman
authors.initials: G
authors.lastname: Silva Lázaro
authors.forename: Leila Souza
authors.initials: LS
authors.lastname: Conegero
authors.forename: Luís Eduardo
authors.initials: LE
authors.lastname: Almeida
authors.forename: Ledjane Silva
authors.initials: LS
authors.lastname: Barreto
authors.forename: Nivan Bezerra
authors.initials: NB
authors.lastname: da Costa
authors.forename: Iara F
authors.initials: IF
authors.lastname: Gimenez
mesh_terms: D000073738:2-Hydroxypropyl-beta-cyclodextrin; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004094:Dihydropteroate Synthase / Q000037:antagonists & inhibitors; D004337:Drug Carriers / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D044367:Phase Transition; D012995:Solubility; D013329:Structure-Activity Relationship; D013411:Sulfadiazine / Q000737:chemistry*; D013696:Temperature; D014867:Water / Q000737:chemistry; D014961:X-Ray Diffraction; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D004337:Drug Carriers; D004791:Enzyme Inhibitors; D047392:beta-Cyclodextrins; D014867:Water; D013411:Sulfadiazine; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D004094:Dihydropteroate Synthase