title: Solubility and bioavailability enhancement of ciprofloxacin by induced oval-shaped mono-6-deoxy-6-aminoethylamino-β-cyclodextrin.
abstract: Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic used to treat bacterial infections; however, its limited aqueous solubility inhibits its broader clinical uses. This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin. During complexation, the oval-shaped cavity induced by mono-aminoethylamine substitution on the primary rim of β-cyclodextrin, was considered to be a key factor according to NMR spectroscopy and molecular modeling studies. The ciprofloxacin with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin complex was characterized using FE-SEM, DSC, FT-IR, T1 relaxation, 2D NOESY, and DOSY NMR spectroscopy and molecular modeling studies. The solubility property of ciprofloxacin complexed with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin was enhanced by seven-fold compared to that of pure ciprofloxacin. Furthermore antibacterial activity of that complex against methicillin-resistant Staphylococcus aureus was enhanced and it clearly showed the growth inhibition. The mono-6-deoxy-6-aminoethylamino-β-cyclodextrin has the potential to be utilized for other oblong guest molecules besides ciprofloxacin based on the novel induced elliptical cavity.
authors.affiliation: Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Jae Min
authors.initials: JM
authors.lastname: Choi
authors.affiliation: Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Kyeonghui
authors.initials: K
authors.lastname: Park
authors.affiliation: Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Benel
authors.initials: B
authors.lastname: Lee
authors.affiliation: Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Daham
authors.initials: D
authors.lastname: Jeong
authors.affiliation: Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Someshwar D
authors.initials: SD
authors.lastname: Dindulkar
authors.affiliation: Departments of Food Science and Technology, BioChip Research Center, Hoseo University, Chungcheongnam-do, Republic of Korea.
authors.forename: Youngjin
authors.initials: Y
authors.lastname: Choi
authors.affiliation: Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea.
authors.forename: Eunae
authors.initials: E
authors.lastname: Cho
authors.affiliation: Department of Applied Chemistry, Dongduk Women's University, Seoul, Republic of Korea.
authors.forename: Seyeon
authors.initials: S
authors.lastname: Park
authors.affiliation: Departments of Bacteriology and Genetics, University of Wisconsin-Madison, Madison, WI, United States.
authors.forename: Jae-Hyuk
authors.initials: JH
authors.lastname: Yu
authors.affiliation: Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea. Electronic address: shjung@konkuk.ac.kr.
authors.forename: Seunho
authors.initials: S
authors.lastname: Jung
mesh_terms: D001682:Biological Availability; D002939:Ciprofloxacin / Q000493:pharmacokinetics*; D009682:Magnetic Resonance Spectroscopy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D047392:beta-Cyclodextrins; D002939:Ciprofloxacin
keywords: -cyclodextrin; Ciprofloxacin; Complexation; Molecular modeling; Mono-6-deoxy-6-aminoethylamino-&beta; NOESY; Oval-shaped cavity