Correlating Physicochemical Properties of Boronic Acid-Chitosan Conjugates to Glucose Adsorption Sensitivity.docVIP

Pharmaceutics 2013, 5, 69-80; doi:10.3390/pharmaceutics5010069 OPEN ACCESS pharmaceutics ISSN 1999-4923 /journal/pharmaceutics Article Correlating Physicochemical Properties of Boronic Acid-Chitosan Conjugates to Glucose Adsorption Sensitivity 1 2 2 1, Yaa Asantewaa , Jonathan Aylott , Jonathan C. Burley , Nashiru Billa * and Clive J. Roberts 2 1 School of Pharmacy, The University of Nottingham, Malaysia Campus, Jalan Broga Semenyih, 43500 Selangor, Malaysia; E-Mail: khyx1yaa@.my 2 School of Pharmacy, The University of Nottingham, University Park Campus, NG7 2RD, UK; E-Mails: jon.aylott@nottingham.ac.uk (J.A.); jonathan.burley@nottingham.ac.uk (J.C.B.); clive.roberts@nottingham.ac.uk (C.J.R.) * Author to whom correspondence should be addressed; E-Mail: Nashiru.Billa@.my; Tel.: +60-3-8964-8211; Fax: +60-3-8964-8018. Received: 28 August 2012; in revised form: 10 December 2012 / Accepted: 18 December 2012 / Published: 27 December 2012 Abstract: Phenyl boronic acid (PBA), which is known to interact with glucose, was covalently bonded to chitosan by direct reductive N-alkylation of chitosan with 4-formylphenylboronic acid (4-FPBA). Evidence of PBA bonding on chitosan was assessed by FTIR, ToF-SIMS, SEM, DSC and glucose adsorption sensitivity measurements. FTIR spectra showed strong signals at 1560 and 630 cm?1 indicating the formation of p-substituted benzene. Similarly, ToF-SIMS analyses on the conjugates ? registered fragments of boron ion (B ) at 11.0 m/z whose intensity increased in proportion to 4-FPBA loading. The degree to which PBA was bonded to chitosan was related to the 4-FPBA load used in the reaction (termed F1 through to F6 with increasing 4-FPBA load). Glucose adsorption sensitivity to PBA-bonded chitosan was directly related to the amount of PBA functionality within the conjugates and the physical nature of the matrices (porous or crystalline).