Spray-dried mucoadhesives for intravesical drug delivery using N-acetylcysteine- and glutathione-glycol chitosan conjugates

Acta Biomaterialia - Tập 43 - Trang 170-184 - 2016
Nunzio Denora1, Angela Lopedota1, Mara Perrone1, Valentino Laquintana1, Rosa M. Iacobazzi1,2, Antonella Milella3, Elisabetta Fanizza3,4, Nicoletta Depalo4, Annalisa Cutrignelli1, Antonio Lopalco5, Massimo Franco1
1Department of Pharmacy – Drug Sciences, University of Bari “A. Moro”, Orabona, St. 4, 70125 Bari, Italy
2Istituto Tumori IRCCS “Giovanni Paolo II”, Flacco, St. 65, 70124 Bari, Italy
3Department of Chemistry, University of Bari “A. Moro”, Orabona, St. 4, 70125 Bari, Italy
4CNR-Institute for Physical and Chemical Processes UOS, Bari, Italy
5Department of Pharmaceutical Chemistry, University of Kansas, Lawrence, Kansas 66047, USA

Tài liệu tham khảo

Singla, 2000, Potential applications of carbomer in oral mucoadhesive controlled drug delivery system: a review, Drug Dev. Ind. Pharm., 26, 913, 10.1081/DDC-100101318 Smart, 2005, The basics and underlying mechanisms of mucoadhesion, Adv. Drug Delivery Rev., 57, 1556, 10.1016/j.addr.2005.07.001 Barthelmes, 2013, Thiolated particles as effective intravesical drug delivery systems for treatment of bladder-related diseases, Nanomedicine, 8, 65, 10.2217/nnm.12.76 Štorha, 2013, Synthesis of thiolated and acrylated nanoparticles using thiolene click chemistry: towards novel mucoadhesive materials for drug delivery, RSC Adv., 3, 12275, 10.1039/C3RA42093K Barthelmes, 2011, Development of a mucoadhesive nanoparticulate drug delivery system for a targeted drug release in the bladder, Int. J. Pharm., 416, 339, 10.1016/j.ijpharm.2011.06.033 GuhaSarkar, 2010, Intravesical drug delivery: challenges, current status, opportunities and novel strategies, J. Control. Release, 148, 147, 10.1016/j.jconrel.2010.08.031 Evans, 2005, Intravesical therapy for overactive bladder, Curr. Urol. Rep., 6, 429, 10.1007/s11934-005-0037-y Makhlof, 2010, Nanoparticles of glycol chitosan and its thiolated derivative significantly improved the pulmonary delivery of calcitonin, Int. J. Pharm., 397, 92, 10.1016/j.ijpharm.2010.07.001 Kafedjiiski, 2005, Synthesis and in vitro evaluation of a novel chitosan–glutathione conjugate, Pharm. Res., 22, 1480, 10.1007/s11095-005-6248-6 Trapani, 2014, Mucoadhesive properties and interaction with P-glycoprotein (P-gp) of thiolated-chitosans and -glycol chitosans and corresponding parent polymers: a comparative study, Biomacromolecules, 15, 882, 10.1021/bm401733p Beamson, 1992 Li, 2010, Nanoparticles by spray drying using innovative new technology: the Büchi nano spray dryer B-90, J. Control. Release, 147, 304, 10.1016/j.jconrel.2010.07.113 Beri, 1993, Characterization of chitosans via coupled size-exclusion chromatography and multiple-angle laser light-scattering technique, Carbohydr. Res., 238, 11, 10.1016/0008-6215(93)87002-A Fee, 2003, Correlation of SEC/MALLS with ultracentrifuge and viscometric data for chitosans, Eur. Biophys. J., 32, 457, 10.1007/s00249-003-0317-8 Nguyen, 2009, Fractionation and characterization of chitosan by analytical SEC and 1H NMR after semi-preparative SEC, Carbohydr. Polym., 75, 636, 10.1016/j.carbpol.2008.09.002 Schmitz, 2008, Synthesis and characterization of a chitosan-N-acetyl cysteine conjugate, Int. J. Pharm., 347, 79, 10.1016/j.ijpharm.2007.06.040 Loretz, 2007, Role of sulfhydryl groups in transfection? A case study with chitosan-NAC nanoparticles, Bioconjugate Chem., 18, 1028, 10.1021/bc0603079 D.F. Putnam, Composition and Concentrative Properties of Human Urine, NASA Contractor Report N° NASA CR-1802, 1971. He, 1998, In vitro evaluation of the mucoadhesive properties of chitosan microspheres, Int. J. Pharm., 166, 75, 10.1016/S0378-5173(98)00027-1 Takeuchi, 2005, Novel mucoadhesion tests for polymers and polymer-coated particles to design optimal mucoadhesive drug delivery systems, Adv. Drug Delivery Rev., 57, 1583, 10.1016/j.addr.2005.07.008 Vehring, 2008, Pharmaceutical particle engineering via spray drying, Pharm. Res., 25, 999, 10.1007/s11095-007-9475-1 Albrecht, 2006, Preparation of thiomer microparticles and in vitro evaluation of parameters influencing their mucoadhesive properties, Drug Dev. Ind. Pharm., 32, 1149, 10.1080/03639040600712334 Albrecht, 2006, Comparative in vivo mucoadhesion studies of thiomer formulations using magnetic resonance imaging and fluorescence detection, J. Control. Release, 115, 78, 10.1016/j.jconrel.2006.06.023 Overberger, 1962, Oxidation of monomeric and polymeric sulfhydryl compounds, J. Org. Chem., 27, 3539, 10.1021/jo01057a032 Li, 1995, Chemical instability of protein pharmaceuticals: mechanism of oxidation and strategies for stabilization, Biotechnol. Bioeng., 48, 490, 10.1002/bit.260480511 Haupstein, 2014, Synthesis and characterization of pH tolerant and mucoadhesive (thiol-polyethylene glycol) chitosan graft polymer for drug delivery pharmaceutics, J. Pharm. Sci., 103, 594, 10.1002/jps.23832 Cassettari, 2010, Effect of PEGylation on the toxicity and permeability enhancement of chitosan, Biomacromolecules, 11, 2854, 10.1021/bm100522c Dünnhaupt, 2012, S-protonated thiolated chitosan for oral delivery of hydrophilic macromolecules: evaluation of permeation enhancing and efflux pump inhibitory properties, Mol. Pharm., 9, 1331, 10.1021/mp200598j Kubota, 1997, Facile preparation of water-soluble N-acetylated chitosan and molecular weight dependence of its water-solubility, Polym. J., 29, 123, 10.1295/polymj.29.123 Sakloetsakun, 2011, Thiolated chitosans: influence of various sulfhydryl ligands on permeation-enhancing and P-gp inhibitory properties, Drug Dev. Ind. Pharm., 37, 648, 10.3109/03639045.2010.534484 Mortazavi, 1993, An investigation into the role of water movement and mucus gel dehydration in mucoadhesion, J. Control. Release, 25, 197, 10.1016/0168-3659(93)90078-J Rossi, 2000, Characterization of chitosan hydrochloride-mucin interaction by means of viscosimetric and turbidimetric measurements, Eur. J. Pharm. Sci., 10, 251, 10.1016/S0928-0987(00)00065-8 Grabovac, 2005, Comparison of mucoadhesive properties of various polymers, Adv. Drug Delivery Rev., 57, 1713, 10.1016/j.addr.2005.07.006 Bernkop-Schnürch, 2005, Thiomers: a new generation of muco-adhesive polymers, Adv. Drug Delivery Rev., 57, 1569, 10.1016/j.addr.2005.07.002 Leitner, 2003, Thiolated polymers: evidence for the formation of disulphide bonds with mucus glycoproteins, Eur. J. Pharm. Biopharm., 56, 207, 10.1016/S0939-6411(03)00061-4 Lehr, 1992, In vitro evaluation of mucoadhesive properties of chitosan and some other natural polymers, Int. J. Pharm., 78, 43, 10.1016/0378-5173(92)90353-4 Deepak, 2012, Thiolated chitosan: modified advanced generation of mucoadhesive polymers, Int. J. Recent Adv. Pharm. Res., 2, 31 Zhu, 2012, Synthesis of thiolated chitosan and preparation nanoparticles with sodium alginate for ocular drug delivery, Mol. Vis., 18, 1973 Bernkop-Schnürch, 2004, Thiomers: potential excipients for non-invasive peptide delivery systems, Eur. J. Pharm. Biopharm., 58, 253, 10.1016/j.ejpb.2004.03.032 He, 1999, Chitosan microspheres prepared by spray drying, Int. J. Pharm., 187, 53, 10.1016/S0378-5173(99)00125-8 Asada, 2004, Theophylline particle design using chitosan by the spray drying, Int. J. Pharm., 270, 167, 10.1016/j.ijpharm.2003.11.001 Draheim, 2015, A design of experiment study of nanoprecipitation and nano-microparticles with defined sizes and size distributions, Pharm. Res., 32, 2609 Burjak, 2001, The study of drug release from microspheres adhered on pig vesical mucosa, Int. J. Pharm., 224, 123, 10.1016/S0378-5173(01)00748-7 Cook, 2015, Synthesis of mucoadhesive thiol-bearing microgels from 2-(acetylthio)ethylacrylate and 2-hydroxyethylmethacrylate: novel drug delivery systems for chemotherapeutic agents to the bladder, J. Mater. Chem. B, 3, 6599, 10.1039/C5TB00834D Zhang, 2014, Functionalized mesoporous silica nanoparticles with mucoadhesive and sustained drug release properties for potential bladder cancer therapy, Langmuir, 30, 6151, 10.1021/la500746e