Mechanochemical activation of vincamine mediated by linear polymers: Assessment of some “critical” steps

European Journal of Pharmaceutical Sciences - Tập 50 - Trang 56-68 - 2013
Dritan Hasa1, Beatrice Perissutti1, Mario Grassi2, Michele R. Chierotti3, Roberto Gobetto3, Valerio Ferrario1, Davide Lenaz4, Dario Voinovich1
1Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, I-34127 Trieste, Italy
2Department of Industrial Engineering and Information Technology, Via Valerio 6/A, I-34127 Trieste, Italy
3Department of Chemistry, University of Torino, Laboratory of NMR Spectroscopy, Via P. Giuria 7, I-10125 Torino, Italy
4Department of Geosciences, University of Trieste, Via Weiss 8, I-34127 Trieste, Italy

Tài liệu tham khảo

Bergese, 2002, Assessment of the X-ray diffraction–absorption method for quantitative analysis of largely amorphous composites, J. Appl. Cryst., 36, 74, 10.1107/S002188980201926X Bergese, 2004, Melting of nanostructured drugs embedded into a polymeric matrix, J. Phys. Chem. B., 108, 15488, 10.1021/jp048762u Braga, 2006, A solid-gas route to polymorph conversion in crystalline [Fe-II(5–C5H4COOH)2]. A diffraction and solid-state NMR study, Organomet, 25, 4627, 10.1021/om060468w Braga, 2007, Polymorphism in crystalline cinchomeronic acid, Chem. Eur. J., 13, 1222, 10.1002/chem.200600760 Breitkreutz, 1998, Prediction of intestinal drug absorption properties by three-dimensional solubility parameters, Pharm. Res., 15, 1370, 10.1023/A:1011941319327 Colombo, 2009, Drug mechanochemical activation, J. Pharm. Sci., 98, 3961, 10.1002/jps.21733 Food and Drug Administration CDER, Revision 1, 2003. Guidance for industry, bioavailability and bioequivalence studies for orally administered drug products-general considerations. <http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM070124.pdf> (accessed 30.03.12). Forster, 2001, Selection of ecxipients for melt extrusion with two poorly water–soluble drugs by solubility parameter calculation and thermal analysis, Int. J. Phar., 226, 147, 10.1016/S0378-5173(01)00801-8 Goodford, 1985, A computational procedure for determining energetically fovorable binding sites on biologically important macromolecules, J. Med. Chem., 28, 849, 10.1021/jm00145a002 Hancock, 1997, The use of solubility parameters in pharmaceutical dosage form design, Int. J. Pharm., 148, 1, 10.1016/S0378-5173(96)04828-4 Hansen, 1969, The universality of the solubility parameter, Ind. Eng. Chem. Res., 8, 2, 10.1021/i360029a002 Hasa, 2011, Multidisciplinary approach on characterizing a mechanochemically activated composite of vinpocetine and crospovidone, J. Pharm. Sci., 100, 915, 10.1002/jps.22331 Hasa, 2012, Mechanochemically induced disordered structures of vincamine: the different mediation of two cross-linked polymers, Int. J. Pharm., 436, 41, 10.1016/j.ijpharm.2012.06.024 Hasa, D., Perissutti, B., Dall’Acqua, S., Chierotti, M.R., Gobetto, R., Grabnar, I., Cepek, C., Voinovich, V., 2012b. Rationale of using Vinca minor Linne dry extract phytocomplex as a vincamine’s oral bioavailability enhancer, Eur. J. Pharm. Biopharm. http://dx.doi.org/10.1016/j.ejpb.2012.11.025. Hsia, 1977, Determination of energy change associated with dissolution of a solid, J. Pharm. Sci., 66, 961, 10.1002/jps.2600660715 Huey, 2007, A semiempirical free energy force field with charge-based desolvation, J. Comput. Chem., 28, 1145, 10.1002/jcc.20634 James, 2012, Mechanochemistry: opportunities for new and cleaner synthesis, Chem. Soc. Rev., 41, 413, 10.1039/C1CS15171A Karpati, 2002, Investigation of vasoactive agents with indole skeletons at Richter Ltd., Act. Pharm. Hung., 72, 25 Lipinski, 1997, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev., 1, 179 Long, 1994, Molecular dynamics and magic angle spinning NMR, J. Am. Chem. Soc., 116, 11950, 10.1021/ja00105a039 Maincent, 1986, Disposition kinetics and oral bioavailability of Vincamine loaded polyalkyl cyanoacrilate nanoparticles, J. Pharm. Sci., 75, 955, 10.1002/jps.2600751009 Mazak, 2003, Lipophilicity of vinpocetine and related compounds characterised by reverse-phase thin-layer chromatography, J. Chromat. A, 996, 195, 10.1016/S0021-9673(03)00617-4 Morris, 1998, Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function, J. Comput. Chem., 19, 1639, 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B Morris, 2009, AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility, J. Comput. Chem., 16, 2785, 10.1002/jcc.21256 Shakhtshneider, 1999, Mechanochemical synthesis and mechanical activation of drugs, 271 Sun, 2012, Enhanced kinetic solubility profiles of indomethacin amorphous solid dispersions in poly(2-hydroxyethyl methacrylate) hydrogels, Eur. J. Pharm. Biopharm., 81, 149, 10.1016/j.ejpb.2011.12.016 Taylor, 1997 Van Eerdenbrugh, 2011, Influence of particle size on the ultraviolet Spectrum of particulate-containing solutions: implications for in-situ concentration monitoring using UV/Vis fiber-optic probes, Pharm. Res., 28, 1643, 10.1007/s11095-011-0399-4 Van Krevelen, 1990 Vas, 2005, Eburnamine derivatives and the brain, Med. Res. Rev., 25, 737, 10.1002/med.20043 Vereczkey, 1985, Pharmacokinetics and metabolism of vincamine and related compounds, Eur. J. Drug Metab. Pharmacokinet., 10, 89, 10.1007/BF03189702 Voinovich, 2009, Solid state mechanochemical activation of Silybum Marianum dry extract with betacyclodextrins: characterization and bioavailability of the coground systems, J. Pharm. Sci., 98, 4119, 10.1002/jps.21704 Voinovich, 2009, Solid state mechanochemical simultaneous activation of the constituents of the silybum marianum phytocomplex with crosslinked polymers, J. Pharm. Sci., 98, 215, 10.1002/jps.21417 York, 1999, Solubility parameters as predictors of miscibility in solid dispersions, J. Pharm. Sci., 88, 1182, 10.1021/js9900856