Use of 1H NMR STD, WaterLOGSY, and Langmuir monolayer techniques for characterization of drug-zein protein complexes

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 85, Issue 3 PART A, 2013, Pages 790-798

  Sousa, F F O ^a,b   Luzardo Alvarez A ^a   Blanco Mendez J ^a   Otero Espinar, F J ^a   Martin Pastor M ^a   Sandez Macho I ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b FEDERAL UNIVERSITY OF AMAPÁ   (Brazil)

Author keywords

Biopolymers; Brewster angle microscopy; Drug protein complexes; Indomethacin; Maize protein; NMR; Tetracycline; Zein; A isotherm

Indexed keywords

INDOMETACIN; TETRACYCLINE; ZEIN; BIOPOLYMER; DRUG CARRIER;

ANALYTIC METHOD; ARTICLE; CONTROLLED STUDY; DRUG PROTEIN BINDING; DYNAMIC LIGHT SCATTERING; LANGMUIR MONOLAYER TECHNIQUE; LIGHT SCATTERING; PI A ISOTHERM; PROTON NUCLEAR MAGNETIC RESONANCE; SATURATION TRANSFERRED DIFFERENCE; WATER LIGAND OBSERVED VIA GRADIENT SPECTROSCOPY; Π-A ISOTHERM; BREWSTER ANGLE MICROSCOPY; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG-PROTEIN COMPLEXES; FEASIBILITY STUDY; LIGHT; MAIZE PROTEIN; MEDICINAL CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHARMACEUTICS; RADIATION SCATTERING;

Π-A ISOTHERM; BIOPOLYMERS; BREWSTER ANGLE MICROSCOPY; DRUG-PROTEIN COMPLEXES; INDOMETHACIN; MAIZE PROTEIN; NMR; TETRACYCLINE; ZEIN;

CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; FEASIBILITY STUDIES; INDOMETHACIN; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; SCATTERING, RADIATION; TECHNOLOGY, PHARMACEUTICAL; TETRACYCLINE; ZEIN;

EID: 84888381697     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2013.07.008     Document Type: Article

References (49)

1. A. Gennadios, and L.C. Weller Edible films and coatings from wheat and corn proteins Food Technol. 44 1990 63 69
2. Y. Matsuda, T. Suzuki, E. Sato, M. Sato, S. Koizumi, K. Unno, T. Kato, and K. Nakai Novel preparation of zein microspheres conjugated with P S-K available for cancer immunotherapy Chem. Pharm. Bull. 37 1989 757 759
3. T. Suzuki, E. Sato, Y. Matsuda, H. Tada, K. Unno, and T. Kato Preparation of zein microspheres conjugated with antitumor drugs available for selective cancer chemotherapy and development of a simple colorimetric determination of drugs in microspheres Chem. Pharm. Bull. 37 1989 1051 1054
4. X. Liu, Q. Sun, H. Wang, L. Zhang, and J.Y. Wang Microspheres of corn protein, zein, for an ivermectin drug delivery system Biomaterials 26 2005 109 115
5. H.J. Wang, Z.X. Lina, X.M. Liub, S.Y. Shenga, and J.Y. Wang Heparin-loaded zein microsphere film and hemocompatibility J. Control. Release 105 2005 120 131
6. J. Dong, Q. Sung, and J.Y. Wang Basic study of corn protein, zein, as a biomaterial in tissue engineering, surface, morphology and biocompatibility Biomaterials 25 2004 4691 4697
7. F.F. Sousa, A. Luzardo-Alvarez, A Pérez-Estévez, R. Seoane-Prado, and J Blanco-Méndez Development of a novel AMX-loaded PLGA/zein microsphere for root canal disinfection Biomed. Mater. 5 2010 1 10 055008
8. F.F. Sousa, J. Blanco-Méndez, A. Pérez-Estévez, R. Seoane-Prado, and A. Luzardo-Álvarez Effect of zein on biodegradable inserts for the delivery of tetracycline within periodontal pockets J. Biomater. Appl. 2 2012 187 200
9. R.L. Phillips, and B.A. McClure Elevated protein-bound methionine in seeds of a maize line resistant to lysine plus threonine Cereal Chem. 62 1985 213 218
10. K.A. Tilley, R.E. Benjamin, K.E. Bagorogoza, B.M. Okot-Kotber, O. Prakash, and H. Kwen Tyrosine cross-links: molecular basis of gluten structure and function J. Agric. Food Chem. 49 2001 2627 2632
11. Y. Wang, A.M. Rakotonirainy, and G.W. Padua Thermal behavior of zein-based biodegradable films Starch - Stärke 55 2003 25 29
12. B.L. Hsu, Y.M. Weng, Y.H. Liao, and W. Chen Structural investigation of edible zein films/coatings and directly determining their thickness by J. Agric. Food Chem. 53 2005 5089 5095
13. Q. Wang, P Geil, and G. Padua Role of hydrophilic and hydrophobic interactions in structure development of zein films J. Polym. Environ. 12 2004 197 202
14. E. Forgács, T. Cserháti, Z. Deyl, and I. Miksík Binding of substituted phenol and aniline derivatives to the corn protein zein studied by high-performance liquid chromatography J. Chromatogr. B, Biomed. Sci. 753 2001 79 86
15. T. Cserháti, and E. Forgács Effect of pH and salts on the binding of free amino acids to the corn protein zein studied by thin-layer chromatography Amino acids 28 2005 99 103
16. N. Matsushima, G. Danno, H. Takezawa, and Y. Izumi Three-dimensional structure of maize alpha-zein proteins studied by small-angle X-ray scattering Biochim. Biophys. Acta 1339 1997 14 22
17. F.F. Sousa, A. Luzardo-Álvarez, J. Blanco-Méndez, and M. Martí-n-Pastor NMR techniques in drug delivery: application to zein protein complexes Int. J. Pharm. 439 2012 41 48
18. B.L. Hsu, Y.M. Weng, Y.H. Liao, and W. Chen Structural investigation of edible zein films/coatings and directly determining their thickness by FT-Raman spectroscopy J Agric. Food Chem. 53 2005 5089 5095
19. M.R. Bugs, L.A. Forato, R.K. Bortoleto-Bugs, H. Fischer, Y.P. Mascarenhas, R.J. Ward, and L.A. Colnago Spectroscopic characterization and structural modeling of prolamin from maize and pearl millet Eur. Biophys. J. 33 2004 335 343
20. L.A. Forato, C. Bicudo Tde, and L.A. Colnago Conformation of alpha zeins in solid state by Fourier transform IR Biopolymers 72 2003 421 426
21. V. Cabra, R. Arreguin, R. Vazquez-Duhalt, and A. Farres Effect of temperature and pH on the secondary structure and processes of oligomerization of 19 kDa alpha-zein Biochim. Biophys. Acta 1764 2006 1110 1118
22. C. Gao, M. Stading, N. Wellner, M.L. Parker, T.R. Noel, E.N. Mills, and P.S. Belton Plasticization of a protein-based film by glycerol: a spectroscopic, mechanical, and thermal study J. Agric. Food Chem. 54 2006 4611 4616
23. L.A. Forato, R. Bernardes-Filho, and L.A. Colnago Protein structure in KBr pellets by infrared spectroscopy Anal. Biochem. 259 1998 136 141
24. D.J. Sessa, A. Mohamed, and J.A. Byars Chemistry and physical properties of melt-processed and solution-cross-linked corn zein J. Agric. Food Chem. 56 2008 7067 7075
25. K. Shi, J.L. Kokini, and Q. Huang Engineering zein films with controlled surface morphology and hydrophilicity J. Agric. Food Chem. 57 2009 2186 2192
26. D.M. Georget, S.A. Barker, and P.S. Belton A study on maize proteins as a potential new tablet excipient Eur. J. Pharm. Biopharm. 69 2008 718 726
27. Y. Mizutani, Y. Matsumura, H. Murakami, and T. Mori Effects of heating on the interaction of lipid and zein in a dry powder system J. Agric. Food Chem. 52 2004 3570 3576
28. S. Subramanian, and S. Sampath Adsorption of zein on surfaces with controlled wettability and thermal stability of adsorbed zein films Biomacromolecules 8 2007 2120 2128
29. P. Argos, K. Pedersen, M.D. Marks, and B.A. Larkins A structural model for maize zein proteins J. Biol. Chem. 257 1982 9984 9990
30. B. Meyer, and T. Peters NMR spectroscopy techniques for screening and identifying ligand binding to protein receptors Angew. Chem. Int. Ed. Engl. 42 2003 864 890
31. J.C. Cobas, and F. Sardina Nuclear magnetic resonance data processing. MestRe-C: a software package for desktop computers., J Concepts Magn. Reson. 19A 2003 80 96
32. M. Mayer, and B. Meyer Characterization of ligand binding by saturation transfer difference NMR spectroscopy Angew. Chem. Int. Ed. 38 1999 1784 1788
33. B. Meyer, and T. Peters NMR spectroscopy techniques for screening and identifying ligand binding to protein receptors Angew. Chem. Int. Ed. 42 2003 864 890
34. C. Dalvit, G. Fogliatto, A. Stewart, M. Veronesi, and B. Stockman WaterLOGSY as a method for primary NMR screening: practical aspects and range of applicability J. Biomol. NMR 21 2001 349 359
35. E.C. Johnson, V.A. Feher, J.W. Peng, J.M. Moore, and J.R. Williamson Application of NMR SHAPES screening to an RNA target J. Am. Chem. Soc. 125 2003 15724 15725
36. P. Toimil, G. Prieto, J. Miñones Jr., J.M. Trillo, and F.l. Sarmiento Monolayer and Brewster angle microscopy study of human serum albumin/dipalmitoyl phosphatidyl choline mixtures at the air/water interface Colloids Surf. B: Biointerf. 92 2012 64 73
37. C.B. Post Exchange-transferred NOE spectroscopy and bound ligand structure determination Curr. Opin. Struct. Biol. 13 2003 581 588
38. C. Dalvit, P. Pevarello, M. Tato, M. Veronesi, A. Vulpetti, and M. Sundström Identification of compounds with binding affinity to proteins via magnetization transfer from bulk water J. Biomol. NMR 18 2000 65 68
39. P. Thordarson Determining association constants from titration experiments in supramolecular chemistry Chem. Soc. Rev. 40 2011 1305 1323
40. J. Angulo, P.M. Enríquez-Navas, and P.M. Nieto Ligand-receptor binding affinities from saturation transfer difference (STD) NMR spectroscopy: the binding isotherm of std initial growth rates Chem. - Eur. J. 16 2010 7803 7812
41. C. Ludwig, P.J.A. Michiels, X. Wu, K.L. Kavanagh, E. Pilka, A. Jansson, U. Oppermann, and U.L. Günther SALMON: solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy J. Med. Chem. 51 2007 1 3
42. D.F. Cheesman, J.T. Davies, M.L. Anson, and T.E. John Physicochemical and biological aspects of proteins at interfaces Advances in Protein Chemistry 1954 Academic Press 439 501
43. J.M. Trillo, E.I. Jado, S.G.a. Fernández, and S.S. Pedrero Monolayers of human serum albumin Kolloid-Z. Z. Polym. 250 1972 318 324
44. I. Pezron, L. Galet, and D. Clausse Surface interaction between a protein monolayer and surfactants and its correlation with skin irritation by surfactants J. Colloid Interface Sci. 180 1996 285 289
45. J.S. Mitchell The structure of protein monolayers Trans. Faraday Soc. 33 1937 1129 1139
46. T.S. Wiedmann, T. Trouard, S.C. Shekar, M. Polikandritou, and Y.-E. Rahman Interaction of cyclosporin A with dipalmitoylphosphatidylcholine Biochim. Biophys. Acta (BBA) - Biomembr. 1023 1990 12 18
47. J.T. Davies, and E.K. Rideal Interfacial Phenomena 1963 Academic Press
48. F.A. Quiocho Carbohydrate-binding proteins: tertiary structures and protein-sugar interactions Annu. Rev. Biochem. 55 1986 287 315
49. N.R. Syme, C. Dennis, A. Bronowska, G.C. Paesen, and S.W. Homans Comparison of entropic contributions to binding in a "hydrophilic" versus "hydrophobic" ligand-protein interaction J. Am. Chem. Soc. 132 2010 8682 8689