Preparation and characterization of insulin-surfactant complexes for loading into lipid-based drug delivery systems

Journal of Pharmaceutical Sciences

Volumn 102, Issue 8, 2013, Pages 2689-2698

  Li, Ping ^a   Nielsen, Hanne Mørck ^a   Fano, Mathias ^a   Müllertz, Anette ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

CD; DSC; FTIR; Lipids; Lyophilization; Oral drug delivery; Proteins; Solubility; Surfactants; X ray powder diffractometry

Indexed keywords

BROMINE DERIVATIVE; DIMETHYL SULFOXIDE; DISTEARYLDIMETHYLAMMONIUM BROMIDE; INSULIN; LIPID; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; SURFACTANT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CIRCULAR DICHROISM; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DELIVERY SYSTEM; FREEZE DRYING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTEIN PROCESSING; PROTEIN SECONDARY STRUCTURE; SCANNING ELECTRON MICROSCOPY; SOLID STATE; X RAY POWDER DIFFRACTION;

EID: 84881027795     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23640     Document Type: Article

References (36)

1. Li P, Nielsen HM, Mullertz A. 2012. Oral delivery of peptides and proteins using lipid-based drug delivery systems. Expert Opin Drug Deliv 9:1289-1304.
2. Gao J, Zhong W, He JQ, Li HM, Zhang H, Zhou GC, Li BH, Lu Y, Zou H, Kou G, Zhang DP, Wang H, Guo YJ, Zhong YQ. 2009. Tumor-targeted PE38KDEL delivery via PEGylated anti-HER2 immunoliposomes. Int J Pharm 374:145-152.
3. Cheng MB, Wang JC, Li YH, Liu XY, Zhang X, Chen DW, Zhou SF, Zhang Q. 2008. Characterization of water-in-oil microemulsion for oral delivery of earthworm fibrinolytic enzyme. J Control Release 129:41-48.
4. Zhang N, Ping QN, Huang GH, Xu WF. 2005. Investigation of lectin-modified insulin liposomes as carriers for oral administration. Int J Pharm 294:247-259.
5. Liu J, Gong T, Wang CG, Zhong ZR, Zhang ZR. 2007. Solid lipid nanoparticles loaded with insulin by sodium cholate-phosphatidylcholine-based mixed micelles: Preparation and characterization. Int J Pharm 340:153-162.
6. Li CL, Deng YJ. 2004. Oil-based formulations for oral delivery of insulin. J Pharm Pharmacol 56:1101-1107.
7. Sarmento B, Martins S, Ferreira D, Souto EB. 2007. Oral insulin delivery by means of solid lipid nanoparticles. Int J Nanomed 2:743-749.
8. Dai WG, Dong LC. 2007. Characterization of physiochemical and biological properties of an insulin/lauryl sulfate complex formed by hydrophobic ion pairing. Int J Pharm 336:58-66.
9. Rao SPVR, Shao J. 2008. Self-nanoemulsifying drug delivery systems (SNEDDS) for oral delivery of protein drugs I. Formulation development. Int J Pharm 362:2-9.
10. Wang T, Wang N, Hao AJ, He X, Li TF, Deng YJ. 2010. Lyophilization of water-in-oil emulsions to prepare phospholipid-based anhydrous reverse micelles for oral peptide delivery. Eur J Pharm Sci 39:373-379.
11. Zhang Q, He N, Zhang L, Zhu F, Chen Q, Qin Y, Zhang Z, Zhang Q, Wang S, He Q. 2012. The in vitro and in vivo study on self-nanoemulsifying drug delivery system (SNEDDS) based on insulin-phospholipid complex. J Biomed Nanotechnol 8:90-97.
12. Cui F, Shi K, Zhang L, Tao A, Kawashima Y. 2006. Biodegradable nanoparticles loaded with insulin-phospholipid complex for oral delivery: Preparation, in vitro characterization and in vivo evaluation. J Control Release 114:242-250.
13. Matsuura J, Powers ME, Manning MC, Shefter E. 1993. Structure and stability of insulin dissolved in 1-octanol. J Am Chem Soc 115:1261-1264.
14. Wangikar PP, Michels PC, Clark DS, Dordick JS. 1997. Structure and function of subtilisin BPN' solubilized in organic solvents. J Am Chem Soc 119:70-76.
15. Yoo HS, Choi HK, Park TG. 2001. Protein-fatty acid complex for enhanced loading and stability within biodegradable nanoparticles. J Pharm Sci 90:194-201.
16. Cosic I. 1994. Macromolecular bioactivity: Is it resonant interaction between macromolecules?-Theory and applications. IEEE TransBiomed Eng 41:1101-1114.
17. Kabsch W, Sander C. 1983. Dictionary of protein secondary structure: Pattern recognition of hydrogen-bonded and geometrical features. Biopolymers 22:2577-2637.
18. Pace CN, Trevino S, Prabhakaran E, Scholtz JM. 2004. Protein structure, stability and solubility in water and other solvents. Phil Trans R Soc B 359:1225-1234.
19. Stevenson CL. 2000. Characterization of protein and peptide stability and solubility in non-aqueous solvents. Curr Pharm Biotechnol 1:165-182.
20. Huang P, Dong AC, Caughey WS. 1995. Effects of dimethyl-sulfoxide, glycerol, and ethylene-glycol on secondary structures of cytochrome-C and lysozyme as observed by infrared-spectroscopy. J Pharm Sci 84:387-392.
21. Smith Korsholm K, Agger EM, Foged C, Christensen D, Dietrich J, Andersen CS, Geisler C, Andersen P. 2007. The adjuvant mechanism of cationic dimethyldioctadecylammonium liposomes. Immunology 121:216-226.
22. Leal C, Moniri E, Pegado L, Wennerstrom H. 2007. Electrostatic attraction between DNA and a cationic surfactant aggregate. The screening effect of salt. J Phys Chem B 111:5999-6005.
23. Fricker G, Kromp T, Wendel A, Blume A, Zirkel J, Rebmann H, Setzer C, Quinkert RO, Martin F, Muller-Goymann C. 2010. Phospholipids and lipid-based formulations in oral drug delivery. Pharm Res 27:1469-1486.
24. Meyer JD, Manning MC, Carpenter JF. 2004. Effects of potassium bromide disk formation on the infrared spectra of dried model proteins. J Pharm Sci 93:496-506.
25. Hussain A, Majumder QH, Ahsan F. 2006. Inhaled insulin is better absorbed when administered as a dry powder compared to solution in the presence or absence of alkylglycosides. Pharm Res 23:138-147.
26. Agarwal V, Khan MA, Nazzal S. 2008. Polymethacrylate based microparticulates of insulin for oral delivery, part II: Solid state characterization. Pharmazie 63:122-128.
27. Pikal MJ, Rigsbee DR. 1997. The stability of insulin in crystalline and amorphous solids: Observation of greater stability for the amorphous form. Pharm Res 14:1379-1387.
28. Todo H, Okamoto H, Iida K, Danjo K. 2004. Improvement of stability and absorbability of dry insulin powder for inhalation by powder-combination technique. Int J Pharm 271:41-52.
29. Wang T, Wang N, Jin X, Zhang K, Lie TF. 2009. A novel procedure for preparation of submicron liposomes-lyophilization of oil-in-water emulsions. J Liposome Res 19:231-240.
30. Jorgensen L, Vermehren C, Bjerregaard S, Froekjaer S. 2003. Secondary structure alterations in insulin and growth hormone water-in-oil emulsions. Int J Pharm 254:7-10.
31. Sarmento B, Ferreira DC, Jorgensen L, Van De Weert M. 2007. Probing insulin's secondary structure after entrapment into alginate/chitosan nanoparticles. Eur J Pharm Biopharm 65:10-17.
32. Wei J, Lin YZ, Zhou JM, Tsou CL. 1991. FTIR Studies of secondary structures of bovine insulin and its derivatives. Biochim Biophys Acta 1080:29-33.
33. Donsmark J, Jorgensen L, Mollmann S, Frokjaer S, Rischel C. 2006. Kinetics of insulin adsorption at the oil water interface and diffusion properties of adsorbed layers monitored using fluorescence correlation spectroscopy. Pharm Res 23:148-155.
34. Kwon YM, Baudys M, Knutson K, Kim SW. 2001. In situ study of insulin aggregation induced by water-organic solvent interface. Pharm Res 18:1754-1759.
35. Tiyaboonchai W, Woiszwillo J, Sims RC, Middaugh CR. 2003. Insulin containing polyethylenimine-dextran sulfate nanoparticles. Int J Pharm 255:139-151.
36. Griebenow K, Klibanov AM. 1995. Lyophilization-induced reversible changes in the secondary structure of proteins. P Natl Acad Sci USA 92:10969-10976.