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Original Article

Design of high payload PLGA nanoparticles containing melittin/sodium dodecyl sulfate complex by the hydrophobic ion-pairing technique

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Pages 959-968 | Received 16 Jul 2008, Accepted 31 Dec 2008, Published online: 19 May 2009

References

  • Allaouiattarki K, Fattal E, Pecquet S, Trolle S, Chachaty E, Couvreur P, (1998). Mucosal immunogenicity elicited in mice by oral vaccination with phosphrylcholine encapsulated in poly(d,l-lactide-coglycolide) microspheres. Vaccine, 16:685–91.
  • Araujo L, Sheppard M, Lobenberg R, Kreuter J. (1999). Uptake of PMMA nanoparticles from the gastrointestinal tract after oral administration to rats: Modification of the body distribution after suspension in surfactant solutions and in oil vehicles. Int J Pharm, 176:209–44.
  • Bowersock TL, HogenEsch H, Suckow M, Guimond P, Martin S, Borie D, (1999). Oral vaccination of animals with antigens encapsulated in alginate microspheres. Vaccine, 17:1804–11.
  • Hussain N, Jani PU, Florence AT. (1997). Enhanced oral uptake of tomato lectin conjugated nanoparticles in the rat. Pharm Res, 14:613–8.
  • Kato Y, Hosokawa T, Ito K. (1993). Influence of liposomes on tryptic digestion of insulin. Biol Pharm Bull, 16:457–61.
  • Lee VHL, Yamamoto A, Kompella UB. (1991). Mucosal penetration enhancers for facilitation of peptides and protein drug absorption. Crit Rev Ther Drug Carrier Syst, 8:91–192.
  • Liu X, Chen D-W, Xie L-P, Zhang R-Q. (2003). Oral colon-specific drug delivery for bee venom peptide: Development of a coated calcium alginate gel beads-entrapped liposome. J Control Release, 93:293–300.
  • Muramatsu K, Maitani Y, Takayama K, Nagai T. (1999). The relationship between the rigidity of the liposomal membrane and the absorption of insulin after nasal administration of liposomes modified with an enhancer containing insulin in rabbits. Drug Dev Ind Pharm, 25:1099–105.
  • Clean SM, Prosser E, Meehan E, Malley DO, Clarke N, Ramtoola Z, (1998). Binding and uptake of biodegradable poly-d,l-lactide micro and nanoparticles in intestinal epithelia. Eur J Pharm Sci, 6:153–63.
  • Jung T, Kamm W, Breitenbach A, Kaiserling E, Xiao JX, Kissel T. (2000). Biodegradable nanoparticles for oral delivery of peptides: Is there a role for polymers to affect mucosal uptake. Eur J Pharm Biopharm, 50:147–60.
  • Romero-Cano MS, Vincent B. (2002). Controlled release of 4-nitroanisole from poly(lactic acid) nanoparticles. J Control Release, 82:127–35.
  • Sakuma S, Suzuki N, Kikuchi H, Hiwatari K, Arikawa K, Kishida A, (1997). Oral peptide delivery using administered salmon calcitonin by polystyrene nanoparticles having poly(N-isopropylacrylamide) branches on their surfaces. Int J Pharm, 158:69–78.
  • Takeuchi H, Yamomoto H, Kawashima Y. (2001). Mucoadhesive nanoparticulate systems for peptide drug delivery. Adv Drug Deliv Rev, 47:39–54.
  • Niwa T, Takeuchi H, Hino T, Kunuo N, Kawashima Y. (1994). In vitro drug release behaviour of d,l-lactide/glycolide copolymer (PLGA) nanospheres with nafarelin acetate prepared by a novel spontaneous emulsification solvent diffusion method. J Pharm Sci, 83:727–32.
  • Park TG, Lu W, Crotts G. (1995). Importance of in vitro experimental conditions on protein release kinetics, stability and polymer degradation in protein encapsulated poly(d,l-lactic-co-glycolic acid) microspheres. J Control Release, 33:211–22.
  • 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.
  • Meyer JD, Mark MC. (1998). Hydrophobic ion pairing: Altering the solubility properties of biomolecules. Pharm Res, 15:188–93.
  • Quintanar-Guerrero D, Allemann E, Fessi H, Doelker E. (1997). Applications of the ion-pair concept to hydrophilic substances with special emphasis on peptides. Pharm Res, 14:119–27.
  • Adjei A, Rao S, Garren J, Menon G, Vadnere M. (1993). Effect of ionpairing on 1-octanol–water partitioning of peptide drugs. I: The nonapeptide leuprolide acetate. Int J Pharm, 90:141–9.
  • Matsuura J, Powers ME, Manning MC, Shefter E. (1993). Structure and stability of insulin dissolved in 1-octanol. J Am Chem Soc, 115:1261–4.
  • Paradkar VM, Dordick JS. (1994). Mechanism of extraction of chymotrypsin into isooctane at very low concentrations of aerosol OT in the absence of reversed micelles. Biotechnol Bioeng, 43:529–40.
  • Powers ME, Matsuura J, Brassell J, Manning MC, Shefter E. (1993). Enhanced solubility of proteins and peptides in nonpolar solvents through hydrophobic ion pairing. Biopolymers, 33:927–32.
  • Falk R, Randolph TW, Meyer JD, Kelly RM, Manning MC. (1997). Controlled release of ionic compounds from poly(l-lactide) microspheres produced by precipitation with a compressed antisolvent. J Control Release, 44:77–85.
  • 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.
  • Bradshaw JP. (1997). Phophatidylglycerol promotes bilayer insertion of salmon calcitonin. Biophys J, 72:2180–96.
  • Dua R, Duncan M, Zia H, Needham TE. (1998). The influence of the enhancer dimyristoylphosphatidylglycerol and formulation factor on the nasal absorption of salmon calcitonin. Drug Deliv, 5:127–34.
  • Angelika N, David AT. (2001). Self-association and membrane-binding behavior of melittins containing trifluoroleucine. J Am Chem Soc, 123:7407–13.
  • Jutel MN, Pichler WJ, Skribic D, Urwyler A, Dahinden C. (1995). Bee venom immunotherapy results in decrease of IL-4 and IL-5 and increase of IFN-gamma secretion in specific allergen-stimulated T cell cultures. J Immunol, 154:4187–94.
  • Thomas GR, Hiley CR. (1988). Cardiovascular effect of intracerebroventricular bradykinin and melittin in the rat. J Pharm Pharmacol, 40:721–3.
  • Pogliani EM, Cofrancesco E. (1983). Thrombotic thrombocytopenic purpura. Haematologica, 68:546–57.
  • Liu X, Chen D-W, Xie L-P, Zhang R-Q. (2002). Effect of honey bee venom on proliferation of K1736M2 mouse melanoma cell in-vitro and growth of murine B16 melanomas in-vivo. J Pharm Pharmacol, 54:1–8.
  • Lo WC, Henk WG, Enright FM. (1997). Light-microscopic studies of 3T3 cell plasma membrane alterations mediated by melittin. Toxicon, 35:15–26.
  • Laine RO, Morgan BP, Esser AF. (1988). Comparison between complement and melittin hemolysis: Anti-melittin antibodies inhibit complement lysis. Biochemistry, 27:5308–14.
  • Tosteson MT, Tosteson DC. (1981). The sting melittin forms channels in lipid bilayers. Biophys J, 36:109–16.
  • Vogel H, Jahnig F. (1986). The structure of melittin in membranes. Biophys J, 50:573–82.
  • Benachir T, Lafleur M. (1995). Study of vesicle leakage induced by melittin. Biochim Biophys Acta, 1235:452–60.
  • Pawlak M, Meseth U, Dhanapal B. (1994). Template-assembled melittin: Structural and functional characterization of a designed, synthetic channel forming protein. Protein Sci, 3:1788–805.
  • Räder K, Wildfeuer A, Wintersberger F, Bossinger P, Mücke HW. (1987). Characterization of bee venom and its main components by high performance liquid chromatography. J Chromatogr, 408:341–8.
  • Lowry OH, Rosebrough N J, Farr AL, Randall RL. (1951). Protein measurement with the Folin phenol reagent. J Biol Chem, 193:265–75.
  • Sah H. (1997). A new strategy to determine the actual protein content of poly (lactide-co-glycolide) microspheres. J Pharm Sci, 86:1315–8.
  • Gevod VS, Birdi KS. (1984). Melittin and the 8–26 fragment. Differences in ionophoric properties as measured by monolayer method. Biophys J, 45:1079–83.
  • Terwillinger TC, Eisenberg D. (1982). The structure of melittin. 2. Interpretation of the structure. J Biol Chem, 257:6016–22.
  • Meek JL, Rossettio ZL. (1981). Factors affecting retention and resolution of peptides in high performance liquid chromatography. J Chromatogr, 211:15–28.
  • Hegg PO. (1979). Precipitation of egg white proteins below their isoelectric points by sodium dodecyl sulfate and temperature. Biochim Biophys Acta, 579:73–87.
  • Bello J, Bello HR, Granados E. (1982). Conformation and aggregation of melittin: Dependence on pH and concentration. Biochemistry, 21:461–5.
  • Sessa G, Freer JH, Colacicco G, Weismann G. (1969). Interaction of a lytic polypeptide, melittin, with lipid membrane systems. J Biol Chem, 244:3575–82.
  • Choi SH, Park TG. (2000). Hydrophobic ion pair formation between leuprolide and sodium oleate for sustained release from biodegradable polymeric microspheres. Int J Pharm, 203:193–202.
  • Yoo HS, Park TG. (2004). Biodegradable nanoparticles containing protein–fatty acid complexes for oral delivery of salmon calcitonin. J Pharm Sci, 93:488–95.
  • Akyü S, Severcan F. (1988). Melittin–lipid interactions: A FT-IR spectroscopic study. J Mol Struct, 175:371–6.
  • Dorkoosh FA, Verhoef JC, Ambagts MHC, Rafiee-Tehrani M, Borchard G, Junginger HE. (2002). Peroral delivery systems based on superorous hydrogel polymer: Release characteristics for the peptide drugs buserelin, octreotide and insulin. Eur J Pharm Sci, 15(5):433–9.
  • Gaikar VG, Padalkar KV, Aswal VK. (2008). Characterization of mixed micelles of structural isomers of sodium butyl benzene sulfonate and sodium dodecyl sulfate by SANS, FTIR spectroscopy and NMR spectroscopy. J Mol Liq, 138(1–3):155–67.
  • Haris PI, Chapman D. (2004). Analysis of polypeptide and protein structures using Fourier transform infrared spectroscopy. Methods Mol Biol, 22:183–202.
  • Yang H, Yan X-H, Wang Z-L, Cheng R-S. (2001). The crystallizing behavior of sodium dodecyl sulfate under a electrostatic field. Chem J Chinese Universities, 22:666–8.
  • Sun SP, Cui FD, Kawashima Y, Liang N, Zhang LQ, Shi K, (2008). A novel insulin–sodium oleate complex for oral administration: Preparation, characterization and in vivo evaluation. J Drug Del Sci Tech, 18(4):239–43.
  • Brandts JF, Hunt L. (1967). The thermodynamics of protein denaturation. III. The denaturation of ribonuclease in water and in aqueous urea and aqueous ethanol mixture. J Am Chem Soc, 89:4826–38.
  • Pace CN. (1975). The stability of globular proteins. CRC Crit Rev Biochem, 3(1):1–43.
  • Boye JI, Ma CY, Ismail A. (2004). Thermal stability of beta-lactoglobulins A and B: Effect of SDS, urea, cysteine and N-ethylmaleimide. J Dairy Res, 71(2):207–15.
  • Lengsfeld CS, Pitera D, Manning M, Randolph TW. (2002). Dissolution and partitioning behavior of hydrophobic ion-paired compounds. Pharm Res, 19:1572–6.
  • Kendrick BS, Meyer JD, Matsuura JE, Carpenter JF, Manning MC. (1997). Hydrophobic ion pairing as a method for enhancing structure and activity of lyophilized subtilisin BPN' suspended in isooctane. Arch Biochem Biophys, 347:113–8.
  • Cui FD, Shi K, Zhang LQ, Tao AJ, Kawashima Y. (2006). Biodegradable nanoparticles loaded with insulin–phospholipid complex for oral delivery: Preparation, in vitro characterization and in vivo evaluation. J Control Release, 114:242–50.

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