Development of an in situ forming PLGA drug delivery system. I. Characterization of a non-aqueous protein precipitation

European Journal of Pharmaceutical Sciences

Volumn 35, Issue 4, 2008, Pages 283-292

  Körber, Martin ^a   Bodmeier, Roland ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Biodegradable polymers; FTIR; Injectables; Microencapsulation; Polymeric drug delivery systems; Precipitation; Protein aggregation; Protein delivery; Protein formulation; Stability

Indexed keywords

ACETIC ACID ETHYL ESTER; DIMETHYL SULFOXIDE; EGG WHITE; LYSOZYME; POLYGLACTIN;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG DELIVERY SYSTEM; HEN; MICROENCAPSULATION; PRECIPITATION; PRIORITY JOURNAL; PROTEIN AGGREGATION; SOLUBILITY;

ACETATES; CHEMISTRY, PHARMACEUTICAL; DIMETHYL SULFOXIDE; DRUG DELIVERY SYSTEMS; LACTIC ACID; MICROCOCCUS; MURAMIDASE; NANOPARTICLES; NEPHELOMETRY AND TURBIDIMETRY; PARTICLE SIZE; PHOTONS; POLYGLYCOLIC ACID; POLYMERS; PROTEINS; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS; WATER;

EID: 53849090614     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2008.07.007     Document Type: Article

References (48)

1. Bittner B., Morlock M., Knoll H., Winter G., and Kissel T. Recombinant human erythropoietin (rhEPO) loaded poly(lactide-co-glycolide) microspheres: influence of the encapsulation technique and polymer purity on microsphere characteristics. Eur. J. Pharm. Biopharm. 45 (1998) 295-305
2. Bodmeier, R., 2000. Multiphasensystem. EP 0,996,426 A1.
3. Brodbeck K.J., Desnoyer J.R., and Mchugh A.J. Phase inversion dynamics of PLGA solutions related to drug delivery. Part II. The role of solution thermodynamics and bath-side mass transfer. J. Control. Release 62 (1999) 333-344
4. Carrasquillo K.G., Stanley A.M., APONTE-Carro J.C., De Jèsus P., Constantino H.R., Bosques C.J., and Griebenow K. Non-aqueous encapsulation of excipient-stabilized spray-freeze dried BSA into poly(lactide-co-glycolide) microspheres results in release of native protein. J. Control. Release 76 (2001) 199-208
5. Castellanos I.J., Carrasquillo K.G., De Jèsus Lòpez J., Alvarez M., and Griebenow K. Encapsulation of bovine serum albumin in poly(lactide-co-glycolide) microspheres by the solid-in-oil-in-water technique. J. Pharm. Pharmacol. 53 (2001) 167-178
6. Chang N., Hen S.J., and Klibanov A.M. Protein separation and purification in neat dimethyl sulfoxide. Biochem. Biophys. Res. Commun. 176 (1991) 1462-1468
7. Chin J.T., Wheeler S.L., and Klibanov A.M. On protein solubility in organic solvents. Biotechnol. Bioeng. 44 (1994) 140-145
8. Claudy P., Lètoffè J.M., Bayol A., Bonnet M.C., and Maurizot J.C. Denaturation versus pH of lyzozyme and biosynthetic human growth hormone by differential scanning calorimetry and circular dichroism: a comparative study. Thermochim. Acta 207 (1992) 227-237
9. Costantino H.R., Firouzabadian L., Hogeland K., Wu C., Beganski C., Carrasquillo K.G., Còrdova M., Griebenow K., Zale S.E., and Tracy M.A. Protein spray-freeze drying. Effect of atomization conditions on particle size and stability. Pharm. Res. 17 (2000) 1374-1383
10. Costantino H.R., Firouzabadian L., Wu C., Carrasquillo K.G., Griebenow K., Zale S.E., and Tracy M.A. Protein spray freeze drying. 2. Effect of formulation variables on particle size and stability. J. Pharm. Sci. 91 (2002) 388-395
11. Costantino H.R., Griebenow K., Mishra P., Langner R., and Klibanov A.M. Fourier-transform infrared spectroscopic investigation of protein stability in the lyophilized form. Biochim. Biophys. Acta 1253 (1995) 69-74
12. Costantino, H.R., Jaworowiscz, W., Tracy, M., Beganski, C., 2001. Method of producing submicron particles of biologically active agents such as proteins and peptides.
13. Costantino H.R., Johnson O.L., and Zale S.E. Relationship between encapsulated drug particle size and initial release of recombinant human growth hormone from biodegradable microspheres. J. Pharm. Sci. 93 (2004) 2624-2634
14. Dunn, R.L., Tipton, A.J., 1997. Polymeric compositions useful as controlled release implants. US 5,702,716.
15. Galkin O., and Vekilov P.G. Control of protein crystal nucleation around the metastable liquid-liquid phase boundary. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 6277-6281
16. Ghaderi R., and Carlfors J. Biological activity of lysozyme after entrapment in poly(d,l-lactide-co-glycolide)-microspheres. Pharm. Res. 14 (1997) 1556-1562
17. Graham P.D., Brodbeck K.J., and Mchugh A.J. Phase inversion dynamics of PLGA solutions related to drug delivery. J. Control. Release 58 (1999) 233-245
18. Griebenow K., and Klibanov A.M. On protein denaturation in aqueous-organic mixtures but not in pure organic solvents. J. Am. Chem. Soc. 118 (1996) 11695-11700
19. Houen P.G. The solubility of proteins in organic solvents. Acta Chem. Scand. 50 (1996) 68-70
20. Jackson M., and Mantsch H.H. Beware of proteins in DMSO. Biochim. Biophys. Acta (1991) 231-235
21. Jaganathan K.S., Rao Y.U.B., Singh P., Prabakaran D., Gupta S., Jain A., and Vyas S.P. Development of a single dose tetanus toxoid formulation based on polymeric microspheres: a comparative study of poly(d,l-lactic-co-glycolic acid) versus chitosan microspheres. Int. J. Pharm. 294 (2005) 23-32
22. Johnson, O., Ganmukhi, H., Bernstein, H., Auer, H., 2000. Composition for sustained release of human growth hormone.
23. Kang F., Jiang G., Hinderliter A., Deluca P.P., and Singh J. Lysozyme stability in primary emulsion for PLGA microsphere preparation: effect of recovery methods and stabilizing excipients. Pharm. Res. 19 (2002) 629-633
24. Kim H.K., and Park T.G. Microencapsulation of human growth hormone within biodegradable polyester microspheres: protein aggregation stability and incomplete release mechanism. Biotechnol. Bioeng. 65 (1999) 659-667
25. Kim H.K., and Park T.G. Microencapsulation of dissociable human growth hormone aggregates within poly(d,l-lactic-co-glycolic acid) microparticles for sustained release. Int. J. Pharm. 229 (2001) 107-116
26. Knubovets T., Osterhout J.J., and Klibanov A.M. Structure of lysozyme dissolved in neat organic solvents as assessed by NMR and CD spectroscopies. Biotechnol. Bioeng. 63 (1999) 242-246
27. Kranz H., Brazeau G.A., Napaporn J., Martin R.L., Millard W., and Bodmeier R. Myotoxicity studies of injectable biodegradable in-situ forming drug delivery systems. Int. J. Pharm. 212 (2001) 11-18
28. Krishnamurthy R., Lumpkin J.A., and Sridhar R. Inactivation of lysozyme by sonication under conditions relevant to microencapsulation. Int. J. Pharm. 205 (2000) 23-34
29. Lambert W.J., and Peck K.D. Development of an in situ forming biodegradable poly-lactide-coglycolide system for the controlled release of proteins. J. Control. Release 33 (1995) 189-195
30. Lu W., and Park T.G. Protein release from poly(lactic-co-glycolic acid) microspheres: protein stability problems. J. Pharm. Sci. Technol. 49 (1995) 13-19
31. Maa Y.F., and Hsu C.C. Effect of primary emulsions on microsphere size and protein-loading in the double emulsion process. J. Microencapsul. 14 (1997) 225-241
32. Morita T., Horikiri Y., Suzuki T., and Yoshino H. Preparation of gelatin microparticles by co-lyophilization with poly(ethylene glycol): characterization and application to entrapment into biodegradable microspheres. Int. J. Pharm. 219 (2001) 127-137
33. Morita T., Horikiri Y., Yamahara H., Suzuki T., and Yoshino H. Formation and isolation of spherical fine protein microparticles through lyophilization of protein-poly(ethylene glycol) aqueous mixture. Pharm. Res. 17 (2000) 1367-1373
34. Morlock M., Koll H., Winter G., and Kissel T. Microencapsulation of rh-erythropoietin, using biodegradable poly(d,l-lactide-co-glycolide): protein stability and the effects of stabilizing excipients. Eur. J. Pharm. Biopharm. 43 (1997) 29-36
35. Moshashaèe S., Bisrat M., Forbes R.T., Nyqvist H., and York P. Supercritical fluid processing of proteins. I. Lysozyme precipitation from organic solution. Eur. J. Pharm. Sci. 11 (2000) 239-245
36. Park T.G., Lee H.Y., and Nam Y.S. A new preparation method for protein loaded poly(d,l-lactic-coglycolic acid) microspheres and protein release mechanism study. J. Control. Release 55 (1998) 181-191
37. 2/water interface and upon water-in-oil-in-water encapsulation in PLGA microspheres. J. Control. Release 89 (2003) 71-85
38. Pèrez C., Castellanos I.J., Costantino H.R., Al-Azzam W., and Griebenow K. Recent trends in stabilizing protein structure upon encapsulation and release from bioerodible polymers. J. Pharm. Pharmacol. 54 (2002) 301-313
39. Pèrez C., De Jèsus P., and Griebenow K. Preservation of lysozyme structure and function upon encapsulation and release from poly(lactic-co-glycolic) acid microspheres prepared by the water-in-oil-in-water method. Int. J. Pharm. 248 (2002) 193-206
40. Platz, R.M., Ip, A., Whitham, C.L., 1994. Process for preparing micronized polypeptide drugs. US 5,354,562.
41. Prestrelski S.J., Tedeschi N., Arakawa T., and Carpenter J.F. Dehydration-induced conformational transitions in proteins and their Inhibition by stabilizers. Biophys. J. 65 (1993) 661-671
42. Royals M.A., Fujita S.M., Yewey G.L., Rodriguez J., Schultheiss P.C., and Dunn R.L. Biocompatibility of a biodegradable in situ forming implant system in rhesus monkeys. J. Biomed. Mater. Res. 45 (1999) 231-239
43. Schwendeman S.P., Tobio M., Joworowicz M., Alonso M.J., and Langer R. New strategies for the microencapsulation of tetanus vaccine. J. Microencapsul. 15 (1998) 299-318
44. Shugar D. The measurement of lysozyme activity and the ultra-violet inactivation of lysozyme. Biochim. Biophys. Acta 8 (1952) 302-309
45. Thiering R., Dehghani F., Dillow A., and Foster N.R. The influence of operating conditions on the dense gas precipitation of model proteins. J. Chem. Technol. Biotechnol. 75 (2000) 29-41
46. Van de Weert M., Hoechstetter J., Hennink W.E., and Crommelin D.J.A. The effect of a water/organic solvent interface on the structural stability of lysozyme. J. Control. Release 68 (2000) 351-359
47. Winters M., Knutson B.L., Debenedetti P.G., Sparks H.G., Prybycien T.M., Stevenson C.L., and Prestrelski S.J. Precipitation of proteins in supercritical carbon dioxide. J. Pharm. Sci. 85 (1996) 586-594
48. Wolf M., Wirth M., Pittner F., and Gabor F. Stabilisation and determination of the biological activity of l-asparaginase in poly(d,l-lactide-co-glycolide) nanospheres. Int. J. Pharm. 256 (2003) 141-152