PEGylated bioactive molecules in biodegradable polymer microparticles

Expert Opinion on Biological Therapy

Volumn 7, Issue 9, 2007, Pages 1427-1436

  Schmidt, Paul G ^a   Campbell, Kathleen M ^a   Hinds, Kenneth D ^b   Cook, Gary P ^c  

^a PR Pharmaceuticals Inc   (United States)

^b CENTOCOR INC   (United States)

^c Jerini Ophthalmic Inc   (United States)

Author keywords

Acylation; Insulin; Microencapsulation; Pegaptanib; Site specific PEGylation

Indexed keywords

ALPHA INTERFERON; ANGIOPEPTIN; ANTIBIOTIC AGENT; ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; ARESTIN; ATYPICAL ANTIPSYCHOTIC AGENT; BROMOCRIPTINE MESILATE; BUSERELIN ACETATE; CHYMOTRYPSIN A; EPIDERMAL GROWTH FACTOR RECEPTOR; HORSERADISH PEROXIDASE; HUMAN GROWTH HORMONE; INSULIN; LEUPRORELIN; LYSOZYME; MACROGOL; MINOCYCLINE; OCTREOTIDE; PAMORELIN; PEGAPTANIB; POLYGLACTIN; RISPERIDONE; TRIPTORELIN; UNCLASSIFIED DRUG;

ACYLATION; BINDING AFFINITY; BIODEGRADABILITY; CAPILLARY ELECTROPHORESIS; DRUG ABSORPTION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROENCAPSULATION; NONHUMAN; REVIEW; SUSTAINED DRUG RELEASE;

ABSORBABLE IMPLANTS; ANIMALS; BIOCOMPATIBLE MATERIALS; DRUG CARRIERS; DRUG IMPLANTS; HUMANS; POLYETHYLENE GLYCOLS;

EID: 34748880897     PISSN: 14712598     EISSN: None     Source Type: Journal    
DOI: 10.1517/14712598.7.9.1427     Document Type: Review

References (58)

1. CHIU Y, SOBEL S: Protein and peptide drug delivery systems: a regulatory viewpoint. In: Therapeutic Peptides and Proteins: Formulation, Delivery, and Targeting. Marshak D, Liu D (Eds), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, USA (1989):187-193.
2. TICE T: Delivering with depot formulations. Drug Delivery Technol. (2004) 4:44-47.
3. BECK L, COWSAR D, LEWIS D et al.: A new long-acting injectable microcapsule system for the administration of progesterone. Fertil. Steril. (1979) 31:545-551.
4. LEWIS D: Controlled release of bioactive agents from lactide/glycolide polymers. In: Biodegradable Polymers as Drug Delivery Systems. Chasin M, Langer R (Eds), Marcel Dekker, Inc., Baltimore, Cambridge, USA (2001): 1-41.
5. BECK L, POPE V, FLOWERS C et al.: Poly(D,L-Lactide-co-glycolide)/ norethisterone microcapsules: an injectable biodegradable contraceptive. Biol. Reprod. (1983) 28:186-195.
6. KEMP S, FIELDER P, ATTIE K et al.: Pharmacokinetic and pharmacodynamic characteristics of a long-acting growth hormone (GH) preparation (Nutropin Depot) in GH-Deficient children. J. Clin. Endocrinol. Metab. (2004) 89:3234-3240.
7. CROTTS G, SAH H, PARK T: Adsorption determines in vitro protein release rate from biodegradable microspheres: quantitative analysis of surface area during degradation. J. Control Release (1997) 47:101-111.
8. TSAI T, MEHTA R, DELUCA P: Adsorption of peptides to poly(D,L-lactide-co- glycolide). 1. Effect of physical factors on the adsorption. Int. J. Pharm. (1996) 127:31-42.
9. DE JONG S, ARIAS E, RIJKERS D, VAN NOSTRUM C, KETTENES-VAN DEN BOSCH J, HENNINK W: New insights into the hydrolytic degradation of poly (lactic acid): participation of the alcohol terminus. Polymer (2001) 42:2795-2802.
10. BRUNNER A, MADER K, GOPFERJCH A: pH and osmotic pressure inside biodegradable microspheres during erosion. Pharm. Res. (1999) 16:847-853.
11. DING A, SCHWENDEMAN S: Determination of water-soluble acid distribution in poly(lactide-co-glycolide). J. Pharm. Sci. (2004) 93:322-331.
12. LAI M, HAGEMAN M, SCHOWEN R, BORCHARDT R, LAIRD B, TOPP E: Chemical stability of peptides in polymers. 2. Discriminating between solvent and plasticizing effects of water on peptide deamidation in poly(vinylpyrrolidone). J. Pharm. Sci. (1999) 88:1081-1089.
13. KROGMEIER S, REDDY S, VANDERVELDE D et al.: Deamidation of model b-turn cyclic peptides in the solid state. J. Pharm. Sci. (2005) 94:2616-2631.
14. JOSHI A, SAWAI M, KEARNEY W, KIRSCH L: Studies on the mechanism of aspartic acid cleavage and glutamine deamidation in the acidic degradation of glucagon. J. Pharm. Sci. (2005) 94:1912-1927.
15. IBRAHIM M, ISMAIL A, FETOUH M, GOPFERICH A: Stability of insulin during the erosion of poly(lactic acid) and poly(lactic-co-glycolic acid) microspheres. J. Control. Release (2005) 106:241-252.
16. DE BONT R, VAN LAREBEKE N: Endogenous DNA damage in humans: a review of quantitative data. Mutagenesis (2004) 19:169-185.
17. VAN DE WEERT M, HENNINK W, JISKOOT W: Protein instability in poly(lactic-co-glycolic acid) microparticles. Pharm. Res. (2000) 17:1159-1167.
18. JIANG W, SCHWENDEMAN S: Stabilization and controlled release of bovine serum albumin encapsulated in poly(D,L-lactide) and polyethylene glycol) microsphere blends. Pharm. Res. (2001) 18:878-885.
19. SHAO P, BAILEY L: Stabilization of pH-induced degradation of porcine insulin in biodegradable polyester microspheres. Pharm. Develop. Technol. (1999) 4:633-642.
20. ZHU G, MALLERY S, SCHWENDEMAN S: Stabilization of proteins encapsulated in injectable poly(lactide-co-glycolide). Nat. Biotechnol. (2000) 18:52-57.
21. LUCRE A, KIERMAIER J, GOPFERICH A: Peptide acylation by poly(a-hydroxy esters). Pharm. Res. (2002) 19:175-181.
22. NA D, YOUN Y, LEE S et al.: Monitoring of peptide acylation inside degrading PLGA microspheres by capillary electrophoresis and MALDI-TOF mass spectrometry. J. Control. Release (2003) 92:291-299.
23. MURTY S, GOODMAN J, THANOO B, DELUCA P: Identification of chemically modified peptide from poly(D,L-lactide-co-glycolide) microspheres under in vitro release conditions. AAPS Pharm. Sci. Tech. (2003) 4:E49.
24. CALICETI P, VERONESE F: Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates. Adv. Drug Deliv. Rev. (2003) 55:1261-1277.
25. KOZLOWSKI A, CHARLES S, HARRIS J: Development of PEGylated interferons for the treatment of chronic hepatitis C. BioDrugs (2001) 15:419-429.
26. HINDSK, KIM S: Effects of PEG conjugation on insulin properties. Adv. Drug Deliv. Rev. (2002) 54:505-530.
27. ROBERTS M, BENTLEY M, HARRIS J: Chemistry for peptide and protein PEGylation. Adv. Drug Deliv. Rev. (2002) 54:459-476.
28. GREENWALD R, CHOE Y, MCGUIRE J, CONOVER C: Effective drug delivery by PEGylated drug conjugates. Adv. Drug Deliv. Rev. (2003) 55:217-250.
29. DELGADO C, FRANCIS GE, FISHER D: The uses and properties of PEG-linked proteins. Crit. Rev. Ther. Drug Carrier Syst. (1992) 9:249-304.
30. DIWAN M, PARK T: PEGylation enhances protein stability during encapsulation in PLGA microspheres. J Control. Release (2001) 73:233-244.
31. DIWAN M, PARK T: Stabilization of recombinant interferon-α by PEGylation for encapsulation in PLGA microspheres. Int. J. Pharm. (2003) 252:111-122.
32. KIM T, LEE H, PARK T: PEGylated recombinant human epidermal growth factor (rhEGF) for sustained release from biodegradable PLGA microspheres. Biomaterials (2002) 23:2311-2317.
33. AL-AZZAM W, PASTRANA E, KING B, MENDEZ J, GRIEBENOW K: Effect of the covalent modification of horseradish peroxidase with poly(ethylene glycol) on the activity and stability upon encapsulation in polyester microspheres. J Pharm. Sci. (2005) 94:1808-1819.
34. CASTELLANOS I, AL-AZZAM W, GRIEBENOW K: Effect of the covalent modification with polyfethylene glycol) on a-chymotrypsin stability upon encapsulation in poly(lactic-co-glycolic) microspheres. J. Pharm. Sci. (2005) 94:327-340.
35. CAMPBELL K, HINDS K, HOLLAND K, LEWIS D: PEG-insulin conjugates for optimal microsphere formulations. Proc. Intern. Symp. Control. Rel. Bioact. Mater. (2004) 31:484.
36. HINDS K, CAMPBELL K, HOLLAND K, LEWIS D, PICHE C, SCHMIDT P: PEGylated insulin in PLGA microparticles. In vivo and in vitro analysis. J. Control. Release (2005) 104:447-460.
37. KELLNER K, TESSMAR J, MILZ S et al.: PEGylation does not impair insulin efficacy in three-dimensional cartilage culture: an investigation toward biomimetic polymers. Tissue Eng. (2004) 10:429-440.
38. COOK G: Evaluation of PLGA microspheres for intraocular sustained delivery of pegaptanib. Proc. Intern. Symp. Control. Rel. Bioact. Mater. (2006) 33:56.
39. INADA Y, NISHIMURA H, TAKAHASHI K, YOSHIMOTO T, SAHA AR, SAITO Y: Ester synthesis catalyzed by polyethylene glycol-modified lipase in benzene. Biochem. Biophys. Res. Commun. (1984) 122:845-850.
40. MARSAC Y, CRAMER J, OLSCHEWSKI D, ALEXANDROV K, BECKER CF: Site-specific attachment of polyethylene glycol-like oligomers to proteins and peptides. Bioconj. Chem. (2006) 17:1492-1498.
41. WIRTH P, SOUPPE J, TRITSCH D, BIELLMANN J: Chemical modification of horseradish peroxidase with ethanal-methoxypolyethylene glycol: solubility in organic solvents, activity, and properties. Bioorg. Chem. (1991) 19:133-142.
42. MURTY S, THANOO B, WEI Q, DELUCA P: Impurity formation studies with peptide-loaded polymeric microspheres Part II. In vitro evaluation. Int. J. Pharm. (2005) 297:62-72.
43. MURTY S, WEI Q, THANOO B, DELUCA P: Impurity formation studies with peptide-loaded polymeric microspheres Part I. In vivo evaluation. Int. J. Pharm. (2005) 297:50-61.
44. NA D, DELUCA P: PEGylation of Octreotide. I. Separation of positional isomers and stability against acylation by poly(D.L-lactide-co-glycolide). Pharm. Res. (2005) 22:736-742.
45. NA D, LEE K, DELUCA P: PEGylation of Octreotide. II. Effect of N-terminal mono-PEGylation on biological activity and pharmacokinetics. Pharm. Res. (2005) 22:743-749.
46. NA D, MURTY S, LEE K, THANOO B, DELUCA P: Preparation and stability of poly(ethylene glycol) (PEG)ylated octreotide for application to microsphere delivery. AAPS Pharm. Sci. Tech. (2003) 4:E72.
47. YEO Y, PARK K: Control of encapsulation efficiency and initial burst in polymeric microparticle systems. Arch. Pharm. Res. (2004) 27:1-12.
48. YAMAGUCHI Y, TAKENAGA M, KITAGAWA A, OGAWA Y, MIZUSHIMA Y, IGARASHI R: Insulin-loaded biodegradable PLGA microcapsules: Initial burst release controlled by hydrophilic additives. J. Control. Release (2002) 81:235-249.
49. FUK, HARRELL R, ZINSKI K et al.: A potential approach for decreasing the burst effect of protein from PLGA microspheres. J. Pharm. Sci. (2003) 92:1582-1591.
50. VERONESE F, MORPURGO M: Bioconjugation in pharmaceutical chemistry. Farmaco (1999) 54:497-516.
51. TSUBERY H, MIRONCHIK M, FRIDKIN M, SHECHTER Y: Prolonging the action of protein and peptide drugs by a novel approach of reversible polyethylene glycol modification. J. Biol. Chem. (2004) 279:38118-38124.
52. YOUN Y, NA D, LEE K: High-yield production of biologically active mono-PEGylated salmon calcitonin by site-specific PEGylation. J Control. Release (2007) 117:371-379.
53. YEH MK: The stability of insulin in biodegradable microparticles based on blends of lactide polymers and polyethylene glycol. J Microencapsul. (2000) 17:743-756.
54. HINDS K, KOH J, JOSS L, LIU F, BAUDYS M, KIM S: Synthesis and characterization of poly(ethylene glycol) - insulin conjugates. Bioconjug. Chem. (2000) 11:195-201.
55. THIEL K: Oligo oligarchy - the suprisingly small world of aptamers. Nat. Biotechnol (2004) 22:649-651.
56. TUCKER C, CHEN L, JUDKINS M, FARMER J, GILL S, DROLET D: Detection and plasma pharmacokinetics of an anti-vascular endothelial growth factor oligonucleotide-aptamer (NX1838) in Rhesus monkeys. J. Chromatogr. B. (1999) 732:203-212.
57. DROLET D, NELSON J, TUCKER C et al.: Pharmacokinetics and safety of an anti-vascular endothelial growth factor aptamer (NX1838) following injection into the vitreous humor of Rhesus monkeys. Pharm. Res. (2000) 17:1503-1510.
58. GRAGOUDAS E, ADAMIS A, CUNNINGHAM E, FEINSOD M, GUYER D: Pegaptanib for neovascular age-related macular degeneration. N. Engl. J. Med. (2004) 351:2805-2816.