Application of solid phase peptide synthesis to engineering PEO-peptide block copolymers for drug delivery

Colloids and Surfaces B: Biointerfaces

Volumn 30, Issue 4, 2003, Pages 323-334

  Van Domeselaar, Gary H ^a   Kwon, Glen S ^b   Andrew, Lena C ^a   Wishart, David S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Block copolymer; Drug delivery; Micelle; Nano engineering; Peptide synthesis

Indexed keywords

BIOCOMPATIBILITY; BLOCK COPOLYMERS; LIGHT SCATTERING; MASS SPECTROMETRY; POLYPEPTIDES; TRANSMISSION ELECTRON MICROSCOPY;

DRUG DELIVERY SYSTEMS;

DRUG THERAPY;

ANTINEOPLASTIC AGENT; COPOLYMER; DOXORUBICIN; MACROGOL;

ARTICLE; BIOCOMPATIBILITY; CORRELATION ANALYSIS; DRUG DELIVERY SYSTEM; DRUG STABILITY; LIGHT SCATTERING; MASS SPECTROMETRY; MICELLE; NANOTECHNOLOGY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0038499320     PISSN: 09277765     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0927-7765(03)00125-5     Document Type: Article

References (37)

1. Tuzar Z., Kratochvil P. Block and graft copolymer micelles in solution. Adv. Colloid Interface Sci. 6:1976;201-232.
2. Kwon G.S., Kataoka K. Block-copolymer micelles as long-circulating drug vehicles. Adv. Drug Deliv. Rev. 16:1995;295-309.
3. Kataoka K., Kwon G.S., Yokoyama M., Okano T., Sakurai Y. Block copolymer micelles as vehicles for drug delivery. J. Controlled Release. 24:1993;119-132.
4. Allen C., Maysinger D., Eisenberg A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf. B. 16:1999;3-27.
5. Yamamoto Y., Nagasaki Y., Kato Y., Sugiyama Y., Kataoka K. Long-circulating poly(ethylene glycol)-poly(D,L-lactide) block copolymer micelles with modulated surface charge. J. Controlled Release. 77:2001;27-38.
6. Kabanov A.V., Chekhonin V.P., Alakhov V.Y., Betrakova E.V., Lebedev A.S., Melik-Nubarov N.S., Arzhakov S., Levashov A.V., Morozov G.V., Severin E.S., Kabanov V.A. The neuroleptic activity of haloperidol increases after its solubilization in surfactant micelles-micelles as microcontainers for drug targeting. FEBS Lett. 258:1989;343-345.
7. Hagan Ha S.A., Coombes A.G., Garnett M.C., Dunn S.E., Davies M.C., Illum L., Davis S.S., Harding S.E., Purkiss S., Gellert P.R. Polylactide-poly(ethylene glycol) copolymers as drug delivery systems. I. Characterization of water dispersible micelle-forming systems. Langmuir. 12:1996;2153-2161.
8. Inoue T., Chen G., Nakamae K., Hoffman S.A. An AB block copolymer of oligo (methylmethacrylate) and poly(acrylic acid) for micellar delivery of hydrophobic drugs. J. Controlled Release. 51:1998;221-229.
9. Abuchowski A., van Es T., Palczuk N.C., McCoy J.R., Davis F.F. Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase. J. Biol. Chem. 252:1977;3582-3586.
10. Shin I.G., Kim S.Y., Lee Y.M., Cho C.S., Sung Y.K. Methoxy poly(ethylene glycol) ε-caprolactone amphiphilic block copolymeric micelle containind indomethacin. I. Preparation and characterization. J. Controlled Rel. 51:1998;1-11.
11. Miller D.W., Batrakova E.V., Waltner T.O., Alakhov V.Y., Kabanov A.V. Interactions of pluronic block copolymers with brain microvessel endothelial cells: evidence of two potential pathways for drug absorption. Bioconjugate Chem. 8:1997;649-657.
12. Yokoyama M., Miyauchi M., Yamada N., Okano T., Sakurai Y., Kataoka K., Inoue S. Characterization and anticancer activity of the micelle-forming polymeric anticancer drug adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer. Cancer Res. 50:1990;1693-1700.
13. Kataoka K., Matsumoto T., Yokoyama M., Okano T., Sakurai Y., Fukushima S., Okamoto K., Kwon G.S. Doxorubicin-loaded poly(ethylene glycol)-poly(β-benzyl-L-aspartate) copolymer micelles: their pharmaceutical characterization and biological significance. Control. Release. 64:2000;143-153.
14. Jeong Y.I., Cheon J.B., Kim S.H., Nah J.W., Lee Y.M., Sung Y.K., Akaike T., Cho C.S. Clonazepam release from core-shell type nanoparticles in vitro. J. Controlled Release. 51:1998;169-178.
15. Harada A., Togawa H., Kataoka K. Physicochemical properties and nuclease resistance of antisense-oligodeoxynucleotides entrapped in the core of polyion complex micelles composed of poly(ethylene glycol)-poly(L-lysine) block copolymers. Eur. J. Pharm. Sci. 13:2001;35-42.
16. Fields C.G., Lloyd D.H., Macdonald R.L., Otteson K.M., Noble R.L. HBTU activation for automated Fmoc solid-phase peptide synthesis. Peptide Res. 4:1991;95-101.
17. Kaiser E., Colescott R.L., Bossinger C.D., Cook P.I. Color test for detection of free terminal amino groups in the solid phase synthesis of peptides. Anal. Biochem. 34:1970;595-598.
18. Tancrede P., Barwicz J., Jutras S., Gruda I.B. The effect of surfactants on the aggregation state of amphotericin B. Biochim. Biophys. Acta. 1030:1990;289-295.
19. Li Y., Kwon G.S. Micelle-like structures of poly(ethylene oxide)-block-poly(2-hydroxyethylaspartamide)-methotrexate conjugates. Colloids Surf. B. 16:1999;217-226.
20. Kwon G.S., Naito M., Yokoyama M., Okano T., Sakurai Y., Kataoka K. Entrapment of adriamycin in ab block copolymer micelles. Pharm. Res. 12:1995;200-203.
21. Pechar M., Ulbrich K., Subr V., Seymour L.W., Schacht E.H. Poly(ethylene glycol) multiblock copolymer as a carrier of the anticancer drug doxorubicin. Bioconjugate Chem. 11:2000;131-139.
22. Onuchic J., Luthey-Schulten Z., Wolynes P. Theory of protein folding: the energy landscape perspective. Ann. Rev. Phys. Chem. 48:1997;545-600.
23. α-pegylated peptides using Fmoc strategy. Peptide Res. 6:1993;140-146.
24. Munch M., Gast A. Block copolymers at interfaces. I. Micelle formation. Macromolecules. 21:1988;1360-1366.
25. Alexandridis P., Hatton T.A. Poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block-copolymer surfactants in aqueous solution and at interfaces - thermodynamics, structure, dynamics and modeling. Colloids Surf. A. 96:1995;1-46.
26. Kwon G.S., Naito M., Yokoyama M., Okano T., Sakurai Y., Kataoka K. Micelles based on AB block copolymers of poly(ethylene oxide) and poly(β-benzyl-L-aspartate). Langmuir. 9:1993;945-949.
27. La S., Okano T., Kataoka K. Preparation and characterization of the micelle-forming polymeric drug indomethacin-incorporated poly(ethylene oxide)-poly(β-benzyl-L-aspartate). J. Pharm. Sci. 85:1996;85-90.
28. Lavasanifar A., Samuel J., Kwon G.S. The effect of alkyl core structure on micellar properties of poly(ethylene oxide)-block-poly(L-aspartamide) derivatives. Colloids Surf. B. 22:2001;115-126.
29. Fauchere J.L., Pliska V. Hydrophobic parameters-π of amino acid side-chains from the partitioning of N-acetyl aminoacid amides. Eur. J. Med. Chem. 18:1983;369-375.
30. Chothia C. Nature of accessible and buried surfaces in proteins. J. Mol. Biol. 105:1976;1-12.
31. Cammas S., Harada A., Nagasaki Y., Kataoka K. Poly(ethylene oxide-co-β-benzyl-L-aspartate) block copolymers: influence of the poly(ethylene oxide) block on the conformation of the poly(β-benzyl-L-aspartate) segment in organic solvents. Macromolecules. 23:1996;3227-3231.
32. Harada A., Cammas S., Kataoka K. Stabilized a-helix structure of poly(L-lysine)-block-poly(ethylene glycol) in aqueous medium through supramolecular assembly. Macromolecules. 29:1996;6183-6188.
33. Kwon G.S., Naito M., Yokoyama M., Okano T., Sakrai Y., Kataoka K. Black copolymer micelles for drug delivery: loading and release of doxorubicin. J. Controlled Release. 48:1997;195-201.
34. Cao T., Munk P., Ramireddy C., Tuzar Z., Webber S.E. Fluorescence studies of amphiphilic poly(methacrylic acid)-block-polystyrene-block-poly(methacrylic acid) micelles. Macromolecules. 24:1991;6300-6305.
35. Zareie H.M., Kaitian X., Piskin E. STM images of PDLLA-PEG copolymer micelles. Colloids Surf. A. 112:1996;19-24.
36. Halperin A., Alexander S. Polymeric micelles - their relaxation kinetics. Macromolecules. 22:1989;2403-2412.
37. Nakamura K., Endo R., Takeda M. Study of molecular-motion of block copolymers in solution by high-resolution proton magnetic resonance. J. Polym. Sci. Part B: Polym. Phys. 15:1977;2095-2101.