Multimeric, multifunctional derivatives of poly(ethylene glycol)

Polymers

Volumn 3, Issue 3, 2011, Pages 1076-1090

  Zacchigna, Marina ^a   Cateni, Francesca ^a   Drioli, Sara ^a   Bonora, Gian Maria ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Conjugation; Drug delivery; Multifunctional polymers; Poly(ethylene glycol)

Indexed keywords

ACTIVE DRUGS; CONJUGATION; DRUG DELIVERY SYSTEM; HIGH MOLECULAR WEIGHT; MULTIFUNCTIONAL POLYMER; MULTIMERIC;

DENDRIMERS; DRUG DELIVERY; ETHYLENE; FUNCTIONAL POLYMERS; GLYCOLS;

POLYETHYLENE GLYCOLS;

EID: 83655182342     PISSN: None     EISSN: 20734360     Source Type: Journal    
DOI: 10.3390/polym3031076     Document Type: Review

References (57)

1. Davis, F.F. The origin of PEGnology. Adv. Drug Deliv. Rev. 2007, 54, 457-458.
2. Maeda, H.; Seymour, L.W.; Miyamoto, Y. Conjugates of anticancer agents and polymers: Advantages of macromolecular therapeutics in vivo. Bioconjug. Chem. 2007, 3, 351-362.
3. Harris, J.M.; Chess, R.B. Effect of pegylation on pharmaceuticals. Nat. Rev. 2003, 2, 214-221.
4. Maeda, H.; Wu, J.; Sawa, T.; Matsumura, Y.; Hori, K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: A review. J. Control. Release 2000, 65, 271-284.
5. Yamaoka, T.; Tabata, Y.; Ikada, Y. Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. J. Pharm. Sci. 1994, 83, 601-606.
6. Yamaoka, T.; Tabata, Y.; Ikada, Y. Fate of water-soluble polymers administered via different routes. J. Pharm. Sci. 1995, 84, 349-354.
7. Bentley, M.D.; Harris, J.M.; Kozlowski, A. Heterobifunctional Polyethylene Glycol Derivatives and Methods for Their Preparation. U.S. Patent 2,010,063,328, 11 March 2010.
8. Pasut, G.; Veronese, F.M. Polymer-drug conjugation, recent achievements and general strategies. Prog. Polym. Sci. 2007, 32, 933-961.
9. Kopecek, J.; Kopeckova, P.; Minko, T.; Lu, Z. HPMA copolymer-anticancer drug conjugates: Design, activity, and mechanism of action. Eur. J. Pharm. Biopharm. 2000, 50, 61-81.
10. Li, C. Poly(L-glutamic acid)-anticancer drug conjugates poly(L-glutamic acid)-anticancer drug conjugates. Adv. Drug Delivery Rev. 2002, 54, 695-713.
11. Choe, Y.H.; Conover, C.D.; Wu, D.; Royzen, M.; Gervacio, Y; Borowski, V. Anticancer drug delivery systems: Multiloaded N4-acyl poly(ethylene glycol) prodrugs of ara-C: II. Efficacy in ascites and solid tumors. J. Control Release 2002, 79, 55-70.
12. Pasut, G.; Scaramuzza, S.; Schiavon, O.; Mendichi, R.; Veronese, F.M. PEG-epirubicin conjugates with high loading. J. Bioac. Comp. Pol. 2005, 20, 13-30.
13. Berna, M.; Dalzoppo, D.; Pasut, G.; Manunta, M.; Izzo, L.; Jones, A.T. Novel monodisperse PEG-dendrons as new tools for targeted drug delivery: Synthesis, characterization and cellular uptake. Biomacromolecules 2006, 7, 146-153.
14. Gajbhiye, V.; Kumar, P.V.; Tekade, R.K.; Jain, N.K. Pharmaceutical and biomedical potential of PEGylated dendrimers. Curr. Pharm. Des. 2004, 13, 415-429.
15. Nathan, A.; Zalipsky, S.; Kohn, J. Strategies for covalent attachment of doxorubicin to PEG. J. Bioact. Compat. Polym. 1994, 9, 239-251.
16. Pechar, M.; Ulbrich, K.; Subr, V.; Seymour, L.W.; Schacht, E.H. Poly(ethylene glycol) multiblock copolymer as a carrier of anti-cancer drug doxorubicin. Bioconjugate Chem. 2000, 11, 131-139.
17. Cheng, J.; Khin, K.T.; Jensen, G.S.; Liu, A.; Davis, M.E. Synthesis of linear, β-Cyclodextrin-based polymers and their camptothecin conjugates. Bioconjugate Chem. 2003, 14, 1007-1017.
18. Kumar, R.; Chen, M.H.; Parmar, V.S.; Samuelson, L.A.; Kumar, J.; Nicolosi, R.; Yoganathan, S.; Watterson. A.C. Supramolecular assemblies based on copolymers of PEG600 and functionalized aromatic diesters for drug delivery applications. J. Am. Chem. Soc. 2004, 126, 10640-10644.
19. De Jesus, O.L.P.; Ihre, H.R.; Gagne, L.; Fréchet, J.M.L.; Szoka, F.C. Olyester dendritic system for drug delivery applications: In vitro and in vivo evaluations. Bioconjugate Chem. 2002, 13, 453-461.
20. Gillies, E.R.; Fréchet, J.M.L. Designing macromolecules for therapeutic applications: Polyester dendrimer-poly(ethylene oxide) "bow-tie" hybrids with tunable molecular weight and architecture. J. Am. Chem. Soc. 2002, 124, 14137-14146.
21. Giullaudeu, S.J.; Fox, E.M.; Haidar, Y.M.; Dy, E.; Szoka, F.C.; Fréchet, J.M.L. PEGylated dendrimers with core functionality for biological applications. Bioconjugate Chem. 2008, 19, 461-469.
22. Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Ressel, S. Synthesis of new poly(ethyleneglycol)s with a high loading capacity. J. Org. Chem. 1998, 63, 8628-8629.
23. Reed, N.N.; Janda, K.D. Steath star polymers: A new high-loading scaffold for liquid-phase organic synthesis. Org. Lett. 2000, 2, 1311-1313.
24. Guiotto, A.; Pozzobon, M.; Sanavio, C.; Schiavon, O.; Orsolini, P.; Veronese, F.M. An improved procedure for the synthesis of branched polyethylene glycols (PEGs) with the reporter dipeptide Met-beta Ala for protein conjugation. Bioorg. Med. Chem. Lett. 2002, 12, 177-180.
25. Monfardini, C.; Schiavon, O.; Caliceti, P.; Morpurgo, M.; Harris, M.J.; Veronese, F.M. A branched monomethoxypoly(ethylene glycol) for protein modification. Bioconjugate Chem. 1995, 6, 62-69.
26. Harris, J.M.; Veronese, F.M.; Caliceti, P.; Schiavon, O. Multiarmed, Monofunctional Polymer for Coupling to Molecules and Surfaces. U.S. Patent 5,932,462, 3 August 1999.
27. Fishman, M.; Farrah, E.; Zhong, J.H.; Paramanantham, S.; Carrera, C.; Lee-Ruff, E. Synthesis and investigation of novel branched PEG-based soluble polymer supports. J. Org. Chem. 2003, 68, 9843-9846.
28. Gillies, E.R.; Fréchet, J.M. Dendrimers and dendritic polymers in drug delivery. Drug Discov. Today 2005, 10, 35-43.
29. Haag, R.; Sunder, A.; Stumbé, J.F. An approach to glycerol dendrimers and pseudo-dendritic polyglycerols. J. Am. Chem. Soc. 2000, 122, 2954-2955.
30. Ihe, H.; De Jesús, O.L.P.; Fréchet, J.M. Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling. J. Am. Chem. Soc. 2001, 123, 5908-5917.
31. Sunder, A.; Mülhaupt, R.; Haag, R.; Frey, H. Chiral hyperbranched dendron-analogs. Macromolecules 2000, 33, 253-254.
32. Liu, X.M.; Thakur, A.; Wang, D. Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. Biomacromolecules 2007, 8, 2653-2658.
33. Ballico, M.; Drioli, S.; Bonora, G.M. MultiPEG: High molecular weight multifunctional poly(ethylen glycol)s assembled by a dendrimer-like approach. Eur. J. Org. Chem. 2005, 2005, 2064-2073.
34. Zacchigna, M.; Di Luca, G.; Cateni, F.; Maurich, V.; Ballico, M.; Bonora, G.M.; Drioli, S. New MultiPEG-conjugated theophylline derivatives: Synthesis and pharmacological evaluations. Eur. J. Pharm. Sci. 2007, 30, 343-350.
35. Drioli, S.; Bonora, G.M.; Ballico, M. Synthesis and characterization of new multifunctional high-molecular weight PEG derivatives (MultiPEG)s. Open Org. Chem. J. 2008, 2, 17-25.
36. Chabot, G.G. Clinical pharmacokinetics of irinotecan. Clin. Pharmacokinet. 1997, 33, 245-259.
37. Zhang, J.A.; Xuan, T.; Parmar, M.; Ma, L.; Ugwu, S.; Ali, S.; Ahmad, I. Development and characterization of a novel liposome-based formulation of SN-38. Int. J. Pharm. 2004, 270, 93-107.
38. Zhao, H.; Rubio, B.; Sapra, P.; Wu, D.; Reddy, P.; Sai, P.; Martinez, A.; Gao, Y.; Lozanguiez, Y.; Longley, C.; et al. Novel prodrugs of SN38 using multiarm poly(ethylene glycol) linkers. Bioconjugate Chem. 2008, 19, 849-859.
39. Johnson, J.A.; Finn, M.G.; Koberstein, J.T.; Turro, N.J. Construction of linear polymers, dendrimers, networks, and other polymeric architectures by copper-catalyzed azide-alkyne cycloaddition "click" chemistry. Macromol. Rapid Commun. 2008, 29, 1052-1072.
40. Lee, B.P.; Dalsin, J.L.; Messersmith, P.B. Enzymatic and non-enzymatic pathways to formation of Dopa-modified PEG hydrogels. Polym. Prepr. 2001, 42, 151-152.
41. Bertuglia, S.; Veronese, F.M.; Pasut, G. Polyethylene glycol and a novel developed polyethylene glycol-nitric oxide normalize arteriolar response and oxidative stress in ischemia-reperfusion. Am. J. Physiol. Heart Circ. Physiol. 2006, 291, 1536-1544.
42. Schiavon, O.; Pasut, G.; Moro, S.; Orsolini, P.; Guiotto, A.; Veronese, F.M. PEG-Ara-C conjugates for controlled release. Eur. J. Med. Chem. 2004, 39, 123-133.
43. Bonora, G.M.; Drioli, S.; Ballico, M. Multifunctional Polyethylene Glycol Derivatives: Preparation and Use. WO 03/093346 A1, 13 November 2003.
44. Zacchigna, M.; Di Luca, G.; Cateni, F.; Zorzet, S.; Maurich, V. Improvement of physicochemical and biopharmaceutical properties of theophylline by poly(ethylene glycol) conjugates. Farmaco 2003, 58, 1307-1312.
45. Grassi, M.; Bonora, G.M.; Drioli, S.; Cateni, F.; Zacchigna, M. Pharmacokinetic analysis of multi PEG-theophylline conjugates. Biopharm. Drug Dispos. 2011, submitted.
46. Pasut, G.; Veronese, F.M. PEG conjugates in clinical development or use as anticancer agents: An overview. Adv. Drug Delivery Rev. 2009, 61, 1177-1188.
47. Yoo, H.S.; Park, T.G. Folate-receptor-targeted delivery of doxorubicin nano-aggregates stabilized by doxorubicin-PEG-folate conjugate. J. Control. Release 2004, 100, 247-256.
48. Canal, F.; Vicent, M.J.; Pasut, G.; Schiavon, O. Relevance of folic acid/polymer ratio in targeted PEG-epirubicin conjugates. J. Control. Release 2010, 146, 388-399.
49. Pasut, G.; Canal, F.; Dalla Via, L.; Arpicco, S.; Veronese, F.M.; Schiavon, O. Antitumoral activity of PEG-gemcitabine prodrugs targeted by folic acid. J. Control. Release 2008, 127, 239-248.
50. Thomas, M.; Klibanov, A. Conjugation to gold nanoparticles enhances polyethylenimine's transfer of plasmid DNA into mammalian cells. Proc. Natl. Acad. Sci. USA 2003, 100, 9138-9143.
51. Shenoy, D.; Fu, W.; Li, J.; Crasto, C.; Jones, G.; DiMarzio, C.; Sridhar, S.; Amiji, M. Surface functionalization of gold nanoparticles using hetero-bifunctional poly(ethylene glycol) spacer for intracellular tracking and delivery. Int. J. Nanomed. 2006, 1, 51-57.
52. Li, J.; Crasto, C.F.; Weinberg, J.S.; Amiji, M.; Shenoy, D.; Sridhar, S.; Bubley, G.J.; Jones, G.B. An approach to heterobifunctional poly(ethyleneglycol) bioconjugates. Bioorg. Med. Chem. Lett. 2005, 15, 5558-5561.
53. Sun, C.; Fang, C.; Stephen, Z.; Veiseh, O.; Hansen, S.; Lee, D.; Ellenbogen, R.G.; Olson, J.; Zhang, M. Tumor-targeted drug delivery and MRI contrast enhancement by chlorotoxin-conjugated iron oxide nanoparticles. Nanomedicine 2008, 3, 495-505.
54. Vaidya, A.; Sun, Y.; Feng, Y.; Emerson, L.; Jeong, E.; Lu, Z. Contrast-enhanced MRI-guided photodynamic cancer therapy with a PEGylated bifunctional polymer conjugate. Pharm. Res. 2008, 25, 2002-2011.
55. Lanciotti, J.; Song, A.; Doukas, J.; Sosnowski, B.; Pierce, G.; Gregory, R.; Wadsworth, S.; Riordan, C. Targeting adenoviral vectors using heterofunctional polyethylene Glicol FGF2 Conjugates. Mol. Ther. 2003, 8, 99-107.
56. Campaner, P.; Drioli, S.; Bonora, G.M. Synthesis of selectively end-modified high-molecular weight polyethylenglycol. Lett. Org. Chem. 2006, 10, 773-779.
57. Niculescu-Duvaz, D.; Getaz, J.; Springer, C.J. Long functionalized poly(ethylene glycol)s of defined molecula weight: Synthesis and application in solid-phase synthesis of conjugates. Bioconjugate Chem. 2008, 19, 973-981.