Diels-Alder hydrogels with enhanced stability: First step toward controlled release of bevacizumab

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 96, Issue , 2015, Pages 217-225

  Kirchhof, Susanne ^a   Gregoritza, Manuel ^a   Messmann, Viktoria ^a   Hammer, Nadine ^a   Goepferich, Achim M ^a   Brandl, Ferdinand P ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Bevacizumab; Controlled release; Degradation; Diels Alder reaction; Hydrogel; Poly(ethylene glycol)

Indexed keywords

AMINOCAPROIC ACID; BEVACIZUMAB; LYSINE; MALEIMIDE; MONOMER; ANGIOGENESIS INHIBITOR; DELAYED RELEASE FORMULATION; FURAN DERIVATIVE; HYDROGEL; MACROGOL DERIVATIVE; MALEIMIDE DERIVATIVE; VASCULOTROPIN;

ARTICLE; CONTROLLED DRUG RELEASE; DIELS ALDER REACTION; DRUG DEGRADATION; DRUG STABILITY; FLOW KINETICS; GELATION; HYDROGEL; HYDROLYSIS; HYDROPHOBICITY; KINETICS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; ADMINISTRATION AND DOSAGE; ANALYSIS; ANTAGONISTS AND INHIBITORS; CHEMICAL PHENOMENA; CHEMISTRY; COMPARATIVE STUDY; DELAYED RELEASE FORMULATION; DRUG FORMULATION; DRUG RELEASE; DRUG STORAGE; POROSITY; PROTEIN STABILITY; VISCOSITY;

ANGIOGENESIS INHIBITORS; BEVACIZUMAB; DELAYED-ACTION PREPARATIONS; DRUG COMPOUNDING; DRUG LIBERATION; DRUG STABILITY; DRUG STORAGE; FURANS; HYDROGELS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; MALEIMIDES; POLYETHYLENE GLYCOLS; POROSITY; PROTEIN STABILITY; VASCULAR ENDOTHELIAL GROWTH FACTORS; VISCOSITY;

EID: 84939502781     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2015.07.024     Document Type: Article

References (35)

1. M.S. Ip, I.U. Scott, G.C. Brown, M.M. Brown, A.C. Ho, S.S. Huang, and et al. Anti-vascular endothelial growth factor pharmacotherapy for age-related macular degeneration Ophthalmology 115 2008 1837 1846 10.1016/j.ophtha.2008.08.012
2. A.C. Ho, I.U. Scott, S.J. Kim, G.C. Brown, M.M. Brown, M.S. Ip, and et al. Anti-vascular endothelial growth factor pharmacotherapy for diabetic macular edema Ophthalmology 119 2012 2179 2188 10.1016/j.ophtha.2012.07.058
3. D. Schweizer, T. Serno, and A.M. Goepferich Controlled release of therapeutic antibody formats Eur. J. Pharm. Biopharm. 88 2014 291 309 10.1016/j.ejpb.2014.08.001
4. K.M. Sampat, and S.J. Garg Complications of intravitreal injections Cur. Opin. Ophthalmol. 21 2010 178 183 10.1097/ICU.0b013e328338679a
5. C.-C. Lin, and K.S. Anseth PEG hydrogels for the controlled release of biomolecules in regenerative medicine Pharm. Res. 26 2009 631 643 10.1007/s11095-008-9801-2
6. T. Vermonden, R. Censi, and W.E. Hennink Hydrogels for protein delivery Chem. Rev. 112 2012 2853 2888 10.1021/cr200157d
7. S. Kirchhof, F.P. Brandl, N. Hammer, and A.M. Goepferich Investigation of the Diels-Alder reaction as a cross-linking mechanism for degradable poly(ethylene glycol) based hydrogels J. Mater. Chem. B 1 2013 4855 4864 10.1039/c3tb20831a
8. S. Kirchhof, A. Strasser, H.-J. Wittmann, V. Messmann, N. Hammer, A.M. Goepferich, and et al. New insights into the cross-linking and degradation mechanism of Diels-Alder hydrogels J. Mater. Chem. B 3 2015 449 457 10.1039/C4TB01680G
9. J.J. Kang, and W.F. Derwent Mieler Thermoresponsive hydrogels as a new ocular drug delivery platform to the posterior segment of the eye Trans. Am. Ophthalmol. Soc. 106 2008 206 214
10. S.B. Turturro, M.J. Guthrie, A.A. Appel, P.W. Drapala, E.M. Brey, V.H. Pérez-Luna, and et al. The effects of cross-linked thermo-responsive PNIPAAm-based hydrogel injection on retinal function Biomaterials 32 2011 3620 3626 10.1016/j.biomaterials.2011.01.058
11. B.M. Rauck, T.R. Friberg, C.A. Medina Mendez, D. Park, V. Shah, R.A. Bilonick, and et al. Biocompatible reverse thermal gel sustains the release of intravitreal bevacizumab in vivo Invest. Ophthalmol. Vis. Sci. 55 2014 469 476 10.1167/iovs.13-13120
12. S. Matsui, and H. Aida Hydrolysis of some N-alkylmaleimides J. Chem. Soc., Perkin Trans. 2 1978 1277 1280 10.1039/P29780001277
13. C.P. Ryan, M.E.B. Smith, F.F. Schumacher, D. Grohmann, D. Papaioannou, G. Waksman, and et al. Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis Chem. Commun. 47 2011 5452 10.1039/c1cc11114k
14. R.I. Nathani, V. Chudasama, C.P. Ryan, P.R. Moody, R.E. Morgan, R.J. Fitzmaurice, and et al. Reversible protein affinity-labelling using bromomaleimide-based reagents Org. Biomol. Chem. 11 2013 2408 2411 10.1039/C3OB40239H
15. R.P. Lyon, J.R. Setter, T.D. Bovee, S.O. Doronina, J.H. Hunter, M.E. Anderson, and et al. Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates Nat. Biotechnol. 32 2014 1059 1062 10.1038/nbt.2968
16. C.M. Nimmo, and M.S. Shoichet Regenerative biomaterials that "click": simple, aqueous-based protocols for hydrogel synthesis, surface immobilization, and 3D patterning Bioconj. Chem. 22 2011 2199 2209 10.1021/bc200281k
17. C.M. Nimmo, S.C. Owen, and M.S. Shoichet Diels-Alder click cross-linked hyaluronic acid hydrogels for tissue engineering Biomacromolecules 12 2011 824 830 10.1021/bm101446k
18. X. Liu, P. Du, L. Liu, Z. Zheng, X. Wang, T. Joncheray, and et al. Kinetic study of Diels-Alder reaction involving in maleimide-furan compounds and linear polyurethane Polym. Bull. 70 2013 2319 2335 10.1007/s00289-013-0954-8
19. G.M. Kavanagh, and S.B. Ross-Murphy Rheological characterisation of polymer gels Prog. Polym. Sci. 23 1998 533 562 10.1016/S0079-6700(97)00047-6
20. S.K. Li, M.R. Liddell, and H. Wen Effective electrophoretic mobilities and charges of anti-VEGF proteins determined by capillary zone electrophoresis J. Pharm. Biomed. Anal. 55 2011 603 607 10.1016/j.jpba.2010.12.027
21. N. Hammer, F.P. Brandl, S. Kirchhof, V. Messmann, and A.M. Goepferich Protein compatibility of selected cross-linking reactions for hydrogels Macromol. Biosci. 15 2015 405 413 10.1002/mabi.201400379
22. A.P. Chapman PEGylated antibodies and antibody fragments for improved therapy: a review Adv. Drug Deliv. Rev. 54 2002 531 545 10.1016/S0169-409X(02)00026-1
23. M. Abrishami, S. Zarei-Ghanavati, D. Soroush, M. Rouhbakhsh, M.R. Jaafari, and B. Malaekeh-Nikouei Preparation, characterization, and in vivo evaluation of nanoliposomes-encapsulated bevacizumab (avastin) for intravitreal administration Retina 29 2009 699 703 10.1097/IAE.0b013e3181a2f42a
24. J.S. Andrew, E.J. Anglin, E.C. Wu, M.Y. Chen, L. Cheng, W.R. Freeman, and et al. Sustained release of a monoclonal antibody from electrochemically prepared mesoporous silicon oxide Adv. Funct. Mater. 20 2010 4168 4174 10.1002/adfm.201000907
25. F. Li, B. Hurley, Y. Liu, B. Leonard, and M. Griffith Controlled release of bevacizumab through nanospheres for extended treatment of age-related macular degeneration Open Ophthalmol. J. 6 2012 54 58 10.2174/1874364101206010054
26. C.K. Pan, C. Durairaj, U.B. Kompella, O. Agwu, S.C.N. Oliver, H. Quiroz-Mercado, and et al. Comparison of long-acting bevacizumab formulations in the treatment of choroidal neovascularization in a rat model J. Ocul. Pharmacol. Ther. 27 2011 219 224 10.1089/jop.2010.0158
27. P. Tyagi, M. Barros, J.W. Stansbury, and U.B. Kompella Light-activated, in situ forming gel for sustained suprachoroidal delivery of bevacizumab Mol. Pharm. 10 2013 2858 2867 10.1021/mp300716t
28. C.-H. Wang, Y.-S. Hwang, P.-R. Chiang, C.-R. Shen, W.-H. Hong, and G.-H. Hsiue Extended release of bevacizumab by thermosensitive biodegradable and biocompatible hydrogel Biomacromolecules 13 2012 40 48 10.1021/bm2009558
29. X. Xu, Y. Weng, L. Xu, and H. Chen Sustained release of Avastin® from polysaccharides cross-linked hydrogels for ocular drug delivery Int. J. Biol. Macromol. 60 2013 272 276 10.1016/j.ijbiomac.2013.05.034
30. J. Yu, X. Xu, F. Yao, Z. Luo, L. Jin, B. Xie, and et al. In situ covalently cross-linked PEG hydrogel for ocular drug delivery applications Int. J. Pharm. 470 2014 151 157 10.1016/j.ijpharm.2014.04.053
31. Y. Yu, and Y. Chau Formulation of in situ chemically cross-linked hydrogel depots for protein release: from the blob model perspective Biomacromolecules 16 2015 56 65 10.1021/bm501063n
32. Y. Yu, L.C.M. Lau, A.C.-Y. Lo, and Y. Chau Injectable chemically crosslinked hydrogel for the controlled release of bevacizumab in vitreous: a 6-month in vivo study Trans. Vis. Sci. Technol. 4 2015 5 10.1167/tvst.4.2.5
33. J. Qu, D. Wang, and C.L. Grosskreutz Mechanisms of retinal ganglion cell injury and defense in glaucoma Exp. Eye Res. 91 2010 48 53 10.1016/j.exer.2010.04.002
34. S.E. Quaggin Turning a blind eye to anti-VEGF toxicities J. Clin. Invest. 122 2012 3849 3851 10.1172/JCI65509
35. K.M. Ford, M. Saint-Geniez, T.E. Walshe, and P.A. D'Amore Expression and role of VEGF-A in the ciliary body Invest. Ophthalmol. Vis. Sci. 53 2012 7520 7527 10.1167/iovs.12-10098