PH-responsive, dynamically restructuring hydrogels formed by reversible crosslinking of PVA with phenylboronic acid functionalised PPO-PEO-PPO spacers (Jeffamines®)

Soft Matter

Volumn 7, Issue 23, 2011, Pages 11111-11118

  Piest, Martin ^a   Zhang, Xiaolin ^a   Trinidad, Jeffrey ^a   Engbersen, Johan F J ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; BORONIC ESTERS; CROSS-LINKERS; CROSSLINKS; END-GROUPS; GEL PROPERTIES; GEL STRENGTHS; JEFFAMINES; PH RANGE; PH-RESPONSIVE; PHENYLBORONIC ACIDS; PPO-PEO-PPO; REDUCTIVE COUPLINGS; REVERSIBLE CROSSLINKING; REVERSIBLE FORMATION; SECONDARY AMINO GROUP; SELF-HEALING;

ALKALINITY; ESTERIFICATION; ESTERS; GELS; HYDROGELS; MOLECULAR STRUCTURE; PH EFFECTS;

ORGANIC ACIDS;

EID: 81355135354     PISSN: 1744683X     EISSN: 17446848     Source Type: Journal    
DOI: 10.1039/c1sm06230a     Document Type: Article

References (29)

1. P. Gupta K. Vermani S. Garg Hydrogels: from controlled release to pH-responsive drug delivery Drug Discovery Today 2002 7 569
2. A. S. Hoffman Hydrogels for biomedical applications Adv. Drug Delivery Rev. 2002 54 3
3. N. A. Peppas P. Bures W. Leobandung H. Ichikawa Hydrogels in pharmaceutical formulations Eur. J. Pharm. Biopharm. 2000 50 27
4. N. A. Peppas J. Z. Hilt A. Khademhosseini R. Langer Hydrogels in biology and medicine: from molecular principles to bionanotechnology Adv. Mater. 2006 18 1345
5. G. H. Deng C. M. Tang F. Y. Li H. F. Jiang Y. M. Chen Covalent cross-linked polymer gels with reversible sol-gel transition and self-healing properties Macromolecules 2010 43 1191
6. M. C. Roberts M. C. Hanson A. P. Massey E. A. Karren P. F. Kiser Dynamically restructuring hydrogel networks formed with reversible covalent crosslinks Adv. Mater. 2007 19 2503
7. S. J. Rowan S. J. Cantrill G. R. L. Cousins J. K. M. Sanders J. F. Stoddart Dynamic covalent chemistry Angew. Chem., Int. Ed. 2002 41 898
8. A. South L. Lyon Autonomic self-healing of hydrogel thin films Angew. Chem., Int. Ed. 2010 49 767
9. D. G. Hall, Boronic Acids - Preparation and Applications in Organic Synthesis and Medicine, John Wiley & Sons, 2005
10. T. D. James Saccharide-selective boronic acid based photoinduced electron transfer (PET) fluorescent sensors Top. Curr. Chem. 2007 277 107
11. A. E. Ivanov H. Larsson I. Y. Galaev B. Mattiasson Synthesis of boronate-containing copolymers of N,N-dimethylacrylamide, their interaction with poly(vinyl alcohol) and rheological behaviour of the gels Polymer 2004 45 2495
12. S. Kitano K. Kataoka Y. Koyama T. Okano Y. Sakurai Glucose-responsive complex-formation between poly(vinyl alcohol) and poly(N-vinyl-2-pyrrolidone) with pendent phenylboronic acid moieties Makrom. Chem., Rapid Commun. 1991 12 227
13. M. C. Roberts A. Mahalingam M. C. Hanson P. F. Kiser Chemorheology of phenylboronate-salicylhydroxamate cross-linked hydrogel networks with a sulfonated polymer backbone Macromolecules 2008 41 8832
14. H. Duel H. Neukom Uber die Reaktion von Borsaure und Borax mit Polysacchariden und anderen hochmolekularen Polyoxy-verbindungen Makromol. Chem. 1949 3 13
15. E. Pezron L. Leibler A. Ricard F. Lafuma R. Audebert Complex-formation in polymer ion solutions 1. Polymer concentration effects Macromolecules 1989 22 1169
16. S. W. Sinton Complexation chemistry of sodium-borate with poly(vinyl-alcohol) and small diols - a B-11 NMR-study Macromolecules 1987 20 2430
17. W. Agut A. Brulet D. Taton S. Lecommandoux Thermoresponsive micelles from Jeffamine-b-poly(L-glutamic acid) double hydrophilic block copolymers Langmuir 2007 23 11526
18. S. L. Wiskur J. J. Lavigne H. Ait-Haddou V. Lynch Y. H. Chiu J. W. Canary E. V. Anslyn pK(a) values and geometries of secondary and tertiary amines complexed to boronic acids - implications for sensor design Org. Lett. 2001 3 1311
19. G. Springsteen B. H. Wang Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates Chem. Commun. 2001 17 1608 1609 (Pubitemid 32808017)
20. G. Springsteen B. H. Wang A detailed examination of boronic acid-diol complexation Tetrahedron 2002 58 5291
21. P. Abiman G. G. Wildgoose A. Crossley J. H. Jones R. G. Compton Contrasting pK(a) of protonated bis(3-aminopropyl)-terminated polyethylene glycol "Jeffamine" and the associated thermodynamic parameters in solution and covalently attached to graphite surfaces Chem.-Eur. J. 2007 13 9663
22. J. Yan G. Springsteen S. Deeter B. H. Wang The relationship among pK(a), pH, and binding constants in the interactions between boronic acids and diols - it is not as simple as it appears Tetrahedron 2004 60 11205
23. H. R. Mulla N. J. Agard A. Basu 3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH Bioorg. Med. Chem. Lett. 2004 14 25
24. M. Bishop N. Shahid J. Z. Yang A. R. Barron Determination of the mode and efficacy of the cross-linking of guar by borate using MAS B-11 NMR of borate cross-linked guar in combination with solution B-11 NMR of model systems Dalton Trans. 2004 2621
25. R. G. Loughlin M. M. Tunney R. F. Donnelly D. F. Murphy M. Jenkins P. A. McCarron Modulation of gel formation and drug-release characteristics of lidocaine-loaded poly(vinyl alcohol)-tetraborate hydrogel systems using scavenger polyol sugars Eur. J. Pharm. Biopharm. 2008 69 1135
26. G. Wulff Selective binding to polymers via covalent bonds - the construction of chiral cavities as specific receptor-sites Pure Appl. Chem. 1982 54 2093
27. S. Iwatsuki S. Nakajima M. Inamo H. D. Takagi K. Ishihara Which is reactive in alkaline solution, boronate ion or boronic acid? Kinetic evidence for reactive trigonal boronic acid in an alkaline solution Inorg. Chem. 2007 46 354
28. M. Rietjens P. A. Steenbergen Crosslinking mechanism of boric acid with diols revisited Eur. J. Inorg. Chem. 2005 1162
29. C. Miyamoto K. Suzuki S. Iwatsuki M. Inamo H. D. Takagi K. Ishihara Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols Inorg. Chem. 2008 47 1417