Swelling, Mechanics, and Thermal/Chemical Stability of Hydrogels Containing Phenylboronic Acid Side Chains
Abstract
:1. Introduction
2. Results
2.1. Equilibrium Swelling
2.2. Mechanics
2.3. Thermal Stability
3. Discussion
4. Conclusions
5. Materials and Methods
5.1. Synthesis of MPBA
5.2. p(AAm-co-MPBA) Hydrogels
5.3. Swelling Studies
5.4. Mechanical Measurements
5.5. Thermal Degradation
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Lorand, J.P.; Edwards, J.O. Polyol Complexes and Structure of Benzeneboronate Ion. J. Org. Chem. 1959, 24, 769–774. [Google Scholar] [CrossRef]
- James, T.D.; Sandanayake, K.; Shinkai, S. Saccharide sensing with molecular receptors based on boronic acid. Angew. Chem. Int. Ed. 1996, 35, 1911–1922. [Google Scholar] [CrossRef]
- Barker, S.A.; Hatt, B.W.; Sommers, P.J.; Woodbury, R.R. The use of poly(4-vinylbenzeneboronic acid) resin in the fractionation and interconversion of carbohydrates. Carbohydr. Res. 1973, 26, 55–64. [Google Scholar] [CrossRef]
- Koyama, T.; Terauchi, K. Synthesis and application of boronic acid-immobilized porous polymer particles: A novel packing for high-performance liquid affinity chromatography. J. Chromatogr. B Biomed. Appl. 1996, 679, 31–40. [Google Scholar] [CrossRef]
- Li, Y.; Jeppsson, J.O.; Jornten-Karlsson, M.; Linne Larsson, E.; Jungvid, H.; Galaev, I.Y.; Mattiasson, B. Application of shielding boronate affinity chromatography in the study of the glycation pattern of haemoglobin. J. Chromatogr. B 2002, 776, 149–160. [Google Scholar] [CrossRef]
- Kataoka, K. High-capacity cell separation by affinity selection on synthetic solid-phase matrices. In Cell Separation Science and Technology; Kompala, D.S., Todd, P., Eds.; American Chemical Society: Washington, DC, USA, 1991; pp. 159–174. [Google Scholar]
- Asher, S.A.; Alexeev, V.L.; Goponenko, A.V.; Sharma, A.C.; Lednev, I.K.; Wilcox, C.S.; Finegold, D.N. Photonic Crystal Carbohydrate Sensors: Low Ionic Strength Sugar Sensing. J. Am. Chem. Soc. 2003, 125, 3322–3329. [Google Scholar] [CrossRef] [PubMed]
- Alexeev, V.L.; Sharma, A.C.; Goponenko, A.V.; Das, S.; Lebedev, I.K.; Wilcox, C.S.; Finegold, D.N.; Asher, S.A. High Ionic Strength Glucose-Sensing Photonic Crystal. Anal. Chem. 2003, 75, 2316–2323. [Google Scholar] [CrossRef] [PubMed]
- Alexeev, V.; Das, S.; Finegold, D.; Asher, S. Photonic Crystal Glucose-Sensing Material for Noninvasive Monitoring of Glucose in Tear Fluid. Clin. Chem. 2004, 50, 2353–2360. [Google Scholar] [CrossRef] [PubMed]
- Muscatello, M.; Stunja, L.E.; Asher, S.A. Polymerized Crystalline Colloidal Array Sensing of High Glucose Concentration. Anal. Chem. 2009, 81, 4978–4986. [Google Scholar] [CrossRef] [PubMed]
- Kabilan, S.; Marshall, A.J.; Sartain, F.K.; Lee, M.-C.; Hussain, A.; Yang, X.; Blyth, J.; Karangu, N.; James, K.; Zeng, J.; et al. Holographic Glucose Sensors. Biosens. Bioelectron. 2005, 20, 1602–1610. [Google Scholar] [CrossRef] [PubMed]
- Yang, X.; Lee, M.-C.; Sartain, F.; Pan, X.; Lowe, C.R. Designed Boronate Ligands for Glucose-Selective Holographic Sensors. Chem. Eur. J. 2006, 12, 8491–8497. [Google Scholar] [CrossRef] [PubMed]
- Yang, X.; Pan, X.; Blyth, J.; Lowe, C.R. Towards the Real-time Monitoring of Glucose in Tear Fluid: Holographic Glucose Sensors with Reduced Interference from Lactate and pH. Biosens. Bioelectron. 2008, 23, 899–905. [Google Scholar] [CrossRef] [PubMed]
- Lin, G.; Chang, S.F.; Hao, H.; Tathireddy, P.; Orthner, M.; Magda, J.J.; Solzbacher, F. Osmotic Swelling Pressure Response of Smart Hydrogels Suitable for Chronically Implantable Glucose Sensors. Sens. Actuators B Chem. 2010, 144, 332–336. [Google Scholar] [CrossRef] [PubMed]
- Orthner, M.; Lin, G.; Avula, M.; Buetefisch, S.; Magda, J.J.; Rieth, L.W.; Solzbacher, F. Hydrogel Based Sensor Arrays (2 × 2) with Perforated Piezoresistive Diaphragms for Metabolic Monitoring (In Vitro). Sens. Actuators B Chem. 2010, 145, 807–816. [Google Scholar] [CrossRef] [PubMed]
- Horkay, F.; Cho, S.H.; Tathireddy, P.; Rieth, L.; Solzbacher, F.; Magda, J. Thermodynamic analysis of the selectivity enhancement obtained by using smart hydrogels that are zwitterionic when detecting glucose with boronic acid moieties. Sens. Actuators B Chem. 2011, 160, 1363–1371. [Google Scholar] [CrossRef] [PubMed]
- Baldi, A.; Lei, M.; Gu, Y.; Siegel, R.A.; Ziaie, B. A Microstructured Silicon Membrane with Entrapped Hydrogels for Environmentally Sensitive Fluid Gating. Sens. Actuators B Chem. 2006, 114, 9–18. [Google Scholar] [CrossRef] [Green Version]
- Lei, M.; Baldi, A.; Nuxoll, E.; Siegel, R.A.; Ziaie, B. A Hydrogel Based Implantable Micromachined Transponder for Wireless Glucose Measurement. Diabetes Technol. Ther. 2006, 8, 112–122. [Google Scholar] [CrossRef] [PubMed]
- Lei, M.; Ziaie, B.; Nuxoll, E.; Ivan, K.; Noszticzius, Z.; Siegel, R.A. Integration of Hydrogels with Hard and Soft Nanostructures. J. Nanosci. Nanotechnol. 2007, 7, 780–789. [Google Scholar] [CrossRef] [PubMed]
- Lei, M.; Baldi, A.; Nuxoll, E.E.; Siegel, R.A.; Ziaie, B. Hydrogel-Based Microsensors for Wireless pH Monitoring. Biomed. Microdevices 2009, 11, 529–538. [Google Scholar] [CrossRef] [PubMed]
- Siegel, R.A.; Gu, Y.; Lei, M.; Baldi, A.; Nuxoll, E.; Ziaie, B. Hard and Soft Micro- and Nanofabrication: An Integrated Approach to Hydrogel Based Sensing and Drug Delivery. J. Control. Release 2010, 141, 303–313. [Google Scholar] [CrossRef] [PubMed]
- Tierney, S.; Falch, B.M.; Hjelme, D.R.; Stokke, B.T. Determination of glucose levels using a functionalized hydrogel-optical fiber biosensor: Toward continuous monitoring of blood glucose in vivo. Anal. Chem. 2009, 81, 3630–3636. [Google Scholar] [CrossRef] [PubMed]
- Tierney, S.; Hjelme, D.R.; Stokke, B.T. Determination of Swelling of Responsive Gels with Nanometer Resolution. Fiber-Optic Based Platform for Hydrogels as Signal Transducers. Anal. Chem. 2008, 80, 5086–5093. [Google Scholar] [CrossRef] [PubMed]
- Tierney, S.; Volden, S.; Stokke, B.T. Glucose sensors based on a responsive gel incorporated as a Fabry-Perot cavity on a fiber-optic readout platform. Biosens. Bioelectron. 2009, 24, 2034–2039. [Google Scholar] [CrossRef] [PubMed]
- Kikuchi, A.; Suzuki, K.; Okabayashi, O.; Hoshino, H.; Kataoka, K.; Sakurai, Y.; Okano, T. Glucose-sensing electrode coated with polymer complex gel containing phenylboronic acid. Anal. Chem. 1996, 68, 823–828. [Google Scholar] [CrossRef] [PubMed]
- Matsumoto, A.; Sato, N.; Sakata, T.; Kataoka, K.; Miyahara, Y. Glucose-sensitive field effect transistor using totally synthetic compounds. J. Solid State Electrochem. 2009, 13, 165–170. [Google Scholar] [CrossRef]
- Lee, Y.-J.; Pruzinsky, S.A.; Braun, P.V. Glucose-Sensitive Inverse Hydrogel Opals: Analysis of Optical Diffraction Response. Langmuir 2004, 20, 3096–3106. [Google Scholar] [CrossRef] [PubMed]
- Zhang, C.; Losego, M.D.; Braun, P.V. Hydrogel-Based Glucose Sensors: Effects of Phenylboronic Acid Chemical Structure on Response. Chem. Mater. 2013, 25, 3239–3250. [Google Scholar] [CrossRef]
- Mesch, M.; Zhang, C.; Braun, P.V.; Giessen, H. Functionalized hydrogel on plamonic nanoantennas for noninvasive glucose sensing. ACS Photonics 2015, 2, 475–480. [Google Scholar] [CrossRef]
- Shibata, H.; Heo, Y.J.; Okitsu, T.; Matsunaga, Y.; Kawanishi, T.; Takeuchi, S. Injectable hydrogel microbeads for fluorescence-based in vivo coninuous glucose monitoring. Proc. Natl. Acad. Sci. USA 2010, 107, 17894–17898. [Google Scholar] [CrossRef] [PubMed]
- Hisamitsu, I.; Kataoka, K.; Okano, T.; Sakurai, Y. Glucose-responsive gel from phenylborate polymer and poly(vinyl alcohol): Prompt response at physiological pH through the interaction of borate with amino group in the gel. Pharm. Res. 1997, 14, 289–293. [Google Scholar] [CrossRef] [PubMed]
- Shiino, D.; Koyama, Y.; Kataoka, K.; Yokoyama, M.; Okano, T.; Sakurai, Y. Design of glucose responsive, insulin releasing device using polymers containing boronic acid groups. J. Artif. Organs 1992, 21, 1196–1198. [Google Scholar]
- Shiino, D.; Kataoka, K.; Koyama, Y.; Yokoyama, M.; Okano, T.; Sakurai, Y. A self-regulated insulin delivery system using boronic acid gel. J. Intell. Mater. Syst. Struct. 1994, 5, 311–314. [Google Scholar] [CrossRef]
- Baldi, A.; Gu, Y.; Loftness, P.; Siegel, R.A.; Ziaie, B. A Hydrogel-Actuated Environmentally-Sensitive Microvalve for Active Flow Control. IEEE J. Microelectromech. Syst. 2003, 12, 613–621. [Google Scholar] [CrossRef]
- Siegel, R.A.; Gu, Y.; Baldi, A.; Ziaie, B. Novel Swelling/Shrinking Behaviors of Glucose-Binding Hydrogels and their Potential Use in a Microfluidic Delivery System. Macromol. Symp. 2004, 208, 249–256. [Google Scholar] [CrossRef]
- Matsumoto, A.; Ishii, T.; Nishida, J.; Matsumoto, H.; Kataoka, K.; Miyahara, Y. A Synthetic Approach Toward a Self-Regulated Insulin Delivery System. Angew. Chem. Int. Ed. 2012, 51, 2124–2128. [Google Scholar] [CrossRef] [PubMed]
- Kim, A.; Mujumdar, S.K.; Siegel, R.A. Swelling Properties of Hydrogels Containing Phenylboronic Acids. Chemosensors 2014, 2, 1–12. [Google Scholar] [CrossRef]
- Springsteen, G.; Wang, B. A detailed examination of boronic acid-diol complexation. Tetrahedron 2002, 58, 5291–5300. [Google Scholar] [CrossRef]
- Horgan, A.M.; Marshall, A.J.; Kew, S.J.; Dean, K.E.S.; Creasey, C.D.; Kabilan, S. Crosslinking of phenylboronic acid receptors as a means of glucose selective holographic detection. Biosens. Bioelectron. 2006, 21, 1838–1845. [Google Scholar] [CrossRef] [PubMed]
- English, A.; Tanaka, T.; Edelman, E.R. Equilibrium and non-equilibrium phase transitions in copolymer polyelectrolyte hydrogels. J. Chem. Phys. 1997, 107, 1645–1654. [Google Scholar] [CrossRef]
- Flory, P.J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, NY, USA, 1953. [Google Scholar]
- Angell, C.A.; Ngai, K.L.; McKenna, G.B.; McMillan, P.F.; Martin, S.W. Relaxation in Glassforming Liquids and Amorphous Solids. Appl. Phys. Rev. 2000, 88, 3113–3157. [Google Scholar] [CrossRef]
- Xing, S.; Guan, Y.; Zhang, Y. Kinetics of glucose-induced swelling of P(NIPAM-AAPBA) microgels. Macromolecules 2011, 44, 4479–4486. [Google Scholar] [CrossRef]
- Hall, D.G. Structure, properties, and preparation of boronic acid derivatives. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2), 2nd ed.; Hall, D.G., Ed.; Wiley-VCH: Weinheim, Germany, 2011. [Google Scholar]
- Shiino, D.; Kubo, A.; Murata, Y.; Koyama, Y.; Kataoka, K.; Kikuchi, A.; Sakurai, Y.; Okano, T. Amine effect on phenylboronic acid complex with glucose under physiological pH in aqueous solution. J. Biomater. Sci. Polym. Ed. 1996, 7, 697–705. [Google Scholar] [CrossRef] [PubMed]
- Cifferi, A. Bond scrambling and network elasticity. Chemistry 2009, 15, 6920–6925. [Google Scholar] [CrossRef] [PubMed]
- Wojtecki, R.J.; Meador, M.A.; Rowan, S.J. Using the dynamic bond to access macroscopically responsive structurally dynamic polymers. Nat. Mater. 2010, 10, 14–26. [Google Scholar] [CrossRef] [PubMed]
- Meng, F.; Pritchard, R.H.; Terentjev, E.M. Stress Relaxation, Dynamics, and Plasticity of Transient Polymer Networks. Macromolecules 2016, 49, 2843–2852. [Google Scholar] [CrossRef]
- Campbell, D.S. Exchange reactions as a basis of thermoplastic behaviour in crosslinked polymers. Polym. Int. 1973. [Google Scholar] [CrossRef]
- Flory, P.J. Elasticity of Polymer Networks Cross-linked in States of Strain. Trans. Faraday Soc. 1960, 56, 722–743. [Google Scholar] [CrossRef]
- Fricker, H.S. On the theory of stress relaxation by cross-link reorganization. Proc. R. Soc. A 1973, 335, 289–300. [Google Scholar] [CrossRef]
- Fricker, H.S. The effects on rubber elasticity of the addition and scission of cross-links under strain. Proc. R. Soc. Lond A 1973, 335, 267–287. [Google Scholar] [CrossRef]
- Rottach, D.R.; Curro, J.G.; Budzien, J.; Grest, G.S.; Evervaers, R. Molecular dynamics simulation of polymer networks undergoing sequential cross-linking and scission. Macromolecules 2010, 40, 131–139. [Google Scholar] [CrossRef]
- Scanlan, J. Cross-link breakdown and re-formation in strained polymer networks. Trans. Faraday Soc. 1961, 57, 839–845. [Google Scholar] [CrossRef]
- Colvin, A.E.; Jiang, H. Increased In Vivo Stability and Functional Lifetime of an Implantable Glucose Sensor through Platinum Catalysis. J. Biomed. Mater. Res. Part A 2012, 101, 1274–1282. [Google Scholar]
Fixed Parameters | Fitted Parameters: 95% CI |
---|---|
= 0.553 mol/cm3 | χ = 0.61 ± 0.01 |
= 0.242 | = 7.26 ± 1.29 mmol/cm3 |
Csalt = 0.155 mol/L | pKa = 8.20 ± 0.10 |
KS = 0.09 mmol/L |
pH | (Pa) | d/d0 | Calculated (mM) | |
---|---|---|---|---|
pH 10 | 0 mM | 3012 | 2.05 | 7.45 |
F9 mM | 2460 | 2.02 | 5.99 | |
G9 mM | 5042 | 1.54 | 9.35 | |
pH 7.4 | 0 mM | 5131 | 1.13 | 6.96 |
F9 mM | 3200 | 1.86 | 7.19 | |
G9 mM | 5031 | 1.26 | 7.62 |
(s) | τ (95% CI) (s) | β (95% CI) (Dimensionless) |
---|---|---|
1 | 3.75 ± 0.13 | 0.495 ± 0.011 |
10 | 3.68 ± 0.21 | 0.549 ± 0.013 |
100 | 15.49 ± 0.26 | 0.753 ± 0.016 |
© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Kim, A.; Lee, H.; Jones, C.F.; Mujumdar, S.K.; Gu, Y.; Siegel, R.A. Swelling, Mechanics, and Thermal/Chemical Stability of Hydrogels Containing Phenylboronic Acid Side Chains. Gels 2018, 4, 4. https://doi.org/10.3390/gels4010004
Kim A, Lee H, Jones CF, Mujumdar SK, Gu Y, Siegel RA. Swelling, Mechanics, and Thermal/Chemical Stability of Hydrogels Containing Phenylboronic Acid Side Chains. Gels. 2018; 4(1):4. https://doi.org/10.3390/gels4010004
Chicago/Turabian StyleKim, Arum, Heelim Lee, Clinton F. Jones, Siddharthya K. Mujumdar, Yuandong Gu, and Ronald A. Siegel. 2018. "Swelling, Mechanics, and Thermal/Chemical Stability of Hydrogels Containing Phenylboronic Acid Side Chains" Gels 4, no. 1: 4. https://doi.org/10.3390/gels4010004