Smart Boronate-Containing Copolymers and Gels at Solid-Liquid Interfaces, Cell Membranes, and Tissues

Smart Polymers: Applications in Biotechnology and Biomedicine

Volumn , Issue , 2007, Pages 299-329

  Ivanov, Alexander E ^a   Galaev, Igor Yu ^a   Mattiasson, Bo ^a  

^a CHEMICAL CENTER   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77953244846     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420008623-15     Document Type: Chapter

References (72)

1. Boeseken, J., The use of boric acid for the determination of the configuration of carbohydrates, Adv. Carbohydr. Chem., 4, 189-210, 1949.
2. Kuivila, H.G., Keough, A.H., and Soboczenski, E.J., Areneboronates from diols and polyols, J. Org. Chem., 19, 780-783, 1954.
3. Lorand, J.P. and Edwards, J.O., Polyol complexes and structure of the benzeneboronate ion, J. Org. Chem., 24, 769-774, 1959.
4. Bergold, A. and Scouten, W.H., Borate chromatography, in Solid Phase Biochemistry:Analytical and Synthetic Methods, Scouten, W.H., Ed., John Wiley and Sons, London, 1983, pp. 149-187.
5. James, T.D. and Shinkai, S., Artificial receptors as chemosensors for carbohydrates, Topics Curr. Chem., 218, 159-200, 2002.
6. Miyata, T., Uragami, T., and Nakamae, K., Biomolecule-sensitive hydrogels, Adv. Drug Delivery Rev., 54, 79-98, 2002.
7. Ding, Z.L., Chen, G.H., and Hoffman, A.S., Synthesis and purification of thermally sensitive oligomer-enzyme conjugates of poly(N-isopropylacrylamide)- trypsin, Bioconjugate Chem., 7, 121-125, 1996.
8. Ding, Z.L., Chen, G.H., and Hoffman, A.S., Unusual properties of thermally sensitive oligomer-enzyme conjugates of poly(N-isopropylacrylamide)- trypsin, J. Biomed. Mater. Res., 39, 498-505, 1998.
9. Uludag, H., Norrie, B., Kousinioris, N., and Gao, T., Engineering temperaturesensitive poly(N-isopropylacrylamide) polymers as carriers of therapeutic properties, Biotechnnol. Bioeng., 73, 510-521, 2001.
10. Mammen, M., Choi, S.-K., and Whitesides, G.M., Polyvalent interactions in biological systems: implication for design and use of multivalent ligands and inhibitors, Angew. Chem. Int. Ed., 37, 2754-2794, 1998.
11. Kumar, A., Galaev, I.Yu., and Mattiasson, B., Affinity precipitation of amylase inhibitor from wheat meal by metal chelate affinity binding using Cu(II)-loaded copolymers of 1-vinylimidazole with N-isopropylacrylamide, Biotechnol. Bioeng., 59, 695-704, 1998.
12. Ivanov, A.E., Galaev, I.Yu., Kazakov, S.V., and Mattiasson, B., Thermosensitive copolymers of N-vinylimidazole as displacers of proteins in immobilized metal affinity chromatography, J. Chromatogr. A, 907, 115-130, 2001.
13. Arvidsson, P., Ivanov, A.E., Galaev, I.Y., and Mattiasson, B., Polymer versus monomer as displacer in immobilized metal affinity chromatography, J. Chromatogr. B: Biomed. Sci. Appl., 753, 279-285, 2001.
14. Cunliffe, D., Pennadam, S., and Alexander, C., Synthetic and biological polymers:merging the interface, Eur. Polym. J., 40, 5-25, 2004.
15. Hubble, J.A., Elbert, D.L., and Winblade, N.D., Methods and compositions to prevent formation of adhesions in biological tissues, PCT Int. Appl. WO9910022, 1999, C.A. 130, 213676, 1999.
16. Kataoka, K., Miyazaki, H., Okano, T., and Sakurai, Y., Sensitive glucose-induced change of the lower critical solution temperature of poly[N, N-dimethylacrylamideco-3-(acrylamido)phenylboronic acid] in physiological saline, Macromolecules, 27, 1061-1062, 1994.
17. Miyazaki, H., Kikuchi, A., Koyama, Y., Okano, T., Sakurai, Y., and Kataoka, K., Boronate-containing polymer as novel mitogen for lymphocytes, Biochem. Biophys. Res. Commun., 195, 829-836, 1993.
18. Uchimura, E., Otsuka, H., Okano, T., Sakurai, Y., and Kataoka, K., Totally synthetic polymer with lectin-like function: induction of killer cells by the copolymer of 3-acrylamidophenylboronic acid with N, N-dimethylacrylamide, Biotechnol. Bioeng., 72, 307-314, 2001.
19. Kuzimenkova, M.V., Ivanov, A.E., and Galaev, I.Yu., Boronate-containing copolymers: polyelectrolyte properties and sugar-specific interaction with agarose gel, Macromol. Biosci., 6, 170-178, 2006.
20. Shiomori, K., Ivanov, A.E., Galaev, I.Yu., Kawano, Y., and Mattiasson, B., Thermoresponsive properties of sugar sensitive copolymer of N-isopropylacrylamide and 3-(acrylamido)phenylboronic acid, Macromol. Chem. Phys., 205, 27-34, 2004.
21. Pezron, E., Richard, A., Lafuma, F., and Audebert, R., Reversible gel formation induced by ion complexation, 1: borax-galactomannan interactions, Macromolecules, 21, 1121-1125, 1988.
22. Matsumoto, A., Yoshida, R., and Kataoka, K., Glucose-responsive polymer gel bearing phenylboronate derivative as a glucose-sensing moiety operating at the physiological pH, Biomacromolecules, 5, 1038-1045, 2004.
23. Yan, J., Springsteen, G., Deeter, S., and Wang, B., The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols:it is not as simple as it appears, Tetrahedron, 60, 11205-11209, 2004.
24. Hisamitsu, I., Kataoka, K., Okano, T., and 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., 14, 289-293, 1997.
25. Ivanov, A.E., Larsson, H., Galaev, I.Yu., and Mattiasson, B., Synthesis of boronate- containing copolymers of N, N-dimethylacrylamide, their interaction with poly(vinyl alcohol) and rheological behaviour of the gels, Polymer, 45, 2495-2505, 2004.
26. Otsuka, H., Uchimura, E., Koshino, H., Okano, T., and Kataoka, K., Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH, J. Am. Chem. Soc., 125, 3493-3502, 2003.
27. Kitano, S., Kataoka, K., Koyama, Y., Okano, T., and Sakurai, Y., Glucose-responsive complex formation between poly(vinyl alcohol) and poly(N-vinyl-2-pyrrolidone) with pendent phenylboronic acid moieties, Makromol. Chem. Rapid Commun., 12, 227-233, 1991.
28. Kitano, S., Koyama, Y., Kataoka, K., Okano, T., and Sakurai, Y., A novel drug delivery system utilising a glucose responsive polymer complex between poly(vinyl alcohol) and poly(N-vinyl-2-pyrrolidone) with a phenylboronic acid moiety, J. Control. Release, 19, 161-170, 1992.
29. Aoki, T., Nagao, Y., Sanui, K., Ogata, N., Kikuchi, A., Sakurai, Y., Kataoka, K., and Okano, T., Glucose-sensitive lower critical solution temperature changes of copolymers composed of N-isopropylacrylamide and phenylboronic acid moieties, Polym. J., 28, 371-374, 1996.
30. Kataoka, K., Miyazaki, H., Bunya, M., Okano, T., and Sakurai, Y., Totally synthetic polymer gels responding to external glucose concentration: their preparation and application to on-off regulation of insulin release, J. Am. Chem. Soc., 120, 12694-12695, 1998.
31. Ivanov, A.E., Shiomori, K., Kawano, Y., Galaev, I.Yu., and Mattiasson, B., Effects of polyols, saccharides and glycoproteins on thermoprecipitation of phenylboronate- containing copolymers, Biomacromolecules, 7, 1017-1024, 2006.
32. Ivanov, A.E., Galaev, I.Yu., and Mattiasson, B., Binding of adenosine to pendant phenylboronate groups of thermoresponsive polymer: a quantitative study, Macromol. Biosci., 5, 795-800, 2005.
33. Alexeev, V.L., Sharma, A.C., Goponenko, A.V., Das, S., Lednev, I.K., Wilcox, C.S., Finegold, D.N., and Asher, S.A., High ionic strength glucose-sensing photonic crystal, Anal. Chem., 75, 2316-2323, 2003.
34. Norrild, J.C. and Eggert, H., Evidence for mono- and bisdentate boronate complexes of glucose in the furanose form: application of 1J C-C coupling constants as a structural probe, J. Am. Chem. Soc., 117, 1479-1484, 1995.
35. Takeuchi, M., Mizuno, T., Shinkai, S., Shirakami, S., and Itoh, T., Chirality sensing of saccharides using a boronic acid-appended chiral ferrocene derivative, Tetrahedron: Asymmetry, 11, 3311-3322, 2000.
36. Lee, M.-C., Kabilan, S., Hussain, A., Yang, X., Blyth, J., and Lowe, C.R., Glucosesensitive holographic sensors for monitoring bacterial growth, Anal. Chem., 76, 5748-5755, 2004.
37. Davis, A.P. and Wareham, R.S., Carbohydrate recognition through noncovalent interaction: a challenge for biomimetic and supramolecular chemistry, Angew. Chem. Int. Ed., 38, 2978-2999, 1999.
38. Kikuchi, A., Suzuki, K., Okabayashi, O., Hoshino, H., Kataoka, K., Sakurai, Y., and Okano, T., Glucose-sensing electrode coated with polymer complex gel containing phenylboronic acid, Anal. Chem., 68, 823-828, 1996.
39. Nicholls, M.P. and Paul, P.K.C., Structures of carbohydrate-boronic acid complexes determined by NMR and molecular modelling in aqueous alkaline media, Org. Biomol. Chem., 2, 1434-1441, 2004.
40. van den Berg, R., Peters, J.A., and van Bekkum, H., The structure and local stability constants of borate esters of mono- and di-saccharides as studied by 11B and 13C NMR spectroscopy, Carbohydr. Res., 253, 1-12, 1994.
41. Gabai, R., Sallacan, N., Chegel, V., Bourenko, T., Katz, E., and Willner, I., Characterization of the swelling of acrylamidophenylboronic acid-acrylamide hydrogels upon interaction with glucose by Faradaic impedance spectroscopy, chronopotentiometry, quartz-crystal microbalance (QCM), and surface plasmon resonance (SPR) experiments, J. Phys. Chem., 105, 8196-8202, 2001.
42. Sallacan, N., Zayats, M., Bourenko, T., Kharitonov, A.B., and Willner, I., Imprinting of nucleotide and monosaccharide recognition sites in acrylamidephenylboronic acid-acrylamide copolymer membranes associated with electronic transducers, Anal. Chem., 74, 702-712, 2002.
43. Asher, S.A., Alexeev, V.L., Goponenko, A.V., Sharma, A.C., Lednev, I.K., Wilcox, C.S., and Finegold, D.N., Photonic crystal carbohydrate sensors: low ionic strength sugar sensing, J. Am. Chem. Soc., 125, 3322-3329, 2003.
44. Thammakhet, C., Ivanov, A.E., Thavarungkul, P., Kanatharana, P., Galaev, I.Yu., and Mattiasson, B., Monitoring of glucose and other carbohydrates using phenylboronate-containing copolymer gels, submitted for publication, 2007.
45. Shoji, E. and Freund, M.S., Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid), J. Am. Chem. Soc., 124, 12486-12493, 2002.
46. Ball, I.J., Huang, S.C., Wolf, R.A., Shimano, J.Y., and Kaner, R.B., pervaporation studies with polyaniline membranes and blends, J. Membr. Sci, 174, 161-176, 2000.
47. Lide, D.R., Frederikse, H.P.R., Eds., CRC Handbook of Chemistry and Physics, 75th Ed., CRC Press, Boca Raton, 1995, p. 253.
48. Ma, Y. and Yang, X., One saccharide sensor based on the complex of the boronic acid and the monosaccharide using electrochemical impedance spectroscopy, J. Electoanal. Chem., 580, 348-352, 2005.
49. Soh, N., Sonezaki, M., and Imato, T., Modification of a thin gold film with boronic acid membrane and its application to a saccharide sensor based on surface plasmon resonance, Electroanalysis, 15, 1281-1290, 2003.
50. Winblade, N.D., Nikolic, I.D., Hoffman, A.S., and Hubbell, J.A., Blocking adhesion to cell and tissue surfaces by the chemisorption of a poly-L-lysinegraft- (poly(ethylene glycol), phenylboronic acid) copolymer, Biomacromolecules, 1, 523-533, 2000.
51. Holmes-Farley, S.R., Mandeville, H.W., Dhal, P.K., Huval, C.C., Li, X., and Polomoscanik, S.C., Aryl boronate functionalized polymers for treating obesity, PCT Patent Appl. WO 03/002571, 2003, C.A., 138: 90649.
52. Wang, B., Gao, X., Yang, W., Fang, H., and Yan, Y., Water soluble boronic acid fluorescent reporter compounds and methods of use thereof, PCT Int. Appl. WO 2005024416, 2005, C.A., 142: 308776.
53. Verchere, J.F. and Hlaibi, M., Stability constants of borate complexes of oligosaccharides, Polyhedron, 6, 1415-1420, 1987.
54. Chapelle, S. and Verchere, J.-F., A 11B and 13C NMR determination of the structures of borate complexes of pentoses and related sugars, Tetrahedron, 44, 4469-4482, 1988.
55. Morin, G.T., Paugam, M.-F., Hughes, M.P., and Smith, B.D., Boronic acid mediates glycoside transport through a liquid organic membrane via reversible formation of trigonal boronate esters, J. Org. Chem., 59, 2724-2728, 1994.
56. Sugasaki, A., Sugiyasu, K., Ikeda, M., Takeuchi, M., and Shinkai, S., First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism, J. Am. Chem. Soc., 123, 10239-10244, 2001.
57. Pezron, E., Richard, A., Lafuma, F., and Audebert, R., Reversible gel formation induced by ion complexation, 1: borax-galactomannan interactions, Macromolecules, 21, 1121-1125, 1988.
58. Winblade, N.D., Schmökel, H., Baumann, M., Hoffman, A.S., and Hubbell, J.A., Sterically blocking adhesion of cells to biological surfaces with a surface-active copolymer containing poly(ethylene glycol) and phenylboronic acid, J. Biomed. Mater. Res., 59, 618-631, 2002.
59. Yu, L.G., Fernig, D.G., Smith, J.A., Milton, J.D., and Rhodes, J.M., Reversible inhibition of proliferation of epithelial cell lines by Agaricus bisporus (edible mushroom) lectin, Cancer Res., 53, 4627-4632, 1993.
60. Szul, D., Ivanov, A., Galaev, I., and Hallmann, R., The Endothelial Cell Surface Glycocalix, a Regulator of Leukocyte Adhesion, Lund Immunology Seminar Minisymposium, Lund, Sweden, Dec. 2004.
61. Ivanov, A.E., Szul, D., Hallmann, R., Galaev, I.Yu., and Mattiasson, B., Boronate-Containing Copolymers as Carbohydrate-Specific Reagents and Regulators of Cell Adhesion, FBPS 05, 6th International Symposium on Frontiers in Biomedical Polymers, Granada, Spain, June 16-19, 2005, Book of Abstracts, P-9.
62. Hahne, M., Jäger, U., Isenmann, S., Hallmann, R., and Vestweber, D., Five TNFinducible cell adhesion mechanisms on the surface of mouse endothelioma cells mediate the binding of leukocytes, J. Cell Biol., 121, 655-664, 1993.
63. Hammel, M., Weitz-Schmidt, G., Krause, A., Moll, T., Vestweber, D., Zerwes, H., and Hallmann, R., Species-specific and conserved epitopes on mouse and human E-selectin important for leukocyte adhesion, Exp. Cell Res., 269, 266-274, 2001.
64. Davis, S.S., Nasal vaccines, Adv. Drug Delivery Rev., 51, 21-42, 2001.
65. Kvanvilkar, K., Donovan, M.D., and Flanagan, D.R., Drug transfer through mucus, Adv. Drug Delivery Rev., 48, 173-193, 2001.
66. Lehr, C.-M., From sticky stuff to sweet receptors: achievements, limits and novel approaches to bioadhesion, Eur. J. Drug Metab. Pharm., 21, 39-48, 1996.
67. Schmitt, E.E., Occlusion of channels in living mammals, PCT Int. Appl. WO 9405342 A1, 1994, C.A., 120: 307569.
68. Mawad, M.E., Cekirge, S., Ciceri, E., and Saatci, I., Endovascular treatment of giant and large intracranial aneurisms by using a combination of stent placement and liquid polymer injection, J. Neurosurg., 96, 474-482, 2002.
69. Piotin, M., Mandal, S., Sugiu, K., Gailloud, P., and Rufenacht, D.A., Endovascular treatment of cerebral aneurysms: an in vitro study with detachable platinum coils and triacetate cellulose polymer, Am. J. Roentgenol., 176, 235-239, 2001.
70. Leibler, L., Pezron, E., and Pincus, P.A., Viscosity behaviour of polymer solutions in the presence of complexing ions, Polymer, 29, 1105-1109, 1988.
71. Tao, S.L., Lubeley, M.W., and Desai, T.A., Bioadhesive poly(methyl methacrylate) microdevices for controlled drug delivery, J. Control. Release, 88, 215-228, 2003.
72. Ivanov, A.E., Ahmad Panahi, H., Kuzimenkova, M.V., Nilsson, L., Bergenståhl, B., Waqif, H.S., Jahanshahi, M., Galaev, I.Yu., and Mattiasson, B., Affinity adhesion of carbohydrate particles and yeast cells to boronate-containing polymer brushes grafted onto siliceous supports, Chem. Eur. J., 12, 7204-7214, 2006.