Boronate-containing copolymers: Polyelectrolyte properties and sugar-specific interaction with agarose gel
(2006) In Macromolecular Bioscience 6(2). p.170-178- Abstract
- Copolymers of N-acryloyl-m-aminophenylboronic acid (NAAPBA) with acryamide (AA), N,N-dimethylacrylamide (DMAA), and N-isopropylacrylamide (NIPAM) were found to adsorb on cross-linked agarose gel (Sepharose CL-6B) in the pH range from 7.5-9.2, due to specific boronate-sugar interactions. The molar percentages of phenylboronic acid (PBA) groups in the boronate-containing copolymers (BCCs), as estimated by H-1 NMR spectroscopy, were 13, 10, and 16%, respectively, whereas the apparent ionization constants, the pK(a) values, of the copolymers were similar and equal to 9.0 +/- 0.2 at 20 degrees C. The copolymers adsorption capacities were in the range of 15-30 mg center dot ml(-1) gel (14-36 mu mol pendant PBA ml(-1) gel) at pH 9.2 and decreased... (More)
- Copolymers of N-acryloyl-m-aminophenylboronic acid (NAAPBA) with acryamide (AA), N,N-dimethylacrylamide (DMAA), and N-isopropylacrylamide (NIPAM) were found to adsorb on cross-linked agarose gel (Sepharose CL-6B) in the pH range from 7.5-9.2, due to specific boronate-sugar interactions. The molar percentages of phenylboronic acid (PBA) groups in the boronate-containing copolymers (BCCs), as estimated by H-1 NMR spectroscopy, were 13, 10, and 16%, respectively, whereas the apparent ionization constants, the pK(a) values, of the copolymers were similar and equal to 9.0 +/- 0.2 at 20 degrees C. The copolymers adsorption capacities were in the range of 15-30 mg center dot ml(-1) gel (14-36 mu mol pendant PBA ml(-1) gel) at pH 9.2 and decreased with decreasing pH value. The interaction of monomeric NAAPBA with Sepharose CL-6B was characterized by an equilibrium association constant of 53 +/- 17 m(-1), the chromatographic capacity factor k ' = 1.8, and a total content of binding sites of 27 +/- 10 mu mol center dot ml(-1) gel at pH 9.2. The weak reversible binding of monomeric NAAPBA and almost irreversible binding of NAAPBA copolymers to the gel at pH 9.2 suggested a multivalent character of the copolymer adsorption. At pH 7.5, the maximal adsorption capacity was displayed by the AA-NAAPBA copolymer (45 mg center dot ml(-1) gel). All the BCCs could be completely desorbed from the gel by 0.1 m fructose in aqueous buffered media with pH values from 7.5-9.2. The strong adsorption of AA-NAAPBA on agarose gel probably relates to the conformation of the copolymer in aqueous solution and provides opportunities for biomedical applications of the copolymer under physiological conditions. Multivalent, weak-affinity adsorption of BCCs to the agarose gel seems to be a tentative model for the copolymers' binding to oligo- and polysaccharides of cell membranes and mucosal surfaces. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/417071
- author
- Kuzimenkova, Marina LU ; Ivanov, Alexander LU and Galaev, Igor LU
- organization
- publishing date
- 2006
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- polymers, hydrophilic, drug delivery systems, biomimetic, chromatography, molecular recognition
- in
- Macromolecular Bioscience
- volume
- 6
- issue
- 2
- pages
- 170 - 178
- publisher
- John Wiley & Sons Inc.
- external identifiers
-
- wos:000235641700006
- pmid:16456876
- scopus:33644614535
- pmid:16456876
- ISSN
- 1616-5195
- DOI
- 10.1002/mabi.200500185
- language
- English
- LU publication?
- yes
- id
- 1fdd0e71-2918-477b-a6e2-6110987dadf7 (old id 417071)
- date added to LUP
- 2016-04-01 11:47:54
- date last changed
- 2022-02-10 21:42:02
@article{1fdd0e71-2918-477b-a6e2-6110987dadf7,
abstract = {{Copolymers of N-acryloyl-m-aminophenylboronic acid (NAAPBA) with acryamide (AA), N,N-dimethylacrylamide (DMAA), and N-isopropylacrylamide (NIPAM) were found to adsorb on cross-linked agarose gel (Sepharose CL-6B) in the pH range from 7.5-9.2, due to specific boronate-sugar interactions. The molar percentages of phenylboronic acid (PBA) groups in the boronate-containing copolymers (BCCs), as estimated by H-1 NMR spectroscopy, were 13, 10, and 16%, respectively, whereas the apparent ionization constants, the pK(a) values, of the copolymers were similar and equal to 9.0 +/- 0.2 at 20 degrees C. The copolymers adsorption capacities were in the range of 15-30 mg center dot ml(-1) gel (14-36 mu mol pendant PBA ml(-1) gel) at pH 9.2 and decreased with decreasing pH value. The interaction of monomeric NAAPBA with Sepharose CL-6B was characterized by an equilibrium association constant of 53 +/- 17 m(-1), the chromatographic capacity factor k ' = 1.8, and a total content of binding sites of 27 +/- 10 mu mol center dot ml(-1) gel at pH 9.2. The weak reversible binding of monomeric NAAPBA and almost irreversible binding of NAAPBA copolymers to the gel at pH 9.2 suggested a multivalent character of the copolymer adsorption. At pH 7.5, the maximal adsorption capacity was displayed by the AA-NAAPBA copolymer (45 mg center dot ml(-1) gel). All the BCCs could be completely desorbed from the gel by 0.1 m fructose in aqueous buffered media with pH values from 7.5-9.2. The strong adsorption of AA-NAAPBA on agarose gel probably relates to the conformation of the copolymer in aqueous solution and provides opportunities for biomedical applications of the copolymer under physiological conditions. Multivalent, weak-affinity adsorption of BCCs to the agarose gel seems to be a tentative model for the copolymers' binding to oligo- and polysaccharides of cell membranes and mucosal surfaces.}},
author = {{Kuzimenkova, Marina and Ivanov, Alexander and Galaev, Igor}},
issn = {{1616-5195}},
keywords = {{polymers; hydrophilic; drug delivery systems; biomimetic; chromatography; molecular recognition}},
language = {{eng}},
number = {{2}},
pages = {{170--178}},
publisher = {{John Wiley & Sons Inc.}},
series = {{Macromolecular Bioscience}},
title = {{Boronate-containing copolymers: Polyelectrolyte properties and sugar-specific interaction with agarose gel}},
url = {{http://dx.doi.org/10.1002/mabi.200500185}},
doi = {{10.1002/mabi.200500185}},
volume = {{6}},
year = {{2006}},
}