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Boronate-containing copolymers: Polyelectrolyte properties and sugar-specific interaction with agarose gel

Kuzimenkova, Marina LU ; Ivanov, Alexander LU and Galaev, Igor LU (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)
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author
; and
organization
publishing date
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 and Sons
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
2021-08-04 03:40:51
@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},
  language     = {eng},
  number       = {2},
  pages        = {170--178},
  publisher    = {John Wiley and Sons},
  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},
}