Synthesis of a new poly(carboxybetaine) with peptide main chain

Nagaya, Jiro; Uzawa, Hirotaka; Minoura, Norihiko

doi:10.1002/(sici)1521-3927(19991101)20:11<573::aid-marc573>3.0.co;2-t

Cited by 13 publications

(16 citation statements)

References 7 publications

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“…On the basis of the IR spectrum of the P(DMAPrAAm) homopolymer (cf. Infrared Spectroscopy section), the peak at 2778 cm −1 in the IR spectrum of P(DMAPrAAm‐ r ‐R f PEGA)‐ b ‐PS ( 2 ) was attributed to >N(CH 3 ) 2 CH stretching vibrations 45. After reactions with bromoacetic acid, 1,3‐propanesultone, and methyl‐2‐bromoacetate, this peak disappeared; this indicated that the tertiary amine groups had undergone the quaternization reaction.…”

Section: Resultsmentioning

confidence: 98%

Carboxybetaine, sulfobetaine, and cationic block copolymer coatings: A comparison of the surface properties and antibiofouling behavior

Jasiński

Krishnan

2011

J of Applied Polymer Sci

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Two different zwitterionic block copolymers (BCs) and a cationic BC were synthesized from the same BC precursor, which consisted of a polystyrene (PS) block and a poly[N-(3-dimethylamino-1-propyl)acrylamide] block. The zwitterionic BCs contained the dimethylammonioacetate (carboxybetaine) and dimethylammoniopropyl sulfonate (sulfobetaine) groups. Thin films cast from these polymers were investigated for surface wettability, surface charge, and protein adsorption. Surface-energy parameters calculated with advancing contact angle (y a ) and receding contact angle (y r ) of different probe liquids showed that it was y r and not y a that was representative of the polar/ionic groups in the near-surface regions of the coatings. Electrophoretic mobility was used to characterize the influence of pH on the net surface charge. In aqueous dispersions, the carboxybetaine polymer showed an ampholyte behavior with an isoelectric point of 6, whereas the sulfobetaine polymer was found to be anionic at all pH values between 2 and 10. Protein adsorption on the carboxybetaine BC was relatively independent of the net charges on the protein or the polymer, but the negatively charged sulfobetaine polymer showed a higher adsorption of positively charged protein molecules. Regardless of the net protein charge, both zwitterionic coatings adsorbed less protein compared to the PS and poly(2,3,4,5,6-pentafluorostyrene) controls. The sulfobetaine and cationic BCs adsorbed higher amounts of oppositely charged protein molecules than like-charged protein molecules. However, the adsorption of oppositely charged protein was much higher on the cationic surface than on the sulfobetaine surface. The zwitterionic BCs, particularly the carboxybetaine polymer, from this article are expected to function as stable, low-fouling surface modifiers in different biological environments.

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Section: Resultsmentioning

confidence: 98%

Carboxybetaine, sulfobetaine, and cationic block copolymer coatings: A comparison of the surface properties and antibiofouling behavior

Jasiński

Krishnan

2011

J of Applied Polymer Sci

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“…Besides the conventional acrylate backbone (homopolymer or block copolymer) with acetate, , propionate, butanoate, , and hexanoate at the quaternized nitrogen some special structures were investigated. Laschewsky and co-workers dealt with salt-free synthesis of zwitterionic derivatives of the well-known cyclopolymer poly(diallyldimethylammonium chloride). , The salt-free procedure was successfully introduced in order to prepare and investigate homogeneous mixtures of polyzwitterions with low molecular weight salt and ionic dyes, respectively. , Minuora et al reported on a synthesis of a polycarboxybetaine from poly(γ-methyl l -glutamate) …”

Section: Introductionmentioning

confidence: 99%

Charge Interaction of Synthetic Polycarboxybetaines in Bulk and Solution

et al. 2002

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Various polycarboxybetaines were synthesized using controlled radical polymerization processes followed by polymer analogous transformations. Structural variation of these exclusively aromatic or heteroaromatic systems includes distance between charges, hybridization and substitution of the ammonium moiety, and additional alkyl chains between the charges. For the first time capillary electrophoresis was used for systematic characterization of the solution properties. It was found to be a very sensitive method to detect even small structural differences and the resulting pH-dependent solution behavior. The electrophoretical mobility compared with an internal standard and the amount of its pH dependence are direct measures for the interaction of charges of polycarboxybetaines in solution. This method clearly reveals a gradual and more or less predictable content of “free” cationic charges dependent on structural and solution parameters. Results obtained coincide in a fairly good way with data from FTIR measurement and charge titration.

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“…Polyzwitterions are a specific type of ion-containing polymer that possesses both cationic and anionic groups in their polymeric repeating unit . Typically, the cationic group is a quaternary ammonium, and the anionic groups are sulfonate (sulfobetaine), carboxylate (carboxylbetaine), or phosphonate (phosphobetaine) . Due to their unique chemistry, these materials exhibit strong protein antifouling properties, making them excellent candidates for biomedical applications. − A significant amount of literature, including many reviews, has focused on their synthesis and the basis for their significant antifouling abilities. ,− Briefly, the ionic nature of zwitterions allows for high concentrations of water to be bound to the functional groups, preventing fouling of the surface.…”

Section: Introductionmentioning

confidence: 99%

“…Polyzwitterions are a specific type of ion-containing polymer that possesses both cationic and anionic groups in their polymeric repeating unit. 8 Typically, the cationic group is a quaternary ammonium, and the anionic groups are sulfonate (sulfobetaine), 9 carboxylate (carboxylbetaine), 10 or phosphonate (phosphobetaine). 11 Due to their unique chemistry, these materials exhibit strong protein antifouling properties, making them excellent candidates for biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

Polyzwitterions as a Versatile Building Block of Tough Hydrogels: From Polyelectrolyte Complex Gels to Double-Network Gels

Yin

King

Sun

et al. 2020

ACS Appl. Mater. Interfaces

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The high water content of hydrogels makes them important as synthetic biomaterials, and tuning the mechanical properties of hydrogels to match those of natural tissues without changing chemistry is usually difficult. In this study, we have developed a series of hydrogels with varied stiffness, strength and toughness based on a combination of poly(2-acrylamido-2-methylpropane sulfonic acid) (PAMPS), a strong acidic polyelectrolyte, and poly-N-polyzwitterion with weak acidic moiety. We demonstrate that modifying the true molar ratio, R, of PCDME to PAMPS results in four unique categories of hydrogels with different swelling ratio and Young's modulus. When R < 1, a negatively charged polyelectrolyte gel (PE) is formed; when 1 < R < 3, a tough and viscoelastic polyelectrolyte complex gel (PEC) is formed; when 3 < R < 6.5, a conventional, elastic interpenetrating network gel (IPN) is formed; and when R > 6.5 a tough and stiff double-network gel (DN) is formed. Both the PEC and DN gels exhibit high toughness and fracture stress, up to 1.8 MPa and 1.5 MPa, respectively. Importantly, the PEC gels exhibit strong recovery properties along with high toughness, distinguishing them from DN gels. Without requiring a change in chemistry, we can tune the mechanical response of hydrogels over a wide spectrum, making this a useful system of soft and hydrated biomaterials.

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Synthesis of a new poly(carboxybetaine) with peptide main chain

Cited by 13 publications

References 7 publications

Carboxybetaine, sulfobetaine, and cationic block copolymer coatings: A comparison of the surface properties and antibiofouling behavior

Carboxybetaine, sulfobetaine, and cationic block copolymer coatings: A comparison of the surface properties and antibiofouling behavior

Charge Interaction of Synthetic Polycarboxybetaines in Bulk and Solution

Polyzwitterions as a Versatile Building Block of Tough Hydrogels: From Polyelectrolyte Complex Gels to Double-Network Gels

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