Mixed charge copolymers and hydrogels

Patent metadata

Field	Value
Publication number	US-10301413-B2
Application number	US-201514698721-A
Country	US
Kind code	B2
Filing date	Apr 28, 2015
Priority date	Aug 7, 2006
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

Nonfouling copolymers and hydrogels comprising positively charged repeating units or latent positively charged repeating units and negatively charged units or latent positively charged units.

First claim

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A non-fouling peptide, comprising:
(a) a plurality of negatively charged repeating units polymerized from amino acid monomers selected from the group consisting of aspartic acid and glutamic acid; and
(b) a plurality of positively charged repeating units polymerized from lysine, and
wherein
the non-fouling peptide comprises at least 3 pairs of repeating units, each pair formed of a negatively charged repeating unit adjacent to a positively charged repeating unit; and
the peptide is substantially electronically neutral at pH 7.4.

2. The non-fouling peptide of claim 1 , wherein the peptide is crosslinked.

3. The non-fouling peptide of claim 1 further comprising a plurality of repeating units each having a hydrophobic pendant group.

4. The non-fouling peptide of claim 1 , wherein the negatively charged repeating unit is polymerized from glutamic acid.

5. A copolymer, consisting of:
(a) a plurality of first repeating units selected from
negatively charged repeating units polymerized from monomers selected from 2-carboxyethyl acrylate, 2-carboxyethyl acrylate, 3-sulfopropyl methacrylate, lauryl methacrylate, and D-glucuronic acid, and
repeating units having latent negatively charged groups polymerized from monomers selected from isobutyl methacrylate, 2,2,2-trifluoroethyl methacrylate, and ethyl glycolate methacrylate, reactive to provide negatively charged groups; and

(b) a plurality of second repeating units selected from
positively charged repeating units polymerized from monomers selected from 2-(dimethylamino)ethyl methacrylate, 2-(diethylamino)ethyl methacrylate, [2-(methacryloyloxy)ethyl]trimethylammonium chloride, 2-aminoethyl methacrylate hydrochloride, and N-acetylglucosamine; and
repeating units having latent positively charged groups polymerized from monomers selected from a monomer comprising an imide and a monomer comprising an oxyimino group, reactive to provide positively charged groups,
wherein:
when the copolymer consists of a plurality of negatively charged repeating units and a plurality of positively charged repeating units, the copolymer is substantially electronically neutral at pH 7.4;
when the copolymer consists of a plurality of positively charged repeating units and a plurality repeating of units having latent negatively charged groups reactive to provide negatively charged groups, the copolymer is substantially electronically neutral at pH 7.4 when the latent negatively charged groups are converted to negatively charged groups;
when the copolymer consists of a plurality of negatively charged repeating units and a plurality of repeating units having latent positively charged groups reactive to provide positively charged groups, the copolymer is substantially electronically neutral at pH 7.4 when the latent positively charged groups are converted to positively charged groups; and
when the copolymer consists of a plurality of repeating units having latent negatively charged groups reactive to provide negatively charged groups and a plurality of repeating units having latent positively charged groups reactive to provide positively charged groups, the copolymer is substantially electronically neutral at pH 7.4 when the latent negatively charged groups are converted to negatively charged groups and the latent positively charged groups are converted to positively charged groups.

6. The copolymer of claim 5 , wherein the copolymer is selected from the group consisting of:
(a) a copolymer consisting of repeating units having a latent negatively charged group derived from isobutyl methacrylate, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate;
(b) a copolymer consisting of repeating units having a latent negatively charged group derived from 2,2,2-trifluoroethyl methacrylate, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate; and
(c) a copolymer consisting of repeating units having a latent negatively charged group derived from ethyl glycolate methacrylate, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate.

7. The copolymer of claim 5 , wherein the copolymer is selected from the group consisting of:
(a) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate;
(b) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-(diethylamino)ethyl methacrylate;
(c) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from [2-(methacryloyloxy)ethyl]trimethylammonium chloride;
(d) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-aminoethyl methacrylate hydrochloride;
(e) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units are derived from 2-(dimethylamino)ethyl methacrylate;
(f) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units are derived from [2-(methacryloyloxy)ethyl]trimethylammonium chloride;
(g) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units are derived from 2-(diethylamino)ethyl methacrylate;
(h) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units derived from 2-aminoethyl methacrylate hydrochloride;
(i) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate;
(j) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-(diethylamino)ethyl methacrylate;
(k) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from [2-(methacryloyloxy)ethyl]trimethylammonium chloride;
(l) a copolymer consisting of negatively charged repeating units derived from 2-carboxyethyl acrylate, and positively charged repeating units derived from 2-aminoethyl methacrylate hydrochloride;
(m) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units derived from 2-(dimethylamino)ethyl methacrylate;
(n) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units derived from [2-(methacryloyloxy)ethyl ]trimethylammonium chloride;
(o) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units derived from 2-(diethylamino)ethyl methacrylate; and
(p) a copolymer consisting of negatively charged repeating units derived from 3-sulfopropyl methacrylate potassium salt, and positively charged repeating units derived from 2-aminoethyl methacrylate hydrochloride.

8. The copolymer of claim 5 , wherein the ratio of the number of the negatively charged repeating units or the repeating units hav

Assignees

• Univ Washington

Inventors

• Jiang Shaoyi
• Chen Shengfu

Classifications

• A61K38/10

  Peptides having 12 to 20 amino acids {(A61K38/043 - A61K38/046 take precedence)} · CPC title

• B29C39/20

  Making multilayered or multicoloured articles {(B29C39/142 takes precedence)} · CPC title

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C08L51/04

  grafted on to rubbers · CPC title

• C08F220/34 Primary

  Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate} · CPC title