Biotin-containing monomers and articles formed therefrom

Patent metadata

Field	Value
Publication number	US-12528824-B2
Application number	US-202017755946-A
Country	US
Kind code	B2
Filing date	Nov 23, 2020
Priority date	Nov 25, 2019
Publication date	Jan 20, 2026
Grant date	Jan 20, 2026

Abstract

Biotin-containing monomers, polymeric materials formed from the biotin-containing monomers, articles containing the polymeric materials, methods of making the articles, and methods of using the articles are provided. The articles can be used, for example, for affinity capture of biotin-binding proteins, including biotin-binding fusion proteins (i.e., a biotin-binding protein fused to another biomaterial). Articles that contain captured biotin-binding proteins can be further used for affinity capture of various biotin-containing biomaterials such as biotinylated proteins. The articles can also be used, for example, for affinity capture of biotin-binding fusion proteins where the fusion protein includes, for example, an enzyme or antibody.

First claim

What is claimed is:

1 . A polymeric material comprising monomeric units derived from a monomer of Formula (I)

in an amount ranging from 1 to 100 mole percent based on total moles of monomeric units in the polymeric material,
wherein
Q is oxygen or NH;
X is —(CO)—O— or —(CO)—NH—
Y is —NH—(CO)—, —NH—(CO)—NH—, —O—(CO)—NH—, or —O—(CO)—;
Z is —O— or —NH—;
R 1 is hydrogen or methyl; and
R 2 is an alkylene, alkylene substituted with an aryl, or heteroalkylene, with the proviso that if the polymeric material is a homopolymer and Y is equal to —NH—(CO)—, then R 2 has greater than 2 carbon atoms; and
each R 3 and R 4 is each independently a (hetero) alkylene.

2 . The polymeric material of claim 1 , wherein the polymeric material comprises 1 to 99 mole percent monomeric units derived from the monomer of Formula (I) and 1 to 99 mole percent monomeric units derived from a hydrophilic second monomer having a single ethylenically unsaturated group and/or derived from a hydrophilic crosslinking monomer having a plurality of ethylenically unsaturated groups, wherein each amount is based on total moles of monomeric materials in the polymeric material.

3 . The polymeric material of claim 2 , wherein the polymeric material comprises 1 to 50 mole percent monomeric units derived from the monomer of Formula (I) and 50 to 99 mole percent monomeric units derived from the hydrophilic second monomer having a single ethylenically unsaturated group and/or derived from the hydrophilic crosslinking monomer having a plurality of ethylenically unsaturated groups, wherein each amount is based on total moles of monomeric material in the polymeric material.

4 . The polymeric material of claim 1 , wherein Z is —O—.

5 . The polymeric material of claim 1 , wherein the monomer of Formula (I) is of Formula (I-D-1)

wherein
R 2 is an alkylene, alkylene substituted with an aryl, or heteroalkylene, with the proviso that if the polymeric material is a homopolymer and Y is equal to —NH—(CO)—, then R 2 has greater than 2 carbon atoms; and
R 3 is a (hetero) alkylene.

6 . An article comprising:
a substrate; and a polymeric material disposed on the substrate, the polymeric material comprising monomeric units derived from a monomer of Formula (I)

in an amount ranging from 1 to 100 mole percent based on total moles of monomeric units in the polymeric material,
wherein
Q is oxygen or NH;
X is —(CO)—O— or —(CO)—NH—
Y is —NH—(CO)—, —NH—(CO)—NH—, —O—(CO)—NH—, or —O—(CO)—;
Z is —O— or —NH—;
R 1 is hydrogen or methyl;
R 2 is an alkylene, alkylene substituted with an aryl, or heteroalkylene; and
each R 3 and R 4 is each independently a (hetero) alkylene.

7 . The article of claim 6 , wherein Z is —O—.

8 . The article of claim 6 , wherein the substrate is porous.

9 . The article of claim 6 , wherein the substrate is a membrane and wherein the membrane with the polymeric material disposed thereon is flexible.

10 . The article of claim 6 , wherein the polymeric material is irreversibly attached to the substrate.

11 . The article of claim 6 , wherein the polymeric material comprises 1 to 99 mole percent monomeric units derived from the monomer of Formula (I) and 1 to 99 mole percent monomeric units derived from a hydrophilic second monomer having a single ethylenically unsaturated group and/or derived from a hydrophilic crosslinking monomer having a plurality of ethylenically unsaturated groups, wherein each amount is based on total moles of monomeric material in the polymeric material.

12 . The article of claim 11 , wherein the polymeric material comprises 1 to 50 mole percent monomeric units derived from the monomer of Formula (I) and 50 to 99 mole percent monomeric units derived from the hydrophilic second monomer having a single ethylenically unsaturated group and/or derived from the hydrophilic crosslinking monomer having a plurality of ethylenically unsaturated groups, wherein each amount is based on total moles of monomeric material in the polymeric material.

13 . The article of claim 6 , wherein the monomer of Formula (I) is of Formula (I-D-1)

wherein
R 2 is an alkylene, alkylene substituted with an aryl, or heteroalkylene, with the proviso that if the polymeric material is a homopolymer and Y is equal to —NH—(CO)—, then R 2 has greater than 2 carbon atoms; and
R 3 is a (hetero) alkylene.

14 . A method of separating biotin-binding proteins from other proteins, the method comprising:
providing an article according to claim 6 ; exposing the article to a mixture comprising biotin-binding proteins and non-biotin-binding biomaterials; and binding the biotin-binding proteins to the article.

15 . A monomer of Formula (I)

wherein
Q is oxygen or NH;
X is —(CO)—O— or —(CO)—NH—
Y is —NH—(CO)—, —NH—(CO)—NH—, —O—(CO)—NH—, or —O—(CO)—;
Z is —O—;
R 1 is hydrogen or methyl;
R 2 is an alkylene, alkylene substituted with an aryl, or heteroalkylene with the proviso that if Y is —NH—(CO)—, then R 2 has greater than 2 carbon atoms; and
each R 3 and R 4 is each independently a (hetero) alkylene.

16 . The monomer of claim 15 , wherein the monomer of Formula (I) is of Formula (I-D-1).

17 . The monomer of claim 16 , wherein the monomer of Formula (I-D-1) is of Formula (I-D-3), Formula (I-D-4), or Formula (I-D-5)

Assignees

• Solventum Intellectual Properties Company
• Thermo Fisher Bioprocessing Inc

Inventors

• Rasmussen Jerald K

Classifications

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• C08F20/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• B01D71/66

  Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only · CPC title

• B01D69/10

  Supported membranes; Membrane supports · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title