Amphipols

Patent metadata

Field	Value
Publication number	US-12534550-B2
Application number	US-201917298328-A
Country	US
Kind code	B2
Filing date	Dec 3, 2019
Priority date	Dec 3, 2018
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

The invention relates to polymeric compounds of formula I

which allow the solubilization and/or stabilization of membrane proteins, it relates in particular to the complexes they form with membrane proteins and the method of solubilizing and/or stabilizing membrane proteins comprising the use of these compounds.

First claim

The invention claimed is:

1 . A water-soluble membrane protein-amphiphilic vinyl polymer complex comprising the amphiphilic vinyl polymer of formula I:

wherein:
M + is an alkali metal,
R 1 , R 4 , R 5 , R 8 are each independently a hydrogen atom or a methyl radical,
R 2 , R 6 , R 9 are each independently a group selected from a hydrogen atom, linear (C1-C8) alkyls, and branched (C3-C8) alkyls,
R 10 is a group selected from linear (C1-C5) alkyls and branched (C3-C5) alkyls,
R 3 and R 7 are each independently a group selected from the group consisting of:
hydrogen, with X then being a single bond,
linear or branched alkyls of at least 6 carbon atoms, linear or branched alkenyls of at least 6 carbon atoms, linear or branched alkynyls of at least 6 carbon atoms, with X then being a single bond,
(C3-C10) cycloalkyls or (C3-C10) (hetero) cycloalkyls, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (3-C8) alkenylenes, linear (C2-C8) alkynylenes and branched (C3-C8) alkynylenes,
(C3-C10) cycloalkenyls or (C3-C10) (hetero) cycloalkenyls, poly or monounsaturated, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C2-C8) alkenylenes, linear (C2-C8) alkynylenes and branched (C2-C8) alkynylenes,
poly or monounsaturated polycycles, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes or branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C2-C8) alkenylenes, linear (C2-C8) alkynylenes and branched (C3-C8) alkynylenes, and
phenyl, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C3-C8) alkenylenes, linear (C2-C8) alkynylenes, and branched (C3-C8) alkynylenes,

with w, x, y, z corresponding to the respective percentages of the units,
with x being between 20 and 90%,
with y being between 0 and 80%,
with w being between 0 and 80%, and
with z being between 0 and 60%, provided that w+x+y+z=100%, and that y or w is at least 10%,

provided that when one of the groups R 3 or R 7 is a linear or branched alkyl of at least 6 carbon atoms, a linear or branched alkenyl of at least 6 carbon atoms, a linear or branched alkynyl of at least 6 carbon atoms, or a hydrogen atom, with X being a single bond, then w and y are different from 0 and the other group R 3 or R 7 is selected from the group consisting of:
C3-C10) cycloalkyls or (C3-C10) (hetero) cycloalkyls, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C3-C8) alkenylenes, linear (C2-C8) alkenylenes and branched (C3-C8) alkynylenes,
(C3-C10) cycloalkenyls or (C3-C10) (hetero) cycloalkenyls, poly or monounsaturated, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes or branched (C3-C8) alkenylenes, linear (C2-C8) alkynylenes, and branched (C3-C8) alkynylenes,
poly or monounsaturated polycycles, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C3-C8) alkenylenes, linear (C2-C8) alkynylenes, and branched (C3-C8) alkynylenes, and
phenyl, unsubstituted or substituted by one or more radicals selected from linear, cyclic or branched (C1-C8) alkyls, linear or branched (C2-C8) alkenyls, and linear or branched (C2-C8) alkynyls, with X then being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C3-C8) alkenylenes, linear (C2-C8) alkynylenes, and branched (C3-C8) alkynylenes.

2 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I, M + is Na + .

3 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I, at least one of w or y is greater than or equal to 25% and less than or equal to 80%.

4 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I, R 10 is an isopropyl group.

5 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I, x is at least 20% and less than or equal to 75%.

6 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I, at least one of w or y is between 25% and 50%, and z is between 0% and 40%.

7 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I:
at least one of R 3 or R 7 is (C 6 -C 8 ) cycloalkyls, or at least one of R 3 or R 7 is phenyl,
with X being selected from a single bond, linear (C2-C8) alkylenes, branched (C3-C8) alkylenes, linear (C2-C8) alkenylenes, branched (C3-C8) alkenylenes, linear (C2-C8) alkynylenes, and branched (C3-C8) alkynylenes.

8 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein in the amphiphilic vinyl polymer of formula I:
each of R 1 , R 2 , R 4 , R 5 , R 6 , R 8 , and R 9 , is a hydrogen atom, at least one of R 3 or R 7 is (C 6 -C 8 ) cycloalkyl, and X is a single bond, R 10 is an isopropyl group, x is equal to 35% or 50%, y is greater than or equal to 25%, w is equal to 0%, or 25%, and z is equal to 0%, 15% or 40%, provided that w+x+y+z=100%.

9 . The water-soluble membrane protein-amphiphilic vinyl polymer complex according to claim 1 , wherein the amphiphilic vinyl polymer is selected from:

10 . The water-soluble membrane protein-amphiphil

Assignees

• Centre Nat Rech Scient
• Univ Paris

Inventors

• Zoonens Manuela
• Marconnet Anaïs
• Giusti Fabrice

Classifications

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• G01N33/6803

  General methods of protein analysis not limited to specific proteins or families of proteins · CPC title

• C08F20/56 Primary

  Acrylamide; Methacrylamide · CPC title

• C08F8/44

  Preparation of metal salts or ammonium salts · CPC title

• C08F8/32 Primary

  by reaction with amines · CPC title