Surfactant compounds-clips for extraction and stabilization in solution of membrane proteins

Patent metadata

Field	Value
Publication number	US-11440932-B2
Application number	US-201716492005-A
Country	US
Kind code	B2
Filing date	Dec 27, 2017
Priority date	Mar 9, 2017
Publication date	Sep 13, 2022
Grant date	Sep 13, 2022

Abstract

The present invention relates to a compound of formula (I): (I) as defined in the description. The present invention also relates to a method for extracting biological membrane-associated membrane proteins, comprising a step of bringing an aqueous solution of biological membrane-associated membrane proteins into contact with at least one compound of the invention. The present invention also relates to a method for stabilizing membrane proteins in solution in an aqueous solution, comprising a step (i) consisting in bringing an aqueous solution of a membrane protein in solution into contact with at least one compound of the invention.

First claim

The invention claimed is:

1. A compound or a pharmaceutically acceptable salt thereof, chosen from:

2. A process for extracting membrane proteins, comprising bringing an aqueous solution of membrane proteins associated with a biological membrane into contact with at least one compound or a pharmaceutically acceptable salt thereof chosen from:

3. The process according to claim 2 , wherein the membrane protein is present in a biological membrane fraction originating from a prokaryotic or eukaryotic organism.

4. The process according to claim 2 , wherein the membrane protein is a transport protein.

5. The process according to claim 4 , wherein the transport protein is an ABC transporter selected from the group consisting of P-glycoproteins (Pgp/ABCB1), MRP1/ABCC1, MRP2/ABCC2, BCRP/ABCG2 and BmrA.

6. The process according to claim 2 , wherein the bringing of an aqueous solution comprising the membrane protein to be extracted into contact with the at least one of the compounds or a pharmaceutically acceptable salt thereof is carried out at a pH ranging from 5.5 to 10.

7. A process for stabilizing membrane proteins in solution in an aqueous solution, comprising bringing an aqueous solution of an extracted membrane protein into contact with at least one compound or a pharmaceutically acceptable salt thereof chosen from:

8. The process according to claim 7 , wherein the membrane proteins are extracted by bringing an aqueous solution of membrane proteins associated with a biological membrane into contact with at least one of the compounds or a pharmaceutically acceptable salt thereof.

9. The process according to claim 7 , wherein said protein in solution is stabilized at a temperature of from 0° C. to 10° C. for a duration of greater than 1 day.

10. The process according to claim 7 , wherein the membrane proteins are extracted by detergent.

Assignees

• Centre Nat Rech Scient
• Univ Claude Bernard Lyon
• Univ Grenoble Alpes

Inventors

• Falson Pierre
• Dauvergne Julien
• Boumendjel Ahcène
• Peuchmaur Marine
• Nguyen Kim Anh
• Magnard Sandrine

Classifications

• C07C237/12

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups (peptides C07K) · CPC title

• C07H15/14 Primary

  attached to a sulfur, selenium or tellurium atom of a saccharide radical · CPC title

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• C07K1/145

  by extraction or solubilisation · CPC title

• C07C237/22

  having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K) · CPC title