ACTIVE CARRIER, ITS PRODUCTION AND ITS USE

• US 20100022415A1
• Filed: 08/21/2007
• Published: 01/28/2010
• Est. Priority Date: 08/22/2006
• Status: Abandoned Application

• Current Assignee: Avicor Ket
• Original Assignee: Avicor Ket
• Inventors: Molnar, Eszter, Puskas, Laszlo
• Application Number:
  US12/310,306
• Publication Number:
  US 20100022415A1
• Time in Patent Office: Days
• US Class Current: 506/23
• CPC Class Codes: G01N 33/54353 with ligand attached to the carrier via a chemical coupling agent coatings G01N33/54393

Abstract

Active carrier that consists of a carrier base (1) and attached linkers containing activated linker functional groups. The active carrier contains two or more different activated linker functional groups. A process for the production of the active carrier that comprises a carrier base (1) and linkers containing activated linker functional groups. Steps of the process: a) binding of a linker containing one or more linker functional groups to the carrier base (1), through the carrier functional groups; and b) reacting the linker functional groups of the linkers bound to the carrier base in step a) with two or more different activating reagents simultaneously. Use of the active carrier, during which the surface of the active carrier is contacted with one or more solution of small molecules.

Claims

1. An active carrier for surface immobilization of low molecular weight compounds comprising a carrier base (1) and attached linkers containing activated linker functional groups, characterized by that the active carrier contains two or more different activated linker functional groups.

2. An active carrier according to claim 1, characterized by that said carrier contains two, three, four or five different activated linker functional groups.

3. An active carrier according to claim 2, characterized by that said carrier contains two or three different activated linker functional groups.

4. An active carrier according to claim 1, characterized by that the material of the said carrier base (1) is glass, natural polymer or artificial polymer.

5. An active carrier according to claim 4, characterized by that the material of the carrier base (1) is glass.

6. An active carrier according to claim 4, characterized by that the material of the carrier base (1) is polypropylene.

7. An active carrier according to claim 1, characterized by that said linker is straight chained or branch chained, and it contains primer and/or secondary and/or tertiary amino group(s).

8. An active carrier according to claim 7, characterized by that said linker is a straight chain or branch chain polyamine.

9. An active carrier according to claim 1, characterized by that said linker contains maximum twenty substituted or unsubstituted linker functional groups.

10. An active carrier according to claim 1, characterized by that said linker is according to the general formula 1

wherein

the meaning of A is Si;

the meaning of B′

is O;

the meaning of R¹ is independently H, hydroxyl, —

C₁-C₂₀-alkyl or —

OC—

C₀-C₂₀-alkyl, —

C₃-C₆-cycloalkyl, where the alkyl advantageously is methyl, ethyl or propyl;

the meaning of R² is independently H, —

C₁-C₂₀-alkyl, —

OC—

C₀-C₂₀-alkyl, —

C₃-C₆-cycloalkyl, nitrile, isocyanate, thiocyanate, isothiocyanate, which, in a given case, with the exception of H, can be substituted with one or more groups selected from the following, include, but not limited to;

thiol, amino, carboxyl, hydroxyl, phenyl, aldehyde, keto, sulphonyl, phosphate, ester, sulpho, nitrile, epoxide, amidoalkyl halogenide, acrylamide, acid anhydride, isocyanate, isothiocyanate, azide, —

(N(R³)CH₂)_m—

N(R³)₂, halogenide, acid halogenide, where the halogenide can be chlorine, bromine, iodine;

the meaning of R³ is independently H, —

C₁-C₂₀-alkyl, —

OC—

C₀-C₂₀-alkyl, —

C₃-C₆-cycloalkyl, nitrile, isocyanate, thiocyanate, isothiocyanate, which, in a given case, with the exception of H, can be substituted with one or more groups selected from the following list, include, but not limited to;

thiol, amino, carboxyl, hydroxyl, phenyl, aldehyde, keto, sulphonyl, phosphate, ester, sulpho, nitrile, epoxide, amidoalkyl halogenide, acrylamide, acid anhydride, isocyanate, isothiocyanate, azide, —

(N(R⁴)CH₂)_m—

N(R⁴)₂, halogenide, acid halogenide, where the halogenide can be chlorine, bromine, iodine;

the meaning of R⁴ is independently H, —

C₁-C₂₀-alkyl, —

OC—

C₀-C₂₀-alkyl, —

C₃-C₆-cycloalkyl, nitrile, isocyanate, thiocyanate, isothiocyanate, which, in a given case, with the exception of H, can be substituted with one or more groups selected from the following list, include, but not limited to;

thiol, amino, carboxyl, hydroxyl, phenyl, aldehyde, keto, sulphonyl, phosphate, ester, sulpho, nitrile, epoxide, amidoalkyl halogenide, acrylamide, acid anhydride, isocyanate, isothiocyanate, azide, halogenide, acid halogenide, where the halogenide can be chlorine, bromine, iodine;

the value of n can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

the value of m can be independently 0, 1, 2, 3, 4, 5, 6, 7, 8; and

the linker is attached to the carrier base through the atom marked B′

, advantageously to the surface Si atom of glass carrier, or to the surface C or N atom of polymer carrier.

11. A process for the production of active carrier for surface immobilization of low molecular weight compounds comprising a carrier base (1) and attached linkers containing activated linker functional groups, characterized by that it consists of the following steps:

a) binding of a linker containing one or more linker functional groups to the carrier base through the carrier functional groups; and

b) reacting the linker functional groups of the linkers bound to the carrier base in step a) with two or more different activating reagents simultaneously.

12. A process according to claim 11, characterized by that said linkers are bound to the surface of the carrier by sililization.

13. A process according to claim 12, characterized by that the sililization is performed with 3,3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane.

14. A process according to claim 12, characterized by that the said sililization is performed with N-(2-aminoethyl)-3-aminopropyl-trimethoxysilane.

15. A process according to claim 11, characterized by that said linker functional groups are reacted with two, three, four or five activating reagents simultaneously.

16. A process according to claim 15, characterized by that said linker functional groups are reacted with two or three activating reagents simultaneously.

17. A process according to claim 11, characterized by that the activating agents are selected from the following compounds:

acrylic acid chloride, epichlorohydrin, chloroacetonitrile, chloroacetic acid chloride, bromoacetic acid chloride, chloroformic acid chloride, bromoformic acid chloride, chloroacetic acid anhydride, bromoacetic acid anhydride, iodoacetic acid chloride, iodoacetic acid anhydride, chloroformic acid anhydride, bromoformic acid anhydride, iodoformic acid anhydride, acrylic acid anhydride, 1,4-butanediol-diglycidyl ether, chloroacetic acid isocyanate, bromoacetic acid isocyanate, iodoacetic acid isocyanate, acrylic acid nitrile, chloroacetaldehyde, bromoacetaldehyde, iodoacetaldehyde, 4-chlorobutyric acid chloride, 4-bromobutyric acid chloride, 4-iodobutyric acid, 4-chlorobutyric acid anhydride, 4-bromobutyric acid anhydride, 4-iodobutyric acid anhydride, chloroacetic acid isothiocyanate, bromoacetic acid isothiocyanate, iodoacetic acid isothiocyanate, 3-chloropropanic acid chloride, 3-bromopropanic acid chloride, 3-iodopropanic acid chloride, N-chlorocarbonyl isocyanate, phenyl diisothiocyanate, disuccinimidyl-carbonate, disuccinimidyl-oxalate, dimethyl suberimidate and 4-nitrophenyl chloroformate.

18. The use of the active carrier for surface immobilization of low molecular weight compounds comprising a carrier base (1) and attached linkers containing two or more different activated linker functional groups, characterized by that the surface of the active carrier is contacted with one or more solutions of small molecules.

19. The use according to claim 18, characterized by that different points of the surface of the active carrier are contacted with two or more different solutions of small molecules for the production of a chemical microarray.

20. The use according to claim 18, characterized by that chromatographic column loads are used as active carriers and small molecules are bound to these for the production of affinity columns.