Functionalized silicon compounds and methods for their synthesis and use

• US 6,743,882 B2
• Filed: 10/29/2002
• Issued: 06/01/2004
• Est. Priority Date: 10/13/1998
• Status: Expired due to Term

• Current Assignee: Affymetrix, Inc. (Thermo Fisher Scientific Incorporated)
• Original Assignee: Affymetrix, Inc. (Thermo Fisher Scientific Incorporated)
• Inventors: Forman, Jonathan Eric, McGall, Glenn
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US10/282,979
• Publication Number:
  US 20030077650A1
• Time in Patent Office: 581 Days
• Field of Search: 528/10, 528/25, 528/28, 528/33, 435/6, 524/588
• US Class Current: 528/10
• CPC Class Codes: C03C 17/30 with silicon-containing compounds
• CPC Class Codes: C03C 2218/113 by sol-gel processes
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08G 73/0206 Polyalkylene(poly)amines
• CPC Class Codes: C09D 179/02 Polyamines
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C09D 183/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Provided are functionalized silicon compounds and methods for their synthesis and use. The functionalized silicon compounds include at least one activated silicon group and at least one derivatizable functional group. Exemplary derivatizable functional groups include hydroxyl, amino, carboxyl and thio, as well as modified forms thereof, such as activated or protected forms. The functionalized silicon compounds may be covalently attached to surfaces to form functionalized surfaces which may be used in a wide range of different applications. In one embodiment, the silicon compounds are attached to the surface of a substrate comprising silica, such as a glass substrate, to provide a functionalized surface on the substrate, to which molecules, including polypeptides and nucleic acids, may be attached. In one embodiment, after covalent attachment of a functionalized silicon compound to the surface of a solid silica substrate to form a functionalized coating on the substrate, an array of nucleic acids may be covalently attached to the substrate. Thus, the method permits the formation of high density arrays of nucleic acids immobilized on a substrate, which may be used, for example, in conducting high volume nucleic acid hybridization assays.

Claims

1. A functionalized silicon compound having Formula 4:

wherein, B is —

SiR₁R₂R₃, wherein R₁, R₂ and R₃ are independently alkoxy, halo or alkyl;

wherein x, y, and z are independently 2 to 3;

wherein L₁, L₂ and L₃ are independently —

(CH₂)_q—

, wherein q is 2-10;

wherein A and C are independently moieties comprising derivatizable functional groups; and

wherein n is about 10 to 10,000.

2. The functionalized silicon compound of claim 1, wherein x, y and z are each 2.

3. The functionalized silicon compound of claim 1, wherein L₁, L₂ and L₃ are —

(CH₂)_q—

, wherein q is 2 or 3.

4. The functionalized silicon compound of claim 1, wherein R₁ and R₂ are independently alkoxy or halo.

5. The functionalized silicon compound of claim 4, wherein R₁ and R₂ are independently —

OCH₃, or —

OCH₂CH₃, and R₃ is alkoxy, halo or alkyl.

6. The functionalized silicon compound of claim 5, wherein R₁, R₂, and R₃ are each —

OCH₃.

7. The functionalized silicon compound of claim 5, wherein R₁, R₂, and R₃ are each —

OCH₂CH₃.

8. The functionalized silicon compound of claim 1, wherein A and C comprise a plurality of derivatizable functional groups.

9. The functionalized silicon compound of claim 8, wherein the derivatizable functional groups are selected from the group consisting of hydroxyl, amino, amido, carboxyl, thio, halo, and sulfonate.

10. The functionalized silicon compound of claim 9, wherein the derivatizable functional groups are hydroxyl, or amino, or modified forms thereof.

11. The functionalized silicon compound of claim 10, wherein the derivatizable functional groups are —

OH.

12. The functionalized silicon compound of claim 1, wherein n is about 1000 to about 10,000.

13. The functionalized silicon compound of claim 1, wherein B is —

Si(OCH₃)₃;

x, y, and z are 2;

L₁ and L₃ are —

(CH₂)₂—

;

L₂ is —

(CH₂)₃—

;

A and C are moieties comprising derivatizable functional groups; and

n is about 10 to 10,000.

14. A functionalized silicon compound of Formula 6:

wherein R₁, R₂ and R₃ are independently alkoxy, halo or alkyl; and

wherein g is about 1 to 5, and n is about 10 to 10,000.

15. The functionalized silicon compound of claim 14, wherein R₁, and R₂ are independently alkoxy or halo and R₃ is alkoxy, halo, or alkyl.

16. The functionalized silicon compound of claim 15, wherein R₁, and R₂ are independently, —

OCH₃ or —

OCH₂CH₃, and R₃ is —

CH₃.

17. A functionalized silicon compound of Formula 8:

wherein R₁, R₂ and R₃ are independently alkoxy, halo or alkyl;

and n is about 10 to 10,000.

18. The functionalized silicon compound of claim 17, wherein R₁, and R₂ are independently alkoxy or halo and R₃ is a alkoxy, halo, or alkyl.

19. The functionalized silicon compound of claim 18, wherein R₁, and R₂ are independently, —

OCH₃ or —

OCH₂CH₃, and R₃ is —

CH₃.

20. A functionalized silicon compound of Formula 9:

wherein R₁, R₂ and R₃ are independently alkoxy, halo or alkyl; and

and n is about 10 to 10,000.

21. The functionalized silicon compound of claim 20, wherein R₁, and R₂ are independently alkoxy or halo and R₃ is a alkoxy, halo, or alkyl.

22. The functionalized silicon compound of claim 21, wherein R₁, and R₂ are independently, —

OCH₃ or —

OCH₂CH₃, and R₃ is —

CH₃.

23. A functionalized silicon compound of Formula 12:

wherein R₁, R₂ and R₃ are independently alkoxy, halo or alkyl;

G is a leaving group;

p is about 1 to 10; and

n is about 10 to 10,000.

24. The functionalized silicon compound of claim 23, wherein R₁, and R₂ are independently alkoxy or halo and R₃ is a alkoxy, halo, or alkyl.

25. The functionalized silicon compound of claim 24, wherein R₁, and R₂ are independently, —

OCH₃ or —

OCH₂CH₃, and R₃ is —

CH₃.

26. The functionalized silicon compound of claim 25, wherein G is hydroxyl, protected hydroxyl, —

Cl or —

Br.

27. The functionalized silicon compound of claim 26, wherein G is —

N(CH₂CH₂—

OH)₂.