Functionalized silicon compounds and methods for their synthesis and use

• US 7,098,286 B2
• Filed: 05/28/2004
• Issued: 08/29/2006
• 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:
  US10/857,283
• Publication Number:
  US 20040214019A1
• Time in Patent Office: 823 Days
• Field of Search: 528/10, 528/25, 528/28, 528/33
• 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 thiol, 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 method of functionalizing a surface, the method comprising covalently attaching to the surface a functionalized silicon compound of Formulas 17, 18, 19, or 20:

2. The method of claim 1, wherein the method comprises covalently attaching a plurality of functionalized silicon compounds to the surface;

and forming an array of nucleic acids covalently attached to the functionalized silicon compounds on the surface.

3. The method of claim 1, wherein the derivatizable groups are hydroxyl groups or modified forms thereof.

4. The method of claim 1, wherein the compound is selected from the group consisting of

5. The method of claim 1, wherein the surface is the surface of a substrate comprising silica.

6. The method of claim 1, wherein R₃ is a substituted alkyl group.

7. The method of claim 1, wherein R₁, R₂, and R₃, are independently, —

OCH₃, or —

OCH₂CH₃.

8. The method of claim 7, wherein R₁, R₂ and R₃ are each —

OCH₃.

9. The method of claim 1, wherein R₁, and R₂, are independently, —

OCH₃ or —

OCH₂CH₃, and R₃ is —

CH₃, or a substituted alkyl group.

10. The method of claim 1, wherein L₁, L₂, and L₃ are independently, C_1-25 alkyl;

or a heteroalkyl; and

the derivatizable groups are hydroxyl or amino.

11. The method of claim 10, wherein L₁, L₂, and L₃ are independently, —

(CH₂)_n—

, wherein n is an integer from 2 to 10.

12. The method of claim 11, wherein L₁, L₂, and L₃ are independently, —

(CH₂)_n—

, wherein n is 2, 3, or 4.

13. The method of claim 1, wherein A₁ and A₂ independently comprise, a linear or branched alkyl or linear or branched heteroalkyl, having 1, 2, or 3 derivatizable groups.

14. The method of claim 13, wherein the derivatizable groups are amino, or hydroxyl.

15. The method of claim 1, wherein A₁ and A₂ are independently —

CH₂CH₂OH, or an amide.

16. The method of claim 1, wherein B₁ and B₂ are independently C_1-12 alkyl, branched C_1-12 alkyl, a heteroatom, or branched C_1-12 heteroalkyl.

17. The method of claim 1, wherein L₄ is C_1-12 alkyl or C_1-12 heteroalkyl optionally comprising one more derivatizable groups.

18. The method of claim 1, wherein acyl is HC(═

CH₂)CO—

or MeC(═

CH₂)CO—

.