Methods of attaching biological compounds to solid supports using triazine

• US 20060127930A1
• Filed: 11/10/2005
• Published: 06/15/2006
• Est. Priority Date: 12/17/2003
• Status: Active Grant

• Current Assignee: Illumina Incorporated
• Original Assignee: Illumina Incorporated
• Inventors: Steinberg-Tatman, Galina, Kozlov, Igor, Zhao, Chanfeng
• Granted Patent: US 7,504,499 B2
• Time in Patent Office: Days
• US Class Current: 435/6
• CPC Class Codes: C07D 251/12 having three double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: Y10T 428/139 Open-ended, self-supporting conduit, cylinder, or tube-type article

Abstract

Disclosed are methods of attaching biologically active compounds to a solid surface, comprising modifying the solid surface using triazine chloride and attaching the biologically active compound to the triazine moiety.

Claims

1. A compound of Formula XX

2. The compound of claim 1, wherein V is NH.

3. The compound of claim 1, wherein V is —

NH—

(CH₂)_p—

Si(O)₃ and p is an integer greater than or equal to zero.

4. The compound of claim 1, wherein D is selected from the group consisting of RNA, DNA, a polypeptide, RNA having one or more non-naturally occurring bases, DNA having one or more non-naturally occurring bases, and a polypeptide having one or more non-naturally occurring amino acids.

5. The compound of claim 1, wherein Q is selected from the group consisting of resin, microbead, glass, controlled pore glass (CPG), polymer support, membrane, paper, plastic, plastic tube or tablet, plastic bead, glass bead, slide, ceramic, silicon chip, multi-well plate, nylon membrane, and PVDF membrane.

6. The compound of claim 1, wherein D is DNA.

9. The compound of claim 1, wherein the compound of Formula XX is selected from the group consisting of:

7. A compound of the Formula XXI:

8. A compound of the Formula XXVII:

10. A compound of Formula XXVI

11. A method of synthesizing a compound of Formula XXII

12. The method of claim 11, wherein said group reactive towards cyanuric chloride is a nucleophile.

13. The method of claim 12, wherein said nucleophile is selected from the group consisting of hydrazine, amine, thiol, and hydroxyl.

14. A method of synthesizing a compound of Formula XXII

15. A method of synthesizing a compound of Formula XXI

17. The method of claim 15, wherein the aldehyde modified biologically active polymer is selected from the group consisting of RNA, DNA, a polypeptide, RNA having one or more non-naturally occurring bases, DNA having one or more non-naturally occurring bases, and a polypeptide having one or more non-naturally occurring amino acids.

18. The method of claim 15, wherein the aldehyde modified biologically active polymer is selected from the group consisting of 5′

modified RNA, 3′

modified RNA, 5′

modified DNA, 3′

modified DNA, N-terminal modified polypeptide, and C-terminal modified polypeptide.

19. The method of claim 15, wherein the aldehyde modified biologically active polymer is an aldehyde modified DNA.

20. The method of claim 19, wherein the aldehyde modified DNA is modified on the 5′

or 3′

base of the DNA molecule.

21. The method of claim 19, wherein the modified 5′

or 3′

base on the aldehyde modified DNA is

22. The method of claim 15, wherein the silanating compound is selected from the group consisting of R—

Si(OR′

)₃, R₁(R₂)—

Si—

(OR′

)₂, and R₁(R₂)(R₃)—

Si—

(OR′

);

R, R₁, R₂, and R₃ are each independently selected from the group consisting of optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxy, and optionally substituted aryloxy;

R, R₁, R₂, and R₃, each independently contain one or more of —

NH—

, —

(CH₂)_p—

, —

C(O)—

and —

O—

, wherein p is an integer greater than or equal to zero; and

R′

is selected from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxy, and optionally substituted aryloxy.

23. The method of claim 15, wherein the silanating compound is aminopropyltrimethoxysilane.

16. A method of synthesizing a compound of Formula XXVII

24. A method of synthesizing a compound of the Formula XXV

25. A method of obtaining a solid surface to which a plurality of biologically active polymers are attached, and having a structure of Formula XXIV,