Compounds and methods for labeling oligonucleotides

• US 7,803,936 B2
• Filed: 11/23/2009
• Issued: 09/28/2010
• Est. Priority Date: 05/20/2005
• Status: Active Grant

• Current Assignee: Integrated DNA Technologies (Danaher Corporation)
• Original Assignee: Integrated DNA Technologies (Danaher Corporation)
• Inventors: Laikhter, Andrei, Yong, Yawfui, Walder, Joseph A., Behlke, Mark, Podyminogin, Mikhail
• Primary Examiner(s): Riley; Jezia
• Application Number:
  US12/623,811
• Publication Number:
  US 20100076181A1
• Time in Patent Office: 309 Days
• Field of Search: 536/23.1, 536/26.6, 540/6, 540/464, 435/6, 435/7.1, 435/7.2, 530/350, 422/61
• US Class Current: 536/26.6
• CPC Class Codes: C07C 245/10 with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: C12Q 1/6818 involving interaction of two or more labels, e.g. resonant energy transfer

Abstract

The invention provides a novel method of labeling oligonucleotides, with reporter moieties, including but not limited to, quenchers, fluorophores, biotin, digoxigenin, peptides and proteins. In addition, this invention provides a method of detecting hybridization of oligonucleotides. This invention also provides novel azo quenchers having the general formula shown below.

The invention further provides compositions comprising labeled oligonucleotides and solid supports. The invention also provides kits comprising at least one composition of the present invention.

Claims

1. A composition comprising a reporter moiety linked to a solid support through an oxime bond.

2. The composition of claim 1 wherein the reporter moiety is a compound of Formula (I)

3. The composition of claim 2, comprising:

4. The composition of claim 2, comprising:

5. The composition of claim 4, wherein the nucleobase is selected from the group consisting of adenine, guanine, cytosine, uracil and thymine.

6. The composition of claim 5, wherein the nucleobase is uracil.