Compounds and methods for labeling oligonucleotides

• US 7,605,243 B2
• Filed: 01/12/2009
• Issued: 10/20/2009
• 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:
  US12/352,125
• Publication Number:
  US 20090118482A1
• Time in Patent Office: 281 Days
• Field of Search: 536/23.1, 536/24.3, 536/26.6, 435/6, 422/68.1
• US Class Current: 536/23.1
• 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 labeled oligonucleotide comprising at least two different reporter moieties linked to different nucleotides of the oligonucleotide, wherein one of the reporter moieties is a quencher linked through an oxime bond.

2. The composition of claim 1, wherein the reporter moieties are independently selected from the group consisting of quenchers, fluorophores, biotin, digoxigenin, peptides, proteins, antibodies, glycoproteins and sugars.

3. The composition of claim 2, wherein one of the reporter moieties is selected from the group consisting of compound 34, compound 35, compound 36 and compound 37.

4. A kit comprising the composition of claim 1.

5. The kit of claim 4, further comprising instructions for the use of the composition.