Compounds and methods for labeling oligonucleotides

• US 8,258,276 B2
• Filed: 09/02/2011
• Issued: 09/04/2012
• 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, Walder, Joseph A., Behlke, Mark, Podyminogin, Mikhail, Yong, Yawfui
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US13/224,571
• Publication Number:
  US 20110319606A1
• Time in Patent Office: 368 Days
• Field of Search: 536/23.1, 536/24.3, 536/26.6, 435/6
• 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

A compound having the general formula shown below:

where R_1-6 are independently selected from the group consisting of an electron withdrawing group, an alkyl group, an aryl group, hydrogen, a heteroaryl group, and a five or six member ring structure formed from the R₁ and R₂ pair, the R₃ and R₄ pair, the R₄ and R₅ pair, or the R₅ and R₆ pair; R₇ is a substituted or unsubstituted aryl group; and Y is a nucleophile.

Claims

1. A composition comprising a reporter moiety linked to an oligonucleotide through an oxime bond, wherein the reporter moiety is a compound of Formula (I):

2. The composition of claim 1, wherein the oxime forming nucleophile includes an aminooxy group.

3. The composition of claim 1, wherein the reporter moiety is

4. The composition of claim 1, wherein the oligonucleotide is linked to a solid support.

5. The composition of claim 1, wherein the reporter moiety is linked to a 3′

end of the oligonucleotide.

6. The composition of claim 1, wherein the reporter moiety is linked to a 5′

end of the oligonucleotide.

7. The composition of claim 1, wherein the reporter moiety is linked to an internal nucleotide of the oligonucleotide.

8. The composition of claim 1, further wherein the reporter moiety is a first reporter moiety, and further comprising a second reporter moiety linked to the oligonucleotide.

9. The composition of claim 1, wherein the oxime forming nucleophile includes a hydrazine group.

10. A kit comprising the composition of claim 1.

11. The kit of claim 1, further comprising instructions for the use of the composition.