Fluorescence quenching azo dyes, their methods of preparation and use

• US 8,084,588 B2
• Filed: 10/16/2008
• Issued: 12/27/2011
• Est. Priority Date: 11/14/2003
• Status: Active Grant

• Current Assignee: Integrated DNA Technologies (Danaher Corporation)
• Original Assignee: Integrated DNA Technologies (Danaher Corporation)
• Inventors: Laikhter, Andrei, Behlke, Mark Aaron, Walder, Joseph, Roberts, Kevin William, Yong, Yawfui
• Primary Examiner(s): Powers, Fiona T
• Application Number:
  US12/252,721
• Publication Number:
  US 20090053821A1
• Time in Patent Office: 1,167 Days
• Field of Search: None
• US Class Current: 534/876
• 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: C07F 9/091 with hydroxyalkyl compounds with further substituents on alkyl
• CPC Class Codes: C07F 9/2408 of hydroxyalkyl compounds
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: C09B 29/00 Monoazo dyes prepared by diazotising and coupling
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]

Abstract

Disclosed is a group of azo quencher compositions useful as fluorescence quenchers having the general structure of formula 1, methods of making or using the compositions, and kits comprising the composition.

Claims

1. A composition, comprising:

a compound for quenching emission of light of the structure of Formula 1;

2. The composition of claim 1 wherein the substance linked to the compound of Formula 1 further comprises a fluorophore.

3. The composition of claim 1 wherein either R₈ or R₉ is a phosphoramidite group.

4. The composition of claim 1 wherein the substance is an oligonucleotide.

5. The composition of claim 4 wherein the compound of Formula 1 is linked to the 3′

-terminus of the oligonucleotide.

6. The composition of claim 4 wherein the compound of Formula 1 is linked to the 5′

-terminus of the oligonucleotide.

7. The composition of claim 1 wherein the substance is a solid support.

8. The composition of claim 7 wherein the solid support is capable of supporting oligonucleotide synthesis.

9. The composition of claim 7 wherein the solid support is controlled pore glass.

10. The composition of claim 1, wherein the compound of formula 1 is the compound of Formula 13,

11. The composition of claim 1, wherein the compound of Formula 1 is the compound of Formula 14,