Polar dyes

• US 8,546,590 B2
• Filed: 08/17/2010
• Issued: 10/01/2013
• Est. Priority Date: 03/09/2005
• Status: Expired due to Fees

• Current Assignee: Cepheid (Danaher Corporation)
• Original Assignee: Cepheid (Danaher Corporation)
• Inventors: Gall, Alexander A.
• Primary Examiner(s): NORTHINGTON DAVIS, ZINNA
• Application Number:
  US12/858,367
• Publication Number:
  US 20110053155A1
• Time in Patent Office: 1,141 Days
• Field of Search: None
• US Class Current: 549/334
• CPC Class Codes: C09B 11/24 Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
• CPC Class Codes: C09B 23/0066 the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
• CPC Class Codes: C09B 23/083 five >CH- groups
• CPC Class Codes: C09B 29/00 Monoazo dyes prepared by diazotising and coupling
• CPC Class Codes: C09B 43/00 Preparation of azo dyes from other azo compounds
• CPC Class Codes: C09B 56/005 Azo-nitro dyes
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/02 Coumarine dyes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: Y10T 436/143333 Saccharide [e.g., DNA, etc.]

Abstract

The present invention relates to novel polar fluorescent and quenchers dyes, and minor groove binder with enhanced polarity. The present invention further relates to methods of preparing oligonucleotide probes labeled with polar arsonate dyes under the condition of automated synthesis and method of using such probes.

Claims

1. A compound of Formula (VIII):

2. An oligonucleotide conjugate comprising an oligonucleotide conjugated to a dye of Formula (VIII):

3. The oligonucleotide of claim 2 wherein the dye is a fluorescent dye having an excitation between 340 nm and 1100 nm and fluorescence emission maximum between 440 and 1150 nm.

4. The oligonucleotide of claim 2 further comprising a minor groove binder (MGB) group.

5. The oligonucleotide of claim 4 wherein the minor groove binder (MGB) group is substituted with a polar arsonate group.

6. A method of preparing an oligonucleotide in an automated synthesis, comprising:

performing automated synthesis of oligonucleotide using phosphoramidite method by conjugating an oligonucleotide to a compound of Formula (VIII);

7. The method of claim 6 further comprising a step of conjugating a minor groove binder (MGB) in the oligonucleotide.

8. The method of claim 7 wherein the minor groove binder (MGB) is substituted with an arsonate group.