Nucleic acid labeling compounds

• US 8,026,057 B2
• Filed: 06/27/2008
• Issued: 09/27/2011
• Est. Priority Date: 03/12/2001
• Status: Expired due to Fees

• Current Assignee: Affymetrix, Inc. (Thermo Fisher Scientific Incorporated)
• Original Assignee: Affymetrix, Inc. (Thermo Fisher Scientific Incorporated)
• Inventors: Barone, Anthony Dale, McGall, Glenn Hugh
• Primary Examiner(s): Ward; Paul V.
• Application Number:
  US12/163,528
• Publication Number:
  US 20080287667A1
• Time in Patent Office: 1,187 Days
• Field of Search: 544/63, 435/6, 536/23.1
• US Class Current: 435/6
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 239/47 One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 7/00 Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
• CPC Class Codes: C07H 7/06 Heterocyclic radicals
• CPC Class Codes: C12Q 1/6816 characterised by the detection means C12Q1/6804 takes precedence

Abstract

Nucleic acid labeling compounds are disclosed. The compounds are synthesized by condensing a heterocyclic derivative with a cyclic group (e.g. a ribofuranose derivative). The labeling compounds are suitable for enzymatic attachment to a nucleic acid, either terminally or internally, to provide a mechanism of nucleic acid detection.

Claims

1. A nucleic acid labeling compound having the formula:

2. The nucleic acid labeling compound of claim 1, wherein A is H or H₄O₉P₃—

;

wherein X₁ is O;

wherein X₂ is a bond; and

wherein G is —

C(O)NR₃—

(CH₂)_m—

(CH₂CH₂O)_n—

CH₂CH₂—

C(O)NR₃—

, wherein R₃ is hydrogen or alkyl, and wherein m and n are independently an integer from 1 to 15.

3. The nucleic acid labeling compound of claim 2, wherein G is —

C(O)NH—

(CH₂)_m—

(CH₂CH₂O)_n—

CH₂CH₂—

C(O)NH—

;

wherein m is from 1 to 6; and

wherein n is from 1 to 4.

4. The nucleic acid labeling compound of claim 1, wherein A is H or H₄O₉P₃—

;

wherein X₁ is O;

wherein X₂ is CH₂; and

wherein G is —

C(O)NR₃—

(CH₂)_m—

(CH₂CH₂O)_n—

CH₂CH₂—

C(O)NR₃—

, wherein R₃ is hydrogen or alkyl, and wherein m and n are independently an integer from 1 to 15.

5. The nucleic acid labeling compound of claim 4, wherein G is —

C(O)NH—

(CH₂)_m—

(CH₂CH₂O)_n—

CH₂CH₂—

C(O)NH—

, wherein m is from 1 to 6, and wherein n is from 1 to 4.