Nucleic acid labeling compounds

• US 20040210045A1
• Filed: 05/11/2004
• Published: 10/21/2004
• Est. Priority Date: 01/23/1996
• Status: Abandoned Application

• Current Assignee: Anthony D. Barone, Glenn McGall
• Original Assignee: Anthony D. Barone, Glenn McGall
• Inventors: Barone, Anthony D., McGall, Glenn
• Application Number:
  US10/842,778
• Publication Number:
  US 20040210045A1
• Time in Patent Office: Days
• US Class Current: 536/25.32
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 19/052 Imidazole radicals
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/12 Triazine radicals
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• 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 1/6809 Methods for determination or identification of nucleic acids involving differential detection
• CPC Class Codes: C12Q 1/6816 characterised by the detection means C12Q1/6804 takes precedence
• CPC Class Codes: C12Q 1/6837 using probe arrays or probe chips C12Q1/6874 takes precedence
• CPC Class Codes: C12Q 2561/125 Ligase Detection Reaction [LDR]
• CPC Class Codes: C12Q 2565/501 being an array of oligonucleotides
• CPC Class Codes: C12Q 2600/156 Polymorphic or mutational markers
• CPC Class Codes: C40B 40/00 Libraries per se, e.g. arrays, mixtures

Abstract

Nucleic acid labeling compounds containing heterocyclic derivatives are disclosed. The heterocyclic derivative containing 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

1-49. -49. (canceled)

53-67. -67. (canceled)

71-169. -169. (canceled)

170. A nucleic acid labeling compound of the following structure:

172. the compound of claim 170, wherein A is H or H₄O₉P₃—

;

X is O;

Y is H or OR₉, wherein R₉ is H, alkyl or aryl;

Z is H, N₃, F or OR₁₀, wherein R₁₀ is H, alkyl or aryl;

L is —

(CH₂)_nC(O)—

, wherein n is an integer ranging from about 1 to about 10;

Q is biotin or a fluorescein; and

, a first M is —

NH(CH₂)_nNH—

, wherein n is an integer from about 2 to about 10, and a second M is —

CO(CH₂)₅NH—

, wherein m is 1 or 2.

173. The nucleic acid labeling compound of claim 170, wherein Y is H or OH;

Z is H or OH;

L is —

(CH₂)₂C(O)—

, Q is biotin or a carboxyfluorescein; and

a first M is —

NH(CH₂)₂NH—

, and a second M is —

CO(CH₂)₅NH—

, wherein m is 2.

174. The nucleic acid labeling compound of claim 170, wherein Y is OH;

Z is OH;

L is —

(CH₂)₂C(O)—

, Q is a carboxyfluorescein; and

, a first M is —

NH(CH₂)₂NH—

, and a second M is —

CO(CH₂)₅NH—

, wherein m is 2.

175. The nucleic acid labeling compound of claim 170, wherein Y is OH;

Z is OH;

L is —

(CH₂)₂C(O)—

, Q is or biotin; and

, a first M is —

NH(CH₂)₂NH—

, and a second M is —

CO(CH₂)₅NH—

, wherein m is 2.

176. A nucleic acid labeling compound according to claim 170, having the structure:

177. A nucleic acid labeling compound according to claim 170, having the structure:

171. (canceled)

50. A nucleic acid derivative produced by coupling a nucleic acid labeling compound according to claim 171 with a nucleic acid.

51. A hybridization product, wherein the hybridization product comprises the nucleic acid derivative according to claim 50 bound to a complementary probe.

52. The hybridization product according to claim 51, wherein the probe is attached to a glass chip.

68. A method of synthesizing a labeled nucleic acid comprising attaching a nucleic acid labeling compound according to claim 171 to a nucleic acid.

69. A method of detecting a nucleic acid comprising incubating a nucleic acid derivative according to claim 50 with a probe.

70. A method according to claim 69, wherein the probe is attached to a glass chip.