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US 2001/0044531 A1Published application
Nucleic acid labeling compounds
AssigneeAffymetrix, Inc.
InventorsGlenn McGall, Anthony D. Barone
Life of this patent
Estimating the term…
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.
Claims168
A nucleic acid labeling compound of the following structure:
- 48
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amido alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 49
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 50
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 51
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 52
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 53
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 54
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amido alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 55
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound ofthe following structure:
- 56
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 57
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 58
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl allyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 59
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 60
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amido alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 61
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 62
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 63
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is amino alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 64
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
A nucleic acid labeling compound of the following structure:
- 65
- wherein
- A is H or a functional group that permits the attachment of the nucleic acid labeling compound to a nucleic acid;
- X is O, S, NR1 or CHR2, wherein R1 and R2 are, independently, H, alkyl or aryl;
- Y is H, N3, F, OR9, SR9 or NHR9, wherein R9 is H, alkyl or aryl;
- Z is H, N3, F or OR10, wherein R10 is H, alkyl or aryl;
- L is functionalized alkyl, alkenyl alkyl or alkynyl alkyl;
- Q is a detectable moiety;
- and
- M is a connecting group, wherein m is an integer ranging from 0 to about 3.
7 more elements
Dependencies are inferred from the claim text.