초록 ▼

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 attachme

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.

대표청구항 ▼

The invention claimed is: 1. A nucleic acid labeling compound comprising the formula: 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,

The invention claimed is: 1. A nucleic acid labeling compound comprising the formula: 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. 2. A nucleic acid labeling compound according to claim 1, 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--NH(CH2)nNH--, wherein n is an integer ranging from about 2 to about 10; Q is biotin or carboxyfluorescein; and M is--CO(CH2)5NH--or--CO(CH2)5NHCO(CH2)5NH--, wherein m is 1 or 0. 3. A nucleic acid labeling compound according to claim 2, wherein Y is H or OH; Z is H or OH; L is--NH(CH2)4NH--; Q is biotin; and M is--CO(CH2)5NH--, wherein m is 1. 4. A nucleic acid labeling compound according to claim 2, wherein Y is H or OH; Z is H or OH; L is--NH(CH2)4NH--; Q is 5-carboxyfluorescein; and M is--CO(CH2)5NH--, wherein m is 1. 5. A nucleic acid labeling compound according to claim 2, wherein A is H; Y is OH; Z is OH; L is--NH(CH2)4NH--; Q is biotin; and M is--CO(CH2)5NH, wherein m is 1. 6. A nucleic acid labeling compound according to claim 2, wherein A is H4O9P3--; Y is OH; Z is OH; L is--NH(CH2)4NH--; Q is biotin; and M is--CO(CH2)5NH, wherein m is 1. 7. A nucleic acid labeling compound according to claim 2, wherein A is H; Y is OH; Z is OH; L is--NH(CH2)4NH--; Q is 5-carboxyfluorescein; and M is--CO(CH2)5NH, wherein m is 1. 8. A nucleic acid labeling compound according to claim 2, wherein A is H4O9P3--; Y is OH; Z is OH; L is--NH(CH2)4NH--; Q is 5-carboxyfluorescein; and M is--CO(CH2)5NH, wherein m is 1. 9. A nucleic acid labeling compound comprising the formula: 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. 10. A nucleic acid labeling compound according to claim 9, 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--CH═CH(CH2)nNH--, wherein n is an integer ranging, from about 1 to about 10; Q is biotin or carboxyfluorescein; and M is--CO(CH2)5NH--or--CO(CH2)5NHCO(CH2)5NH--, wherein m is 1 or 0. 11. A nucleic acid labeling compound according to claim 10, wherein Y is H or OH; Z is H or OH; L is--CH═CHCH2NH--; Q is biotin; and m is 0. 12. A nucleic acid labeling compound according to claim 10, wherein Y is H or OH; Z is H or OH; L is--CH═CHCH2NH--; Q is 5-carboxyfluorescein; and m is 0. 13. A nucleic acid labeling compound comprising the formula: 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. 14. A nucleic acid labeling compound according to claim 13, 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--CH═CH(CH2)nNH--, wherein n is an integer ranging from about 1 to about 10; Q is biotin or carboxyfluorescein; and M is--CO(CH2)5NH--or--CO(CH2)5NHCO(CH2)5NH--, wherein m is 1 or 0. 15. A nucleic acid labeling compound according to claim 14, wherein Y is H or OH; Z is H or OH; L is--CH═CHCH2NH--; Q is biotin; and m is 0. 16. A nucleic acid labeling compound according to claim 14, wherein Y is H or OH; Z is H or OH; L is--CH═CHCH2NH--; Q is 5-carboxyfluorescein; and m is 0. 17. A nucleic acid labeling compound according to claim 1, wherein the compound has the formula: 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. 18. A nucleic acid labeling compound according to claim 9, wherein the compound has the formula: 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. 19. A nucleic acid labeling compound according to claim 13, wherein the compound has the formula: 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. 20. A nucleic acid labeling compound according to claim 1, wherein the compound has the formula: 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. 21. A nucleic acid labeling compound according to claim 9, wherein the compound has the formula: 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. 22. A nucleic acid labeling compound according to claim 13, wherein the compound has the formula: 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. 23. A nucleic acid labeling compound according to claim 1, wherein the compound has the formula: 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. 24. A nucleic acid labeling compound according to claim 9, wherein the compound has the formula: 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. 25. A nucleic acid labeling compound according to claim 13, wherein the compound has the formula: 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.