Nucleoside analogues
AssigneeAmersham Pharmacia Biotech UK Limited
InventorsDaniel Brown, David Loakes, Alan Hamilton, Adrian Simmonds, Clifford Smith
Life of this patent
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Abstract
Nucleoside analogues in which a group M replaces the natural base where M is (1) or (2) or (3), where each of X1, X2 and X3 are C or N, each of R6 and R7 is the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)n(R8)2, halogen, or a reporter moiety, each of R8 and R9 is H or hydrocarbyl or a reporter moiety, and n is 0-4. The analogues are substrates for polymerase and terminal transferase enzymes.
Claims12
A nucleoside analogue of the formula:
- where Z is O, S, Se, SO NR9 or CH2,
- R1, R2, R3 and R4 are the same or different and each is H, OH, F, NH2, N3, O-hydrocarbyl or a reporter moiety,
- R5 is OH or mono-, di- or tri-phosphate or -thiophosphate or corresponding boranophosphate,
- or one of R2 and R5 is a phosphoramidite or other group for incorporation in a polynucleotide chain,
- and M is:
- where X1, X2 and X3 are the same or different and each is C or N, when X3 is N, there is no R7 group,
- R6 and R7 are the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)nN(R8)2, halogen, or a reporter moiety,
- each of R8 and R9 is H or hydrocarbyl or a reporter moiety,
- and n is 0, 1, 2, 3 or 4,
- provided that when R5 is not triphosphate, then the nucleoside analogue comprises a reporter moiety
- and provided that, when M is benzimidazolyl and a reporter moiety is absent, the M has the structure:
- and R6 is not H,
- and further provided that when M is:
- then R5 is not OH.
A method of detecting a nucleic acid which contains a residue of a nucleoside analogue of the formula:
- where Z is O, S, Se, SO, NR9 or CH2,
- R1, R2, R3 and R4 are the same or different and each is H, OH, F, NH2, N3, O-hydrocarbyl or a reporter moiety,
- R5 is OH or mono-, di- or tri-phosphate or -thiophosphate or corresponding boranophosphate,
- or one of R2 and R5 is a phosphoramidite or other group for incorporation in a polynucleotide chain,
- and M is:
- where X1, X2 and X3 are the same or different and each is C or N, when X3 is N, there is no R7 group,
- R6 and R7 are the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)nN(R8)2, halogen, or a reporter moiety,
- each of R8 and R9 is H or hydrocarbyl or a reporter moiety,
- and n is 0, 1, 2, 3 or 4,
- which method comprises using for detection an antibody which binds to M.
[1-(2′-deoxy-β-D-ribofuranosyl)-pyrrole-3,4-dicarboxamide]5′-triphosphate.
Dependencies are inferred from the claim text.