Nucleobase-functionalized conformationally restricted nucleotides and oligonucleotides for targeting nucleic acids
AssigneeUniversity of Idaho
InventorsPatrick Jerzy Hrdlicka, Pawan Kumar, Michael E. Østergaard
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Abstract
Embodiments are disclosed herein that involve C5-functionalized nucleic acids, which can be used for detecting a target in a nucleic acid. Particular embodiments disclose methods for making these compounds, wherein the compounds can be formed by coupling of an intermediate with a linker. Certain embodiments disclose the use of these compounds for detecting single nucleotide polymorphisms, and for increasing the thermal affinity of nucleic acid complements as compared to unmodified nucleic acid complements. In addition, the disclosed compounds can decrease enzymatic degradation of nucleic acids.
Claims20
A compound having a formula
- or a pharmaceutically acceptable salt, a hydrate, a solvate, or combinations thereof, where:
- R1 is selected from aliphatic, heteroaliphatic, aryl, heteroaryl, charged moieties, or metal complexes;
- R2 is selected from hydrogen, aliphatic, heteroaliphatic, aryl, heteroaryl, functional group protecting groups, oligonucleotides, a phosphorous-containing compound, a sulfur-containing compound, a nitrogen-containing compound, an oxygen-containing compound, a metal-containing compound, or a selenium-containing compound;
- R3 is selected from hydrogen, oligonucleotides, a phosphorous-containing compound, a sulfur-containing compound, a nitrogen-containing compound, an oxygen-containing compound, a metal-containing compound, or a selenium-containing compound;
- R4 is selected from
- wherein each X is independently nitrogen, carbon, or any combination thereof;
- Y is selected from oxygen, sulfur, or N(R5) where R5 is selected from hydrogen, aliphatic, aryl, heteroaliphatic, or heteroaryl;
- Z is selected from ether, thioether, hydroxyl, sulfhydryl or N(R5)2 where each R5 is independently selected from hydrogen, aliphatic, aryl, heteroaliphatic, heteroaryl, or any combination thereof;
- linker is selected from aliphatic, aryl, heteroaliphatic, or heteroaryl;
- each Y is independently selected from oxygen, sulfur, or NR5 where R5 is selected from hydrogen, aliphatic, aryl, heteroaliphatic, or heteroaryl, or any combination thereof;
- and
- m+n=2 to 4.
Dependencies are inferred from the claim text.