Nitrodiarylethenes as fluorescence quenchers for nucleic acid probes
AssigneeElitechgroup B.V.
InventorsEugeny A. Lukhtanov, Noah Scarr
Life of this patent
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Abstract
Fluorescence quenching nitrodiarylethene analogs are useful in oligonucleotide conjugates and probes. These analogs, whose absorption spectra are substantially blue-shifted relatively to emission spectra of common fluorophores (such as fluorescein), do not need to rely on spectral overlap of quencher absorbance and fluorophore's emission for their quenching abilities. The oligonucleotide-quencher conjugates may be used in detection methods for nucleic acid targets.
Claims9
A quencher reagent for oligonucleotide labeling having the formula:
- (R1)(R2)Y-(—Ar1—CR3═CR4—)n-Ar2
- wherein Ar1 is a substituted phenyl and Ar2 is a substituted naphthyl, wherein Ar1 and Ar2 are independently substituted with one or more of H, (C1-C8)alkyl, halogen, alkyloxy, phenyl, or combinations thereof, and at least one of Ar1 and Ar2 is substituted with one or more NO2 groups;
- R3 and R4 are independently H or (C1-C8)alkyl;
- n is 1;
- Y is a linking group connecting Ar1 with R1 and R2 and having from 1 to 100 main chain atoms selected from C, N, O, S, P and Si;
- R1 is a phosphoramidite having the formula —OP(N(iPr)2)(OCH2CH2CN)) or a linking group attached to a solid support having the formula —O—C(═O)Z-solid support, wherein iPr is isopropyl, and wherein Z is 1 to 30 main chain atoms in length wherein the main chain atoms are selected from C, N, O, P, and S;
- and
- R2 is H, or a dimethoxytrityl-protected hydroxyl group.
A quencher reagent for oligonucleotide labeling having the formula:
- (R1)(R2)Y-(—Ar1—CR3═CR4—)n-Ar2
- wherein Ar1 is a substituted phenyl and Ar2 is a substituted anthryl, wherein Ar1 and Ar2 are independently substituted with one or more of H, (C1-C8)alkyl, halogen, alkyloxy, phenyl, or combinations thereof, and at least one of Ar1 and Ar2 is substituted with one or more NO2 groups;
- R3 and R4 are independently H or (C1-C8)alkyl;
- n is 1;
- Y is a linking group connecting Ar1 with R1 and R2 and having from 1 to 100 main chain atoms selected from C, N, O, S, P and Si;
- R1 is a phosphoramidite having the formula —OP(N(iPr)2)(OCH2CH2CN)) or a linking group attached to a solid support having the formula —O—C(═O)Z-solid support, wherein iPr is isopropyl, and wherein Z is 1 to 30 main chain atoms in length wherein the main chain atoms are selected from C, N, O, P, and S;
- and
- R2 is H, or a dimethoxytrityl-protected hydroxyl group.
A quencher reagent for oligonucleotide labeling having the formula:
- (R1)(R2)Y-(—Ar1—CR3═CR4—)n-Ar2
- wherein Ar1 is a substituted naphthyl and Ar2 is a substituted phenyl, wherein Ar1 and Ar2 are independently substituted with one or more of H, (C1-C8)alkyl, halogen, alkyloxy, phenyl, or combinations thereof, and at least one of Ar1 and Ar2 is substituted with one or more NO2 groups;
- R3 and R4 are independently H or (C1-C8)alkyl;
- n is 1;
- Y is a linking group connecting Ar1 with R1 and R2 and having from 1 to 100 main chain atoms selected from C, N, O, S, P and Si;
- R1 is a phosphoramidite having the formula —OP(N(iPr)2)(OCH2CH2CN)) or a linking group attached to a solid support having the formula —O—C(═O)Z-solid support, wherein iPr is isopropyl, and wherein Z is 1 to 30 main chain atoms in length wherein the main chain atoms are selected from C, N, O, P, and S;
- and
- R2 is H, or a dimethoxytrityl-protected hydroxyl group.
Dependencies are inferred from the claim text.