US 12,379,315 B2
Nitrodiarylethenes as fluorescence quenchers for nucleic acid probes
Eugeny A. Lukhtanov, Bothell, WA (US); Noah Scarr, Seattle, WA (US); and Viachaslau Bernat, Bothell, WA (US)
Assigned to ELITECHGROUP MDX LLC, Bothell, WA (US)
Filed by ELITechGroup MDX, LLC, Logan, UT (US)
Filed on Dec. 21, 2021, as Appl. No. 17/557,613.
Application 16/844,223 is a division of application No. 15/909,096, filed on Mar. 1, 2018, granted, now 10,738,346, issued on Aug. 11, 2020.
Application 17/557,613 is a continuation in part of application No. 16/844,223, filed on Apr. 9, 2020, granted, now 11,242,554.
Claims priority of provisional application 62/469,063, filed on Mar. 9, 2017.
Prior Publication US 2022/0119424 A1, Apr. 21, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. G01N 21/64 (2006.01); C07F 9/06 (2006.01); C09B 23/14 (2006.01)
CPC G01N 21/6428 (2013.01) [C07F 9/06 (2013.01); C09B 23/14 (2013.01); G01N 2021/6432 (2013.01)] 15 Claims
 
1. 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 acridone, 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.