Quencher and use thereof

Patent metadata

Field	Value
Publication number	US-2023313277-A1
Application number	US-202318332137-A
Country	US
Kind code	A1
Filing date	Jun 9, 2023
Priority date	Dec 9, 2020
Publication date	Oct 5, 2023
Grant date	—

Abstract

The present invention relates to a quencher which exhibits a quenching effect on a fluorescent material exhibiting luminescence at an excited energy level, and various uses thereof.

First claim

What is claimed is:

1 . A quencher represented by Formula 1 or 2 below:

Wherein,
Q is represented by Formula 3 or 4 below,

R 1 to R 6 and R 9 to R 20 are each independently (1) a moiety selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 alkyl, substituted or unsubstituted C 1 -C 40 heteroalkyl having at least one hetero atom, substituted or unsubstituted C 2 -C 40 alkenyl, substituted or unsubstituted C 2 -C 40 alkynyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 3 -C 20 cycloalkenyl, substituted or unsubstituted C 2 -C 20 heterocycloalkyl, hydroxy, oxido (—O—), substituted or unsubstituted C 1 -C 40 alkoxy, substituted or unsubstituted C 3 -C 40 cycloalkyloxy, substituted or unsubstituted C 5 -C 40 aryloxy, substituted or unsubstituted C 2 -C 40 heteroaryloxy, substituted or unsubstituted C 5 -C 50 aryl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 5 -C 50 aralkyl, substituted or unsubstituted C 1 -C 40 alkylthio, substituted or unsubstituted C 5 -C 40 arylthio, substituted or unsubstituted C 3 -C 40 cycloalkylthio, substituted or unsubstituted C 2 -C 40 heteroarylthio, substituted or unsubstituted acylamino, acyloxy, substituted or unsubstituted phosphino, carboxylate (—CO 2 − ), trifluoromethylsulfonyl (—SO 2 CF 3 ), substituted or unsubstituted ammonium, nitro, sulfonic acid (—SO 3 H), sulfonate, substituted sulfonyl, substituted sulfonic ester, substituted or unsubstituted sulfonamide, substituted thioketone, trihalomethyl (—CF 3 , —CCl 3 , —CBr 3 , or —CI 3 ), haloformyl (—COCl, —COBr, or —COI), formyl (—CHO), acyl, carboxyl, substituted ester, substituted or unsubstituted aminocarbonyl, nitro, nitroso (—N═O), fluoro (—F), chloro (—Cl), bromo (—Br), iodo (—I), substituted or unsubstituted germanium, substituted or unsubstituted boron, substituted or unsubstituted aluminum, substituted or unsubstituted silyl, substituted or unsubstituted amide, carbamate, carboxylate, substituted or unsubstituted phosphine, substituted or unsubstituted phosphoric acid, phosphate, phosphonic acid, phosphonate, nitrile, hydrazine, acetal, ketal, and polyalkylene oxide,
(2) a moiety selected from carboxyl, carboxyl derivatives, hydroxyl, haloalkyl, dienophile, aldehyde, substituted ketone, sulfonyl halide, thiol, substituted or unsubstituted amino, sulfhydryl, alkene, alkyne, halogen, hydrazine, azido, imido, ketene, isocyanate, epoxide, and phosphoramidite, or any moiety substituted with the moiety,
(3) a reactive group enabling a covalent bond with a moiety selected from carboxyl, carboxyl derivatives, hydroxyl, haloalkyl, dienophile, aldehyde, substituted ketone, sulfonyl halide, thiol, substituted or unsubstituted amino, sulfhydryl, alkene, alkyne, halogen, hydrazine, azido, imido, ketene, isocyanate, epoxide, and phosphoramidite, or any moiety substituted with the reactive group, or
(4) a protecting group selected from an alcohol-derived protecting group, an amide-derived protecting group, a carbonyl-derived protecting group, a carboxyl acid-derived protecting group, a phosphate-derived protecting group, and an alkyne-derived protecting group,
m and n are each independently an integer of 0 to 3,
X is O, S, CR 7 R 8 , or SiR 7 R 8 ,
Y is O or S,
R 7 and R 8 are each independently selected from substituted or unsubstituted C 1 -C 40 alkyl, substituted or unsubstituted C 1 -C 40 heteroalkyl having at least one hetero atom, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 3 -C 30 heterocycloalkyl having at least one hetero atom, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, or form a ring by bonding them together,
at least one of R 1 to R 20 is
(1) a moiety selected from carboxyl, carboxyl derivatives, hydroxyl, haloalkyl, dienophile, aldehyde, substituted ketone, sulfonyl halide, thiol, substituted or unsubstituted amino, sulfhydryl, alkene, alkyne, halogen, hydrazine, azido, imido, ketene, isocyanate, epoxide, and phosphoramidite, or any moiety substituted with the moiety,
(2) a reactive group enabling a covalent bond with a moiety selected from carboxyl, carboxyl derivatives, hydroxyl, haloalkyls, dienophile, aldehyde, substituted ketone, sulfonyl halide, thiol, substituted or unsubstituted amino, sulfhydryl, alkene, alkyne, halogen, hydrazine, azido, imido, ketene, isocyanate, epoxide, and phosphoramidite, or any moiety substituted with the reactive group, or
(3) a protecting group selected from an alcohol-derived protecting group, an amide-derived protecting group, a carbonyl-derived protecting group, a carboxylic acid-derived protecting group, a phosphate-derived protecting group, and an alkyne-derived protecting group,
R 9 , R 10 , R 15 and R 16 are not electron-withdrawing groups, and
the case in which all of R 9 to R 14 or R 15 to R 19 are hydrogen is excluded.

2 . The quencher of claim 1 , wherein the quencher exists as at least one structure selected from Formula 1 and Formula 5, which is a resonance structure of Formula 1:

3 . The quencher of claim 1 , wherein the quencher exists as at least one structure selected from Formula 2 and Formula 6, which is a resonance structure of Formula 2:

4 . The quencher of claim 1 , wherein R 1 and R 2 are bound with each other to form a substituted or unsubstituted ring.

5 . The quencher of claim 1 , wherein at least one selected from R 1 and R 2 is bound with adjacent R 5 to form a substituted or unsubstituted ring.

6 . The quencher of claim 1 , wherein R 3 and R 4 are bound with each other to form a substituted or unsubstituted ring.

7 . The quencher of claim 4 , wherein the ring is substituted with at least one selected from (1) a moiety selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 40 alkyl, substituted or unsubstituted C 1 -C 40 heteroalkyl having at least one hetero atom, substituted or unsubstituted C 2 -C 40 alkenyl, substituted or unsubstituted C 2 -C 40 alkynyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 3 -C 20 cycloalkenyl, substituted or unsubstituted C 2 -C 20 heterocycloalkyl, hydroxy, oxido (—O − ), substituted or unsubstituted C 1 -C 40 alkoxy, substituted or unsubstituted C 3 -C 40 cycloalkyloxy, substituted or unsubstituted C 5 -C 40 aryloxy, substituted or unsubstituted C 2 -C 40 heteroaryloxy, substituted or unsubstituted C 5 -C 50 aryl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 5 -050 aralkyl, substituted or unsubstituted C 1 -C 40 alkylthio, substituted or unsubstituted C 5 -C 40 arylthio, substituted or unsubstituted C 3 -C 40 cycloalkylthio, substituted or unsubstituted C 2 -C 40 heteroarylthio, substituted or unsubstituted acylamino, acyloxy, substituted or unsubstituted phosphino, carboxylate (—CO 2 − ), trifluoromethylsulfonyl (—SO 2 CF 3 ), substituted or unsubstituted ammonium, nitro, sulfonic acid (—SO 3 H), sulfonate, substituted sulfonyl, substituted sulfonic ester, substituted or unsubstituted sulfonamide, substituted thioketone, trihalomethyl (—CF 3 , —CCl 3 , —CBr 3 , or —CI 3 ), haloformyl (—COCl, —COBr, or —COI), formyl (—CHO), acyl, ca

Assignees

• Sfc Co Ltd

Inventors

• Lee Do Min
• Si Ho Young
• Jo Jae Hyung
• Masanta Goutam
• Song Ju Man
• Eum Min Su
• Je Jong Tae

Classifications

• C12Q1/6818 Primary

  involving interaction of two or more labels, e.g. resonant energy transfer · CPC title

• C09B11/24

  Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C12Q1/6844

  Nucleic acid amplification reactions · CPC title

• C07H21/00

  Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids · CPC title