US 12,215,381 B2
Reporter and uses thereof
Do Min Lee, Cheongju-si (KR); Ho Young Si, Cheongju-si (KR); Jae Hyung Jo, Cheongju-si (KR); Goutam Masanta, Cheongju-si (KR); Ju Man Song, Cheongju-si (KR); Min Su Eum, Cheongju-si (KR); and Jong Tae Je, Cheongju-si (KR)
Assigned to SFC CO., LTD., Cheongju-si (KR)
Filed by SFC CO., LTD., Cheongju-si (KR)
Filed on Sep. 5, 2023, as Appl. No. 18/461,211.
Application 18/461,211 is a continuation of application No. PCT/KR2022/002848, filed on Feb. 28, 2022.
Claims priority of application No. 10-2021-0031308 (KR), filed on Mar. 10, 2021; and application No. 10-2022-0022318 (KR), filed on Feb. 21, 2022.
Prior Publication US 2024/0132940 A1, Apr. 25, 2024
Int. Cl. C09B 23/00 (2006.01); C07H 19/06 (2006.01); C12Q 1/68 (2018.01); C12Q 1/682 (2018.01); C12Q 1/6834 (2018.01); C12Q 1/686 (2018.01); G01N 21/64 (2006.01)
CPC C12Q 1/682 (2013.01) [C07H 19/06 (2013.01); C09B 23/00 (2013.01); C12Q 1/6834 (2013.01); C12Q 1/686 (2013.01); G01N 21/6486 (2013.01)] 12 Claims
 
1. A reporter for labeling a nucleic acid represented by Formula 5 below:

OG Complex Work Unit Chemistry
wherein,
R21 and R22 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C5-C20 aryl, and substituted or unsubstituted C2-C20 heteroaryl,
R23 to R30 are each independently a functional group selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted C2-C20 heterocycloalkyl, hydroxy, oxido (—O−), substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C20 cycloalkyloxy, substituted or unsubstituted C5-C20 aryloxy, substituted or unsubstituted C2-C20 heteroaryloxy, substituted or unsubstituted C5-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted C5-C20 aralkyl, substituted or unsubstituted C1-C10 alkylthio, substituted or unsubstituted C5-C20 arylthio, substituted or unsubstituted C3-C20 cycloalkylthio, substituted or unsubstituted C2-C20 heteroarylthio, substituted or unsubstituted acylamino, acyloxy, substituted or unsubstituted phosphino, trifluoromethylsulfonyl (—SO2CF3), substituted or unsubstituted ammonium, nitro, substituted sulfonyl, substituted sulfonic acid ester, substituted or unsubstituted sulfonamide, substituted thioketone, trihalomethyl (—CF3, —CCl3, —CBr3, or —CI3), haloformyl (—COCl, —COBr, or —COI), formyl (—CHO), acyl, 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, substituted or unsubstituted phosphine, nitrile, hydrazine, acetal, ketal, polyalkyleneoxide, and -L1-R12, or two adjacent functional groups are bonded to each other to form a ring,
R31 to R34 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom, and -L1-R12, and at least one of R31 to R34 is -L1-R12,
L1 includes a single bond or at least one selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 cycloalkenyl, and substituted or unsubstituted C2-C20 heterocycloalkyl, and
R12 is a deoxyribonucleoside represented by Formula 3 below,

OG Complex Work Unit Chemistry
Wherein,
* indicates a location where the deoxyribonucleoside is bonded to L1,
B is a nucleobase,
R13 is selected from hydrogen, deuterium, P(OR15)(N(R16R17), and -L2-R18,
R14 is an alcohol protecting group, hydrogen or P(OR15)(N(R16R17), or a support or nucleic acid to which the reporter is bound, at least one of R13 and R14 is P(OR15)(N(R16R17),
R15 to R17 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom,
L2 is a single bond, or selected from an internucleotide phosphodiester bond, substituted or unsubstituted C1-C10 alkyl and substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom,
R18 is hydroxy or P(OR15)(N(R16R17), or a support or nucleic acid to which the reporter is bound,
Y is CR35, each R35 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl containing at least one hetero atom, fluoro (—F), chloro (—Cl), bromo (—Br), and iodo (—I), and
n is an integer of 1 to 4,
when any functional group of R21 to R35 is a substituted functional group, any substituent other than hydrogen bonded to at least one carbon of the functional group,
wherein the substituent is selected from deuterium, C1-C10 alkyl, C1-C10 heteroalkyl containing at least one hetero atom, C2-C10 alkenyl, C2-C10 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C2-C20 heterocycloalkyl, hydroxy, oxido (—O−), C1-C10 alkoxy, C3-C20 cycloalkyloxy, C5-C20 aryloxy, C2-C20 heteroaryloxy, C5-C20 aryl, C2-C20 heteroaryl, C5-C20 aralkyl, C1-C10 alkylthio, C5-C20 arylthio, C3-C20 cycloalkylthio, C2-C20 heteroarylthio, acylamino, acyloxy, phosphino, trifluoromethylsulfonyl (—SO2CF3), ammonium, nitro, substituted sulfonyl, substituted sulfonic acid ester, sulfonamide, substituted thioketone, trihalomethyl (—CF3, —CCl3, —CBr3, or —CI3), haloformyl (—COCl, —COBr, or —COI), formyl (—CHO), acyl, substituted ester, aminocarbonyl, nitro, nitroso (—N═O), fluoro (—F), chloro (—Cl), bromo (—Br), iodo (—I), germanium, boron, aluminum, silyl, amide, carbamate, phosphine, nitrile, hydrazine, acetal, ketal, polyalkyleneoxide, and -L1-R12.