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US 2026/0234403 A1Published application
Photoactive fluorescent compounds and use thereof for labeling of proteins
OwnerHilary Plake BECK, David Trombley MCSWIGGEN +5inventors
InventorsHilary Plake BECK, David Trombley MCSWIGGEN, Leah Brigit CLEARY, Daniel James ANDERSON, Yihong LI, Anne Ruth SIZEMORE, Nicholas William PINO
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Abstract
Provided herein are novel photoactive fluorescent compounds and their use in labeling proteins, for example, tagged proteins, and their use for visualizing the location and dynamics of proteins in living cells.
Claims33
A compound of Formula (VIII):
- or a salt, a single stereoisomer, a mixture of stereoisomers or an isotopic form thereof,
- wherein:
- R1 is H, or —C(═O)N(C1-3 alkyl)2,
- each L1 is independently:
- —O—C1-6-alkylene-;
- —C(O)NH—, —C1-6-alkylene-N(C1-3-alkyl)(C1-6-alkylene)-, or —C1-6-alkylene-O—C1-6-alkylene-;
- each L2 is —(OCH2CH2)p—;
- p is an integer of 1 to 3;
- a is an integer of 1 or 2;
- b is an integer of 0 to 2;
- and
- Z is
- and
- wherein
- when R1 is H and a is 1, then L1 is not
- wherein the wavy line () represents a point of attachment to the rest of the compound.
13 more elements
A compound of Formula (IX):
- or a salt, a single stereoisomer, a mixture of stereoisomers, or an isotopic form thereof, wherein
- LB is (i) —O—C1-6-alkylene-, —C1-6-alkylene-N(C1-3-alkyl)-, or —C1-6-alkylene-O—.
A compound of Formula (X):
- or a salt, a single stereoisomer, a mixture of stereoisomers, or an isotopic form thereof,
- wherein:
- R1 is H or —C(═O)N(C1-3 alkyl)2.
A method for preparing a compound of Formula (VIII-a):
- wherein:
- R′ is
- R1 is H, or —C(═O)N(C1-3 alkyl)2,
- each L1 is independently:
- —O—C1-6-alkylene-;
- —C(O)NH—, —C(O)NH(C1-3-alkylene)-, —C1-6-alkylene-N(C1-3-alkyl)(C1-6-alkylene)-, or —C1-6-alkylene-O—C1-6-alkylene-;
- each L2 is —(OCH2CH2)p—;
- p is an integer of 1 to 3;
- a is an integer of 1 or 2;
- b is an integer of 0 to 2;
- Z is
- and
- wherein
- when R1 is H and a is 1, then L1 is not
- wherein the wavy line () represents a point of attachment to the rest of the compound, the process comprising:
- converting a compound of the following Formula (a-1):
- wherein:
- R1 is H or —C(═O)N(C1-3 alkyl)2,
- R is —C(═O)OCH3 or —C(═O)NH(C1-3 alkylene)-(OCH2CH2)—Z;
- and wherein
- Z is
- using Ghosez's reagent, in the presence of a diazomethane agent and a solvent, to prepare the compound of Formula (VIII-a).
19 more elements
A method for preparing a compound of Formula (XI):
- wherein:
- R1 is H, or —C(═O)N(C1-3 alkyl)2,
- each L1 is:
- —C(O)NH(C1-3-alkylene)-;
- each L2 is —(OCH2CH2)p—;
- p is an integer of 1 to 3;
- a is an integer of 1 or 2;
- b is an integer of 0 to 2;
- Z is
- the process comprising:
- converting a compound of the following Formula (a-2):
- wherein:
- R1 is H, or —C(═O)N(C1-3 alkyl)2,
- R is —C(═O)OCH3 or —C(═O)NH(C1-3 alkylene)-(OCH2CH2)—Z;
- and wherein
- Z is
- using Ghosez's reagent, in the presence of a diazomethane agent and a solvent, to prepare the compound of Formula (XI).
14 more elements
Dependencies are inferred from the claim text.