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US 12,091,554 B2Granted
Substituted polyfluorene compounds
AssigneeBiolegend, Inc.
InventorsXinshe Xu, Jing Wang
Life of this patent
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Abstract
The present invention provides fluorescent polyfluorene polymers or macromers with unique optical properties that are stable. The polymeric fluorophores are useful in various bioassays formats. The inventive polymers are useful in assays relying on fluorescence resonance energy transfer (FRET) mechanisms where two fluorophores are used.
Claims12
A macromer of formula I:
- wherein adjacent R1 groups on the same carbon atom form an optionally substituted 4-, 5-, or 6-membered ring selected from the group consisting of an optionally substituted C4-C6 cycloalkyl group and an optionally substituted C4-C6 heterocyclyl group, or alternatively, when at least one of R2, R3, R4, R5, R6, or R7 is other than hydrogen on a given monomer, each R1 on the same monomer may be the same of different and is selected from the group consisting of hydrogen, an optionally substituted C1-C18 alkyl, an optionally substituted C1-C18 alkoxy, an optionally substituted C6-C18 aryl, an optionally substituted C4-C18 acyl, an optionally substituted C4-C18 acyloxy, a functional group for conjugation to a molecule or biomolecule, ethylene oxide oligomers and ethylene oxide polymer wherein the compound of Formula I contains at least one or more ethylene oxide oligomers or ethylene oxide polymer;
- each R2, R3, R4, R5, R6, and R7 is independently selected from the group consisting of hydrogen, nitro, cyano, an optionally substituted amino, an optionally substituted C1-C18 alkyl, an optionally substituted C1-C18 alkoxy, optionally substituted C6-C18 aryl, optionally substituted C4-C18 acyl, optionally substituted C4-C18 acyloxy, a water solubilizing group, ethylene oxide oligomers, ethylene oxide polymer, and a functional group for conjugation to a biomolecule or dye, and wherein each of R2, R3, R4, R5, R6, and R7 may be the same or different within o, n and m;
- m is a value selected from the group consisting of 1-200;
- n is a value selected from the group consisting of 1-200;
- o is a value selected from the group consisting of 0-10,000, wherein the monomers within m, n, and o may be the same or different;
- each of A, B, and C can be present or absent and can each be the same or different, and each is selected from the group consisting of an aromatic group or heteroaromatic group, which group completes a n-conjugated backbone and is a divalent substituent member selected from the group consisting of benzene, naphthalene, anthracene, benzodiathiazolyl, fluorene, indenofluorene, thiophene, thienothiophene, dithienothiophene, 3,4-ethylenedioxythiophene, furan, pyridine, pyrrole, fused pyrrole, tetrahydropyrene and oxadiazole, wherein each of the foregoing is optionally substituted with a ethylene oxide oligomers or ethylene oxide polymer;
- and
- E1 and E2 are each independently a member selected from the group consisting of hydrogen, halogen, alkynyl, optionally substituted aryl, optionally substituted heteroaryl, halo, substituted aryl, boronic acid substituted aryl, boronic ester substituted aryl, boronic ester, boronic acid, optionally substituted fluorene and aryl or heteroaryl substituted with one or more pendant chains terminated with:
- i) a functional group selected from amine, carbamate, carboxylic acid, carboxylate, maleimide, activated esters, N-hydroxysuccinimidyl, hydrazines, hydrazids, hydrazones, azide, alkyne, aldehydes, thiols, and protected groups thereof for conjugation to a molecule or biomolecule;
- or ii) a conjugated organic dye or biomolecule, wherein the molecular weight (Mn) of the macromer is about 5000 to about 100,000.
7 more elements
Dependencies are inferred from the claim text.