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US 11,584,883 B2Granted
Conjugated polymers and methods of use
AssigneeBiolegend, Inc.
InventorsXinshe Xu, Jing Wang, Matthew Yerou
Life of this patent
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Abstract
The present disclosure provides fluorescent polyindenofluorene 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.
Claims23
A macromer of formula I or formula II:
- wherein each of R1, R2, R3 and R4 are each independently a member selected from the group consisting of hydrogen, an optionally substituted C1-C10 alkyl, an optionally substituted C1-C18 alkoxy, optionally substituted C6-C18 aryl, optionally substituted C4-C18 acyl, optionally substituted C4-C18 acyloxy, NRaRb, wherein Ra and Rb are each independently hydrogen or lower alkyl, a water soluble group, ethylene oxide oligomers and an ethylene oxide oligomer methyl ether;
- alternatively, R1 and R2 and/or R3 and R4 together with the carbons to which they are attached, join to form a an optionally substituted 4-, 5-, or 6-membered ring;
- each R5 is independently a member selected from the group consisting of halo, alkyl, alkoxy, amino, ethylene oxide oligomers and an ethylene oxide oligomer methyl ether;
- each p is a value from 0-3;
- m is a value selected from the group consisting of 1-10,000, with the proviso that the macromer of Formula I or Formula II contains at least one indenofluorene monomer, wherein p=0 and each of R1, R2, R3 and R4 is CH2CH2CH2R6, wherein R6 is a water-solubilizing group selected from the group consisting of an ethylene oxide oligomer and an ethylene oxide oligomer methyl ether;
- each of A and B, 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 7-conjugated backbone;
- each of 1, 2 and 3 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 7-conjugated backbone;
- n and o are each independently 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;
- 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;
- and
- wherein the macromer of Formula I or II can be an alternating copolymer, a block copolymer, a random copolymer or a graph copolymer between E1 and E2.
10 more elements
Dependencies are inferred from the claim text.