Back to results
US 12,760,180 B2Granted
Polymeric compounds including an acceptor dye and donor luminophore
AssigneeNorth Carolina State University
InventorsJonathan S. Lindsey, Masahiko Taniguchi
Life of this patent
Estimating the term…
Abstract
Described herein are polymeric compounds including an acceptor dye and donor luminophore, a polymer, and optionally a bioconjugate group. A polymeric compound of the present invention may have a structure represented by: A-B-C or C-A-B, wherein A is an acceptor dye; B is a polymer comprising one or more hydrophobic unit(s) and one or more hydrophilic unit(s); and optionally C, wherein C, when present, comprises a bioconjugate group, wherein one or more donor luminophore(s) are each separately attached to a portion of the polymer and/or to a portion of the acceptor dye. Also described herein are compositions comprising the polymeric compounds and methods of preparing and using the same.
Claims19
A compound comprising:
- a polymer having a polymer backbone comprising one or more hydrophobic unit(s) and one or more hydrophilic unit(s), wherein the polymer backbone comprises a first terminus and a second terminus, wherein the first terminus and the second terminus are opposing ends of the polymer backbone, wherein the polymer has a molecular weight in a range of about 5,000 Da to about 175,000 Da;
- a single acceptor dye that is attached to the first terminus or the second terminus of the polymer backbone;
- one or more donor luminophore(s) that are each separately attached to a portion of the polymer or to a portion of the acceptor dye;
- and
- optionally a bioconjugate group,
- wherein at least one of the one or more hydrophobic unit(s) has a structure represented by Formula III:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, —CH2—;
- A is a linker, C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;
- R2 is hydrogen or a halo, ethyne, hydroxyl, carboxyl, amino, formyl, vinyl, epoxy, mercapto, ester, azido, maleimido, isocyanato, or isothiocyanato group, or a donor luminophore;
- and
- p is an integer from 1 to 100,000;
- and
- wherein at least one of the one or more hydrophilic unit(s) has a structure represented by Formula IV:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, or —CH2—;
- R3 is selected from the group consisting of a linker, —(CH2CH2R5)n—, —C1—C6alkyl, —C1—C6alkenyl, —C1—C6alkynyl, —C1—C6alkyl—O—, and —C1—C6alkyl—SO3— or a salt thereof, wherein R5 is —O—or —CH2— and n is an integer from 1 or 5 to 10, 25, 50, 75, 100, 1,000, 5,000, or 10,000;
- R4 is absent or is a hydrogen, alkyl, alkenyl, alkynyl, phosphono, sulfono, phosphatidyl choline, phosphoryl, halo, hydroxyl, carboxyl, amino, ammonio, formyl or ester group or a donor luminophore;
- and
- p is an integer from 1 to 100,000.
19 more elements
A method of preparing a co-polymer comprising:
- polymerizing a hydrophobic monomer and a hydrophilic monomer to provide a co-polymer comprising a hydrophobic unit and a hydrophilic unit, wherein at least one of the hydrophobic unit and the hydrophilic unit comprises a donor luminophore;
- attaching an acceptor dye to a first portion of the co-polymer;
- and
- optionally attaching a bioconjugate group to a second portion of the co-polymer and/or
- optionally cross-linking the compound,
- wherein the hydrophobic unit has a structure represented by Formula III:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, —CH2—;
- A is a linker, C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;
- R2 is hydrogen or a halo, ethyne, hydroxyl, carboxyl, amino, formyl, vinyl, epoxy, mercapto, ester, azido, maleimido, isocyanato, or isothiocyanato group, or a donor luminophore;
- and
- p is an integer from 1 to 100,000;
- and
- wherein the hydrophilic unit has a structure represented by Formula IV:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, or —CH2—;
- R3 is selected from the group consisting of a linker, —(CH2CH2R5)n—, —C1—C6alkyl, —C1—C6alkenyl, —C1—C6alkynyl, —C1—C6alkyl—O—, and —C1—C6alkyl-SO3— or a salt thereof, wherein R5 is —O— or —CH2— and n is an integer from 1 or 5 to 10, 25, 50, 75, 100, 1,000, 5,000, or 10,000;
- R4 is absent or is a hydrogen, alkyl, alkenyl, alkynyl, phosphono, sulfono, phosphatidyl choline, phosphoryl, halo, hydroxyl, carboxyl, amino, ammonio, formyl or ester group or a donor luminophore;
- and
- p is an integer from 1 to 100,000.
19 more elements
A method of preparing a co-polymer comprising:
- polymerizing a hydrophobic monomer and a hydrophilic monomer to provide a co-polymer comprising a hydrophobic unit and a hydrophilic unit;
- attaching an acceptor dye to a first portion of the co-polymer;
- attaching a donor luminophore to a second portion of the co-polymer or to a portion of the acceptor dye;
- and
- optionally attaching a bioconjugate group to a third portion of the co-polymer and/or
- optionally cross-linking the co-polyner,
- wherein the hydrophobic unit has a structure represented by Formula III:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, —CH2—;
- A is a linker, C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;
- R2 is hydrogen or a halo, ethyne, hydroxyl, carboxyl, amino, formyl, vinyl, epoxy, mercapto, ester, azido, maleimido, isocyanato, or isothiocyanato group, or a donor luminophore;
- and
- p is an integer from 1 to 100,000;
- and
- wherein the hydrophilic unit has a structure represented by Formula IV:
- wherein:
- R is hydrogen or a C1-C8 alkyl;
- R1 is absent or is —O—, —NH—, or —CH2—;
- R3 is selected from the group consisting of a linker, —(CH2CH2R5)n—, —C1—C6alkyl, —C1—C6alkenyl, —C1—C6alkynyl, —C1—C6alkyl—O—, and —C1—C6alkyl—SO3— or a salt thereof, wherein R5 is —O — or —CH2— and n is an integer from 1 or 5 to 10, 25, 50, 75, 100, 1,000, 5,000, or 10,000;
- R4 is absent or is a hydrogen, alkyl, alkenyl, alkynyl, phosphono, sulfono, phosphatidyl choline, phosphoryl, halo, hydroxyl, carboxyl, amino, ammonio, formyl or ester group or a donor luminophore;
- and
- p is an integer from 1 to 100,000.
20 more elements
Dependencies are inferred from the claim text.