IP Library Granted Patent US 12,139,617
Granted Patent B2
US 12,139,617 · App. 16/955,152 · Granted Nov 12, 2024

Polymeric fluorophores, compositions comprising the same, and methods of preparing and using the same

Inventors: Jonathan S. Lindsey (Raleigh, NC); Gongfang Hu (Cary, NC); Rui Liu (Cary, NC)
Assignee: North Carolina State University
C09B69/108A61K49/0032A61K49/0054C08F293/005C08L33/08C08F2438/03C08L2207/53
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Quick Facts
Patent No.
US 12,139,617
App. No.
16/955,152
Granted
Nov 12, 2024
Kind
B2
Abstract

Described herein are polymeric fluorophores that include a dye, a polymer, and optionally a bioconjugate group. A polymeric fluorophore may have a structure represented by: A-B-C or C-A-B, wherein A is a 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. Also described herein are compositions comprising the polymeric fluorophores and methods of preparing and using the same.

Claims (40)

1. A compound having a structure represented by:

A-B-C, or

C-A-B

wherein

A is a dye;

B is 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; and

optionally C, wherein C comprises a bioconjugate group,

wherein the dye is covalently attached to the first terminus or the second terminus of the polymer backbone,

wherein the one or more hydrophobic unit(s) have a structure represented by Formula III:

wherein:

R is hydrogen or CH 3 ;

R 1 is —O— or —NH—;

A is a C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;

R 2 is hydrogen or a halo, hydroxyl, carboxyl, amino, formyl, vinyl, epoxy, mercapto, ester, azido, maleimido, isocyanato, or isothiocyanato group; and

p is an integer from 1 to 10, 100, 1,000, 5,000, 10,000, 50,000, or 100,000, and

wherein the one or more hydrophilic unit(s) have a structure represented by Formula IV:

wherein:

R is hydrogen or CH 3 ;

R 1 is —O— or —NH—;

R 3 is selected from the group consisting of —(CH 2 CH 2 O) n —, —C 1 -C 6 alkyl, and —C 1 -C 6 alkyl-SO 3 — or a salt thereof, wherein n is an integer from 1 or 5 to 10, 25, 50, 75, 100, 1,000, 5,000, or 10,000;

R 4 is absent or is a hydrogen, alkyl, phosphono, sulfono, phosphatidyl choline, phosphoryl, halo, hydroxyl, carboxyl, amino, ammonio, formyl or ester group; and

p is an integer from 1 to 10, 100, 1,000, 5,000, 10,000, 50,000, or 100,000.

2. The compound of claim 1 , wherein the one or more hydrophobic unit(s) and the one or more hydrophilic unit(s) are randomly distributed in the polymer.

3. The compound of claim 1 , wherein the one or more hydrophobic unit(s) and the one or more hydrophilic unit(s) are present in the polymer in a ratio of about 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, or 1:10.

4. The compound of claim 1 , wherein the compound is self-folding in an aqueous solution.

5. The compound of claim 1 , wherein the dye is encapsulated by a portion of the compound when the compound is in a folded structure.

6. The compound of claim 1 , wherein the polymer is a telechelic polymer or a heterotelechelic polymer.

7. The compound of claim 1 , wherein the compound has a solubility in water at room temperature in a range of about 1 mg/mL to about 10 mg/mL.

8. The compound of claim 1 , wherein at least one of the one or more hydrophobic unit(s) and/or the one or more hydrophilic unit(s) comprises a pendant functional group, optionally wherein the pendant functional group is a halo, hydroxyl, carboxyl, amino, formyl, vinyl, epoxy, mercapto, ester, azido, maleimido, isocyanato, isothiocyanato, phosphono, sulfono, ammonio, or phosphatidyl choline group.

9. The compound of claim 1 , wherein at least one of the one or more hydrophobic unit(s) comprises an alkyl pendant group and/or at least one of the one or more hydrophilic unit(s) comprise a glycol pendant group.

10. The compound of claim 1 , wherein the polymer is attached to one dye.

11. The compound of claim 1 , wherein, in Formula III,

R is hydrogen;

R 1 is —O—; and

p is an integer from 1 to 50.

12. The compound of claim 1 , wherein, in Formula IV,

R is hydrogen;

R 1 is —O—; and

p is an integer from 1 to 50.

13. A biomolecule comprising a compound of claim 1 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 9, 2024
From: NORTH CAROLINA STATE UNIVERSITY RALEIGH
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 066238/0842 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2020
From: LINDSEY, JONATHAN S.; HU, GONGFANG; LIU, RUI
To: NORTH CAROLINA STATE UNIVERSITY
Reel/Frame 053020/0283 →
Continuity (3)
Provisional Application 62714541 · Aug 3, 2018
Provisional Application 62609494 · Dec 22, 2017
Related Publication 20200385583A1 · Dec 10, 2020