US 12,139,617 B2
Polymeric fluorophores, compositions comprising the same, and methods of preparing and using the same
Jonathan S. Lindsey, Raleigh, NC (US); Gongfang Hu, Cary, NC (US); and Rui Liu, Cary, NC (US)
Assigned to North Carolina State University, Raleigh, NC (US)
Appl. No. 16/955,152
Filed by North Carolina State University, Raleigh, NC (US)
PCT Filed Dec. 18, 2018, PCT No. PCT/US2018/066195
§ 371(c)(1), (2) Date Jun. 18, 2020,
PCT Pub. No. WO2019/126144, PCT Pub. Date Jun. 27, 2019.
Claims priority of provisional application 62/714,541, filed on Aug. 3, 2018.
Claims priority of provisional application 62/609,494, filed on Dec. 22, 2017.
Prior Publication US 2020/0385583 A1, Dec. 10, 2020
Int. Cl. C09B 69/10 (2006.01); A61K 49/00 (2006.01); C08F 293/00 (2006.01); C08L 33/08 (2006.01)
CPC C09B 69/108 (2013.01) [A61K 49/0032 (2013.01); A61K 49/0054 (2013.01); C08F 293/005 (2013.01); C08L 33/08 (2013.01); C08F 2438/03 (2013.01); C08L 2207/53 (2013.01)] 13 Claims
OG exemplary drawing
 
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:

OG Complex Work Unit Chemistry
wherein:
R is hydrogen or CH3;
R1 is —O— or —NH—;
A is a C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl;
R2 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:

OG Complex Work Unit Chemistry
wherein:
R is hydrogen or CH3;
R1 is —O— or —NH—;
R3 is selected from the group consisting of —(CH2CH2O)n—, —C1-C6alkyl, and —C1-C6alkyl-SO3— 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;
R4 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.