Granted Patent
B2
US 12,528,903 · App. 17/198,006 · Granted Jan 20, 2026
Block copolymer and micelle compositions and methods of use thereof
Inventors:
Jinming Gao (Plano, TX); David Boothman; Kejin Zhou (Dallas, TX); Xiaonan Huang (Beijing, CN); Yiguang Wang (Dallas, TX)
C08F293/005A61K9/1075A61K9/1273A61K9/5031A61K31/337A61K31/704A61K47/58A61K47/62A61K47/6811A61K47/6845A61K47/6907A61K49/0032A61K49/0054A61K49/0056A61K49/0082A61P35/00C07D311/92C08F299/024C08G81/025G01N33/582A61K49/005C08F2438/01
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Abstract
Provided herein are block copolymers comprising a hydrophilic polymer segment and a hydrophobic polymer segment, wherein the hydrophilic polymer segment comprises a polymer selected from the group consisting of: poly(ethylene oxide) (PEO), poly(methacrylate phosphatidyl choline) (MPC), and polyvinylpyrrolidone (PVP), wherein the hydrophobic polymer segment comprises wherein R′ is —H or —CH 3 , wherein R is —NR 1 R 2 , wherein R 1 and R 2 are alkyl groups, wherein R 1 and R 2 are the same or different, wherein R 1 and R 2 together have from 5 to 16 carbons, wherein R 1 and R 2 may optionally join to form a ring, wherein n is 1 to about 10, and wherein x is about 20 to about 200 in total. Also provided are pH-sensitive micelle compositions for therapeutic and diagnostic applications.
Claims (28)
1 . A block copolymer capable of forming a pH-sensitive micelle comprising a compound of Formula (I):
wherein R is —NR 1 R 2 , wherein R 1 and R 2 together have from 5 to 16 carbons, and
wherein R 1 and R 2 join to form a ring;
L is a labelling moiety;
R′ is —H or —CH 3 ;
n is 1 to about 10;
x is about 20 to about 200 in total;
m is 1 to about 10;
y is 0 to about 6;
wherein z is such that the PEO is about 2 kD to about 20 kD in size;
wherein R′″ is any suitable moiety; and
wherein the following portion of the structure:
may be arranged in any order.
2 . The block copolymer of claim 1 , wherein the micelles have a pH transition range ΔpH 10-90 % of less than about 1 pH unit.
3 . The block copolymer of claim 1 , wherein R 1 and R 2 join to form a ring having —(CH 2 ) 5 — or —(CH 2 ) 6 —.
4 . The block copolymer of claim 1 , wherein n is 2 and R 1 and R 2 join to form a ring having —(CH 2 ) 5 —.
5 . The block copolymer of claim 4 , wherein the micelles have a pH transition value of about 7.2.
6 . The block copolymer of claim 1 , wherein n is 2 and R 1 and R 2 join to form a ring having —(CH 2 ) 6 —.
7 . The block copolymer of claim 6 , wherein the micelles have a pH transition value about 6.8.
8 . The block copolymer of claim 1 , wherein the block copolymer has a polydispersity index of less than 1.2.
9 . The block copolymer of claim 1 , wherein the block copolymer has a polydispersity index of less than 1.1.
10 . The block copolymer of claim 1 , wherein the micelles have a size of about 10 to about 200 nm.
11 . The block copolymer of claim 1 , wherein the micelles have a size of about 20 to about 100 nm.
12 . The block copolymer of claim 1 , wherein the micelles have a size of about 30 to about 50 nm.
13 . The block copolymer of claim 1 , wherein the fluorescent label is tetramethyl rhodamine (TMR).
14 . The block copolymer of claim 1 , wherein L is a near-infrared (NIR) label.
15 . The block copolymer of claim 14 , wherein the NIR label is cypate or a cypate analog.
16 . The block copolymer of claim 1 , wherein the block copolymer is
Assignments (1)
CONFIRMATORY LICENSE
Recorded Nov 2, 2023
From: UT SOUTHWESTERN MEDICAL CENTER
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 065431/0921 →
Continuity (8)
Continuation
13825518
Provisional Application
61471054
· Apr 1, 2011
Provisional Application
61470441
· Mar 31, 2011
Provisional Application
61385422
· Sep 22, 2010
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