Library of pH responsive polymers and nanoprobes thereof

Patent metadata

Field	Value
Publication number	US-10098971-B2
Application number	US-201615369701-A
Country	US
Kind code	B2
Filing date	Dec 5, 2016
Priority date	Jun 6, 2014
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The present disclosure relates to polymers which contain a hydrophobic and hydrophilic segment which is sensitive to pH. In some aspects, the polymers form a micelle which is sensitive to pH and results in a change in fluorescence based upon the particular pH. In some aspects, the disclosure also provides methods of using the polymers for the imaging of cellular or extracellular environment or delivering a drug.

First claim

What is claimed is:

1. A polymer of the formula:

wherein:
R 1 is an alkyl (C≤12) ;
n is an integer from 10-200;
R 2 and R 2 ′ are each independently methyl;
R 3 is a group of the formula:

wherein:
n x is 1-3;
X 1 is a hydrogen or an alkyl (C≤12) ;
X 2 and X 3 are each hydrogen;
X 4 is pentyl, n-propyl, or ethyl and X 5 is pentyl or n-propyl; or X 4 and X 5 are taken together and are alkanediyl (C≤9) or substituted alkanediyl (C≤9) ;

x is an integer from 30 to 150;
R 4 is a group of the formula:

wherein:
n z is 1-10;
Y 1 , Y 2 , and Y 3 are each independently selected from hydrogen, alkyl (C≤12) , cycloalkyl (C≤12) , substituted alkyl (C≤12) , or substituted cycloalkyl (C≤12) ; and
Y 4 is a dye with the following structure:

y is an integer from 1 to 6; and
R 5 is hydrogen, halo, hydroxy, alkyl (C≤12) , or substituted alkyl (C≤12) .

2. The polymer of claim 1 , wherein R 1 is methyl.

3. The polymer of claim 1 , wherein R 4 is:

4. The polymer of claim 1 , wherein X 1 or Y 1 is alkyl (C≤12) .

5. The polymer of claim 4 , wherein X 1 is methyl.

6. The polymer of claim 4 , wherein Y 1 is methyl.

7. The polymer of claim 1 , wherein the polymer is

8. The polymer of claim 1 , wherein the polymer is

wherein Y 4 is the dye with the following structure:

9. The polymer of claim 1 , wherein the polymer is:

wherein: x is an integer from 30 to 150, y is an integer from 1 to 2; and Y 4 is the dye with the following structure:

10. A composition comprising a micelle formed from a plurality of polymers according to claim 1 .

11. The composition of claim 10 , wherein the micelle has a pH transition point and an emission spectra, wherein the micelle dissociates at a pH below the pH transition point; and wherein Y 4 is a dye with the following structure:

12. The polymer of claim 1 , where n x is an integer from 1-2.

13. The polymer of claim 1 , where n x is 1.

Assignees

• Univ Texas

Inventors

• Gao Jinming
• Huang Gang
• Zhao Tian
• Ma Xinpeng
• Wang Yiguang
• Li Yang
• Sumer Baran D

Classifications

• G01N2021/6441

  with two or more labels · CPC title

• A61K49/0054 Primary

  Macromolecular compounds, i.e. oligomers, polymers, dendrimers · CPC title

• A61K49/0032

  Methine dyes, e.g. cyanine dyes · CPC title

• G01N21/6456

  Spatial resolved fluorescence measurements; Imaging · CPC title

• C09B69/106

  containing an azo dye · CPC title