Photoluminescent hydrogel

Patent metadata

Field	Value
Publication number	US-10653802-B2
Application number	US-201715702923-A
Country	US
Kind code	B2
Filing date	Sep 13, 2017
Priority date	Sep 14, 2016
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

Shown and described is a composition and a method to prepare a dopant-free photoluminescent hydrogel with synthetic polymers are disclosed. The hydrogel can be synthesized in one embodiment by incorporating an amino acid to a citric acid based polyester oligomer followed by multiple crosslinking group functionalization through a transesterification reaction using an enzyme such as Candida antarctica Lipase B (CALB) as a catalyst. The hydrogels are injectable, degradable, and their mechanical and photoluminescent properties are tunable. An in vivo study shows that the hydrogel emits strong fluorescence under visible light excitation and can completely degrade over time.

First claim

What is claimed is:

1. A photoluminescent dopant-free hydrogel having biodegradable properties, comprising:
a dopant-free polyester-based biodegradable photoluminescent hydrogel defined as a citric acid and hexaethylene glycol based polyester oligomer-serine-ethyl thioglycolate-polyethylene glycol (CHPO-Ser-ET-PEG) hydrogel, the hydrogel is synthesized by:
(1) synthesizing a fluorescent oligomer from reacting an amino acid Serine (Ser), a citric acid, and a hexaethylene glycol to form a citric acid and hexaethylene glycol serine based polyester oligomer (CHPO-Ser), followed by a transesterification reaction with a Candida antarctica Lipase B (CALB) first catalyst to functionalize a thiol containing compound ethyl thioglycolate (ET) to the citric acid and the hexaethylene glycol serine based polyester oligomer (CHPO-Ser),

the fluorescent oligomer has at least 5 to 7 thiol groups singularly conjugated thereon through the CALB catalyzed transesterification reaction; and
(2) reacting the oligomer with a multiple arm polyethylene glycol (PEG) second catalyst to form the hydrogel; and

wherein the hydrogel emits a fluorescence under visible light excitation with emissions up to 720 nm.

2. The photoluminescent hydrogel of claim 1 , wherein the multiple arm polyethylene glycol (PEG) second catalyst further includes a maleimide crosslinking agent.

3. The photoluminescent hydrogel of claim 1 , wherein addition of Serine (Ser) is at a molar ratio of 1:0.2 between citric acid and serine (Ser).

4. The photoluminescent hydrogel of claim 3 , wherein the CHPO-Ser-ET/PEG hydrogel is an injectable hydrogel individually that emits the fluorescence under visible light excitation and completely degrades over time.

5. The photoluminescent hydrogel of claim 4 , wherein the CHPO-Ser-ET/PEG hydrogel is an injectable CHPO-Ser-ET/PEG hydrogel that emits fluorescence at excitation of about 488 nm, and an emission of about 525 nm.

6. The photoluminescent hydrogel of claim 1 , wherein the hydrogel functions as both an injectable scaffold and a fluorescent imaging probe with a chemical property that avoids carcinogenesis and toxicity associated with fluorescent dopants.

Assignees

• New Jersey Inst Technology

Inventors

• Xu Xiaoyang
• Tsou Yunghao

Classifications

• C12P17/14

  Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring · CPC title

• C12Y301/01003

  Triacylglycerol lipase (3.1.1.3) · CPC title

• A61K9/0024

  Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L) · CPC title

• A61K49/0054

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

• C08G63/6886

  Dicarboxylic acids and dihydroxy compounds · CPC title