# US 10,370,488 B2 · Stimulus-responsive poly(lactic-co-glycolic)-based polymers and nanoparticles formed therefrom

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- Number: US 10,370,488 B2
- Document ID: US10370488B2
- Status: Granted
- Kind: B2
- Application number: 15/564,693
- Filed: 2016-04-08
- Published: 2018-03-22
- Granted: 2019-08-06
- Earliest claimed: 2015-04-08
- Assignees: The Regents of the University of California
- Applicants: The Regents of the University of California
- Inventors: Adah Almutairi; Jason Olejniczak; Minnie Chan
- Web page: https://patentgrep.com/patent/US10370488B2

## CPC

- C08G 63/685: containing nitrogen
- A61K 9/0002: {Galenical forms characterised by the drug release technique; Application systems commanded by energy}
- A61K 9/5153: {Polyesters, e.g. poly(lactide-co-glycolide)}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

PLGA-based polymers include pendant nucleophiles protected with photocleavable protecting groups. Upon deprotection, the polymers degrade rapidly via intramolecular cyclization into small molecules. The polymer may be formulated as a nanoparticle, with an encapsulated payload, which may be an imaging agent, a bioactive agent or a pharmaceutical agent.

## Claims

### Claim 1

A composition comprising a polymer having a poly(lactide-co-glycolide) backbone and pendant nucleophiles protected by a stimulus-responsive protecting group, wherein the polymer comprises
or a derivative thereof, where X is NH, O or S, and wherein the protecting group is configured to deprotect upon exposure to a stimulus to facilitate degradation by intramolecular cyclization.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the protecting group is photocleavable and the stimulus is light.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the light is UV light.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the protecting group is an ortho-nitrobenzyl (ONB) protecting group.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the polymer degrades according to:
where X is NH, O or S.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the polymer is configured as a plurality of nanoparticles, the composition further comprising a payload encapsulated within each nanoparticle.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the payload is selected from the group consisting of imaging agents, bioactive agents, and pharmaceutical agents.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the pendant nucleophile is an amine.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the pendant nucleophile is an alcohol.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the pendant nucleophile is a thiol.

### Claim 11

A composition comprising a polymer comprising:
a polymer backbone comprising a poly(lactide-co-glycolide) comprising
or a derivative thereof, where X is NH, O or S, and;
pendant nucleophiles linked to the backbone and protected by a photolabile protecting group, wherein the protecting group is configured to deprotect upon exposure to irradiation to facilitate degradation of the nucleophiles to five membered rings by intramolecular cyclization.

### Claim 12 (depends on 11)

The composition of claim 11, wherein the irradiation is UV light.

### Claim 13 (depends on 11)

The composition of claim 11, wherein the protecting group is an ortho-nitrobenzyl (ONB) protecting group.

### Claim 14 (depends on 11)

The composition of claim 11, wherein the polymer degrades according to:
where X is NH, O or S.

### Claim 15 (depends on 11)

The composition of claim 11, wherein the polymer is configured as a plurality of nanoparticles, the composition further comprising a payload encapsulated within each nanoparticle.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the payload is selected from the group consisting of imaging agents, bioactive agents, and pharmaceutical agents.

### Claim 17 (depends on 11)

The composition of claim 11, wherein the pendant nucleophile is an amine.

### Claim 18 (depends on 11)

The composition of claim 11, wherein the pendant nucleophile is an alcohol.

### Claim 19 (depends on 11)

The composition of claim 11, wherein the pendant nucleophile is a thiol.