# US 10,869,940 B2 · Targeted photoacoustic compounds, formulations, and uses thereof

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- Number: US 10,869,940 B2
- Document ID: US10869940B2
- Status: Granted
- Kind: B2
- Application number: 15/180,418
- Filed: 2016-06-13
- Published: 2016-12-15
- Granted: 2020-12-22
- Earliest claimed: 2015-06-12
- Assignees: The Board of Trustees of the Leland Stanford Junior University
- Applicants: The Board of Trustees of the Leland Stanford Junior University
- Inventors: Sanjiv S. Gambhir; Jelena Levi
- Web page: https://patentgrep.com/patent/US10869940B2

## CPC

- A61K 49/221: {characterised by the targeting agent or modifying agent linked to the acoustically-active agent}
- A61K 49/0017: {Fluorescence in vivo}
- 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

Provided herein are targeted photoacoustic compounds and formulations thereof that can contain a photoacoustic signaling moiety operatively coupled to a targeting moiety. Also provided herein are methods of imagining a subject using the targeted photoacoustic compounds and formulations thereof provided herein.

## Claims

### Claim 1

A method of imaging a target cell in a subject in need thereof, comprising:
administering a photoacoustic compound to the subject in need thereof;
applying a light to the area of the subject to be imaged; and
detecting ultrasonic waves emitted from the photoacoustic compound,
wherein the photoacoustic compound consists of a targeting moiety and a photoacoustic signaling molecule, wherein the photoacoustic signaling molecule is coupled to the targeting moiety via a linker, and wherein the photoacoustic signaling molecule is selected from the group consisting of: Evans blue, lymphazurin, methylene blue, ATTO-610, ATTO-620, ATTO-Rho 14, ATTO-633, ATTO-647, ATTO-647N, ATTO-655, ATTO-Oxa12, ATTO-665, ATTO-680, ATTO-700, ATTO, 725, and ATTO-740, and wherein the targeting moiety has a Formula according to any one of Formulas 2-9, and 12:
wherein, in Formula 6, R is H or —O-Me, and in Formula 7, n is between 1 and 50.

### Claim 2 (depends on 1)

The method of claim 1, further comprising the step of converting the ultrasonic waves detected into a visual image.

### Claim 3 (depends on 1)

The method of claim 1, wherein the ultrasonic waves are detected with an ultrasound transducer.

### Claim 4

A compound consisting of a targeting moiety and a photoacoustic signaling molecule, wherein the photoacoustic signaling molecule is coupled to the targeting moiety via a linker, and wherein the photoacoustic signaling molecule is selected from the group consisting of: Evans blue, lymphazurin, methylene blue, ATTO-610, ATTO-620, ATTO-Rho 14, ATTO-633, ATTO-647, ATTO-647N, ATTO-655, ATTO-Oxa12, ATTO-665, ATTO-680, ATTO-700, ATTO, 725, and ATTO-740, and wherein the targeting moiety has a Formula according to any one of Formulas 2-9, and 12:
wherein, in Formula 6, R is H or —O-Me, and in Formula 7, n is between 1 and 50.

### Claim 5

A pharmaceutical formulation comprising a photoacoustic compound consisting of a targeting moiety and a photoacoustic signaling molecule, wherein the photoacoustic signaling molecule is coupled to the targeting moiety via a linker, and wherein the photoacoustic signaling molecule is selected from the group consisting of: Evans blue, lymphazurin, methylene blue, ATTO-610, ATTO-620, ATTO-Rho 14, ATTO-633, ATTO-647, ATTO-647N, ATTO-655, ATTO-Oxa12, ATTO-665, ATTO-680, ATTO-700, ATTO, 725, and ATTO-740, and wherein the targeting moiety has a Formula according to any one of Formulas 2-9, and 12:
wherein, in Formula 6, R is H or —O-Me, in Formula 7, n is between 1 and 50; and
a pharmaceutically acceptable carrier.

### Claim 6 (depends on 4)

The compound of claim 4, wherein the linker is 6-aminohexanoic acid.

### Claim 7 (depends on 4)

The compound of claim 4, wherein the photoacoustic signaling molecule has a formula selected from the group consisting of:

### Claim 8 (depends on 5)

The pharmaceutical formulation of claim 5, wherein the linker is 6-aminohexanoic acid.

### Claim 9 (depends on 5)

The pharmaceutical formulation of claim 5, wherein the photoacoustic signaling molecule has a formula selected from the group consisting of: