# US 10,245,329 B2 · Composition having dye and conjugate of polyethyleneglycol and additive and contrast agent for photoacoustic imaging having the same

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- Number: US 10,245,329 B2
- Document ID: US10245329B2
- Status: Granted
- Kind: B2
- Application number: 14/845,592
- Filed: 2015-09-04
- Published: 2016-03-10
- Granted: 2019-04-02
- Earliest claimed: 2014-09-08
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Tatsuki Fukui; Atsushi Takahashi; Daisuke Sasaguri; Kouichi Kato; Fumiko Tomatsu; Keigo Mizusawa
- Web page: https://patentgrep.com/patent/US10245329B2

## CPC

- A61K 49/22: Echographic preparations; Ultrasonic imaging preparations
- A61K 49/0032: {Methine dyes, e.g. cyanine dyes}
- 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

The present invention provides contrast agents for photoacoustic imaging which exhibit high degrees of accumulation in tumor and low degrees of retention in the blood and can be administered into the blood. The contrast agents for photoacoustic imaging include a conjugate of a dye and a polyethyleneglycol represented by Formula (1), (5), (6), or (7) and an additive represented by Formula (301).

## Claims

### Claim 1

A contrast agent suitable for photoacoustic imaging, comprising: a compound represented by formula (1), (5), (6), or (7); and an additive, which interacts with the compound, wherein the additive is at least one selected from the group consisting of an α-cyclodextrin, a β-cyclodextrin, a hydroxypropyl-β-cyclodextrin, and a γ-cyclodextrin:
wherein R301 to R312 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, —PO3T301, a substituted or unsubstituted phenyl group, thiophene group, or pyridinyl group and a linear or branched alkyl group having 1 to 18 carbon atoms;
T301 is selected from the group consisting of a hydrogen atom, a sodium atom and a potassium atom;
R31 to R34 are each independently selected from the group consisting of a hydrogen atom and a linear or branched alkyl group having 1 to 18 carbon atoms;
A31, B31 and B32 each independently represent a linear or branched alkylene group having 1 to 18 carbon atoms;
L31 to L37 are each independently selected from the group consisting of CH and CR35 and may form a 4- to 6-membered ring;
R35 is selected from the group consisting of a linear or branched alkyl group having 1 to 18 carbon atoms, a halogen atom, a substituted or unsubstituted phenyl group, pyridinyl group, or benzyl group, ST302 and a linear or branched alkylene group having 1 to 18 carbon atoms;
T302 is selected from the group consisting of a linear or branched alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group and a linear or branched alkylene group having 1 to 18 carbon atoms;
Q31 is selected from the group consisting of —CONT31-, —NT31CO—, —NT31(C═O) NT31-, —NT31(C═S) NT31-, —NT31(C═O)O—, —O—, —S—, —S(═O)2NT31-, —OP(═O)(OT31)O—, —S—S—, —CT31=N—, —CT31=N—NH—, —CT31=N—O—, —CT31=N—NH—O—, —CONT31-R37—(C═O)O—, —CONT31-R37—CONT31-, formula (2) and formula (3);
T31 is selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 5 carbon atoms;
R37 is selected from the group consisting of —CH(CO2T37)-, —CH(CH2CO2T37)- and a linear or branched alkylene group having 1 to 18 carbon atoms;
T37 is selected from the group consisting of a hydrogen atom, a sodium atom, a potassium atom and an alkyl group having 1 to 5 carbon atoms;
R38 is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, a hydrogen atom, —OCH3, —NH2, —OH, —CO2T38, —S(═O)2OT38, —P(═O)(OT38)2 and —OP(═O)(OT38)2;
T38 is selected from the group consisting of a hydrogen atom, a sodium atom and a potassium atom;
R39 is selected from the group consisting of a hydrogen atom, —OCH3, —NH2, —OH, —S(═O)2OT39, —CO2T39, —P(═O)(OT39)2, —CONH—CH(CO2T39)-CH2(C═O)OT39, —CONH—CH(CO2T39)-CH2CH2(C═O)OT39 and —OP(═O)(OT39)2;
T39 is selected from the group consisting of a hydrogen atom, a sodium atom and a potassium atom;
q is an integer from 1 to 20;
n is an integer from 2 to 250:

### Claim 2 (depends on 1)

The contrast agent according to claim 1, wherein the compound represented by the formula (1), (5), (6), or (7) has a structure represented by Formula (501) or (601):
wherein j and k are each an integer from 2 to 250.

### Claim 3 (depends on 1)

The contrast agent according to claim 1, wherein the compound has a molar extinction coefficient of 106 M−1 cm−1 at a wavelength of 600 nm to 1300 nm.

### Claim 4 (depends on 1)

The contrast agent according to claim 1, further comprising a dispersion medium.