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Title: Small molecule dye for molecular imaging and photothermal therapy

Abstract

Disclosed is a small molecule dye for use in imaging in the near-infrared window, namely between 1000 nm-1700 nm wavelength. The present dyes are also useful for photoacoustic imaging and photothermal therapy. The dyes have a structure of a D-A-D (donor-acceptor-donor) fluorescent compound core and side chains rendering the compounds water soluble and easily conjugated to hydrophilic polymers and/or targeting ligands. Further disclosed is compound, CH1055 that can be PEGylated, conjugated to a targeting ligand, or conjugated to taurine. Key steps utilized to assemble the core structure of the target included a cross-Suzuki coupling reaction, iron reduction and N-thionylaniline induced ring closure. Four carboxylic acid groups were introduced into the donor-acceptor-donor (D-A-D) type fluorescent compound to impart a certain aqueous solubility and to allow facile conjugation to targeting ligands.

Inventors:
; ; ; ; ;
Issue Date:
Research Org.:
Stanford Univ., CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1494129
Patent Number(s):
10124111
Application Number:
15/051,563
Assignee:
The Board of Trustees of the Leland Stanford Junior University (Stanford, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES
A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
DOE Contract Number:  
SC0008397
Resource Type:
Patent
Resource Relation:
Patent File Date: 2016 Feb 23
Country of Publication:
United States
Language:
English
Subject:
47 OTHER INSTRUMENTATION

Citation Formats

Cheng, Zhen, Hong, Xuechuan, Dai, Hongjie, Chen, Hao, Antaris, Alexander, and Cheng, Kai. Small molecule dye for molecular imaging and photothermal therapy. United States: N. p., 2018. Web.
Cheng, Zhen, Hong, Xuechuan, Dai, Hongjie, Chen, Hao, Antaris, Alexander, & Cheng, Kai. Small molecule dye for molecular imaging and photothermal therapy. United States.
Cheng, Zhen, Hong, Xuechuan, Dai, Hongjie, Chen, Hao, Antaris, Alexander, and Cheng, Kai. Tue . "Small molecule dye for molecular imaging and photothermal therapy". United States. https://www.osti.gov/servlets/purl/1494129.
@article{osti_1494129,
title = {Small molecule dye for molecular imaging and photothermal therapy},
author = {Cheng, Zhen and Hong, Xuechuan and Dai, Hongjie and Chen, Hao and Antaris, Alexander and Cheng, Kai},
abstractNote = {Disclosed is a small molecule dye for use in imaging in the near-infrared window, namely between 1000 nm-1700 nm wavelength. The present dyes are also useful for photoacoustic imaging and photothermal therapy. The dyes have a structure of a D-A-D (donor-acceptor-donor) fluorescent compound core and side chains rendering the compounds water soluble and easily conjugated to hydrophilic polymers and/or targeting ligands. Further disclosed is compound, CH1055 that can be PEGylated, conjugated to a targeting ligand, or conjugated to taurine. Key steps utilized to assemble the core structure of the target included a cross-Suzuki coupling reaction, iron reduction and N-thionylaniline induced ring closure. Four carboxylic acid groups were introduced into the donor-acceptor-donor (D-A-D) type fluorescent compound to impart a certain aqueous solubility and to allow facile conjugation to targeting ligands.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2018},
month = {11}
}

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Works referenced in this record:

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