Small molecule dye for molecular imaging and photothermal therapy

Patent · Tue Jan 19 00:00:00 EST 2021

OSTI ID:1805394

Cheng, Zhen; Hong, Xuechuan; Dai, Hongjie; Chen, Hao; Antaris, Alexander L.; Cheng, Ken

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.

• Research Organization: Stanford Univ., Palo Alto, CA (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: SC0008397
• Assignee: The Board of Trustees of the Leland Stanford Junior University (Stanford, CA)
• Patent Number(s): 10,894,121
• Application Number: 16/186,947
• OSTI ID: 1805394
• Resource Relation: Patent File Date: 11/12/2018
• Country of Publication: United States
• Language: English