Water-soluble near-infrared fluorescent heptamethine dye for lymphatic mapping applications. (1st October 2022)

• Record Type: Journal Article
• Authors: Zhang, Shaohui; Ji, Xin; Zhang, Rong; Zhao, Weili; Dong, Xiaochun
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 73(2022)
• Publication Date: 2022-10-01
• Subjects: Heptamethine cyanine dye -- Sentinel lymph node -- NIR optical imaging; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2022.128910
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The identification of sentinel lymph node (SLN) is an important method for prognostic evaluation and minimally invasive staging of metastatic tumors. Here, we report a series of near-infrared fluorescent heptamethylamine dyes (series A, B and C) with central cycloalkene ring modified by tyrosine or N -Boc tyrosine via ether linkage. N -Boc tyrosine/tyrosine modification provided enhanced absorption coefficient and fluorescence quantum yield in DMSO, however with slight hypsochromic shift compared to the mother dyes in DMSO. In PBS, series A and B were found to be more fluorescent than ICG and showed brighter images. Compound A1 was found to exhibit the most favorable imaging performance among all the dyes investigated and was selected for in vivo sentinel lymph node mapping experiments in mice. A1 showed faster response and stronger fluorescence emission than FDA-approved ICG . The lymph node tracing with A1 could be assisted by MB staining. Ex vivo imaging of harvested organs indicated that similar metabolic characteristics of A1 and ICG . Overall, A1 is advantageous over ICG and is very promising for non-invasive lymph node imaging.