Synthesis of a Single‐Stranded DNA Aptamer Modified Near‐infrared, Water‐Soluble Fluorophore for Lung Cancer Cell Imaging

Abstract

In recent years, aza‐boron dipyrromethene (aza‐BODIPY) derivatives have attracted considerable attention as fluorescent imaging agents. In this work, two polyethylene glycol functionalized water soluble aza‐BODIPY derivatives (a mono cycloaddition product 1PEG‐BOD and a double cycloaddition product 2PEG‐BOD) were synthesized through a cycloaddition click reaction between aza‐BODIPY and N3‐PEG2000‐COOH. The absorption and fluorescence profiles of these two compounds were in near‐infrared region. The fluorescence quantum yield of 2PEG‐BOD was 20 times higher than 1PEG‐BOD in water. The attachment of an A549 lung cancer cell targeting aptamer with 2PEG‐BOD afforded APT‐PEG‐BOD. The average fluorescence intensity of APT‐PEG‐BOD (5 μmol/L) in A549 lung cancer cells calculated from confocal microscopy images was 25–33 times stronger than that in other cell lines, such as MDA‐MB‐231, HT1080 and LO2. These results indicated that APT‐PEG‐BOD shows high affinity to A549 lung cancer cells.

Fluorescent poly(β-amino ester)s containing aza-BODIPYs as theranostic agents for bioimaging and photodynamic therapy

“…Previous studies on aza-BODIPY conjugated with poly(ethylene glycol) (PEG-BODs) reported the ϕ F to be 0.008–0.07 in methanol. 77 ϕ F values of the PBAEs in an aqueous solution ranged between 0.0034 and 0.0255 with respect to the reference PS ( ϕ F of MB: 0.22). Although the values were relatively low, the polymers displayed strong radiation in the NIR region in cell culture experiments.…”