Abstract
A Thiazole Orange conjugated with folate derivative was synthesized in two steps. Firstly, folate was coupled with 1-(3-aminopropyl)-4-methylquinolinium bromide to afford folate-methylquinolinium bromide, which then reacted with benzothiazolium to obtain the title folate-conjugated compound. The compound was evaluated by 1H-NMR MS, TG/DTA and fluorescence spectroscopic methods. The title compound could selectively target folate receptor expressing tumors according to the in vivo fluorescence imaging preliminarily performed on nude mice with breast tumors.
Highlights
An increasing scientific and commercial interest in the synthesis and application as probes of cyanine dyes, whose spectra can reach near-infrared region, has aroused much attention in recent years
Folate compound 2 can be obtained from the reaction of folate and compound 1
Folate compound 2 can be synthesized from NHS-folate and compound 1 in DMSO
Summary
An increasing scientific and commercial interest in the synthesis and application as probes of cyanine dyes, whose spectra can reach near-infrared region, has aroused much attention in recent years These probes can be used as powerful detection or treatment tools in biological systems [1-9], such as tools allowing detection of DNA and RNA in gel by flow cytometry or microscopy. We expected that folic acid conjugated with TO could selectively deliver the organic fluorescence probe to folate-receptor-overexpressing breast cancer cells and utilize TO’s advantages. For targeting purposes, the cyanine dye TO with an amine residue (TO-NH2) was modified by folic acid to obtain a coupled folate-TO (Route 1 in Scheme 1), which was applied to targets to facilitate the identification of cancer cells with extra FR on the membrane cellular surface.
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