The crucial components in successful treatment of cancer are early detection and accurate diagnosis, which rely heavily on the diagnostic method used. Diagnostic processes using near-infrared (NIR) fluorescence can be used to identify superficial tumors, while deep tumors can be detected using MRI. A combination of these two processes would provide a significant advantage over individual methods in accurately diagnosing either superficial or deep tumors. Phthalocyanines (Pcs) are a type of highly conjugated macrocycle that exhibit strong fluorescence and are prepared by a synthetic method that allows for the addition of fluorine atoms. Therefore, Pcs are of interest as dual-mode imaging probes for fluorescence and 19F MRI. Herein we report the synthesis of two types of Pcs, AB3 ([1,4-dioxino[b]-(2R,3R)-2,3-dimethoxy-2,3-dimethyl-dodecafluorophthalocyanine) and B4 (hexadecafluorophthalocyanine) as both the metal-free and Zn2+ forms. New Pcs have been characterized by 1H and 19F NMR, MALDI-MS, UV-vis, and fluorescence spectroscopy. Solubility in biological environments is imperative for practical application; Pc aggregation has been studied by UV-vis spectroscopy. These studies provide insight into identifying a molecule that exhibits the best combination of photophysical properties and solubility for advancement to imaging studies in tumor cells in vitro.

Fluorinated phthalocyanines as dual-mode fluorescent and MRI contrast agents

251st National Meeting (2016)

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