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Synthesis of the C3 and C1 Constitutional Isomers of Trifluorosubphthalocyanine and Their Fluorescence within MDA-MB-231 Breast Tumor Cells

Department of Chemistry, Oakland University, Rochester, MI 48309, USA
Author to whom correspondence should be addressed.
Present Addresses: Department of Chemistry, Duke University, Durham, NC 27708, USA.
Academic Editors: Roman Dembinski, Igor V. Alabugin and Vadim A. Soloshonok
Molecules 2019, 24(21), 3832;
Received: 30 September 2019 / Revised: 15 October 2019 / Accepted: 16 October 2019 / Published: 24 October 2019
(This article belongs to the Special Issue Organic Chemistry in the USA)
Metal tetrapyrrole macrocycles such as porphyrins and chlorins are ubiquitous in nature. Synthetic analogs, including phthalocyanines, have found applications in medicine, particularly as photosensitizers for photodynamic therapy and as fluorescent imaging probes. Tripyrrolic macrocycles, called subphthalocyanines (SPcs) with a smaller boron atom at their core, have similar potential as optical agents. We have recently reported a series of mixed fluorinated SPcs with varying aromaticity, showing that electronic absorption and emission are synthetically tunable across the far visible region, and that the inclusion of 4–12 peripheral fluorine atoms results in strong fluorescence within MDA-MB-231 breast tumor cells. Further probing this system, we report herein the synthesis and characterization of boron trifluorosubphthalocyanine chloride (F3SPc). The constitutional isomers F3SPc(C3) and F3SPc(C1) are readily separable by chromatography, and their identity and purity have been confirmed by 1H NMR, 19F NMR, HR APCI-MS, and HPLC. Unsurprisingly, these structurally similar F3SPcs have identical electronic absorption (λmax = 557 nm; tetrahydrofuran (THF)) and emission (λem = 574 nm; Φf = 0.27–0.28; THF). Strong fluorescence from MDA-MB-231 breast tumor cells was observed following treatment with F3SPc(C3) and F3SPc(C1) (50 µM F3SPc, 15 min), further highlighting the importance of even a limited number of peripheral fluorine atoms for this type of application. View Full-Text
Keywords: fluorescent probes; MDA-MB-231; subphthalocyanine fluorescent probes; MDA-MB-231; subphthalocyanine
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L. Calandrino, R.; J. McAuliffe, K.; E. Dolmage, L.; R. Trivedi, E. Synthesis of the C3 and C1 Constitutional Isomers of Trifluorosubphthalocyanine and Their Fluorescence within MDA-MB-231 Breast Tumor Cells. Molecules 2019, 24, 3832.

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