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Int. J. Mol. Sci. 2017, 18(6), 1177; doi:10.3390/ijms18061177

Low-Symmetry Mixed Fluorinated Subphthalocyanines as Fluorescence Imaging Probes in MDA-MB-231 Breast Tumor Cells

Department of Chemistry, Oakland University, Rochester, MI 48309, USA
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Author to whom correspondence should be addressed.
Academic Editor: Nick Hadjiliadis
Received: 12 May 2017 / Revised: 26 May 2017 / Accepted: 30 May 2017 / Published: 1 June 2017
(This article belongs to the Section Bioinorganic Chemistry)
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Abstract

Boron subphthalocyanines (SPcs) are aromatic macrocycles that possess a combination of physical and optical properties that make them excellent candidates for application as fluorescent imaging probes. These molecules have intense electronic absorption and emission, and structural versatility that allows for specific tuning of physical properties. Herein, we report the synthesis of a series of low-symmetry fluorinated SPcs and compare them to analogous compounds with varying numbers of peripheral fluorine atoms and varied aromaticity. Across the series, with increasing addition of fluorine atoms to the periphery of the ring, a downfield chemical shift in 19F NMR and a bathochromic shift of electronic absorption were observed. Expanding the size of the aromatic ring by replacing peripheral benzo- groups with naphtho- groups prompted a far more drastic bathochromic shift to absorption and emission. Fluorescence quantum yields (Φf) proved to be sufficiently high to observe intracellular fluorescence from MDA-MB-231 breast tumor cells in vitro by epifluorescence microscopy; fluorination proved vital for this purpose to improve solubility. This report lays the groundwork for the future development of these promising SPcs for their ultimate application as near-infrared (NIR) fluorescent imaging probes in biological systems. View Full-Text
Keywords: subphthalocyanine; fluorescence imaging; 19F NMR; fluorescence microscopy subphthalocyanine; fluorescence imaging; 19F NMR; fluorescence microscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

McAuliffe, K.J.; Kaster, M.A.; Szlag, R.G.; Trivedi, E.R. Low-Symmetry Mixed Fluorinated Subphthalocyanines as Fluorescence Imaging Probes in MDA-MB-231 Breast Tumor Cells. Int. J. Mol. Sci. 2017, 18, 1177.

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