Fluorescent Arylphosphonic Acids: Synergic Interactions between Bone and the Fluorescent Core |
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Authors: | Dr Yunus Zorlu Connor Brown Dr Claudia Keil Dr M Menaf Ayhan Prof Dr Hajo Haase Dr Richard B Thompson Dr Imre Lengyel Dr Gündoğ Yücesan |
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Institution: | 1. Department of Chemistry, Faculty of Science, Gebze Technical University, 41400 Gebze-Kocaeli, Turkey;2. Wellcome-Wolfson Institute for Experimental Medicine, School of Medicine, Dentistry and Biomedical Science, Queen's University Belfast, Belfast, BT9 7BL UK;3. Technische Universität Berlin, Chair of Food Chemistry and Toxicology, Straße des 17. Juni 135, 10623 Berlin, Germany;4. Department of Biochemistry and Molecular Biology, University of Maryland School of Medicine, Baltimore, Maryland, 21201 USA |
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Abstract: | Herein, we report the third generation of fluorescent probes (arylphosphonic acids) to target calcifications, particularly hydroxyapatite (HAP). In this study, we use highly conjugated porphyrin-based arylphosphonic acids and their diesters, namely 5,10,15,20-tetrakism-(diethoxyphosphoryl)phenyl]porphyrin ( m -H8TPPA-OEt8 ) and 5,10,15,20-tetrakis m-phenylphosphonic acid]porphyrin ( m -H8TPPA ), in comparison with their positional isomers 5,10,15,20-tetrakisp-(diisopropoxyphosphoryl)phenyl]porphyrin ( p -H8TPPA-iPr8 ) and 5,10,15,20-tetrakis p-phenylphosphonic acid]porphyrin ( p -H8TPPA ), which have phosphonic acid units bonded to sp2 carbon atoms of the fluorescent core. The conjugation of the fluorescent core is thus extended to the (HAP) through sp2-bonded −PO3H2 units, which generates increased fluorescence upon HAP binding. The resulting fluorescent probes are highly sensitive towards the HAP in rat bone sections. The designed probes are readily taken up by cells. Due to the lower reported toxicity of ( p -H8TPPA ), these probes could find applications in monitoring bone resorption or adsorption, or imaging vascular or soft tissue calcifications for breast cancer diagnosis etc. |
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Keywords: | Alzheimer's disease calcifications fluorescent imaging ligand synthesis vascular calcifications |
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