دورية أكاديمية
Development of a Neutral Diketopyrrolopyrrole Phosphine Oxide for the Selective Bioimaging of Mitochondria at the Nanomolar Level.
| العنوان: | Development of a Neutral Diketopyrrolopyrrole Phosphine Oxide for the Selective Bioimaging of Mitochondria at the Nanomolar Level. |
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| المؤلفون: | Abelha TF; School of Pharmacy, The University of Nottingham, University Park, NG72RD, Nottingham, UK., Morris G; School of Computing, Engineering and Physical Sciences, University of the West of Scotland, PA12BE, Paisley, UK., Lima SM; Grupo de Espectroscopia Óptica e Fototérmica, Universidade Estadual de Mato Grosso do Sul, CP 351, 79804-970, Dourados, MS, Brazil., Andrade LHC; Grupo de Espectroscopia Óptica e Fototérmica, Universidade Estadual de Mato Grosso do Sul, CP 351, 79804-970, Dourados, MS, Brazil., McLean AJ; School of Computing, Engineering and Physical Sciences, University of the West of Scotland, PA12BE, Paisley, UK., Alexander C; School of Pharmacy, The University of Nottingham, University Park, NG72RD, Nottingham, UK., Calvo-Castro J; School of Life and Medical Sciences, University of Hertfordshire, AL109AB, Hatfield, UK., McHugh CJ; School of Computing, Engineering and Physical Sciences, University of the West of Scotland, PA12BE, Paisley, UK. |
| المصدر: | Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Mar 09; Vol. 26 (14), pp. 3173-3180. Date of Electronic Publication: 2020 Feb 21. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Weinheim, Germany : Wiley-VCH |
| مواضيع طبية MeSH: | Fluorescent Dyes/*chemistry , Ketones/*chemistry , Mitochondria/*metabolism , Organophosphorus Compounds/*chemistry , Pyrroles/*chemistry, Biosensing Techniques ; Humans ; Light ; MCF-7 Cells ; Membrane Potential, Mitochondrial/physiology ; Molecular Structure ; Optical Imaging ; Organic Chemicals/chemistry ; Structure-Activity Relationship |
| مستخلص: | Development of novel bioimaging materials that exhibit organelle specific accumulation continues to be at the forefront of research interests and efforts. Among the various subcellular organelles, mitochondria, which are found in the cytoplasm of eukaryotic cells, are of particular interest in relation to their vital function. To date, most molecular probes that target mitochondria utilise delocalised lipophilic cations such as triphenylphosphonium and pyridinium. However, the use of such charged motifs is known to be detrimental to the working function of the mitochondrial transmembrane potential and there remains a strong case for development of neutral mitochondrial fluorescent probes. Herein, we demonstrate for the first time the exploitation of diketopyrrolopyrrole-based chemistries for the realisation of a neutral fluorescent probe that exhibits organelle specific accumulation within the mitochondria at the nanomolar level. The synthesised probe, which bears a neutral triphenylphosphine oxide moiety, exhibits a large Stokes shift and high fluorescence quantum yield in water, both highly sought-after properties in the development of bioimaging agents. In vitro studies reveal no interference with cell metabolism when tested for the human MCF7 breast cancer cell and nanomolar subcellular organelle colocalisation with commercially available mitochondrial staining agent Mitotracker Red. In light of its novelty, neutral structure and the preferential accumulation at nanomolar concentrations we anticipate this work to be of significant interest for the increasingly larger community devoted to the realisation of neutral mitochondrial selective systems and more widely to those engaged in the rational development of superior organic architectures in the biological field. (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.) |
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| معلومات مُعتمدة: | 422329/2018- 5 Conselho Nacional de Desenvolvimento Científico e Tecnológico; EP/N03371X/1 Engineering and Physical Sciences Research Council |
| فهرسة مساهمة: | Keywords: diketopyrrolopyrroles; mitochondria staining; nanomolar; neutral probe |
| المشرفين على المادة: | 0 (Fluorescent Dyes) 0 (Ketones) 0 (MitoTracker Red 580) 0 (Organic Chemicals) 0 (Organophosphorus Compounds) 0 (Pyrroles) 0 (diketopyrrolopyrrole dye) Z69161FKI3 (triphenylphosphine oxide) |
| تواريخ الأحداث: | Date Created: 20200222 Date Completed: 20200406 Latest Revision: 20200408 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1002/chem.201905634 |
| PMID: | 32083355 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1521-3765 |
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| DOI: | 10.1002/chem.201905634 |