Fluorescent styrenes for mitochondrial imaging and viscosity sensing.
Cyanostilbenes
nystatin
pentafluorophenyl
sub-cellular imaging
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
22 Feb 2024
22 Feb 2024
Historique:
revised:
12
12
2023
received:
13
09
2023
accepted:
05
01
2024
medline:
22
2
2024
pubmed:
22
2
2024
entrez:
22
2
2024
Statut:
aheadofprint
Résumé
Fluorophores bearing cationic pendants, such as the pyridinium group, tend to preferentially accumulate in mitochondria, whereas those with pentafluorophenyl groups display a distinct affinity for the endoplasmic reticulum. In this study, we designed fluorophores incorporating pyridinium and pentafluorophenyl pendants and examined their impact on sub-cellular localization. Remarkably, the fluorophores exhibited a notable propensity for the mitochondrial membrane. Furthermore, these fluorophores revealed dual functionality by facilitating the detection of viscosity changes within the sub-cellular environment and serving as heavy-atom-free photosensitizers. With easy chemical tunability, wash-free imaging, and a favorable signal-to-noise ratio, these fluorophores are valuable tools for imaging mitochondria and investigating their cellular processes.
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Science and Engineering Research Board
ID : CRG/2022/007048
Organisme : Department of Biotechnology, Minstry of Science and Technology, India
ID : BT/RLF/Re-entry/45/2015
Organisme : Department of Biotechnology, Minstry of Science and Technology, India
ID : BT/PR15214/BRB/10/1449/2015
Organisme : DST-SERB
ID : ECR/2016/000913
Informations de copyright
© 2024 American Society for Photobiology.
Références
Trinh N, Jolliffe KA, New EJ. Dual-functionalisation of fluorophores for the preparation of targeted and selective probes. Angew Chem Int Ed. 2020;59:20290-20301.
Pramanik SK, Das A. Fluorescent probes for imaging bioactive species in subcellular organelles. Chem Commun. 2021;57:12058-12073.
Zhang J, Campbell RE, Ting AY, Tsien RY. Creating new fluorescent probes for cell biology. Nat Rev Mol Cell Biol. 2002;3:906-918.
Dutta T, Pal K, Koner AL. Intracellular physical properties with small organic fluorescent probes: recent advances and future perspectives. Chem Rec. 2022;22:e202200035.
Lin J, Yang K, New EJ. Strategies for organelle targeting of fluorescent probes. Org Biomol Chem. 2021;19:9339-9357.
Zhu H, Fan J, Du J, Peng X. Fluorescent probes for sensing and imaging within specific cellular organelles. Acc Chem Res. 2016;49:2115-2126.
Sasaki S, Drummen GPC, Konishi G-I. Recent advances in twisted intramolecular charge transfer (TICT) fluorscence and related phenomena in materials chemistry. J Mater Chem. 2016;4:2731-2743.
Collot M, Boutant E, Fam KT, Danglot L, Klymchenko AS. Molecular tuning of styryl dyes leads to versatile and efficient plasma membrane probes for cell and tissue imaging. Bioconjug Chem. 2020;31:875-883.
Hong J, Guan X, Chen Y, Tan X, Zhang S, Feng G. Mitochondrial membrane potential independent near-infrared mitochondrial viscosity probes for real-time tracking mitophagy. Anal Chem. 2023;95:5687-5694.
Giepmans BNG, Adams SR, Ellisman MH, Tsien RY. The fluorescent toolbox for assessing protein location and function. Science. 2006;312:217-224.
Chen X, Zhang D, Su N, et al. Visualizing RNA dynamics in live cells with bright and stable fluorescent RNAs. Nat Biotechnol. 2019;37:1287-1293.
Kim MJ, Li Y, Junge JA, Kim NK, Fraser SE, Zhang C. Development of highly fluorogenic styrene probes for visualizing RNA in live cells. ACS Chem Biol. 2023;18:1523-1533.
Goujon A, Colom A, Straková K, et al. Mechanosensitive fluorescent probes to image membrane tension in mitochondria, endoplasmic reticulum, and lysosomes. J Am Chem Soc. 2019;141:3380-3384.
Wagner N, Stephan M, Höglinger D, Nadler A. A click cage: organelle-specific uncaging of lipid messengers. Angew Chem Int Ed. 2018;57:13339-13343.
Danylchuk DI, Jouard P-H, Klymchenko AS. Targeted solvatochromic fluorescent probes for imaging lipid order in organelles under oxidative and mechanical stress. J Am Chem Soc. 2021;143:912-924.
Singh D, Shewale DJ, Sengupta A, Soppina V, Kanvah S. Lutidine derivatives for live-cell imaging of the mitochondria and endoplasmic reticulum. Org Biomol Chem. 2022;20:7047-7055.
Wei X, Zhu Y, Yu X, et al. An endoplasmic reticulum targeting green fluorescent protein chromophore-based probe for the detection of viscosity. Chem Commun. 2022;58:10727-10730.
Sekhar AR, Mallik B, Kumar V, Sankar J. A cell-permeant small molecule for the super-resolution imaging of the endoplasmic reticulum in live cells. Org Biomol Chem. 2019;17:3732-3736.
Ghosh S, Nandi S, Ghosh C, Bhattacharyya K. Fluorescence dynamics in the endoplasmic reticulum of a live cell: time-resolved confocal microscopy. ChemPhysChem. 2016;17:2818-2823.
Chini CE, Fisher GL, Johnson B, Tamkun MM, Kraft ML. Observation of endoplasmic reticulum tubules via TOF-SIMS tandem mass spectrometry imaging of transfected cells. Biointerphases. 2018;13:03B409.
Rajput D, Mahalingavelar P, Soppina V, Kanvah S. Styryl-NIR mitochondrial probes with rapid HOCl detection in live-cells. Chembiochem. 2023;24:e202300084.
Mukherjee T, Soppina V, Ludovic R, et al. Live-cell imaging of the nucleolus and mapping mitochondrial viscosity with a dual function fluorescent probe. Org Biomol Chem. 2021;19:3389-3395.
Zielonka J, Joseph J, Sikora A, et al. Mitochondria-targeted triphenylphosphonium-based compounds: syntheses, mechanisms of action, and therapeutic and diagnostic applications. Chem Rev. 2017;117:10043-10120.
Wang D, Lee MMS, Shan G, et al. Highly efficient photosensitizers with far-red/near-infrared aggregation-induced emission for in vitro and in vivo cancer theranostics. Adv Mater. 2018;30:1802105.
Huang Y, Zhang G, Zhao R, Zhang D. Aggregation-induced emission luminogens for mitochondria-targeted cancer therapy. ChemMedChem. 2020;15:2220-2227.
Karpenko J, Niko Y, Yakubovskyi VP, et al. Push-pull dioxaborine as fluorescent molecular rotor: far-red fluorogenic probe for ligand-receptor interactions. J Mater Chem. 2016;4:3002-3009.
Tang Q, Li H, Hu H, Chen L. New tool for diseases mechanism studies: endoplasmic reticulum-targeted fluorescent probes. Dyes Pigm. 2023;219:111634.
Rafael J, Nicholls DG. Mitochondrial membrane potential monitored in situ within isolated guinea pig brown adipocytes by a styryl pyridinium fluorescent indicator. FEBS Lett. 1984;170:181-185.
Wisnovsky S, Lei EK, Jean SR, Kelley SO. Mitochondrial chemical biology: new probes elucidate the secrets of the powerhouse of the cell. Cell Chem Biol. 2016;23:917-927.
Ma C, Xia F, Kelley SO. Mitochondrial targeting of probes and therapeutics to the powerhouse of the cell. Bioconjug Chem. 2020;31:2650-2667.
McBride HM, Neuspiel M, Wasiak S. Mitochondria: more than just a powerhouse. Curr Biol. 2006;16:R551-R560.
Gökerküçük EB, Tramier M, Bertolin G. Imaging mitochondrial functions: from fluorescent dyes to genetically-encoded sensors. Genes (Basel). 2020;11:125.
Park S-H, Lee H-G, Liu X, Lee SK, Chang Y-T. Quantitative structure-activity relationship of fluorescent probes and their intracellular localizations. Chemosensors. 2023;11:310.
Golf HRA, Reissig H-U, Wiehe A. Nucleophilic substitution on (pentafluorophenyl) dipyrromethane: a new route to building blocks for functionalized BODIPYs and tetrapyrroles. Org Lett. 2015;17:982-985.
Hoppmann C, Maslennikov I, Choe S, Wang L. In situ formation of an azo bridge on proteins controllable by visible light. J Am Chem Soc. 2015;137:11218-11221.
Chai Z, Wu Q, Cheng K, et al. Simultaneous detection of small molecule thiols with a simple 19F NMR platform. Chem Sci. 2021;12:1095-1100.
Smith RAJ, Porteous CM, Coulter CV, Murphy MP. Selective targeting of an antioxidant to mitochondria. Eur J Biochem. 1999;263:709-716.
Dickinson BC, Srikun D, Chang CJ. Mitochondrial-targeted fluorescent probes for reactive oxygen species. Curr Opin Chem Biol. 2010;14:50-56.
Zorov DB, Juhaszova M, Sollott SJ. Mitochondrial reactive oxygen species (ROS) and ROS-induced ROS release. Physiol Rev. 2014;94:909-950.
Liu T, Liu X, Spring DR, Qian X, Cui J, Xu Z. Quantitatively mapping cellular viscosity with detailed organelle information via a designed PET fluorescent probe. Sci Rep. 2014;4:5418.
Fu M, Sun Y, Kenry M, et al. A dual-rotator fluorescent probe for analyzing the viscosity of mitochondria and blood. Chem Commun. 2021;57:3508-3511.
Li S, Wang P, Feng W, Xiang Y, Dou K, Liu Z. Simultaneous imaging of mitochondrial viscosity and hydrogen peroxide in Alzheimer's disease by a single near-infrared fluorescent probe with a large Stokes shift. Chem Commun. 2020;56:1050-1053.
Niu L, Cao Q, Zhang T, Zhang Y, Liang T, Wang J. Simultaneous detection of mitochondrial viscosity and peroxynitrite in livers from subjects with drug-induced fatty liver disease using a novel fluorescent probe. Talanta. 2023;260:124591.
Ma C, Sun W, Xu L, et al. A minireview of viscosity-sensitive fluorescent probes: design and biological applications. J Mater Chem B. 2020;8:9642-9651.
Yang Z, He Y, Lee J-H, et al. A self-calibrating bipartite viscosity sensor for mitochondria. J Am Chem Soc. 2013;135:9181-9185.
Carloni P, Damiani E, Greci L, et al. On the use of 1,3-diphenylisobenzofuran (DPBF). Reactions with carbon and oxygen centered radicals in model and natural systems. Res Chem Intermed. 1993;19:395-405.
Guo X, Yang N, Ji W, et al. Mito-bomb: targeting mitochondria for cancer therapy. Adv Mater. 2021;33:2007778.
Reiniers MJ, van Golen RF, Bonnet S, et al. Preparation and practical applications of 2′,7′-dichlorodihydrofluorescein in redox assays. Anal Chem. 2017;89:3853-3857.