Dynamic covalent chemistry in live cells for organelle targeting and enhanced photodynamic action

Liu, Fei; Danylchuk, Dmytro I.; Andreiuk, Bohdan; Klymchenko, Andrey S.

doi:10.1039/d1sc04770a

Cited by 12 publications

(11 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[35][36][37][38][39][40][41] Here, three hydrazide-bearing ligands were synthesized as shown in Figure 3. [42] One with triphenylphosphonium (Mito-HZ) for mitochondria targeting; one with octyl chains (LD-HZ) for lipid droplet targeting, and one with dodecyl chain and sulfonate (PM-HZ) for plasma membrane targeting. Cells were incubated with Scheme 3.…”

Section: Applications Of the Imine Bondmentioning

confidence: 99%

See 1 more Smart Citation

Recent Progress in Polymers with Dynamic Covalent Bonds

Li,

Peng,

Zhu

et al. 2023

Macro Chemistry & Physics

View full text Add to dashboard Cite

Dynamic covalent bonds have attracted huge interest in the past two decades, particularly in polymer materials, due to their reversibility. The introduction of dynamic covalent bonds into polymers often endows the polymers with unprecedented properties such as self‐healing, shape memory, enhanced mechanical strength, and stimuli responsiveness. Specifically, dynamic covalent bonds offer unique opportunities for self‐healing materials by enabling spontaneous reformation of covalent linkages and restoring structural integrity upon damaged or mechanical stress. Additionally, shape memory behavior allows polymers to retain programmed shapes and undergo reversible transformations triggered by external stimuli. This property finds applications in various fields such as biomedical devices and smart textiles. Furthermore, dynamic covalent bonds enhance mechanical strength, making polymers resilient and durable, thus expanding their applications in structural materials. Their stimuli responsiveness allows for dynamic modulation of properties based on environmental triggers, enabling the development of intelligent materials for sensors, drug delivery systems, and responsive coatings. This review provides an overview of commonly employed dynamic covalent bonds in polymer materials, explaining their dynamic behaviors, reversibility, and stabilities. It also explores the diverse applications that have emerged from harnessing the unique properties of dynamic covalent bond‐based polymers, from self‐healing coatings to shape memory polymers. Through these advancements, the potential for future breakthroughs in materials science becomes evident.This article is protected by copyright. All rights reserved

show abstract

Section: Applications Of the Imine Bondmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Recent Progress in Polymers with Dynamic Covalent Bonds

Li,

Peng,

Zhu

et al. 2023

Macro Chemistry & Physics

View full text Add to dashboard Cite

show abstract

“…Dynamic covalent exchange cascades [1] are emerging as a central process not only to access modern materials [2–15] but also for use in chemical biology, particularly to penetrate cells [16–36] . Exchange cascades operate with dynamic covalent exchangers, which, upon exchange, either produce a new covalently tethered exchanger or offer another exchanger, and thereby continue to exchange.…”

Section: Figurementioning

confidence: 99%

Dynamic Phosphorus: Thiolate Exchange Cascades with Higher Phosphorothioates

Bouffard,

Coelho,

Sakai

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

In this study, we introduce phosphorus, a pnictogen, as an exchange center for dynamic covalent chemistry. Cascade exchange of neutral phosphorotri‐ and ‐tetrathioates with thiolates is demonstrated in organic solvents, aqueous micellar systems, and in living cells. Exchange rates increase with pH, electrophilicity of the exchange center and nucleophilicity of the exchangers. Molecular walking of the dynamic phosphorus along Hammett gradients is simulated by the sequential addition of thiolate exchangers. Compared to phosphorotrithioates, tetrathioates are better electrophiles with higher exchange rates. Dynamic phosphorotri‐ and ‐tetrathioates are non‐toxic to HeLa Kyoto cells and participate in the dynamic networks that account for thiol‐mediated uptake into living cells.

show abstract

“…An alternative organelle-targeting strategy is a bio-orthogonal reaction inside the cells between a targeting ligand and a fluorophore. , For example, the ceramide derivative Ser-TCO can localize in Golgi or ER depending on the temperature and then react with the tetrazine derivative of the spontaneously blinking Si-rhodamine dye HMSiR-Tz, allowing their super-resolution imaging . Recently, we explored dynamic covalent chemistry to couple the Nile Red ketone derivative with hydrazide ligands located in mitochondria, PM, or lipid droplets, which allowed localizing the same dye in organelles of interest. Specific targeting of mitochondria and PM led to significantly higher phototoxicity compared to LDs or nontargeted dyes, showing that the organelle targeting can modulate the biological activity.…”

Section: Lipidic Probes For Organellesmentioning

confidence: 99%

Fluorescent Probes for Lipid Membranes: From the Cell Surface to Organelles

Klymchenko

2022

Acc. Chem. Res.

Self Cite

View full text Add to dashboard Cite

Conspectus Biomembranes are ubiquitous lipid structures that delimit the cell surface and organelles and operate as platforms for a multitude of biomolecular processes. The development of chemical toolsfluorescent probesfor the sensing and imaging of biomembranes is a rapidly growing research direction, stimulated by a high demand from cell biologists and biophysicists. This Account focuses on advances in these smart molecules, providing a voyage from the cell frontierplasma membranes (PM)toward intracellular membrane compartmentsorganelles. General classification of the membrane probes can be based on targeting principles, sensing profile, and optical response. Probes for PM and organelle membranes are designed based on multiple targeting principles: conjugation with natural lipids or synthetic targeting ligands and in situ cell labeling by bio-orthogonal chemistry, conjugation to protein tags, and receptor–ligand interactions. Thus, to obtain membrane probes targeting PM with selectivity to one leaflet, we designed membrane anchor ligands based on a charged group and an alkyl chain. According to the sensing profile, we define basic membrane markers with constant emission and probes for biophysical and chemical sensing. The markers are built from classical fluorophores, exemplified by a series of bright cyanines and BODIPY dyes bearing the PM anchors (MemBright). Membrane probes for biophysical sensing are based on environment-sensitive fluorophores: (1) polarity-sensitive solvatochromic dyes; (2) viscosity-sensitive fluorescent molecular rotors; (3) mechanosensitive fluorescent flippers; and (4) voltage-sensitive electrochromic dyes. Our solvatochromic probes based on Nile Red (NR12S, NR12A, NR4A), Laurdan (Pro12A), and 3-hydroxyflavone (F2N12S) through polarity-sensing can visualize liquid ordered and disordered phases of lipid membranes, sense lipid order and its heterogeneity in cell PM, detect apoptosis, etc. Chemically sensitive probes, combining a dye, membrane-targeting ligand, and molecular recognition unit, enable the detection of pH, ions, redox species, lipids, and proteins at the biomembrane surface. In terms of the optical response profile, we can identify (1) fluorogenic (turn-on) probes, allowing background-free imaging; (2) ratiometric probes, e.g., solvatochromic probes, which enable ratiometric imaging by changing their emission/excitation color; (3) fluorescence lifetime-responsive probes, e.g., fluorescence molecular rotors and flippers, suitable for fluorescence lifetime imaging (FLIM); and (4) switchable probes, important for single-molecule localization microscopy. We showed that combining solvatochromic probes with on–off switching through a reversible binding specifically to cell PM enables the mapping of their biophysical properties with superior resolution. While the majority of efforts have been focused on PM, the probes for cellular organelles, such as endoplasmic reticulum, mitochondria, Golgi apparatus, etc., emerge rapidly. Thus, nontargeted solvatochromic probes can disting...

show abstract

Dynamic covalent chemistry in live cells for organelle targeting and enhanced photodynamic action

Abstract: Organelle-specific targeting enables increasing the therapeutic index of drugs and localizing probes for better visualization of cellular processes. Current targeting strategies require conjugation of a molecule of interest with organelle-targeting...

Cited by 12 publications

References 75 publications

Recent Progress in Polymers with Dynamic Covalent Bonds

Recent Progress in Polymers with Dynamic Covalent Bonds

Dynamic Phosphorus: Thiolate Exchange Cascades with Higher Phosphorothioates

Fluorescent Probes for Lipid Membranes: From the Cell Surface to Organelles

Contact Info

Product

Resources

About