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Fluorescence Quenching Properties and Bioimaging Applications of Readily Accessible Blue to Far-Red Fluorogenic Triazinium Salts Open
Fluorogenic probes, which become fluorescent only upon specific activation, enable no-wash imaging with an excellent signal-to-noise ratio. Despite significant progress in the development of such probes, challenges remain in achieving effi…
Double Disguise: Camouflaging Photocages for Bioorthogonally Controlled Conditional Activation Open
Photocages provide excellent spatiotemporal control over biological processes; however, strategies to restrict their activation to specific conditions remain limited. In this work, we demonstrate that our recently introduced photocages bas…
New Click on the Block: Photocaged Hydroxylamine, an Addition to the Light‐Activatable Bioorthogonal Toolbox Open
A new photoactivatable bioorthogonal function was added to the photoactivatable bioorthogonal toolbox by transiently disabling the bioorthogonal reactivity of the hydroxylamine moiety with a photolabile protecting group. The photocaged bio…
Fluorescence Quenching Properties and Bioimaging Applications of Readily Accessible Blue to Far-Red Fluorogenic Triazinium Salts Open
Fluorogenic probes, which become fluorescent only upon specific activation, enable no-wash imaging with an excel-lent signal-to-noise ratio. Despite significant progress in the development of such probes, challenges remain in achiev-ing ef…
Optically Controlled Drug Delivery Through Microscale Brain–Machine Interfaces Using Integrated Upconverting Nanoparticles Open
The aim of this work is to incorporate lanthanide-cored upconversion nanoparticles (UCNP) into the surface of microengineered biomedical implants to create a spatially controlled and optically releasable model drug delivery device in an in…
I Bind It That Way – Bioorthogonal Unmasking of Pro‐Fluorescent Quinone Methides Open
Proof‐of‐concept studies for the bioorthogonally controlled generation of pro‐fluorescent quinone‐methides are presented here. The novel concept relies on a click‐to‐release tetrazine unit that chemically cages a pro‐fluorescent quinone me…
Bioorthogonal Reactions in Bioimaging Open
Visualization of biomolecules in their native environment or imaging-aided understanding of more complex biomolecular processes are one of the focus areas of chemical biology research, which requires selective, often site-specific labeling…
Bioorthogonally Assisted Phototherapy: Recent Advances and Prospects Open
Photoresponsive materials offer excellent spatiotemporal control over biological processes and the emerging phototherapeutic methods are expected to have significant effects on targeted cancer therapies. Recent examples show that combinati…
Bioorthogonally Assisted Phototherapy: Recent Advances and Prospects Open
Photoresponsive materials offer excellent spatiotemporal control over biological processes and the emerging phototherapeutic methods are expected to have significant effects on targeted cancer therapies. Recent examples show that combinati…
Organic Anion Transporting Polypeptide 3A1 (OATP3A1)-Gated Bio-Orthogonal Labeling of Intracellular Proteins Open
Organic anion transporting polypeptides (OATPs) were found to readily deliver membrane impermeable, tetrazine bearing fluorescent probes into cells. This feature was explored in OATP3A1 conditioned bio-orthogonal labeling schemes of variou…
Turning Red without Feeling Embarrassed─Xanthenium-Based Photocages for Red-Light-Activated Phototherapeutics Open
Herein, we present high-yielding, concise access to a set of xanthenium-derived, water-soluble, low-molecular-weight photocages allowing light-controlled cargo release in the green to red region. Very importantly, these new photocages allo…
Evaluation of bioorthogonally applicable tetrazine–Cy3 probes for fluorogenic labeling schemes Open
Evaluation of tetrazine-modulated fluorogenic Cy3 probes revealed that internal conversion-based quenching of fluorescence results in better fluorogenic performances even in spectral ranges where tetrazines have diminished modulation power.
Cloning and characterization of a novel functional organic anion transporting polypeptide 3A1 isoform highly expressed in the human brain and testis Open
Organic anion transporting polypeptide 3A1 (OATP3A1, encoded by the SLCO3A1 gene) is a prostaglandin, oligopeptide, and steroid/thyroid hormone transporter with wide tissue distribution, expressed, e.g., in the human brain and testis. Alth…
Beyond the Bioorthogonal Inverse-Electron-Demand Diels–Alder Reactions of Tetrazines: 2-Pyrone-Functionalized Fluorogenic Probes Open
The applicability of pyrones as a bioorthogonal platform was explored in inverse-electron-demand Diels–Alder (IEDDA) reactions with a strained cyclooctyne. Studies showed that the pyrones are indeed suitable for IEDDA reactions under physi…
A Bioorthogonal Double Fluorogenic Probe to Visualize Protein–DNA Interaction Open
Two sets of bioorthogonally applicable, double fluorogenic probes, capable of sensing DNA–protein interactions, were prepared by installing an azide or tetrazine motif onto structurally fluorogenic, DNA sensitive frames. Installation of th…
Bioorthogonal Ligation‐Activated Fluorogenic FRET Dyads Open
An energy transfer‐based signal amplification relay concept enabling transmission of bioorthogonally activatable fluorogenicity of blue‐excitable coumarins to yellow/red emitting cyanine frames is presented. Such relay mechanism resulted i…
Bioorthogonal Ligation‐Activated Fluorogenic FRET Dyads Open
An energy transfer‐based signal amplification relay concept enabling transmission of bioorthogonally activatable fluorogenicity of blue‐excitable coumarins to yellow/red emitting cyanine frames is presented. Such relay mechanism resulted i…
Novel Approaches in Biomolecule Labeling Open
The selective functionalization of biomolecules such as proteins, nucleic acids, lipids or carbohydrates is a focus of persistent interest due to their widespread use, ranging from basic chemical biology research to gain insight into biolo…
A Genetically Encoded Isonitrile Lysine for Orthogonal Bioorthogonal Labeling Schemes Open
Bioorthogonal click-reactions represent ideal means for labeling biomolecules selectively and specifically with suitable small synthetic dyes. Genetic code expansion (GCE) technology enables efficient site-selective installation of bioorth…
Synergistic transport of a fluorescent coumarin probe marks coumarins as pharmacological modulators of Organic anion-transporting polypeptide, OATP3A1 Open
Organic anion-transporting polypeptide 3A1 (OATP3A1) is a membrane transporter mediating the cellular uptake of various hormones such as estrone-3-sulfate, prostaglandins E1 and E2 and thyroxine. OATP3A1 is widely expressed in the human bo…
Conditionally Activatable Visible-Light Photocages Open
The proof of concept for conditionally activatable photocages is demonstrated on a new vinyltetrazine-derivatized coumarin. The tetrazine form is disabled in terms of light-induced cargo release, however, bioorthogonal transformation of th…
A Bioorthogonally Applicable, Fluorogenic, Large Stokes-Shift Probe for Intracellular Super-Resolution Imaging of Proteins Open
Herein, we present the synthesis and application of a fluorogenic, large Stokes-shift (>100 nm), bioorthogonally conjugatable, membrane-permeable tetrazine probe, which can be excited at common laser line 488 nm and detected at around 600 …
Microscope laser assisted photooxidative activation of bioorthogonal ClickOx probes Open
A photoactivatable fluorogenic tetrazine-rhodaphenothiazine probe was synthesized and studied in light-assisted, bioorthogonal labeling schemes.
Bioothogonally applicable, π-extended rhodamines for super-resolution microscopy imaging for intracellular proteins Open
A set of new, bioorthogonally applicable tetrazine and polarity modulated double fluorogenic π-extended rhodamine probes were synthesized. Fluorogenicity and cell labeling experiments suggest that combination of the two quenching mechanism…
Green-Light Activatable, Water-Soluble Red-Shifted Coumarin Photocages Open
Easily accessible green-light activatable (>500 nm) photocages based on red-shifted, π-extended coumarin scaffolds are developed with uncaging efficiencies similar to those of recently introduced BODIPY derivatives. The photocages possess …
Copper-free dual labeling of DNA by triazines and cyclopropenes as minimal orthogonal <i>and</i> bioorthogonal functions Open
Two different and small functions for inverse electron demand Diels–Alder reactions were applied for dual labeling of DNA: the 1,2,4-triazine was attached to the 5-position of 2′-deoxyuridine, and the 1-methylcyclopropene to the 7-position…
Fluorogenic probes for super-resolution microscopy Open
Fluorogenic probes efficiently reduce non-specific background signals, which often results in highly improved signal-to-noise ratios.
Tracking down protein–protein interactions<i>via</i>a FRET-system using site-specific thiol-labeling Open
A novel Cys-specific bioorthogonalized linker was synthesized and applied in combination with bioorthogonally applicable fluorescent markers to track down protein–protein (p38-MK2) interactions by FRET.