ArticleJournal of medicinal chemistry2014
Development and bioorthogonal activation of palladium-labile prodrugs of gemcitabine.
Article in Journal of medicinal chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 71 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
71 citing papers in PubMed, 198 citations in OpenAlex.
- Bioorthogonal Gold-Catalyzed Hydrothiolation Leading to Amide Bond Cleavage of Ethynylated Biarylbutanamide Precursors.Journal of the American Chemical Society · 2026Article
- Critical re-evaluation of experimental settings with fluorescent probes for bioorthogonal chemistry with palladium antimony inactivation-resistant catalyst.Scientific reports · 2026Article
- Insights into the activation patterns of 1,2-dithiolane unit in biofunctional molecules.Nature communications · 2026Article
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- Palladium-Catalyzed Tsuji-Trost-Type Reactions in Bioorthogonal Chemistry: From Test Tubes to Living Systems.Topics in current chemistry (Cham) · 2025Review
- Near-Infrared Light-Accelerated Bioorthogonal Drug Uncaging and Photothermal Ablation by Anisotropic Pd@Au Plasmonic Nanorods.Journal of the American Chemical Society · 2025Article
- Micellar "Click" Nanoreactors: Spiking Pluronic-Based Micelles with Polymeric Ligands.Macromolecules · 2024Article
- Tuning singlet oxygen generation with caged organic photosensitizers.Nature communications · 2024Article
- Development of Biocompatible Cu(I)-Microdevices for Bioorthogonal Uncaging and Click Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
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- Interplay of chloride levels and palladium(ii)-catalyzedChemical science · 2024Article
- Modular Fabrication of Bioorthogonal Nanozymes for Biomedical Applications.Advanced materials (Deerfield Beach, Fla.) · 2024Review
- Enhancing Tsuji-Trost deallylation in living cells with an internal-nucleophile coumarin-based probe.RSC advances · 2024Article
- Chemical Reactions in Living Systems.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Review
- Theoretical and experimental study on the photothermal effect of palladium nanoparticles based on a finite element model.Lasers in medical science · 2023Article
- A narrative review: progress in transition metal-mediated bioorthogonal catalysis for the treatment of solid tumors.Translational cancer research · 2023Review
- Expanding Transition Metal-Mediated Bioorthogonal Decaging to Include C-C Bond Cleavage Reactions.Journal of the American Chemical Society · 2023Article
- Article
- Ratiometric optical probes for biosensing.Theranostics · 2023Review
- Hydrogel-Encapsulated Heterogenous Mesoporous Resin Catalyst for In Situ Anti-Cancer Agent Production under Biological Conditions.Biomolecules · 2022Article
11 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
9 authors at 1 institution in 1 country.
Funding
Abstract
Bioorthogonal chemistry has become one of the main driving forces in current chemical biology, inspiring the search for novel biocompatible chemospecific reactions for the past decade. Alongside the well-established labeling strategies that originated the bioorthogonal paradigm, we have recently proposed the use of heterogeneous palladium chemistry and bioorthogonal Pd(0)-labile prodrugs to develop spatially targeted therapies. Herein, we report the generation of biologically inert precursors of cytotoxic gemcitabine by introducing Pd(0)-cleavable groups in positions that are mechanistically relevant for gemcitabine's pharmacological activity. Cell viability studies in pancreatic cancer cells showed that carbamate functionalization of the 4-amino group of gemcitabine significantly reduced (>23-fold) the prodrugs' cytotoxicity. The N-propargyloxycarbonyl (N-Poc) promoiety displayed the highest sensitivity to heterogeneous palladium catalysis under biocompatible conditions, with a reaction half-life of less than 6 h. Zebrafish studies with allyl, propargyl, and benzyl carbamate-protected rhodamines confirmed N-Poc as the most suitable masking group for implementing in vivo bioorthogonal organometallic chemistry.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.