ArticleJournal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry2014
Investigating the cellular fate of a DNA-targeted platinum-based anticancer agent by orthogonal double-click chemistry.
Article in Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Short-Chain and Long-Chain Fatty Acid-Containing Platinum-Acridine Anticancer Prodrugs: Exploiting Alternative Mechanisms of Cellular Internalization.Journal of medicinal chemistry · 2026Article
- Visualizing the Invisible: Dual Click Imaging of Ruthenium-Based Photoactivated Chemotherapy Agents and Their DNA Synthesis Inhibition in Fixed Cancer Cells.Journal of the American Chemical Society · 2025Article
- Novel Platinum(II) Tetrazine Complex Capable of Live-Cell IEDDA Reaction.Chembiochem : a European journal of chemical biology · 2025Article
- A clickable melphalan for monitoring DNA interstrand crosslink accumulation and detecting ICL repair defects in Fanconi anemia patient cells.Nucleic acids research · 2023Article
- Platinum-Acridine Agents with High Activity in Cancers Expressing the Solute Carrier MATE1 (ACS medicinal chemistry letters · 2023Article
- Regium-π Bonds Involving Nucleobases: Theoretical Study and Biological Implications.Inorganic chemistry · 2023Article
- Computational and Experimental Characterization of rDNA and rRNA G-Quadruplexes.The journal of physical chemistry. B · 2022Article
- DNA Adduct Detection after Post-Labeling Technique with PCR Amplification (DNA-ADAPT-qPCR) Identifies the Pre-ribosomal RNA Gene as a Direct Target of Platinum-Acridine Anticancer Agents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Discovery of a Chiral DNA-Targeted Platinum-Acridine Agent with Potent Enantioselective Anticancer Activity.Angewandte Chemie (International ed. in English) · 2020Article
- Exploiting azide-alkyne click chemistry in the synthesis, tracking and targeting of platinum anticancer complexes.Current opinion in chemical biology · 2020Review
- Chromatin Regulates Genome Targeting with Cisplatin.Angewandte Chemie (International ed. in English) · 2017Article
- Click Chemistry in the Development of Contrast Agents for Magnetic Resonance Imaging.Topics in magnetic resonance imaging : TMRI · 2016Review
- A clickable psoralen to directly quantify DNA interstrand crosslinking and repair.Bioorganic & medicinal chemistry · 2016Article
- Cellular Recognition and Repair of Monofunctional-Intercalative Platinum--DNA Adducts.Chemical research in toxicology · 2015Article
- Evaluation of fluorophore-tethered platinum complexes to monitor the fate of cisplatin analogs.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2015Article
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Authors and funding
5 authors.
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Abstract
Confocal fluorescence microscopy was used to study a platinum-based anticancer agent in intact NCI-H460 lung cancer cells. Orthogonal copper-catalyzed azide-alkyne cycloaddition (click) reactions were used to simultaneously determine the cell-cycle-specific localization of the azide-functionalized platinum-acridine agent 1 and monitor its effects on nucleic acid metabolism. Copper-catalyzed postlabeling showed advantages over copper-free click chemistry using a dibenzocyclooctyne (DIBO)-modified reporter dye, which produced high background levels in microscopic images and failed to efficiently label platinum adducts in chromatin. Compound 1 was successfully labeled with the fluorophore DIBO to yield 1* (characterized by in-line high-performance liquid chromatography/electrospray mass spectrometry). 1 and 1* show a high degree of colocalization in the confocal images, but the ability of 1* to target the (compacted) chromatin was markedly reduced, most likely owing to the steric bulk introduced by the DIBO tag. Nuclear platinum levels correlated inversely with the ability of the cells to synthesize DNA and cause cell cycle arrest, as confirmed by bivariate flow cytometry analysis. In addition, a decrease in the level of cellular transcription, shrinkage of the nucleolar regions, and redistribution of RNA into the cytosol were observed. Postlabeling in conjunction with colocalization experiments is a useful tool for studying the cell killing mechanism of this type of DNA-targeted agent.
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