ArticleJournal of the American Chemical Society2016
Nitrodibenzofuran: A One- and Two-Photon Sensitive Protecting Group That Is Superior to Brominated Hydroxycoumarin for Thiol Caging in Peptides.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 73 citations in OpenAlex.
- Tunable Linkers for Dynamic Thiol-Based Bioconjugation Strategies.Biomacromolecules · 2026Review
- Generation of thiyl radicals in a spatiotemporal controlled manner by light: Applied for the cis to trans isomerization of unsaturated fatty acids/phospholipids.Redox biology · 2025Article
- Visible and near-infrared light-induced photoclick reactions.Nature reviews. Chemistry · 2024Review
- Genetically Encoded Lysine Analogues with Differential Light Sensitivity for Activation of Protein Function.ChemPhotoChem · 2024Article
- Phototriggered structures: Latest advances in biomedical applications.Acta pharmaceutica Sinica. B · 2023Review
- Dual photo-controlled release system for fipronil and dinotefuran.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2023Article
- Photoactivatable Fluorophores for Bioimaging Applications.ACS applied optical materials · 2023Article
- The Development and Application of Opto-Chemical Tools in the Zebrafish.Molecules (Basel, Switzerland) · 2022Review
- Directed cell migration towards softer environments.Nature materials · 2022Article
- Recent advances in nanomedicines for photodynamic therapy (PDT)-driven cancer immunotherapy.Theranostics · 2022Review
- Using photocaging for fast time-resolved structural biology studies.Acta crystallographica. Section D, Structural biology · 2021Review
- Photoclick Chemistry: A Bright Idea.Chemical reviews · 2021Review
- A Photolabile Carboxyl Protecting Group for Solid Phase Peptide Synthesis.ChemistryOpen · 2021Article
- Two-photon uncaging of bioactive thiols in live cells at wavelengths above 800 nm.Organic & biomolecular chemistry · 2021Article
- Selective Modification for Red-Shifted Excitability: A Small Change in Structure, a Huge Change in Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.Chemical reviews · 2020Article
- Light: A Magical Tool for Controlled Drug Delivery.Advanced functional materials · 2020Article
- Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.The Journal of organic chemistry · 2020Article
- Methoxy-Substituted Nitrodibenzofuran-Based Protecting Group with an Improved Two-Photon Action Cross-Section for Thiol Protection in Solid Phase Peptide Synthesis.The Journal of organic chemistry · 2020Article
- Photobodies: Light-Activatable Single-Domain Antibody Fragments.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Photoremovable protecting groups are important for a wide range of applications in peptide chemistry. Using Fmoc-Cys(Bhc-MOM)-OH, peptides containing a Bhc-protected cysteine residue can be easily prepared. However, such protected thiols can undergo isomerization to a dead-end product (a 4-methylcoumarin-3-yl thioether) upon photolysis. To circumvent that photoisomerization problem, we explored the use of nitrodibenzofuran (NDBF) for thiol protection by preparing cysteine-containing peptides where the thiol is masked with an NDBF group. This was accomplished by synthesizing Fmoc-Cys(NDBF)-OH and incorporating that residue into peptides by standard solid-phase peptide synthesis procedures. Irradiation with 365 nm light or two-photon excitation with 800 nm light resulted in efficient deprotection. To probe biological utility, thiol group uncaging was carried out using a peptide derived from the protein K-Ras4B to yield a sequence that is a known substrate for protein farnesyltransferase; irradiation of the NDBF-caged peptide in the presence of the enzyme resulted in the formation of the farnesylated product. Additionally, incubation of human ovarian carcinoma (SKOV3) cells with an NDBF-caged version of a farnesylated peptide followed by UV irradiation resulted in migration of the peptide from the cytosol/Golgi to the plasma membrane due to enzymatic palmitoylation. Overall, the high cleavage efficiency devoid of side reactions and significant two-photon cross-section of NDBF render it superior to Bhc for thiol group caging. This protecting group should be useful for a plethora of applications ranging from the development of light-activatable cysteine-containing peptides to the development of light-sensitive biomaterials.
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