ArticleACS medicinal chemistry letters2014
Predicting the reactivity of nitrile-carrying compounds with cysteine: a combined computational and experimental study.
Article in ACS medicinal chemistry letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 101 citations in OpenAlex.
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- Correlating Predicted Reactivities with Experimental Inhibition Data of Covalent ChlaDUB1 Inhibitors.ACS medicinal chemistry letters · 2024Article
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- Development of Novel Peptidyl Nitriles Targeting Rhodesain and Falcipain-2 for the Treatment of Sleeping Sickness and Malaria.International journal of molecular sciences · 2024Article
- 2-cyanopyridine derivatives enable N-terminal cysteine bioconjugation and peptide bond cleavage of glutathione under aqueous and mild conditions.RSC advances · 2024Article
- Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C-H Functionalization.ACS catalysis · 2024Article
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- Evaluation of the Drug-Induced Liver Injury Potential of Saxagliptin through Reactive Metabolite Identification in Rats.Pharmaceutics · 2024Article
- The Nitrile Bis-Thiol Bioconjugation Reaction.Journal of the American Chemical Society · 2024Article
- Targeted modification of furan-2-carboxaldehydes into Michael acceptor analogs yielded long-acting hemoglobin modulators with dual antisickling activities.Chemical biology & drug design · 2024Article
- Solid-Phase Compatible Silane-Based Cleavable Linker Enables Custom Isobaric Quantitative Chemoproteomics.Journal of the American Chemical Society · 2023Article
- Quantum Descriptors for Predicting and Understanding the Structure-Activity Relationships of Michael Acceptor Warheads.Journal of chemical information and modeling · 2023Article
- Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine.Bioconjugate chemistry · 2023Article
- Straightforward Creation of Possibly Prebiotic Complex Mixtures of Thiol-Rich Peptides.Life (Basel, Switzerland) · 2023Article
- Nitriles: an attractive approach to the development of covalent inhibitors.RSC medicinal chemistry · 2023Review
- Discovery of new symmetrical and asymmetrical nitrile-containing 1,4-dihydropyridine derivatives as dual kinases and P-glycoprotein inhibitors: synthesis,Journal of enzyme inhibition and medicinal chemistry · 2022Article
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Here, we report on a mechanistic investigation based on DFT calculations and kinetic measures aimed at determining the energetics related to the cysteine nucleophilic attack on nitrile-carrying compounds. Activation energies were found to correlate well with experimental kinetic measures of reactivity with cysteine in phosphate buffer. The agreement between computations and experiments points to this DFT-based approach as a tool for predicting both nitrile reactivity toward cysteines and the toxicity of nitriles as electrophile agents.
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Registered trials
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