ArticleJournal of the American Chemical Society2012
Azalysine analogues as probes for protein lysine deacetylation and demethylation.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 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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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
17 citing papers in PubMed, 51 citations in OpenAlex.
- Histone probes for reader and eraser investigations.Chemical science · 2025Review
- Mechanism-based inhibitors of SIRT2: structure-activity relationship, X-ray structures, target engagement, regulation of α-tubulin acetylation and inhibition of breast cancer cell migration.RSC chemical biology · 2021Article
- Mitochondria-targeted inhibitors of the human SIRT3 lysine deacetylase.RSC chemical biology · 2021Article
- Photo Cross-Linking Probes Containing ϵ-N-Thioacyllysine and ϵ-N-Acyl-(δ-aza)lysine Residues.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A one-step specific assay for continuous detection of sirtuin 2 activity.Acta pharmaceutica Sinica. B · 2019Article
- NRoyal Society open science · 2019Article
- Hydrazide Mimics for Protein Lysine Acylation To Assess Nucleosome Dynamics and Deubiquitinase Action.Journal of the American Chemical Society · 2018Article
- Mechanism-Based Inhibitors of the Human Sirtuin 5 Deacylase: Structure-Activity Relationship, Biostructural, and Kinetic Insight.Angewandte Chemie (International ed. in English) · 2017Article
- A Fluorescent Probe for Imaging Sirtuin Activity in Living Cells, Based on One-Step Cleavage of the Dabcyl Quencher.Chembiochem : a European journal of chemical biology · 2016Article
- Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3.Angewandte Chemie (International ed. in English) · 2016Article
- Chemical Methods for Encoding and Decoding of Posttranslational Modifications.Cell chemical biology · 2016Review
- Acetyl-CoA and the regulation of metabolism: mechanisms and consequences.Current opinion in cell biology · 2015Review
- Epigenetic pathway targets for the treatment of disease: accelerating progress in the development of pharmacological tools: IUPHAR Review 11.British journal of pharmacology · 2014Review
- A selective phenelzine analogue inhibitor of histone demethylase LSD1.ACS chemical biology · 2014Article
- Design of small molecule epigenetic modulators.Bioorganic & medicinal chemistry letters · 2014Review
- Small molecule epigenetic inhibitors targeted to histone lysine methyltransferases and demethylases.Quarterly reviews of biophysics · 2013Review
- Sirtuin catalysis and regulation.The Journal of biological chemistry · 2012Review
Corrections and comments
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Authors and funding
11 authors at 2 institutions in 1 country.
Funding
Abstract
Reversible lysine acetylation and methylation regulate the function of a wide variety of proteins, including histones. Here, we have synthesized azalysine-containing peptides in acetylated and unacetylated forms as chemical probes of the histone deacetylases (HDAC8, Sir2Tm, and SIRT1) and the histone demethylase, LSD1. We have shown that the acetyl-azalysine modification is a fairly efficient substrate for the sirtuins, but a weaker substrate for HDAC8, a classical HDAC. In addition to deacetylation by sirtuins, the acetyl-azalysine analogue generates a novel ADP-ribose adduct that was characterized by mass spectrometry, Western blot analysis, and nuclear magnetic resonance spectroscopy. This peptide-ADP-ribose adduct is proposed to correspond to a derailed reaction intermediate, providing unique evidence for the direct 2'-hydroxyl attack on the O-alkylimidate intermediate that is formed in the course of sirtuin catalyzed deacetylation. An unacetylated azalysine-containing H3 peptide proved to be a potent inhibitor of the LSD1 demethylase, forming an FAD adduct characteristic of previously reported related structures, providing a new chemical probe for mechanistic analysis.
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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.