ArticleEuropean journal of medicinal chemistry2016
O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1.
Article in European journal of medicinal chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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The trial behind it
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
19 citing papers in PubMed, 36 citations in OpenAlex.
- Design, Synthesis, and Antileishmanial Activity of Novel C6-Substituted Eugenol Derivatives with a Triazole Linker.ACS omega · 2026Article
- Modulating IDO1 and TDO Inhibition Through Structural Modification of Diaryl Hydroxylamines.ChemMedChem · 2026Article
- Article
- Hydroxamic Acid as a Potent Metal-Binding Group for Inhibiting Tyrosinase.Antioxidants (Basel, Switzerland) · 2022Article
- Sodium Tanshinone IIA Sulfonate as a Potent IDO1/TDO2 Dual Inhibitor Enhances Anti-PD1 Therapy for Colorectal Cancer in Mice.Frontiers in pharmacology · 2022Article
- Modulation of immune cell function, IDO expression and kynurenine production by the quorum sensor 2-heptyl-3-hydroxy-4-quinolone (PQS).Frontiers in immunology · 2022Article
- Design, synthesis and biological evaluation of erlotinib-based IDO1 inhibitors.Frontiers in pharmacology · 2022Article
- Novel 1,2,3-Triazole Erlotinib Derivatives as Potent IDO1 Inhibitors: Design, Drug-Target Interactions Prediction, Synthesis, Biological Evaluation, Molecular Docking and ADME Properties Studies.Frontiers in pharmacology · 2022Article
- Discovery and characterization of natural products as novel indoleamine 2,3-dioxygenase 1 inhibitors through high-throughput screening.Acta pharmacologica Sinica · 2020Article
- Discovery of Icotinib-1,2,3-Triazole Derivatives as IDO1 Inhibitors.Frontiers in pharmacology · 2020Article
- 4,5-Disubstituted 1,2,3-triazoles: Effective Inhibition of Indoleamine 2,3-Dioxygenase 1 Enzyme Regulates T cell Activity and Mitigates Tumor Growth.Scientific reports · 2019Article
- Recent advances in the discovery of indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors.MedChemComm · 2019Review
- Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase.European journal of medicinal chemistry · 2019Article
- Discovery of indoleamine 2,3-dioxygenase inhibitors using machine learning based virtual screening.MedChemComm · 2018Article
- Immune-modulating enzyme indoleamine 2,3-dioxygenase is effectively inhibited by targeting its apo-form.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Abnormal kynurenine pathway of tryptophan catabolism in cardiovascular diseases.Cellular and molecular life sciences : CMLS · 2017Review
- Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1.MedChemComm · 2017Article
- Fused Heterocyclic Compounds as Potent Indoleamine-2,3-dioxygenase 1 Inhibitors.ACS medicinal chemistry letters · 2016Article
- Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens.Marine drugs · 2016Article
Corrections and comments
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Authors and funding
12 authors at 4 institutions in 1 country.
Funding
Abstract
Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.
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Registered trials
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