The DOI matches its Crossref record; 48 of the 48 references it cites were found in a registry or an index.
Trace derivatives of kynurenine potently activate the aryl hydrocarbon receptor (AHR)
Open accessAbstract
Cellular metabolites act as important signaling cues, but are subject to complex unknown chemistry. Kynurenine is a tryptophan metabolite that plays a crucial role in cancer and the immune system. Despite its atypical, non-ligand-like, highly polar structure, kynurenine activates the aryl hydrocarbon receptor (AHR), a PER, ARNT, SIM (PAS) family transcription factor that responds to diverse environmental and cellular ligands. The activity of kynurenine is increased 100-1000-fold by incubation or long-term storage and relies on the hydrophobic ligand-binding pocket of AHR, with identical structural signatures for AHR induction before and after activation. We purified trace-active derivatives of kynurenine and identified two novel, closely related condensation products, named trace-extended aromatic condensation products (TEACOPs), which are active at low picomolar levels. The synthesized compound for one of the predicted structures matched the purified compound in both chemical structure and AHR pharmacology. Our study provides evidence that kynurenine acts as an AHR pro-ligand, which requires novel chemical conversions to act as a receptor agonist.
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“On the basis of these novel approaches, recent docking studies not only allowed prediction of the binding modes of several AhR ligands but also led to the discovery of novel AhR agonists and SAhRMs25,27–30.”
From Modeling the binding of diverse ligands within the Ah receptor ligand binding domain (2019) · cites this paper as [29]
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“They may rather function as “pro-ligands” through further conversion to “real” AHR ligands with much higher binding potencies, as exemplified by kynurenine and its trace derivatives52.”
From Structural basis for the ligand-dependent activation of heterodimeric AHR-ARNT complex (2025) · cites this paper as [52]
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Citations
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“As observed previously (14), kynurenine induces a maximum AHR activation that is 40% higher than that induced by FICZ (Fig.”
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“with diverse shape and chemical properties have been reported to bind AHR (28, 29).”
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“Kynurenine (Kyn), along with its metabolites 3-HAA, KA, and L-Kyn, acts as an agonist of the Aryl hydrocarbon receptor (AhR) (Mellor et al., 2017; Seok et al., 2018), a cytoplasmic transcription factor that promotes the activation of Src kinase family members.”
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“Kyn derivatives can potently activate the aryl hydrocarbon receptor, leading to immunosuppression [52].”
Aryl Hydrocarbon Receptor, a Critical Interface between Host Immunity and Microbiota
Rehman, A., & Koh, Y.-S. (2025) · Journal of Bacteriology and Virology · doi:10.4167/jbv.2025.55.4.298 · Cited by 3
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“When kynurenine activates AhR, it translocates to the nucleus (Seok et al. 2018).”
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“Being mostly studied in murine model so far, we concentrated our study in human T cells that have yet to be characterized, using the CRISPR-Cas tool.”
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“Kyn is a key mediator in the Trp-AhR pathway mentioned in the above article, where tryptophan is catalyzed by IDO/TDO to produce Kyn, which undergoes a related enzymatic reaction that produces derivatives and thus acts on the aryl hydrocarbon receptor (AhR) ( Seok et al., 2018 ).”
The aryl hydrocarbon receptor: A modulator of skeletal muscle health and aging
Wimberly, K., & RYAN, T. E. (2025) · Biochimie · doi:10.1016/j.biochi.2025.12.012 · Cited by 2
Commensal bacteria inhibit viral infections via a tryptophan metabolite
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“Although kynurenine does not have direct AhR binding activity, it is an AhR pro-ligand that requires chemical conversions to act as an AhR agonist 74 .”
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InfluentialPositive feedback loop via HIF-1α lactylation driven by kynurenine promotes glycolysis
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“Dysregulation of the host kynurenine pathway, which also produces AHR agonists (Dinatale et al. 2010; Seok et al. 2018; Vyhlídalová et al. 2020), may also be important in pathophysiology of ME/CFS (Anderson et al. 2012; Morris et al. 2016; Kashi et al. 2019; Ormstad et al. 2020; Dehhaghi et al.…”
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“Furthermore, Cheng et al. demonstrated that in sepsis-associated acute thymic atrophy, activation of the IDO1/Kyn/AHR signaling axis induces mitochondrial damage and lipid peroxidation, thereby promoting ferroptosis and leading to substantial thymocyte loss (108).”
InfluentialZhang, J., Tang, Z., Wang, Y., Wan, J., Zhou, Y., Li, J., & Ming, J. (2026) · Cells · doi:10.3390/cells15151422 · Cited by 1
“Kynurenine acts as a high-affinity endogenous ligand for the aryl hydrocarbon receptor (AhR), thereby orchestrating broad immunosuppressive programs within the TME [123].”
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“The assumption that kynurenine itself is the operative AHR ligand has also been challenged: in vitro kynurenine preparations may activate AHR primarily through trace condensation derivatives rather than through the parent molecule, with kynurenine acting as a pro-ligand [114].”
Madella, A. M., van Gerven, C. C. E., Garví, E. S., van Bergenhenegouwen, J., Garssen, J., Masereeuw, R., & Overbeek, S. A. (2026) · Toxins · doi:10.3390/toxins18100451
“These findings suggest that, in this acute in vitro model, UTs may act as relatively weak AhR agonists, or that additional cofactors, stress signals, or longer exposures may be required for robust transcriptional responses [29,30].”
Emerging links between gut dysbiosis, aryl hydrocarbon receptor activation, and Parkinson’s disease
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Metadata
- Authors
- Seok, S.-H., Ma, Z.-X., Feltenberger, J. B., Chen, H., Chen, H., Scarlett, C., Lin, Z., Satyshur, K. A., Cortopassi, M., Jefcoate, C. R., Ge, Y., Tang, W., Bradfield, C. A., & Xing, Y.
- Affiliations
- University of Wisconsin–Madison (US)
- Corresponding author
- Xing, Yongna
- ORCID
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2018-02
- Volume
- 293
- Issue
- 6
- Pages
- 1994-2005
- ISSN
- 0021-9258 (ISSN-L)
- PMC
- PMC5808761
- OpenAlex
- W2779643604
- Cited by
- 157
- References
- 48
- Citations by year
- 2026: 15 · 2025: 27 · 2024: 16 · 2023: 19 · 2022: 16 · 2021: 16 · 2020: 22 · 2019: 16 · 2018: 10
- FWCI
- 4.37
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- DH National Institute for Health Research (NIHR) (R01 GM096060, R35028377)
- Topics
- Life Sciences › Neuroscience › Biological Psychiatry › Tryptophan and brain disorders
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Keywords
- kynurenine, aryl hydrocarbon receptor, tryptophan metabolism, AhR activation, binding pocket, condensation products, transcription factor activation
- MeSH terms
- Animals, Binding Sites, Kinetics, Kynurenine, Ligands, Molecular Structure, Receptors, Aryl Hydrocarbon, Mice
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