In vitro toxicity and in silico docking analysis of two novel selective AH-receptor modulators
Open accessAbstract
The mediator of dioxin toxicity, aryl hydrocarbon receptor (AHR), has also important physiological functions. Selective AHR modulators (SAHRMs) share some effects of dioxins, except for their marked toxicity. We recently characterised toxicologically two novel SAHRMs, prodrugs IMA-08401 and IMA-07101 in rats, demonstrating that they are far less deleterious than the most toxic AHR-agonist, TCDD. Here, we analysed the in vitro toxicity and in silico AHR binding of the respective active, deacetylated metabolites, IMA-06201 (N-ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide) and IMA-06504 (N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide). In H4IIE rat hepatoma cells, IMA-06201 and IMA-06504 induced CYP1A1 with comparable potencies and efficacies to those of TCDD. They had little effect on cell viability as assessed by LDH leakage and MTT reduction assays, and were not mutagenic in the Ames test, but IMA-06504 elicited a maximally 2.7-fold increase in micronuclei. Molecular docking simulations showed that similar to TCDD, they occupy the central region of AHR ligand binding cavity. Hence, while showing low to negligible in vitro toxicity, these novel SAHRMs bind to the AHR qualitatively in a similar fashion to TCDD, and appear comparably powerful AHR agonists. Combined with our earlier results demonstrating that they seem considerably less toxic in vivo than TCDD, these compounds are thus highly interesting new SAHRMs.
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Recent docking studies allowed prediction of the binding modes of several AhR ligands and led to the discovery of novel AhR agonists and SAhRMs.
“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 [30]
The Discussion (section 4; page unavailable) says docking predicted the binding geometries and protein–ligand interactions of two novel SAHRM metabolites. The Abstract says the compounds had been characterized previously, while this study analyzed their binding; it does not show that docking led to their discovery. The paper therefore supports the binding-mode part, but not the claimed discovery by docking. (LLM, conf=0.86)
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Sadhu, S. P., Yarla, N. S., Pragada, R. R., & Konduri, P. (2021) · Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry · doi:10.2174/1871523021666220330143058 · Cited by 1 · see citing works
Ciência da Saúde na Amazônia Ocidental
Meneguetti, D. U. D. O., & Silva, R. P. M. (2019) · Stricto Sensu Editora eBooks · doi:10.35170/ss.ed.9786580261062
Vimala, T. (2022) · International Journal of Zoological Investigations · doi:10.33745/ijzi.2022.v08i02.062
- Authors
- Mahiout, S., Tagliabue, S. G., Nasri, A., Omoruyi, I. M., Pettersson, L., Bonati, L., & Pohjanvirta, R.
- Affiliations
- University of Helsinki (FI)
- University of Milano-Bicocca (IT)
- Corresponding author
- Pohjanvirta, Raimo
- ORCID
- Venue
- Toxicology in Vitro
- Publisher
- Elsevier BV
- Published
- 2018-10
- Volume
- 52
- Pages
- 178-188
- ISSN
- 0887-2333 (ISSN-L)
- OpenAlex
- W2808466150
- Cited by
- 19
- References
- 83
- Citations by year
- 2024: 2 · 2023: 1 · 2022: 4 · 2021: 5 · 2020: 2 · 2019: 5
- FWCI
- 1.60
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Locations
- Toxicology in Vitro (publishedVersion, cc-by)
- PubMed (publishedVersion)
- BOA (University of Milano-Bicocca) (submittedVersion)
- Työväentutkimus Vuosikirja (submittedVersion)
- Greater South Information System
- Funders
- Academy of Finland (Grant no. 261232)
- University of Helsinki Doctoral Programme in Food Chain and Health
- Topics
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Keywords
- aryl hydrocarbon receptor, TCDD, dioxin toxicity, CYP1A1 induction, hepatotoxicity, genotoxicity, micronuclei, molecular docking, quinoline derivatives, prodrugs
- MeSH terms
- Animals, Cell Survival, Mutagenicity Tests, Quinolines, Receptors, Aryl Hydrocarbon, Cytochrome P-450 CYP1A1, Cell Line, Tumor, Rats, Molecular Docking Simulation
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