ArticleACS chemical biology2017
Halogen-π Interactions in the Cytochrome P450 Active Site: Structural Insights into Human CYP2B6 Substrate Selectivity.
Article in ACS chemical biology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 65 citations in OpenAlex.
- Exploring proteins and protein-ligand complexes through residue interaction networks.Nature protocols · 2026Review
- A QM-AI Approach for the Acceleration of Accurate Assessments of Halogen-π Interactions by Training Neural Networks.Journal of chemical information and modeling · 2025Article
- Impact of halogenation on scaffold toxicity assessed using HD-GEM machine learning model.Briefings in bioinformatics · 2025Article
- Comparison of QM Methods for the Evaluation of Halogen-π Interactions for Large-Scale Data Generation.Journal of chemical theory and computation · 2025Article
- Human Defensins: Structure, Function, and Potential as Therapeutic Antimicrobial Agents with Highlights Against SARS CoV-2.Probiotics and antimicrobial proteins · 2025Review
- Innovative Strategies and Methodologies in Antimicrobial Peptide Design.Journal of functional biomaterials · 2024Review
- Development of a high throughput cytochrome P450 ligand-binding assay.The Journal of biological chemistry · 2024Article
- RING 4.0: faster residue interaction networks with novel interaction types across over 35,000 different chemical structures.Nucleic acids research · 2024Article
- Facile Halogenation of Antimicrobial Peptides As Demonstrated by Producing Bromotryptophan-Labeled Nisin Variants with Enhanced Antimicrobial Activity.Journal of natural products · 2024Article
- Design methods for antimicrobial peptides with improved performance.Zoological research · 2023Review
- Bisphenols-A Threat to the Natural Environment.Materials (Basel, Switzerland) · 2023Review
- Optimizing metabolic stability of phosphodiesterase 5 inhibitors: Discovery of a potent N-(pyridin-3-ylmethyl)quinoline derivative targeting synaptic plasticity.Bioorganic & medicinal chemistry letters · 2023Article
- Enantio-Complementary Synthesis of 2-Substituted Pyrrolidines and Piperidines via Transaminase-Triggered Cyclizations.JACS Au · 2023Article
- Vapor Sorption and Halogen-Bond-Induced Solid-Form Rearrangement of a Porous Pharmaceutical.Crystal growth & design · 2023Article
- Four Decades of Cytochrome P450 2B Research: From Protein Adducts to Protein Structures and Beyond.Drug metabolism and disposition: the biological fate of chemicals · 2023Review
- New O- and N-N-Bridging Complexes of Tc(V), the Role of the Nitrogen Atom Position in Aromatic Rings: Reaction Mechanism, Spectroscopy, DTA, XRD and Hirshfeld Surface Analysis.International journal of molecular sciences · 2022Article
- Genetic and Biochemical Characterization of Halogenation and Drug Transportation Genes Encoded in the Albofungin Biosynthetic Gene Cluster.Applied and environmental microbiology · 2022Article
- Cytochrome P450 and P-gp Mediated Herb-Drug Interactions and Molecular Docking Studies of Garcinol.Membranes · 2021Article
- Natural and Synthetic Halogenated Amino Acids-Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics.Molecules (Basel, Switzerland) · 2021Review
- [Adsorption mechanism of typical monohydroxyphenanthrene on polyvinyl chloride microplastics].Se pu = Chinese journal of chromatography · 2021Article
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5 authors at 2 institutions in 1 country.
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Abstract
Numerous cytochrome P450 (CYP) 2B6 substrates including drugs and environmental chemicals are halogenated. To assess the role of halogen-π bonds in substrate selectivity and orientation in the active site, structures of four CYP2B6 monoterpenoid complexes were solved by X-ray crystallography. Bornyl bromide exhibited dual orientations in the active site with the predominant orientation revealing a bromine-π bond with the Phe108 side chain. Bornane demonstrated two orientations with equal occupancy; in both, the C2 atom that bears the bromine in bornyl bromide was displaced by more than 2.5 Å compared with the latter complex. The bromine in myrtenyl bromide π-bonded with Phe297 in CYP2B6, whereas the two major orientations in the active site mutant I114V exhibited bromine-π interactions with two additional residues, Phe108 and Phe115. Analysis of existing structures suggests that halogen-π interactions may be unique to the CYP2B enzymes within CYP family 2 but are also important for CYP3A enzymes.
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