Halogen bonds involved in binding of halogenated ligands by protein kinases

• Authors: Jarosław Poznański , Maria Winiewska , Honorata Czapinska , Anna Poznańska , David Shugar
• Languages of publication: EN

Abstracts

EN

Analysis of 664 known structures of protein kinase complexes with halogenated ligands revealed 424 short contacts between a halogen atom and a potential protein X-bond acceptor, the topology and geometry of which were analyzed according to the type of a halogen atom (X = Cl, Br, I) and a putative protein X-bond acceptor. Among 236 identified halogen bonds, the most represented ones are directed to backbone carbonyls of the hinge region and may replace the pattern of ATP-like hydrogen bonds. Some halogen-π interactions with either aromatic residues or peptide bonds, that accompany the interaction with the hinge region, may possibly enhance ligand selectivity. Interestingly, many of these halogen-π interactions are bifurcated. Geometrical preferences identify iodine as the strongest X-bond donor, less so bromine, while virtually no such preferences were observed for chlorine; and a backbone carbonyl as the strongest X-bond acceptor. The presence of a halogen atom in a ligand additionally affects the properties of proximal hydrogen bonds, which according to geometrical parameters get strengthened, when a nitrogen of a halogenated ligand acts as the hydrogen bond donor.

Keywords

EN

halogen bonding; protein kinase; ligand binding; PDB screening

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2016
• Volume: 63
• Issue: 2
• Pages: 203-214

Dates

published

2016

received

2015-07-15

revised

2016-02-11

accepted

2016-03-11

(unknown)

2016-04-20

Contributors

author

Jarosław Poznański

• Institute of Biochemistry and Biophysics PAS, Warszawa, Poland

author

Maria Winiewska

• Institute of Biochemistry and Biophysics PAS, Warszawa, Poland

author

Honorata Czapinska

• Institute of Biochemistry and Biophysics PAS, Warszawa, Poland
• International Institute of Molecular and Cell Biology, Warszawa, Poland

author

Anna Poznańska

• Department - Center of Population Health Monitoring and Analysis, National Institute of Public Health - National Institute of Hygiene, Warszawa, Poland

author

David Shugar

• Institute of Biochemistry and Biophysics PAS, Warszawa, Poland

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Identifiers

DOI

10.18388/abp.2015_1106