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Literature DB >> 19294721

Evidence for C-Cl/C-Br...pi interactions as an important contribution to protein-ligand binding affinity.

Hans Matter¹, Marc Nazaré, Stefan Güssregen, David W Will, Herman Schreuder, Armin Bauer, Matthias Urmann, Kurt Ritter, Michael Wagner, Volkmar Wehner.

Abstract

Attractive chlorine: Noncovalent interactions between chlorine or bromine atoms and aromatic rings in proteins open up a new method for the manipulation of molecular recognition. Substitution at distinct positions of two factor Xa inhibitors improves the free energy of binding by interaction with a tyrosine unit. The generality of this motif was underscored by multiple crystal structures as well as high-level quantum chemical calculations (see picture).

Entities: Chemical Gene

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Year: 2009 PMID： 19294721 DOI： 10.1002/anie.200806219

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

39 in total

1. A quantum mechanics-based halogen bonding scoring function for protein-ligand interactions.

Authors: Zhuo Yang; Yingtao Liu; Zhaoqiang Chen; Zhijian Xu; Jiye Shi; Kaixian Chen; Weiliang Zhu
Journal: J Mol Model Date: 2015-05-10 Impact factor: 1.810

2. Mapping the binding of GluN2B-selective N-methyl-D-aspartate receptor negative allosteric modulators.

Authors: Pieter B Burger; Hongjie Yuan; Erkan Karakas; Matthew Geballe; Hiro Furukawa; Dennis C Liotta; James P Snyder; Stephen F Traynelis
Journal: Mol Pharmacol Date: 2012-05-17 Impact factor: 4.436

3. Interplay between halogen bonds and hydrogen bonds in OH/SH···HOX···HY (X = Cl, Br; Y = F, Cl, Br) complexes.

Authors: Wenjie Wu; Yanli Zeng; Xiaoyan Li; Xueying Zhang; Shijun Zheng; Lingpeng Meng
Journal: J Mol Model Date: 2012-11-01 Impact factor: 1.810

4. Structural and biophysical characterization of human cytochromes P450 2B6 and 2A6 bound to volatile hydrocarbons: analysis and comparison.

Authors: Manish B Shah; P Ross Wilderman; Jingbao Liu; Hyun-Hee Jang; Qinghai Zhang; C David Stout; James R Halpert
Journal: Mol Pharmacol Date: 2015-01-13 Impact factor: 4.436

Evidence for C-Cl/C-Br...pi interactions as an important contribution to protein-ligand binding affinity.

1. A quantum mechanics-based halogen bonding scoring function for protein-ligand interactions.

2. Mapping the binding of GluN2B-selective N-methyl-D-aspartate receptor negative allosteric modulators.

3. Interplay between halogen bonds and hydrogen bonds in OH/SH···HOX···HY (X = Cl, Br; Y = F, Cl, Br) complexes.

4. Structural and biophysical characterization of human cytochromes P450 2B6 and 2A6 bound to volatile hydrocarbons: analysis and comparison.

5. Effect of external electric field on C-X ··· π halogen bonds.

6. Extending Halogen-based Medicinal Chemistry to Proteins: IODO-INSULIN AS A CASE STUDY.

7. Exploration of conformational transition in the aryl-binding site of human FXa using molecular dynamics simulations.

Review 8. Halogen bonding (X-bonding): a biological perspective.

9. A mammalian reductive deiodinase has broad power to dehalogenate chlorinated and brominated substrates.

Review 10. A medicinal chemist's guide to molecular interactions.