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J Med Chem. 2013 Feb 28;56(4):1363-88. doi: 10.1021/jm3012068. Epub 2013 Jan 3.

Principles and applications of halogen bonding in medicinal chemistry and chemical biology.

Author information

1
Laboratory for Molecular Design and Pharmaceutical Biophysics, Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, Eberhard Karls University, Tuebingen, Auf der Morgenstelle 8, 72076 Tuebingen, Germany.

Abstract

Halogen bonding has been known in material science for decades, but until recently, halogen bonds in protein-ligand interactions were largely the result of serendipitous discovery rather than rational design. In this Perspective, we provide insights into the phenomenon of halogen bonding, with special focus on its role in drug discovery. We summarize the theoretical background defining its strength and directionality, provide a systematic analysis of its occurrence and interaction geometries in protein-ligand complexes, and give recent examples where halogen bonding has been successfully harnessed for lead identification and optimization. In light of these data, we discuss the potential and limitations of exploiting halogen bonds for molecular recognition and rational drug design.

PMID:
23145854
DOI:
10.1021/jm3012068
[Indexed for MEDLINE]
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