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Fragment Molecular Orbital Method Applied to Lead Optimization of Novel Interleukin-2 Inducible T-Cell Kinase (ITK) Inhibitors.

Abstract：

:Inhibition of inducible T-cell kinase (ITK), a nonreceptor tyrosine kinase, may represent a novel treatment for allergic asthma. In our previous reports, we described the discovery of sulfonylpyridine (SAP), benzothiazole (BZT), indazole (IND), and tetrahydroindazole (THI) series as novel ITK inhibitors and how computational tools such as dihedral scans and docking were used to support this process. X-ray crystallography and modeling were applied to provide essential insight into ITK-ligand interactions. However, "visual inspection" traditionally used for the rationalization of protein-ligand affinity cannot always explain the full complexity of the molecular interactions. The fragment molecular orbital (FMO) quantum-mechanical (QM) method provides a complete list of the interactions formed between the ligand and protein that are often omitted from traditional structure-based descriptions. FMO methodology was successfully used as part of a rational structure-based drug design effort to improve the ITK potency of high-throughput screening hits, ultimately delivering ligands with potency in the subnanomolar range.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Heifetz A,Trani G,Aldeghi M,MacKinnon CH,McEwan PA,Brookfield FA,Chudyk EI,Bodkin M,Pei Z,Burch JD,Ortwine DF

doi

10.1021/acs.jmedchem.6b00045

subject

Has Abstract

pub_date

2016-05-12 00:00:00

pages

4352-63

issue

9

eissn

0022-2623

issn

1520-4804

journal_volume

59

pub_type

杂志文章

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