Design of dipicolinic acid derivatives as New Delhi metallo-β-lactamase-1 inhibitors using a combined computational approach

J Biomol Struct Dyn. 2020 Jul;38(11):3384-3395. doi: 10.1080/07391102.2019.1663262. Epub 2019 Sep 24.

Abstract

New Delhi metallo-β-lactamase (NDM-1) is the most recent addition to the class of metallo-β-lactamases (MBLs). This enzyme leads to antibiotic resistance in clinical treatments owing to its exertion of hydrolysis activity in almost all clinically available β-lactam antibiotics. Consequently, inhibitors targeting NDM-1 have attracted considerable research attention. However, progress has been slow regarding the study of the quantitative structure-activity relationship (QSAR) of NDM-1 inhibitors. In this study, a three-dimensional QSAR (3 D-QSAR) for NDM-1 inhibitors was established using Topomer CoMFA. The multiple correlation coefficients of the fitting model, leave-one-out cross validation, and external validation were found to be 0.761, 0.976, and 0.972, respectively. Topomer Search was used to design 16 new molecules that inhibit NDM-1 using R-group search from ZINC databases, 10 of which had comparatively high activities against NDM-1. The results indicate that Topomer CoMFA and Topomer Search can be used to design new NDM-1 inhibitors and guide the design of new NDM-1 drugs with good predictive capability. Furthermore, from molecular modeling and binding free-energy calculation, it was found that the newly designed molecules can bind to the catalytic region of NDM-1. Additionally, the newly designed inhibitors formed strong interactions with Ile35, Met67, Phe70, Trp93, His122, His189, Cys208, and His250 around the Zn2+-centered active region of NDM-1. These findings will facilitate the development of more effective NDM-1 inhibitors for use as potential antibacterial agents.Communicated by Ramaswamy H. Sarma.

Keywords: NDM-1; QSAR; dipicolinic acid; inhibitor.

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Picolinic Acids*
  • beta-Lactamase Inhibitors / pharmacology
  • beta-Lactamases*

Substances

  • Anti-Bacterial Agents
  • Picolinic Acids
  • beta-Lactamase Inhibitors
  • beta-Lactamases
  • beta-lactamase NDM-1
  • dipicolinic acid