Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism

  • Naik, Ravi; 
  • Ban, Hyun Seung; 
  • Jang, Kyusic; 
  • Kim, Inhyub; 
  • Xu, Xuezhen; 
  • ... Lee, Kyeong; 
  • 외 8명
Citations

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32
Citations

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초록

Previously, we reported a hypoxia-inducible factor (HIF)-l inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure?activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1 alpha accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.

키워드

FACTOR (HIF)-1-ALPHA INHIBITORS; HIF-1 INHIBITOR; ASPARTATE SHUTTLE; CHEMICAL PROBES; SMALL-MOLECULE; ACID ANALOGS; TUMOR-GROWTH; CELL-LINE; MORACIN O; HYPOXIA
제목
Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism
저자
Naik, Ravi; Ban, Hyun Seung; Jang, Kyusic; Kim, Inhyub; Xu, Xuezhen; Harmalkar, Dipesh; Shin, Seong-Ah; Kim, Minkyoung; Kim, Bo-Kyung; Park, Jaehyung; Ku, Bonsu; On, Sujin; Won, Misun; Lee, Kyeong
DOI
10.1021/acs.jmedchem.7b01231
발행일
2017-10-26
유형
Article
저널명
Journal of Medicinal Chemistry
권
60
호
20
페이지
8631 ~ 8646