Design, synthesis, biological evaluation study of spirocyclic POM analogues as novel MmpL3 anti-tubercular agent

We present the development of a phenyl oxazole methyl (POM) core structure with spirocyclic derivatives as part of our efforts to discover innovative anti-tuberculosis agents. Derivatives of spirocyclic POM were synthesized and evaluated for their inhibitory effects on M.tuberculosis (M. tb) H37Rv. Notably, compound 5c displayed potent anti-tubercular activity with MIC value of 0.206 μM in culture broth medium. Furthermore MIC values of compound 5c against DS/MDR/pre-XDR clinical isolates ranged from 0.34 to 0.68 μg/mL, 0.17 to 0.68 μg/mL, and 0.17 to 0.34 μg/mL, respectively. Also, compound 5c with favorable ADME and PK properties was not cytotoxic to THP-1 human cells. Based on the spontaneous mutant generation, we have identified the target of compound 5c to be MmpL3. The computational docking study suggested its plausible binding mode against MmpL3. There is no approved drug targeting this target yet, and the outcomes of the presented research will contribute to the future discovery of novel anti-tuberculosis drugs.

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Publication Details

Journal
Bioorganic Chemistry
Published
2024-09-14
DOI
https://doi.org/10.1016/j.bioorg.2024.107823
Citations
5
Primary Topic
Tuberculosis Research and Epidemiology
Type
article
Field-Weighted Citation Impact
1.95

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article

Design, synthesis, biological evaluation study of spirocyclic POM analogues as novel MmpL3 anti-tubercular agent

Jong Seok Lee, S.‐B. PARK, Kyungjong Kim, Seorin Bang et al.
5 citations
Bioorganic Chemistry
Tuberculosis Research and Epidemiology
1.95
article

Design, synthesis, biological evaluation study of spirocyclic POM analogues as novel MmpL3 anti-tubercular agent

Jong Seok Lee, S.‐B. PARK, Kyungjong Kim, Seorin Bang, Yumi Park, Jake Whang, Minji Kang, Lianji Cui, Inhee Choi, Young Mi Kim, Aram Lee, Jeong Seong Yang, Ji Eun Ahn, Mi Ji Jeong, Eun Soon Son
article en
5 citations

Abstract

We present the development of a phenyl oxazole methyl (POM) core structure with spirocyclic derivatives as part of our efforts to discover innovative anti-tuberculosis agents. Derivatives of spirocyclic POM were synthesized and evaluated for their inhibitory effects on M.tuberculosis (M. tb) H37Rv. Notably, compound 5c displayed potent anti-tubercular activity with MIC value of 0.206 μM in culture broth medium. Furthermore MIC values of compound 5c against DS/MDR/pre-XDR clinical isolates ranged from 0.34 to 0.68 μg/mL, 0.17 to 0.68 μg/mL, and 0.17 to 0.34 μg/mL, respectively. Also, compound 5c with favorable ADME and PK properties was not cytotoxic to THP-1 human cells. Based on the spontaneous mutant generation, we have identified the target of compound 5c to be MmpL3. The computational docking study suggested its plausible binding mode against MmpL3. There is no approved drug targeting this target yet, and the outcomes of the presented research will contribute to the future discovery of novel anti-tuberculosis drugs.

Bioorganic ChemistryVol. 153
Institut Pasteur Korea (KR), International Tuberculosis Research Center (KR), Korea National Tuberculosis Association (KR)
Ministry of Science, ICT and Future Planning, Ministry of Health and Welfare, Korea Health Industry Development Institute, National Research Foundation of Korea, Ministry of Science and ICT, South Korea
Zero hunger
Openalex Percentile: Top 14%
Tuberculosis Research and Epidemiology
1.95
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