Structure–activity relationship of 2-aminodibenzothiophene pharmacophore and the discovery of aminobenzothiophenes as potent inhibitors of Mycobacterium smegmatis

Alelaiwi, Sawsan H.; Heindl, Jason E.; Sivaganesh, Vignesh; Peethambaran, Bela; McKee, James R.

doi:10.1016/j.bmcl.2022.128650

Cited by 2 publications

(4 citation statements)

References 31 publications

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“…16,17 M. smegmatis can grows rapidly in the cell culture laboratories, possesses safety, non-pathogenic and eco-friendly properties. 18,19 M. smegmatis has the same cell architecture, physiology, and gene orthologs compara-ble to M. tuberculosis. Therefore, M. smegmatis have been widely used as a surrogate for M. tuberculosis.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, M. smegmatis have been widely used as a surrogate for M. tuberculosis. [18][19][20] The screening of S. wuyuanensis A79 demonstrated good activity against M. smegmatis. Following the bioguide result, compound 1 (indole-3-carboxylic acid) was isolated from the strain culture extract and structurally elucidated.…”

Section: Introductionmentioning

confidence: 99%

“…This bacteria does not live in mammals and not cause infection in humans 16,17 . M. smegmatis can grows rapidly in the cell culture laboratories, possesses safety, non‐pathogenic and eco‐friendly properties 18,19 . M. smegmatis has the same cell architecture, physiology, and gene orthologs comparable to M. tuberculosis .…”

Section: Introductionmentioning

confidence: 99%

“…M. smegmatis has the same cell architecture, physiology, and gene orthologs comparable to M. tuberculosis . Therefore, M. smegmatis have been widely used as a surrogate for M. tuberculosis 18–20 …”

Section: Introductionmentioning

confidence: 99%

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CLPC1 protein inhibition, antimycobacterial, and anti‐inflammatory properties of the metabolite from Streptomyces wuyuanensis collected in Nghe An province, Vietnam

Ni,

Ninh,

Dung

et al. 2024

Vietnam Journal of Chemistry

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Streptomyces wuyuanensis A79 was isolated from the soil samples collected in Quynh Luong mangrove forest, Quynh Luu district, Nghe An province, Vietnam. This strain demonstrated antimycobacterial activity against Mycobacterium smegmatis. Compound 1 (indole‐3‐carboxylic acid) was isolated from the culture extract of S. wuyuanensis (A79). This compound displayed the affection of ATPase activity of the recombinant ClpC1 protein, a regulatory protein of Mycobacterium tuberculosis. In addition, compound 1 exhibited anti‐inflammatory activity through the inhibition of TNF‐α on LPS‐stimulated macrophage RAW264.7. This is the first time compound 1 (indole‐3‐carboxylic acid) has been isolated from S. wuyuanensis. Indole‐3‐carboxylic acid was also reported for the first time its inhibition of M. tuberculosis ClpC1 protein.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

CLPC1 protein inhibition, antimycobacterial, and anti‐inflammatory properties of the metabolite from Streptomyces wuyuanensis collected in Nghe An province, Vietnam

Ni,

Ninh,

Dung

et al. 2024

Vietnam Journal of Chemistry

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Screening for Antimycobacterial Activity of Actinomycetes Collected in Vietnam – Isolation and Activity of Metabolites from Streptomyces alboniger (A121)

Huynh,

Pham,

Tran

et al. 2024

Natural Product Communications

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Objective Actinomycetes have been known to be the great natural sources to explore antibiotics for the treatment of tuberculosis (TB). The isolation of actinomycetes from the samples in Vietnam followed by the screening of their antimycobacterial activity was performed in this study. The metabolites isolated from the most active strain were further evaluated for their antimycobacterial, antimicrobial and cytotoxic activity. Methods Actinomycetes were growth in culture media, isolated and identified by colony, spore chain morphology and 16S rRNA gene sequencing. Agar diffusion assay was used for the screening of the isolated strains against Mycobacterium smegmatis, a safety surrogate for Mycobacterium tuberculosis. The metabolites produced from the most active strain were investigated by actinomycete fermentation, extraction and isolation from biomass and cultures. The structures of the isolated compound were elucidated by spectral data and comparison with the reported literatures. Results 181 strains were isolated from nine regions along the north to central Vietnam. The five most active strains against Mycobacterium smegmatis were detected. Following the bioassay-guided result, the strain A121 ( Streptomyces alboniger) was selected for further isolation of the bioactive metabolites. As a result, obscurolide B2β (1) and chartreusin (2) were obtained and evaluated for their antimycobacterial activity against M. smegmatis. Compound 2 displayed potential antimycobacterial activity, antimicrobial effect against the Gram positive bacteria Staphylococcus aureus, Bacillus subtilis, Lactobacillus fermentum and cytotoxicity against four cancer cell lines KB, HepG-2, Lu-1 and MCF-7. Conclusions Five strains possessing potential antimycobacterial activity were identified from the samples collected in Vietnam. Two compounds including obscurolide B2β (1) and chartreusin (2) were isolated from the most active strain A121 ( Streptomyces alboniger). This is the first time these compounds have been isolated from this strain. Chartreusin (2) exhibited notable antimycobacterial, antimicrobial and cytotoxic activity, making its worthy attention for further drug development, particularly for antituberculosis therapeutic agents.

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Structure–activity relationship of 2-aminodibenzothiophene pharmacophore and the discovery of aminobenzothiophenes as potent inhibitors of Mycobacterium smegmatis

Cited by 2 publications

References 31 publications

CLPC1 protein inhibition, antimycobacterial, and anti‐inflammatory properties of the metabolite from Streptomyces wuyuanensis collected in Nghe An province, Vietnam

CLPC1 protein inhibition, antimycobacterial, and anti‐inflammatory properties of the metabolite from Streptomyces wuyuanensis collected in Nghe An province, Vietnam

Screening for Antimycobacterial Activity of Actinomycetes Collected in Vietnam – Isolation and Activity of Metabolites from Streptomyces alboniger (A121)

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