Crescent-shaped meta-substituted benzene derivatives as a new class of non-nucleoside ribonuclease A inhibitors

Das, Ashrukana; Dasgupta, Swagata; Pathak, Tanmaya

doi:10.1016/j.bmc.2022.116888

Cited by 5 publications

(4 citation statements)

References 46 publications

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“…L929 cells in the logarithmic growth phase were inoculated in 96‐well plates at a density of 1.5 × 10 5 cells/mL. 24 h later, L929 cells were incubated with 2 ng/mL TNF‐ α , 1 μg/mL Actinomycin D, and compound 3 (40, 20, 10, 5, and 2.5 μmol/L) for 24 h. Cell viability was measured using the CCK‐8 kit (Cell counting kit‐8, MCE, Shanghai, China).…”

Section: Methodsmentioning

confidence: 99%

“…Psoriasis is an autoimmune chronic systemic disease and is considered to be the most common immune‐mediated disease significantly affecting the quality of life of nearly 3% of the general population worldwide which brings substantial burdens to individuals and society. [ 1‐5 ] Although the detailed pathogenesis of psoriasis is still unclear, it is generally accepted that the pathogenesis of psoriasis is stimulated by keratinocyte hyperproliferation and excessive inflammatory response. [ 6‐10 ] Previous studies have shown that multiple cytokines, such as interleukin (IL)‐17 and tumor necrosis factor‐alpha (TNF‐ α ) are involved in the pathogenesis of psoriasis vulgaris.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

Hu,

Li,

Shi

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryPsoriasis is a chronic immune‐mediated inflammatory skin disease and the TNF‐α is an important therapeutic target of this disease. In our continuous study of bioactive natural products from fungi, the first ergosterol‐polyether adducts, polyaspers A (1) and B (2), along with two known ergosterols, (3β,5α,6α,22E)‐5,6‐epoxy‐3‐hydroxyergosta‐8,22‐dien‐7‐one (3) and calvasterol B (4), were isolated from Aspergillus sp. TJ507. Structure elucidation was accomplished by extensive spectroscopic analysis and single‐crystal X‐ray diffraction tests. Polyaspers A and B possessing an unequalled 6/6/6/5/5/6/6/6/6 nonacyclic system, and their biosynthetic pathways were proposed to include intermolecular cyclization and Diels‐Alder reactions. Activity screen of these isolates showed that 1—3 could improve the cell viability in an actinomycin D/TNF‐α induced L929 cells death model, with the EC50 values of 49.85, 46.75 and 4.99 μmol/L, respectively, and the activity of 3 was even comparable with that of the positive control SPD304. Further bioactive investigations discovered 3 could suppress the inflammatory response simulated with TNF‐α in HaCaT cells. In an imiquimod‐induced psoriasis murine model, 3 significantly restrained the development of psoriasis symptoms and reduced the expression of IL‐17 and IL‐23, presenting an anti‐psoriatic effect. As such, those ergosterol derivatives, might serve as lead compounds for the development of novel TNF‐α inhibitory agents in the clinical treatment of psoriasis.

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Section: Methodsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

Hu,

Li,

Shi

et al. 2023

Chin. J. Chem.

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“…Leu27, Residue Cys145, and His41 formed bonds with the benzene structure from the ligand. The benzene ring of a com-pound significantly increases the inhibitory properties due to the bulkiness of the benzene structure, which allows for many bonds to occur with the amino acids of the target protein [40]. Jaspamide Q interacted with amino acid residues in the catalytic active site of 3CLpro (fig.…”

Section: -Dimension Visual Interaction (B) 3-dimension Visual Interac...mentioning

confidence: 99%

The Potential of Indonesian Marine Natural Product With Dual Targeting Activity Through Sars-Cov-2 3clpro and Plpro: An in Silico Studies

NAHIR,

PUTRA,

WIBOWO

et al. 2023

Int J App Pharm

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Objective: This research was conducted to find potential candidate compounds from one hundred thirty-seven Indonesian marine natural products capable of preventing SARS-CoV-2 with a computational approach. Methods: The physicochemical properties and Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) profile of compounds were predicted using ADMETLab. The candidate compounds were filtered using AutodockVina. Molecular docking was carried out using AutoDockTools on the SARS-CoV-2 3-Chymotrypsin-like protease (3CLpro) and Papain-like protease (PLpro) that is essential for the SARS-CoV-2 life cycle. Also, AMBER22 was used to perform molecular dynamics simulations in this study. Results: Based on molecular docking results, Pre-Neo-Kaluamine has good activity against 3CLpro with a bond energy value of-10.35 kcal/mol. Cortistatin F showed excellent binding activity on PLpro, with energy value results of-10.62 kcal/mol. Acanthomanzamine C has dual targeting activity and interacts well with protein 3CLpro and PLpro with binding energy values ranging from 10 kcal/mol to 14 kcal/mol. Conclusion: The molecular docking results were corroborated by molecular dynamics simulation results and showed good stability of the candidate ligands, and we found that there were three potential compounds as protease inhibitors of SARS-CoV-2 including Pre-Neo-Kaluamine for 3CLpro, Cortistatin F for PLpro, and Acanthomanzamine C which had dual targeting activity against both proteases.

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“…Compound 2.290 exhibited the highest inhibition efficiency with a Ki value of 12 ± 0.9 µM (Scheme 2.59). 77 Scheme 2.58 Scheme 2.59…”

Section: Author(s) Scheme 255mentioning

confidence: 99%

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

Pathak¹,

Pan²

2022

Arkivoc

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A typical 1,2,3-triazoles are important aromatic heterocyclic compounds with three adjacent nitrogen atoms. These "unnatural" heterocycles found applications in pharmaceutical science, material science and chemical biology. Oligo-1,2,3-triazole linked molecules showed interesting applications in the field of DNA binding, selfassembly, surface modification, supramolecular chemistry etc. In this article, oligo-1,2,3-triazoles are broadly classified into two categories: (i) 1,2,3-triazoles are connected through varieties of organic molecules and (ii) triazole units are connected with one another either by N-(CH)n-C linkages or by amide bonds generated from amino acids. Syntheses and properties of some of these oligomers are reviewed in this article.

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Crescent-shaped meta-substituted benzene derivatives as a new class of non-nucleoside ribonuclease A inhibitors

Cited by 5 publications

References 46 publications

Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

The Potential of Indonesian Marine Natural Product With Dual Targeting Activity Through Sars-Cov-2 3clpro and Plpro: An in Silico Studies

“Copper catalyzed azide alkyne cycloaddition” based synthesis and applications of oligo-1, 2, 3-triazoles connected by suitable building blocks and “N-(CH)n-C” linked triazole oligomers

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