Unknown

Dataset Information

0

Isolation of Nocuolin A and Synthesis of New Oxadiazine Derivatives. Design, Synthesis, Molecular Docking, Apoptotic Evaluation, and Cathepsin B Inhibition.

ABSTRACT: Nocuolin A (1), an oxadiazine, was isolated from the cyanobacterium Nostoc sp. Its chemical structure was elucidated using NMR and mass spectroscopic data. From this compound, two new oxadiazines, 3-[(6R)-5,6-dihydro-4,6-dipentyl-2H-1,2,3-oxadiazin-2-yl]-3-oxopropyl acetate (2) and 4-{3-[(6R)-5,6-dihydro-4,6-dipentyl-2H-1,2,3-oxadiazin-2-yl]-3-oxopropoxy}-4-oxobutanoic acid (3), were synthesised. The chemical structures of these two compounds were elucidated by a combination of NMR and MS analysis. Compound 3 showed cytotoxicity against the ACHN (0.73 ± 0.10 μM) and Hepa-1c1c7 (0.91 ± 0.08 μM) tumour cell lines. Similarly, compound 3 significantly decreased cathepsin B activity in ACHN and Hepa-1c1c7 tumour cell lines at concentrations of 1.52 ± 0.13 nM and 1.76 ± 0.24 nM, respectively. In addition, compound 3 showed no in vivo toxicity in a murine model treated with a dose of 4 mg/kg body weight.

SUBMITTER: Tena Perez V 

PROVIDER: S-EPMC10221466 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Isolation of Nocuolin A and Synthesis of New Oxadiazine Derivatives. Design, Synthesis, Molecular Docking, Apoptotic Evaluation, and Cathepsin B Inhibition.

Tena Pérez Víctor V   Apaza Ticona Luis L   H Cabanillas Alfredo A   Maderuelo Corral Santiago S   Rosero Valencia Diego Fernando DF   Martel Quintana Antera A   Ortega Domenech Montserrat M   Rumbero Sánchez Ángel Á  

Marine drugs 20230429 5

Nocuolin A (<b>1</b>), an oxadiazine, was isolated from the cyanobacterium <i>Nostoc</i> sp. Its chemical structure was elucidated using NMR and mass spectroscopic data. From this compound, two new oxadiazines, 3-[(6<i>R</i>)-5,6-dihydro-4,6-dipentyl-2<i>H</i>-1,2,3-oxadiazin-2-yl]-3-oxopropyl acetate (<b>2</b>) and 4-{3-[(6<i>R</i>)-5,6-dihydro-4,6-dipentyl-2<i>H</i>-1,2,3-oxadiazin-2-yl]-3-oxopropoxy}-4-oxobutanoic acid (<b>3</b>), were synthesised. The chemical structures of these two compoun  ...[more]

Similar Datasets

Unknown Benzimidazole-Based Derivatives as Apoptotic Antiproliferative Agents: Design, Synthesis, Docking, and Mechanistic Studies.
| S-EPMC10819888 | biostudies-literature
Unknown Synthesis of new oxadiazol-phthalazinone derivatives with anti-proliferative activity; molecular docking, pro-apoptotic, and enzyme inhibition profile.
| S-EPMC9048702 | biostudies-literature
Unknown Antiproliferative Effects of the Natural Oxadiazine Nocuolin A Are Associated With Impairment of Mitochondrial Oxidative Phosphorylation.
| S-EPMC6456697 | biostudies-literature
Unknown The Cyanobacterial Oxadiazine Nocuolin A Shows Broad-Spectrum Toxicity Against Protozoans and the Nematode C. elegans.
| S-EPMC11880066 | biostudies-literature
Unknown The cyanobacterial metabolite nocuolin a is a natural oxadiazine that triggers apoptosis in human cancer cells.
| S-EPMC5333925 | biostudies-literature
Unknown New quinoline and isatin derivatives as apoptotic VEGFR-2 inhibitors: design, synthesis, anti-proliferative activity, docking, ADMET, toxicity, and MD simulation studies.
| S-EPMC9387325 | biostudies-literature
Unknown Design, synthesis, characterization and computational docking studies of novel sulfonamide derivatives.
| S-EPMC5938533 | biostudies-literature
Unknown Exploration of the VEGFR-2 inhibition activity of phthalazine derivatives: design, synthesis, cytotoxicity, ADMET, molecular docking and dynamic simulation.
| S-EPMC11229888 | biostudies-literature
Unknown Novel 2-Thiouracil-5-Sulfonamide Derivatives: Design, Synthesis, Molecular Docking, and Biological Evaluation as Antioxidants with 15-LOX Inhibition.
| S-EPMC9963659 | biostudies-literature
Unknown Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives.
| S-EPMC6321598 | biostudies-literature