{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["14(33)"],"submitter":["Nagavath R"],"pubmed_abstract":["We present, for the first time, the organo-<i>N</i>-heterocyclic carbene (NHC) catalyzed 1,3-dipolar cycloaddition of 4β-<i>O</i>-propargyl podophyllotoxin (1) with <i>in situ</i> aromatic nitrile oxides to afford regioselective 4β-isoxazolepodophyllotoxin hybrids (6a-n) in benign aqueous-organic media. Preliminary anticancer activity results showed that compound 6e displayed superior activity against MCF-7, HeLa and MIA PaCa2 human cell lines compared with podophyllotoxin. Compounds 6j and 6n showed greater activity against the MCF-7 cell line than the positive control. Caspase activation studies revealed that compound 6e at 20 μg ml<sup>-1</sup> concentration had greater caspase 3/7 activation in MCF-7 and MIAPaCa2 cells than podophyllotoxin. Furthermore, <i>in vitro</i> tubulin polymerization inhibition studies revealed that compound 6e showed comparable activity with podophyllotoxin. Finally, <i>in silico</i> molecular docking studies of compounds 6e, 6j, 6n and podophyllotoxin on α,β-tubulin (pdb id 1SA0) revealed that compound 6n showed excellent binding energies and inhibition constants compared with podophyllotoxin."],"journal":["RSC advances"],"pagination":["23574-23582"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11276401"],"repository":["biostudies-literature"],"pubmed_title":["Organo NHC catalyzed aqueous synthesis of 4β-isoxazole-podophyllotoxins: <i>in vitro</i> anticancer, caspase activation, tubulin polymerization inhibition and molecular docking studies."],"pmcid":["PMC11276401"],"pubmed_authors":["Nagavath R","Thupurani MK","Badithapuram V","Manchal R","Vasam CS","Thirukovela NS"],"additional_accession":[]},"is_claimable":false,"name":"Organo NHC catalyzed aqueous synthesis of 4β-isoxazole-podophyllotoxins: <i>in vitro</i> anticancer, caspase activation, tubulin polymerization inhibition and molecular docking studies.","description":"We present, for the first time, the organo-<i>N</i>-heterocyclic carbene (NHC) catalyzed 1,3-dipolar cycloaddition of 4β-<i>O</i>-propargyl podophyllotoxin (1) with <i>in situ</i> aromatic nitrile oxides to afford regioselective 4β-isoxazolepodophyllotoxin hybrids (6a-n) in benign aqueous-organic media. Preliminary anticancer activity results showed that compound 6e displayed superior activity against MCF-7, HeLa and MIA PaCa2 human cell lines compared with podophyllotoxin. Compounds 6j and 6n showed greater activity against the MCF-7 cell line than the positive control. Caspase activation studies revealed that compound 6e at 20 μg ml<sup>-1</sup> concentration had greater caspase 3/7 activation in MCF-7 and MIAPaCa2 cells than podophyllotoxin. Furthermore, <i>in vitro</i> tubulin polymerization inhibition studies revealed that compound 6e showed comparable activity with podophyllotoxin. Finally, <i>in silico</i> molecular docking studies of compounds 6e, 6j, 6n and podophyllotoxin on α,β-tubulin (pdb id 1SA0) revealed that compound 6n showed excellent binding energies and inhibition constants compared with podophyllotoxin.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Jul","modification":"2026-06-02T23:12:11.484Z","creation":"2025-04-19T13:11:24.298Z"},"accession":"S-EPMC11276401","cross_references":{"pubmed":["39070249"],"doi":["10.1039/d4ra04297b"]}}