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Synthesis and biological evaluation of bergenin-1,2,3-triazole hybrids as novel class of anti-mitotic agents
- Source :
- Bioorganic Chemistry. 91:103161
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- In continuation of our investigation of pharmacologically-motivated natural products, we have isolated bergenin (1) as a major compound from Mallotus philippensis, which is deployed in different Indian traditional systems of medicine. Here, a series of bergenin-1,2,3-triazole hybrids were synthesized and evaluated for their potentials against a panel of cancer cell lines. Several of the hybrid derivatives were found more potent in comparison to parent compound bergenin (1). Among them, 4j demonstrated potent activity against A-549 and HeLa cell lines with IC50 values of 1.86 µM and 1.33 μM, respectively, and was equipotent to doxorubicin. Cell cycle analysis showed that 4j arrested HeLa cells at G2/M phase and lead to accumulation of Cyclin B1 protein. Cell based tubulin polymerization assays and docking studies demonstrated that 4j disrupts tubulin assembly by occupying colchicine binding pocket of tubulin.
- Subjects :
- Mitosis
Antineoplastic Agents
Antimitotic Agents
01 natural sciences
Biochemistry
Polymerization
HeLa
Structure-Activity Relationship
chemistry.chemical_compound
Tubulin
Drug Discovery
medicine
Humans
Benzopyrans
Doxorubicin
Mallotus philippensis
Cyclin B1
Molecular Biology
Molecular Structure
biology
010405 organic chemistry
Chemistry
Organic Chemistry
Bergenin
Triazoles
biology.organism_classification
Tubulin Modulators
0104 chemical sciences
Molecular Docking Simulation
010404 medicinal & biomolecular chemistry
Chromones
Docking (molecular)
Cell culture
Drug Design
biology.protein
medicine.drug
Subjects
Details
- ISSN :
- 00452068
- Volume :
- 91
- Database :
- OpenAIRE
- Journal :
- Bioorganic Chemistry
- Accession number :
- edsair.doi.dedup.....0e0bdf56ad51d8b58719177394f22636