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Semi-synthesis and in vitro anti-cancer effects evaluation of novel xanthohumol derivatives.
- Source :
-
Molecular diversity [Mol Divers] 2023 Dec 08. Date of Electronic Publication: 2023 Dec 08. - Publication Year :
- 2023
- Publisher :
- Ahead of Print
-
Abstract
- Xanthohumol (Xn) is a chalcone compound isolated from Humulus lupulus Linn., that has various biological activities. In this study, eight Xn derivatives were synthesized by Williamson, Mannich, Reimer-Tiemann, and Schiff base reactions, and evaluated for their in vitro cytotoxic activity against five human cancer cell lines (MDA-MB-231, MCF-7, CNE-2Z, SMMC-7721, and H1975). Among these compounds, 2-((E)-2,4-dihydroxy-5-((E)-3-(4-hydroxyphenyl)acryloyl)-6-methoxy-3-(3- methylbut-2-en-1-yl)benzylidene)hydrazine-1-carboximidamide (8) exhibited the most potent cytotoxic activity against the five cancer cells, with IC <subscript>50</subscript> values ranging from 4.87 to 14.35 µM. Wound-healing and transwell assays showed that compound 8 inhibited the migration and invasion of MDA-MB-231 cells by down-regulation HIF-1α, MMP-2 and MMP-9 protein expression. We further demonstrated that compound 8 induced apoptosis of MDA-MB-231 cells by increasing of Bax/Bcl-2 ratio and down-regulation of Akt protein expression.<br /> (© 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
Details
- Language :
- English
- ISSN :
- 1573-501X
- Database :
- MEDLINE
- Journal :
- Molecular diversity
- Publication Type :
- Academic Journal
- Accession number :
- 38064107
- Full Text :
- https://doi.org/10.1007/s11030-023-10706-7