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3-O-Substituted-3',4',5'-trimethoxyflavonols: Synthesis and cell-based evaluation as anti-prostate cancer agents
- Source :
- Bioorganicmedicinal chemistry. 25(17)
- Publication Year :
- 2017
-
Abstract
- Twenty-two 3- O -substituted-3′,4′,5′-trimethoxyflavonols have been designed and synthesized for their anti-proliferative activity towards three human prostate cancer cell lines. Our results indicate that most of them are significantly more potent than the parent 3′,4′,5′-trimethoxyflavonol in inhibiting the cell proliferation in PC-3 and LNCaP prostate cancer cell models. 3- O -Substituted-3′,4′,5′-trimethoxyflavonols have generally higher potency towards PC-3 and LNCaP cell lines than the DU145 cell line. Incorporation of an ethyl group to 3-OH of 3′,4′,5′-trimethoxyflavonol leads to 3- O -ethyl-3′,4′,5′-trimethoxyflavonol as the optimal derivative with up to 36-fold enhanced potency as compared with the corresponding lead compound 3′,4′,5′-trimethoxyflavonol, but with reversed PC-3 cell apoptotic response. Introduction of a dipentylaminopropyl group to 3-OH increases not only the antiproliferative potency but also the ability in activating PC-3 cell apoptosis. Our findings imply that modification on 3-OH of trimethoxyflavonol can further enhance its in vitro anti-proliferative potency and PC-3 cell apoptosis induction.
- Subjects :
- 0301 basic medicine
Male
Flavonols
Clinical Biochemistry
Cell
Pharmaceutical Science
Antineoplastic Agents
Apoptosis
Biochemistry
Article
03 medical and health sciences
Structure-Activity Relationship
0302 clinical medicine
DU145
Cell Line, Tumor
Drug Discovery
LNCaP
medicine
Potency
Humans
Molecular Biology
Cell Proliferation
Cell growth
Chemistry
Organic Chemistry
Prostatic Neoplasms
Cell Cycle Checkpoints
Cell cycle
Cell biology
030104 developmental biology
medicine.anatomical_structure
Cell culture
030220 oncology & carcinogenesis
Cancer research
Molecular Medicine
Drug Screening Assays, Antitumor
Subjects
Details
- ISSN :
- 14643391
- Volume :
- 25
- Issue :
- 17
- Database :
- OpenAIRE
- Journal :
- Bioorganicmedicinal chemistry
- Accession number :
- edsair.doi.dedup.....11fc873852466bff30aea0862b015b6c