Synthesis of kaempferide Mannich base derivatives and their antiproliferative activity on three human cancer cell lines.

Abstract

Kaempferide (3,5,7-trihydroxy-4'-methoxyflavone, 1), a naturally occurring flavonoid with potent anticancer activity in a number of human tumour cell lines, was first semisynthesized from naringin. Based on Mannich reaction of kaempferide with various secondary amines and formaldehyde, nine novel kaempferide Mannich base derivatives 2-10 were synthesized. The aminomethylation occurred preferentially in the position at C-6 and C-8 of the A-ring of kaempferide. All the synthetic compounds were tested for antiproliferative activity against three human cancer cell lines (Hela, HCC1954, SK-OV-3) by the standard MTT method. The results showed that compounds 1, 2 and 5-10 were more potent against Hela cells with IC50 values of 12.47-28.24 μM than the positive control cis-platin (IC50 41.25 μM), compounds 5, 6, 8 and 10 were more potent against HCC1954 cells with IC50 values of 8.82-14.97 μM than the positive control cis-platin (IC50 29.68 μM), and compounds 2, 3, 5, 6 and 10 were more potent against SK-OV-3 cells with IC50 values of 7.67-18.50 μM than the positive control cis-platin (IC50 21.27 μM).

• Authors: Van-Son Nguyen, Ling Shi, Fang-Qian Luan, Qiu-An Wang
• Journal: Acta biochimica Polonica (Acta Biochim Pol) Vol. 62 Issue 3 Pg. 547-52 ( 2015) ISSN: 1734-154X [Electronic] Poland
• PMID: 26345098 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Kaempferols
• Mannich Bases
• kaempferide
• Cisplatin

Topics

• Antineoplastic Agents (chemistry)
• Breast Neoplasms (pathology)
• Cell Line, Tumor (drug effects)
• Cell Proliferation
• Cisplatin (chemistry)
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor (methods)
• Female
• HeLa Cells
• Humans
• Inhibitory Concentration 50
• Kaempferols (chemical synthesis, pharmacology)
• Mannich Bases (chemistry)
• Models, Chemical
• Ovarian Neoplasms (pathology)
• Temperature
• Uterine Cervical Neoplasms (pathology)