Synthesis, characterization and anticancer activity of kaempferol-zinc(II) complex

Lv-Ying Tu; Jiang Pi; Hua Jin; Ji-Ye Cai; Sui-Ping Deng

doi:10.1016/j.bmcl.2016.03.091

Synthesis, characterization and anticancer activity of kaempferol-zinc(II) complex

Bioorg Med Chem Lett. 2016 Jun 1;26(11):2730-4. doi: 10.1016/j.bmcl.2016.03.091. Epub 2016 Mar 25.

Authors

Lv-Ying Tu¹, Jiang Pi², Hua Jin², Ji-Ye Cai³, Sui-Ping Deng⁴

Affiliations

¹ Department of Chemistry, Jinan University, Guangzhou 510632, PR China.
² State Key Laboratory of Quality Research in Chinese Medicines, Macau University of Science and Technology, Macau 000853, PR China.
³ Department of Chemistry, Jinan University, Guangzhou 510632, PR China; State Key Laboratory of Quality Research in Chinese Medicines, Macau University of Science and Technology, Macau 000853, PR China.
⁴ Department of Chemistry, Jinan University, Guangzhou 510632, PR China. Electronic address: tspdeng@jnu.edu.cn.

PMID: 27080177
DOI: 10.1016/j.bmcl.2016.03.091

Abstract

According to the previous studies, the anticancer activity of flavonoids could be enhanced when they are coordinated with transition metal ions. In this work, kaempferol-zinc(II) complex (kaempferol-Zn) was synthesized and its chemical properties were characterized by UV-VIS, FT-IR, (1)H NMR, elemental analysis, electrospray mass spectrometry (ES-MS) and fluorescence spectroscopy, which showed that the synthesized complex was coordinated with a Zn(II) ion via the 3-OH and 4-oxo groups. The anticancer effects of kaempferol-Zn and free kaempferol on human oesophageal cancer cell line (EC9706) were compared. MTT results demonstrated that the killing effect of kaempferol-Zn was two times higher than that of free kaempferol. Atomic force microscopy (AFM) showed the morphological and ultrastructural changes of cellular membrane induced by kaempferol-Zn at subcellular or nanometer level. Moreover, flow cytometric analysis indicated that kaempferol-Zn could induce apoptosis in EC9706 cells by regulating intracellular calcium ions. Collectively, all the data showed that kaempferol-Zn might be served as a kind of potential anticancer agent.

Keywords: Apoptosis; Atomic force microscopy; EC9706; Kaempferol-Zn; Spectroscopic analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Kaempferols / chemistry
Kaempferols / pharmacology*
Molecular Structure
Organometallic Compounds / chemical synthesis
Organometallic Compounds / chemistry
Organometallic Compounds / pharmacology*
Spectrometry, Fluorescence
Structure-Activity Relationship
Zinc / chemistry
Zinc / pharmacology*

Substances

Antineoplastic Agents
Kaempferols
Organometallic Compounds
kaempferol
Zinc