A New Family of Homoleptic Copper Complexes of Curcuminoids: Synthesis, Characterization and Biological Properties.

William Meza-Morales,Julia Cassani,Yair Alvarez-Ricardo,Marco Obregón-Mendoza,Juan Machado-Rodriguez,Rubén. Toscano,Manuel Soriano-García,Raúl Enríquez,Antonio Nieto-Camacho

doi:10.3390/molecules24050910

Abstract

We report herein the synthesis and crystal structures of five new homoleptic copper complexes of curcuminoids. The scarcity of reports of homoleptic complex structures of curcuminoids is attributed to the lack of crystallinity of such derivatives, and therefore, their characterization by single crystal X-ray diffraction is rare. The ligand design suppressing the phenolic interaction by esterification or etherification has afforded a significant increase in the number of known crystal structures of homoleptic metal complexes of curcuminoids revealing more favorable crystallinity. The crystal structures of the present new copper complexes show four-fold coordination with a square planar geometry. Two polymorphs were found for DiBncOC-Cu when crystallized from DMF. The characterization of these new complexes was carried out using infrared radiation (IR), nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and single crystal X-ray diffraction (SCXRD) and the antioxidant and cytotoxic activity of the obtained complexes was evaluated.

Highlights

Curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-diketone) is a metabolite of the Indian Curcuma species, generated by the rhizome of the perennial herb Curcuma longa, a member of the gingiberacea family widely cultivated in India and China [1]
The synthesis of 5 new homoleptic copper complexes was achieved with 5 different curcuminoid ligands, and their crystal structures reveal a four-fold coordination with square planar geometry
The copper ion did not increase the cytotoxic properties of the complexes with respect to free ligands but instead, high antioxidant activity for compounds

Summary

Introduction

Curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-diketone) is a metabolite of the Indian Curcuma species, generated by the rhizome of the perennial herb Curcuma longa, a member of the gingiberacea family widely cultivated in India and China [1]. Curcumin was isolated for the first time by Vogel and Pelletier more than two centuries ago, and Milobedzka and Lampe first proposed its chemical structure in 1910 [2,3]. This posed the fundamental interest that curcumin awoke gradually and expanded to other compounds that retain similar molecular topology and are denominated curcuminoids. Numerous studies have been performed to better understand the medicinal properties of curcumin, curcuminoids and their metal complexes, with purported antitumor, antimicrobial, anti-inflammatory, Molecules 2019, 24, 910; doi:10.3390/molecules24050910 www.mdpi.com/journal/molecules. Based on the wide medicinal applications reported in the literature for copper complexes, we tried to obtain copper complexes homoleptic structures andastoligands investigate their to biological

Methods

Results

Conclusion