Synthesis of First Copper Metal Complex of C=C Extended Curcuminoid Analogue: Structure, β-Cyclodextrin Association, and Biological Properties
, , , , and Abstract
includes curcuminoids as promising scaffolds. Here, we report the synthesis of a family
of curcuminoid analogue compounds with an extended unsaturated central chain, as follows:
difluoroboron complex 1, the enolised curcuminoid 2, and its homoleptic copper
complex 3, in moderate to good yields (68–90%). Additionally, their β-cyclodextrin (BCD)
association complexes, 4 and 5, were prepared through a mechanochemical method and
characterised by spectroscopic techniques. Complete 1H and 13C NMR assignments and
NOESY correlations revealed unique solvent effects on the conformational disposition of
compound 2, while the copper complex 3 displayed the highest extinction coefficient (1.20
× 105 M−1·cm−1). Furthermore, the authentication of the polymorph of 1 and the new crystal
structures of 2 and 3, determined by single-crystal X-ray analysis, were highlighted. Although
the copper complex 3 initially exhibited the lowest a-glucosidase inhibitory activity
(IC50 > 100 μM), it showed a significant increase (IC50 = 36.27 μM) upon association with
BCD, reaching values comparable to the free ligand (IC50 = 45.63 μM). Compounds 1–5
were non-toxic to healthy cells (COS-7), but compound 5 stands out as a promising candidate
against this metabolic condition.
Share and Cite
Tavera-Hernández, R.; Sánchez-Obregón, R.; Obregón-Mendoza, M.A.; Nieto-Camacho, A.; Ramírez-Apan, M.T.; Pérez-González, L.L.; Enríquez, R.G. Synthesis of First Copper Metal Complex of C=C Extended Curcuminoid Analogue: Structure, β-Cyclodextrin Association, and Biological Properties. Molecules 2025, 30, 3943. https://doi.org/10.3390/molecules30193943
Tavera-Hernández R, Sánchez-Obregón R, Obregón-Mendoza MA, Nieto-Camacho A, Ramírez-Apan MT, Pérez-González LL, Enríquez RG. Synthesis of First Copper Metal Complex of C=C Extended Curcuminoid Analogue: Structure, β-Cyclodextrin Association, and Biological Properties. Molecules. 2025; 30(19):3943. https://doi.org/10.3390/molecules30193943
Chicago/Turabian StyleTavera-Hernández, Rosario, Rubén Sánchez-Obregón, Marco A. Obregón-Mendoza, Antonio Nieto-Camacho, María Teresa Ramírez-Apan, Leidys L. Pérez-González, and Raúl G. Enríquez. 2025. "Synthesis of First Copper Metal Complex of C=C Extended Curcuminoid Analogue: Structure, β-Cyclodextrin Association, and Biological Properties" Molecules 30, no. 19: 3943. https://doi.org/10.3390/molecules30193943
APA StyleTavera-Hernández, R., Sánchez-Obregón, R., Obregón-Mendoza, M. A., Nieto-Camacho, A., Ramírez-Apan, M. T., Pérez-González, L. L., & Enríquez, R. G. (2025). Synthesis of First Copper Metal Complex of C=C Extended Curcuminoid Analogue: Structure, β-Cyclodextrin Association, and Biological Properties. Molecules, 30(19), 3943. https://doi.org/10.3390/molecules30193943
