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Comparative Study
. 2024 Sep 17;25(18):10010.
doi: 10.3390/ijms251810010.

Comparative Study of the Antioxidant Activity of the Conformers of C-tetra(4-methoxyphenyl)calix[4]resorcinarene

Laura Angélica Maldonado-Sanabria  1 , Ivette Nicole Rodriguez-Saavedra  1 , Ingrid Valentina Reyes-Peña  1 , Alver Castillo-Aguirre  1 , Mauricio Maldonado  1 , Almudena Crespo  2 , Miguel A Esteso  2   3
Affiliations
Comparative Study

Comparative Study of the Antioxidant Activity of the Conformers of C-tetra(4-methoxyphenyl)calix[4]resorcinarene

Laura Angélica Maldonado-Sanabria et al. Int J Mol Sci. .

Abstract

C-tetra(4-methoxyphenyl)calix[4]resorcinarene was synthesized by hydrochloric acid-catalysed cyclocondensation of resorcinol and 4-methoxybenzaldehyde. Under these conditions, the reaction produces a conformational mixture of crown and chair structural conformers, which were separated and characterized by chromatographic and spectroscopic techniques. The antioxidant activity of both conformers was measured by using the DPPH assay, through which it was observed that the chair conformer showed greater antioxidant activity (IC50 = 47.46 ppm) than the crown conformer (IC50 = 78.46 ppm). Additionally, it was observed that the mixture of both conformers presented lower antioxidant activity than either conformer in isolation. The results found suggest that the chair conformer has efficient antioxidant activity that makes it a potential target for further research.

Keywords: antioxidant activity; calix[4]resorcinarene; chair conformer; crown conformer.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Scheme 1
Scheme 1
Synthesis of C-tetra(4-methoxyphenyl)calix[4]resorcinarene, including the crown (1a) and chair (1b) conformers.
Figure 1
Figure 1
Chromatograms of the separation, via HPLC, of C-tetra(4-methoxyphenyl)calix[4]resorcinarene: (a) the conformational mixture, (b) the chair conformer and (c) the crown conformer.
Figure 2
Figure 2
1H-NMR C-tetra(4-methoxyphenyl)calix[4]resorcinarene: crown conformer (1a) and chair conformer (1b). Signals a, b and c (in red) correspond to protons a, b and c of the resorcinol residue.
Figure 3
Figure 3
DPPH free radical inhibition for 1:1 conformer mixture, individual C-tetra(4-methoxyphenyl)calix[4]resorcinarene conformers (chair and crown) and positive control (ascorbic acid).
Figure 4
Figure 4
Fa–CI plot of the conformational mixture to evaluate antagonism. The combination index (CI) values are represented on the y-axis and the affected fraction (Fa) on the x-axis.
Figure 5
Figure 5
Hydrogen bonding interactions for 1a (a), 1b (b) and the conformational mixture (c).
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