Abstract

A new family of polyphenolic carbosilane dendrimers functionalized with ferulic, caffeic, and gallic acids has been obtained through a straightforward amidation reaction. Their antioxidant activity has been studied by different techniques such as DPPH (2,2′-diphenyl-1-picrylhydrazyl) radical scavenging assay, FRAP assay (ferric reducing antioxidant power), and cyclic voltammetry. The antioxidant analysis showed that polyphenolic dendrimers exhibited higher activities than free polyphenols in all cases. The first-generation dendrimer decorated with gallic acid stood out as the best antioxidant compound, displaying a correlation between the number of hydroxyl groups in the polyphenol structure and the antioxidant activity of the compounds. Moreover, the antibacterial capacity of these new systems has been screened against Gram-positive (+) and Gram-negative (−) bacteria, and we observed that polyphenolic dendrimers functionalized with caffeic and gallic acids were capable of decreasing bacterial growth. In contrast, ferulic carbosilane dendrimers and free polyphenols showed no effect, establishing a correlation between antioxidant activity and antibacterial capacity. Finally, a viability assay in human skin fibroblasts cells (HFF-1) allowed for corroborating the nontoxicity of the polyphenolic dendrimers at their active antibacterial concentration.

Highlights

  • The accumulation of free radicals caused by oxidative stress has been associated with the aging process as well as several age-related conditions [1]

  • A new family of carbosilane dendrimers functionalized with ferulic, caffeic, and gallic acids has been obtained through a simple and easy protocol based on amidation reactions

  • We observed that the use of the dendritic systems as anchorage platforms for polyphenolic compounds improved their antioxidant capacity, highlighting the first-generation dendrimer functionalized with gallic acid

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Summary

Introduction

The accumulation of free radicals caused by oxidative stress has been associated with the aging process as well as several age-related conditions (i.e., cardiovascular diseases, cancer, and degenerative diseases) [1]. Free radicals produce mutations in biological macromolecules (mainly DNA, lipids, and proteins) that cause structural cell damage [2]. Polyphenols could modulate the activity of different enzymes, and interfere with signaling mechanisms and different cellular processes. This behavior can be attributed to their physicochemical characteristics, which allow them to participate in different redox cellular metabolic reactions. The concept of bioavailability is significant, since they are generally poorly absorbed in the gut, highly metabolized, or rapidly excreted [4]. To overcome this drawback, nanotechnology has become a promising alternative

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