Bioactive (Co)oligoesters as Potential Delivery Systems of p-Anisic Acid for Cosmetic Purposes.

Magdalena Martinka Maksymiak,Grazyna Adamus,Arkadiusz Orchel,Marek Kowalczuk,Monika Musiał-Kulik,Magdalena Zięba

doi:10.3390/ma13184153

Abstract

This article reports the studies on bioactive (co)oligoesters towards their use as controlled delivery systems of p-anisic acid. The objects of the study were oligo[3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate], (p-AA-CH2-HP)n oligoester, and oligo[(3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate)-co-(3-hydroxybutyrate)] [(p-AA-CH2-HP)x-co-(HB)y (co)oligoesters containing p-anisic acid moiety (p-AA, as the bioactive end and side groups) connected to the polymer backbone through the susceptible to hydrolysis ester bonds. A thorough insight into the hydrolysis process of the bioactive (co)oligoesters studied has allowed us to determine the release profile of p-AA as well as to identify polymer carrier degradation products. The p-AA release profiles determined on the basis of high-performance liquid chromatography (HPLC) measurements showed that the release of the bioactive compound from the developed (co)oligoester systems was regular and no burst effect occurred. Biological studies demonstrated that studied (homo)- and (co)oligoesters were well tolerated by HaCaT cells because none of them showed notable cytotoxicity. They promoted keratinocyte growth at moderate concentrations. Bioactive (co)oligoesters containing p-anisic acid moiety had somewhat decreased cell proliferation at the highest concentration (100 µg/mL). The important practical inference of the current study is that the (co)oligoesters developed have a relatively large load of the biologically active substance (p-AA) per polymer macromolecule, which unlocks their potential application in the cosmetic industry.

Highlights

Natural antioxidants offer a host of benefits, especially for our health and general well-being, including anti-aging, anti-carcinogenic, anti-inflammatory, and anti-microbial properties, which promote a growing use in cosmetic products
We provided an overview of the approach for synthesizing bioactiveoligoesters on the basis of anionic homo- and co-polymerization of selected β-substituted β-lactones that contain bioactive species selectively chosen from compounds commonly used in cosmetic industry
We present a further extension study on bioactiveoligoesters that contain p-anisic acid moieties bound along oligomer chains

Summary

Introduction

Natural antioxidants offer a host of benefits, especially for our health and general well-being, including anti-aging, anti-carcinogenic, anti-inflammatory, and anti-microbial properties, which promote a growing use in cosmetic products. The antioxidant activities of natural antioxidants have been largely ascribed to the presence of phenolic content [1,2]. Antioxidants possess very strong preservative properties and they may prevent lipid oxidation in cosmetic products. Sunlight, air and vehicle pollution, and other environmental factors produce free radicals, which could be neutralized by antioxidants. The use of antioxidants in cosmetics aims to create a barrier that helps protect the skin against free radicals produced by oxidative stressors [3].

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