New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential
Ewa Janus,
Luan Ramalho Pinheiro,
Anna Nowak,
Edyta Kucharska,
Ewelina Świątek,
Natalia Podolak,
Magdalena Perużyńska,
Katarzyna Piotrowska,
Wiktoria Duchnik,
Łukasz Kucharski,
Adam Klimowicz
Affiliations
Ewa Janus
Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology in Szczecin, Pulaski Ave. 10, 70-322 Szczecin, Poland
Luan Ramalho Pinheiro
Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology in Szczecin, Pulaski Ave. 10, 70-322 Szczecin, Poland
Anna Nowak
Department of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Edyta Kucharska
Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology in Szczecin, Pulaski Ave. 10, 70-322 Szczecin, Poland
Ewelina Świątek
Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology in Szczecin, Pulaski Ave. 10, 70-322 Szczecin, Poland
Natalia Podolak
Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology in Szczecin, Pulaski Ave. 10, 70-322 Szczecin, Poland
Magdalena Perużyńska
Department of Experimental & Clinical Pharmacology, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Katarzyna Piotrowska
Department of Physiology, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Wiktoria Duchnik
Department of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Łukasz Kucharski
Department of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Adam Klimowicz
Department of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, Poland
Ferulic acid (FA) has been widely used in the pharmaceutical and cosmetics industry due to its, inter alia, antioxidant, antiaging and anti-inflammatory effects This compound added to cosmetic preparations can protect skin because of its photoprotective activity. However, the usefulness of FA as a therapeutic agent is limited due to its low solubility and bioavailability. The paper presents the synthesis, identification, and physicochemical properties of new FA derivatives with propyl esters of three amino acids, glycine (GPr[FA]), L-leucine (LPr[FA]), and L-proline (PPr[FA]). The NMR and FTIR spectroscopy, DSC, and TG analysis were used as analytical methods. Moreover, water solubility of the new conjugates was compared with the parent acid. Both ferulic acid and its conjugates were introduced into hydrogel and emulsion, and the resulting formulations were evaluated for stability. Additionally, in vitro penetration of all studied compounds from both formulations and for comparative purposes using Franz diffusion cells was evaluated from the solution in 70% (v/v) ethanol. Finally, cytotoxicity against murine fibroblasts L929 was tested. All of the analyzed compounds permeated pig skin and accumulated in it. LPr[FA] and PPr[FA] were characterized by much better permeability compared to the parent ferulic acid. Additionally, it was shown that all the analyzed derivatives are characterized by high antioxidant activity and lack of cytotoxicity. Therefore, they can be considered as an interesting alternative to be applied in dermatologic and cosmetic preparations.
