New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential
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 t...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-12-01
|
| Series: | Pharmaceutics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1999-4923/15/1/117 |
| _version_ | 1797437865268871168 |
|---|---|
| author | Ewa Janus Luan Ramalho Pinheiro Anna Nowak Edyta Kucharska Ewelina Świątek Natalia Podolak Magdalena Perużyńska Katarzyna Piotrowska Wiktoria Duchnik Łukasz Kucharski Adam Klimowicz |
| author_facet | Ewa Janus Luan Ramalho Pinheiro Anna Nowak Edyta Kucharska Ewelina Świątek Natalia Podolak Magdalena Perużyńska Katarzyna Piotrowska Wiktoria Duchnik Łukasz Kucharski Adam Klimowicz |
| author_sort | Ewa Janus |
| collection | DOAJ |
| description | 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% (<i>v</i>/<i>v</i>) 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. |
| first_indexed | 2024-03-09T11:27:52Z |
| format | Article |
| id | doaj.art-c25220a7832344e9aedaad0c88ddf9c6 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-09T11:27:52Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-c25220a7832344e9aedaad0c88ddf9c62023-11-30T23:57:54ZengMDPI AGPharmaceutics1999-49232022-12-0115111710.3390/pharmaceutics15010117New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical PotentialEwa Janus0Luan Ramalho Pinheiro1Anna Nowak2Edyta Kucharska3Ewelina Świątek4Natalia Podolak5Magdalena Perużyńska6Katarzyna Piotrowska7Wiktoria Duchnik8Łukasz Kucharski9Adam Klimowicz10Department 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, PolandDepartment 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, PolandDepartment of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandDepartment 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, PolandDepartment 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, PolandDepartment 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, PolandDepartment of Experimental & Clinical Pharmacology, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandDepartment of Physiology, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandDepartment of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandDepartment of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandDepartment of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, 70-111 Szczecin, PolandFerulic 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% (<i>v</i>/<i>v</i>) 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.https://www.mdpi.com/1999-4923/15/1/117antioxidant activityantiagingferulic acidnew ferulic acid and amino acid derivativesskin permeationtoxicity |
| spellingShingle | Ewa Janus Luan Ramalho Pinheiro Anna Nowak Edyta Kucharska Ewelina Świątek Natalia Podolak Magdalena Perużyńska Katarzyna Piotrowska Wiktoria Duchnik Łukasz Kucharski Adam Klimowicz New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential Pharmaceutics antioxidant activity antiaging ferulic acid new ferulic acid and amino acid derivatives skin permeation toxicity |
| title | New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential |
| title_full | New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential |
| title_fullStr | New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential |
| title_full_unstemmed | New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential |
| title_short | New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential |
| title_sort | new ferulic acid and amino acid derivatives with increased cosmeceutical and pharmaceutical potential |
| topic | antioxidant activity antiaging ferulic acid new ferulic acid and amino acid derivatives skin permeation toxicity |
| url | https://www.mdpi.com/1999-4923/15/1/117 |
| work_keys_str_mv | AT ewajanus newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT luanramalhopinheiro newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT annanowak newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT edytakucharska newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT ewelinaswiatek newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT nataliapodolak newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT magdalenaperuzynska newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT katarzynapiotrowska newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT wiktoriaduchnik newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT łukaszkucharski newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential AT adamklimowicz newferulicacidandaminoacidderivativeswithincreasedcosmeceuticalandpharmaceuticalpotential |