Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration

Wound healing is a complex process to restore skin. Plant-derived bioactive compounds might be a source of substances for the treatment of wounds stalled in a non-resolving stage of wound healing. Oleanolic acid (OA), a pentacyclic triterpene, has shown favorable wound healing properties both in vit...

Full description

Bibliographic Details
Main Authors: Javier Stelling-Férez, Santiago López-Miranda, José Antonio Gabaldón, Francisco José Nicolás
Format: Article
Language:English
Published: MDPI AG 2023-10-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:https://www.mdpi.com/1422-0067/24/19/14860
_version_ 1797575732111605760
author Javier Stelling-Férez
Santiago López-Miranda
José Antonio Gabaldón
Francisco José Nicolás
author_facet Javier Stelling-Férez
Santiago López-Miranda
José Antonio Gabaldón
Francisco José Nicolás
author_sort Javier Stelling-Férez
collection DOAJ
description Wound healing is a complex process to restore skin. Plant-derived bioactive compounds might be a source of substances for the treatment of wounds stalled in a non-resolving stage of wound healing. Oleanolic acid (OA), a pentacyclic triterpene, has shown favorable wound healing properties both in vitro and in vivo. Unfortunately, OA cannot be solubilized in aqueous media, and it needs to be helped by the use of dimethyl sulfoxide (DMSO). In this paper, we have shown that cyclodextrins (CDs) are a good alternative to DMSO as agents to deliver OA to cells, providing better features than DMSO. Cyclodextrins are natural macromolecules that show a unique tridimensional structure that can encapsulate a wide variety of hydrophobic compounds. We have studied the cyclodextrin-encapsulated form of OA with OA/DMSO, comparing their stability, biological properties for cell migration, and cell viability. In addition, detailed parameters related to cell migration and cytoskeletal reorganization have been measured and compared. Our results show that OA-encapsulateds compound exhibit several advantages when compared to non-encapsulated OA in terms of chemical stability, migration enhancement, and preservation of cell viability.
first_indexed 2024-03-10T21:42:28Z
format Article
id doaj.art-22f2b056a91242b0a2341bc0c65fff7b
institution Directory Open Access Journal
issn 1661-6596
1422-0067
language English
last_indexed 2024-03-10T21:42:28Z
publishDate 2023-10-01
publisher MDPI AG
record_format Article
series International Journal of Molecular Sciences
spelling doaj.art-22f2b056a91242b0a2341bc0c65fff7b2023-11-19T14:31:42ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-10-0124191486010.3390/ijms241914860Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell MigrationJavier Stelling-Férez0Santiago López-Miranda1José Antonio Gabaldón2Francisco José Nicolás3Department of Nutrition and Food Technology, Health Sciences PhD Program, Universidad Católica de San Antonio Murcia (UCAM), Campus de los Jerónimos n°135, Guadalupe, 30107 Murcia, SpainDepartment of Nutrition and Food Technology, Health Sciences PhD Program, Universidad Católica de San Antonio Murcia (UCAM), Campus de los Jerónimos n°135, Guadalupe, 30107 Murcia, SpainDepartment of Nutrition and Food Technology, Health Sciences PhD Program, Universidad Católica de San Antonio Murcia (UCAM), Campus de los Jerónimos n°135, Guadalupe, 30107 Murcia, SpainRegeneration, Molecular Oncology and TGF-β, Instituto Murciano de Investigación Biosanitaria (IMIB)-Arrixaca, Hospital Clínico Universitario Virgen de la Arrixaca, El Palmar, 30120 Murcia, SpainWound healing is a complex process to restore skin. Plant-derived bioactive compounds might be a source of substances for the treatment of wounds stalled in a non-resolving stage of wound healing. Oleanolic acid (OA), a pentacyclic triterpene, has shown favorable wound healing properties both in vitro and in vivo. Unfortunately, OA cannot be solubilized in aqueous media, and it needs to be helped by the use of dimethyl sulfoxide (DMSO). In this paper, we have shown that cyclodextrins (CDs) are a good alternative to DMSO as agents to deliver OA to cells, providing better features than DMSO. Cyclodextrins are natural macromolecules that show a unique tridimensional structure that can encapsulate a wide variety of hydrophobic compounds. We have studied the cyclodextrin-encapsulated form of OA with OA/DMSO, comparing their stability, biological properties for cell migration, and cell viability. In addition, detailed parameters related to cell migration and cytoskeletal reorganization have been measured and compared. Our results show that OA-encapsulateds compound exhibit several advantages when compared to non-encapsulated OA in terms of chemical stability, migration enhancement, and preservation of cell viability.https://www.mdpi.com/1422-0067/24/19/14860hydroxypropyl cyclodextrins (HP-CDs)oleanolic acid (OA)cell migrationMAP kinasesepidermal growth factor receptor (EGR)c-Jun
spellingShingle Javier Stelling-Férez
Santiago López-Miranda
José Antonio Gabaldón
Francisco José Nicolás
Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
International Journal of Molecular Sciences
hydroxypropyl cyclodextrins (HP-CDs)
oleanolic acid (OA)
cell migration
MAP kinases
epidermal growth factor receptor (EGR)
c-Jun
title Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
title_full Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
title_fullStr Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
title_full_unstemmed Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
title_short Oleanolic Acid Complexation with Cyclodextrins Improves Its Cell Bio-Availability and Biological Activities for Cell Migration
title_sort oleanolic acid complexation with cyclodextrins improves its cell bio availability and biological activities for cell migration
topic hydroxypropyl cyclodextrins (HP-CDs)
oleanolic acid (OA)
cell migration
MAP kinases
epidermal growth factor receptor (EGR)
c-Jun
url https://www.mdpi.com/1422-0067/24/19/14860
work_keys_str_mv AT javierstellingferez oleanolicacidcomplexationwithcyclodextrinsimprovesitscellbioavailabilityandbiologicalactivitiesforcellmigration
AT santiagolopezmiranda oleanolicacidcomplexationwithcyclodextrinsimprovesitscellbioavailabilityandbiologicalactivitiesforcellmigration
AT joseantoniogabaldon oleanolicacidcomplexationwithcyclodextrinsimprovesitscellbioavailabilityandbiologicalactivitiesforcellmigration
AT franciscojosenicolas oleanolicacidcomplexationwithcyclodextrinsimprovesitscellbioavailabilityandbiologicalactivitiesforcellmigration