In Vitro and In Silico Studies of Two 1,4-Naphthoquinones and their Topi- cal Formulation in Bigels
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Imen Khelifi
- Audrey Tourrette
- Daycem Khelifi
- Thomas Efferth
- El Akrem Hayouni
- Riadh Ksouri
- Jalloul Bouajila
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000697682900009&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.2174/1567201818666210618111118
- eISSN
- 1875-5704
- Externe Identifier
- Clarivate Analytics Document Solution ID: US8NP
- PubMed Identifier: 34145994
- ISSN
- 1567-2018
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- CURRENT DRUG DELIVERY
- Schlüsselwörter
- 1,4-Naphthoquinone
- anti-elastase
- bigel
- cytotoxicity
- drug release
- molecular docking
- Paginierung
- 931 - 940
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Titel
- <i>In Vitro</i> and <i>In Silico</i> Studies of Two 1,4-Naphthoquinones and their Topi- cal Formulation in Bigels
- Sub types
- Article
- Ausgabe der Zeitschrift
- 18
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:sec> <jats:title>Background:</jats:title> <jats:p>1,4-Naphthoquinones (1,4-NQs) are secondary plant metabolites with numerous biological activities. 1,4-NQs display low water solubility and poor bioavailability. Bigels are a new technology with great potential, which are designated as drug delivery systems. Biphasic bigels consisting of solid and liquid components represent suitable formulations improving diffusion and bioavailability of NQs into the skin.</jats:p> </jats:sec> <jats:sec> <jats:title>Objective:</jats:title> <jats:p>We evaluated the in silico and in vitro activity of 5,8-dihydroxy-1,4-naphthoquinone (M1) and 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (M2) on elastase and assessed their cytotoxicity towards COLO38 melanoma cells. The 1,4-NQs were loaded into bigels for topical application.</jats:p> </jats:sec> <jats:sec> <jats:title>Methods:</jats:title> <jats:p>Molecular docking was performed, and cytotoxicity was evaluated on COLO38 cells using the resazurin assay. M1 and M2 were separately incorporated into bigels consisting of hydrogel organogel with sweet almond oil as the non-polar solvent and span 65 as an organogelator. Their rheological behavior and microscopic properties were characterized. The diffusion kinetics and permeation of 1,4-NQs from bigels were studied by a paddle-over-extraction cell and a “Franz cell” in vitro permeation model.</jats:p> </jats:sec> <jats:sec> <jats:title>Results:</jats:title> <jats:p> Molecular docking data predicted high interactions between elastase and ligands. Hydrogen bonds with LYS233 were observed for M1, M2, and phosphoramidon (positive control). The average binding energies were -8.5 and -9.7 kcal/mol for M1 and M2 and -12.6 kcal/mol for phosphoramidon. M1 and M2 inhibited the elastase activity by 58.9 and 56.6%, respectively. M1 and M2 were cytotoxic towards COLO38 cells (IC<jats:sub>50</jats:sub> value: 2.6 and 9.8 μM). The M1 release from bigels was faster and more efficient than that of M2.</jats:p> </jats:sec> <jats:sec> <jats:title>Conclusion:</jats:title> <jats:p>M1 and M2 are promising for skin disease treatment. Biphasic organogel-hydrogel bigels are efficient and safe formulations to overcome their low bioavailability.</jats:p> </jats:sec>
- Autoren
- Imen Khelifi
- Audrey Tourrette
- Daycem Khelifi
- Thomas Efferth
- El Akrem Hayouni
- Riadh Ksouri
- Jalloul Bouajila
- DOI
- 10.2174/1567201818666210618111118
- ISSN
- 1567-2018
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Current Drug Delivery
- Sprache
- en
- Paginierung
- 955 - 964
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Herausgeber
- Bentham Science Publishers Ltd.
- Herausgeber URL
- http://dx.doi.org/10.2174/1567201818666210618111118
- Datum der Datenerfassung
- 2021
- Titel
- In Vitro and In Silico Studies of Two 1,4-Naphthoquinones and Their Topical Formulation in Bigels
- Ausgabe der Zeitschrift
- 18
Datenquelle: Crossref
- Abstract
- <h4>Background</h4>1,4-Naphthoquinones (1,4-NQs) are secondary plant metabolites with numerous biological activities. 1,4-NQs display low water solubility and poor bioavailability. Bigels are a new technology with great potential, which are designated as drug delivery systems. Biphasic bigels consisting of solid and liquid components represent suitable formulations improving diffusion and bioavailability of NQs into the skin.<h4>Objective</h4>We evaluated the in silico and in vitro activity of 5,8-dihydroxy-1,4-naphthoquinone (M1) and 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (M2) on elastase and assessed their cytotoxicity towards COLO38 melanoma cells. The 1,4-NQs were loaded into bigels for topical application.<h4>Methods</h4>Molecular docking was performed, and cytotoxicity was evaluated on COLO38 cells using the resazurin assay. M1 and M2 were separately incorporated into bigels consisting of hydrogel organogel with sweet almond oil as the non-polar solvent and span 65 as an organogelator. Their rheological behavior and microscopic properties were characterized. The diffusion kinetics and permeation of 1,4-NQs from bigels were studied by a paddle-over-extraction cell and a "Franz cell" in vitro permeation model.<h4>Results</h4>Molecular docking data predicted high interactions between elastase and ligands. Hydrogen bonds with LYS233 were observed for M1, M2, and phosphoramidon (positive control). The average binding energies were -8.5 and -9.7 kcal/mol for M1 and M2 and -12.6 kcal/mol for phosphoramidon. M1 and M2 inhibited the elastase activity by 58.9 and 56.6%, respectively. M1 and M2 were cytotoxic towards COLO38 cells (IC<sub>50</sub> value: 2.6 and 9.8 μM). The M1 release from bigels was faster and more efficient than that of M2.<h4>Conclusion</h4>M1 and M2 are promising for skin disease treatment. Biphasic organogel-hydrogel bigels are efficient and safe formulations to overcome their low bioavailability.
- Addresses
- Laboratory of Aromatic and Medicinal Plants, Center of Biotechnology at the Ecopark of Borj-Cedria, Hammam Lif, Tunisia.
- Autoren
- Imen Khelifi
- Audrey Tourrette
- Daycem Khelifi
- Thomas Efferth
- El Akrem Hayouni
- Riadh Ksouri
- Jalloul Bouajila
- DOI
- 10.2174/1567201818666210618111118
- eISSN
- 1875-5704
- Externe Identifier
- PubMed Identifier: 34145994
- Open access
- false
- ISSN
- 1567-2018
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Current drug delivery
- Schlüsselwörter
- Naphthoquinones
- Hydrogels
- Drug Delivery Systems
- Rheology
- Molecular Docking Simulation
- Sprache
- eng
- Medium
- Paginierung
- 955 - 964
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Datum der Datenerfassung
- 2021
- Titel
- In Vitro and In Silico Studies of Two 1,4-Naphthoquinones and Their Topical Formulation in Bigels.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 18
Datenquelle: Europe PubMed Central
- Abstract
- BACKGROUND: 1,4-Naphthoquinones (1,4-NQs) are secondary plant metabolites with numerous biological activities. 1,4-NQs display low water solubility and poor bioavailability. Bigels are a new technology with great potential, which are designated as drug delivery systems. Biphasic bigels consisting of solid and liquid components represent suitable formulations improving diffusion and bioavailability of NQs into the skin. OBJECTIVE: We evaluated the in silico and in vitro activity of 5,8-dihydroxy-1,4-naphthoquinone (M1) and 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (M2) on elastase and assessed their cytotoxicity towards COLO38 melanoma cells. The 1,4-NQs were loaded into bigels for topical application. METHODS: Molecular docking was performed, and cytotoxicity was evaluated on COLO38 cells using the resazurin assay. M1 and M2 were separately incorporated into bigels consisting of hydrogel organogel with sweet almond oil as the non-polar solvent and span 65 as an organogelator. Their rheological behavior and microscopic properties were characterized. The diffusion kinetics and permeation of 1,4-NQs from bigels were studied by a paddle-over-extraction cell and a "Franz cell" in vitro permeation model. RESULTS: Molecular docking data predicted high interactions between elastase and ligands. Hydrogen bonds with LYS233 were observed for M1, M2, and phosphoramidon (positive control). The average binding energies were -8.5 and -9.7 kcal/mol for M1 and M2 and -12.6 kcal/mol for phosphoramidon. M1 and M2 inhibited the elastase activity by 58.9 and 56.6%, respectively. M1 and M2 were cytotoxic towards COLO38 cells (IC50 value: 2.6 and 9.8 μM). The M1 release from bigels was faster and more efficient than that of M2. CONCLUSION: M1 and M2 are promising for skin disease treatment. Biphasic organogel-hydrogel bigels are efficient and safe formulations to overcome their low bioavailability.
- Date of acceptance
- 2021
- Autoren
- Imen Khelifi
- Audrey Tourrette
- Daycem Khelifi
- Thomas Efferth
- El Akrem Hayouni
- Riadh Ksouri
- Jalloul Bouajila
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/34145994
- DOI
- 10.2174/1567201818666210618111118
- eISSN
- 1875-5704
- Ausgabe der Veröffentlichung
- 7
- Zeitschrift
- Curr Drug Deliv
- Schlüsselwörter
- 1
- 4-Naphthoquinone
- anti-elastase
- bigel
- cytotoxicity
- drug release
- molecular docking.
- Drug Delivery Systems
- Hydrogels
- Molecular Docking Simulation
- Naphthoquinones
- Rheology
- Sprache
- eng
- Country
- United Arab Emirates
- Paginierung
- 955 - 964
- PII
- CDD-EPUB-116245
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2021
- Titel
- In Vitro and In Silico Studies of Two 1,4-Naphthoquinones and Their Topical Formulation in Bigels.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 18
Datenquelle: PubMed
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