Language:

Potent anti-melanogenic activity and favorable toxicity profile of selected 4-phenyl hydroxycoumarins in the zebrafish model and the computational molecular modeling studies

Veselinović, Jovana B. ; Veselinović, Aleksandar M. ; Ilic-Tomic, Tatjana ; Davis, Reeta ; O'Connor, Kevin ; Pavic, Aleksandar ; Nikodinovic-Runic, Jasmina

Bioorganic & medicinal chemistry, 2017-12, Vol.25 (24), p.6286-6296 [Peer Reviewed Journal]

England: Elsevier Ltd

Full text available

Citations Cited by

Actions
1. Add to e-Shelf
2. Remove from e-Shelf
3. E-mail
4. Print
5. Permalink
6. Citation
7. EasyBib
8. EndNote
9. RefWorks
10. Delicious
11. Export RIS
12. Export BibTeX

Title:
Potent anti-melanogenic activity and favorable toxicity profile of selected 4-phenyl hydroxycoumarins in the zebrafish model and the computational molecular modeling studies
Author: Veselinović, Jovana B. ; Veselinović, Aleksandar M. ; Ilic-Tomic, Tatjana ; Davis, Reeta ; O'Connor, Kevin ; Pavic, Aleksandar ; Nikodinovic-Runic, Jasmina
Subjects: 4-Phenyl hydroxycoumarins ; Animals ; Coumarins - chemistry ; Coumarins - pharmacology ; Dose-Response Relationship, Drug ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Melanocytes ; Melanogenesis ; Models, Animal ; Models, Molecular ; Molecular docking ; Molecular Structure ; Monophenol Monooxygenase - antagonists & inhibitors ; Monophenol Monooxygenase - metabolism ; Structure-Activity Relationship ; Tyrosinase inhibitors ; Zebrafish
Is Part Of: Bioorganic & medicinal chemistry, 2017-12, Vol.25 (24), p.6286-6296
Description: [Display omitted] •4-Phenyl hydroxycoumarins (7C and 5,7C) have anti-melanogenic activity.•7C and 5,7C showed depigmenting and anti-tyrosinase activity in vivo and in vitro.•4-Phenyl hydroxycoumarins are not toxic in vivo on melanocytes and neutrophils.•7C and 5,7C have better pharmacological properties than kojic acid and hydroquinone.•7C and 5,7C target the multiple major regulators of melanogenesis. 7-Hydroxy-4-phenylcoumarin (7C) and 5,7-dihydroxy-4-phenylcoumarin (5,7C) have been evaluated as potential anti-melanogenic agents in the zebrafish (Danio rerio) model in comparison to commercially utilized depigmenting agents hydroquinone and kojic acid. 7C and 5,7C decreased the body pigmentation at 5 µg/mL, while did not affect the embryos development and survival at doses ≤50 µg/mL and ≤25 µg/mL. Unlike hydroquinone and kojic acid, 4-phenyl hydroxycoumarins were no melanocytotoxic, showed no cardiotoxic side effects, neither caused neutropenia in zebrafish embryos, suggesting these compounds may present novel skin-whitening agents with improved pharmacological properties. Inhibition of tyrosinase was identified as the possible mode of anti-melanogenic action. Molecular docking studies using the homology model of human tyrosinase as well as adenylate cyclase revealed excellent correlation with experimentally obtained results.
Publisher: England: Elsevier Ltd
Language: English

Links

View this record in MEDLINE/PubMed

Back to results list

Implemented by: Social Network Logos:

Potent anti-melanogenic activity and favorable toxicity profile of selected 4-phenyl hydroxycoumarins in the zebrafish model and the computational molecular modeling studies

Veselinović, Jovana B. ; Veselinović, Aleksandar M. ; Ilic-Tomic, Tatjana ; Davis, Reeta ; O'Connor, Kevin ; Pavic, Aleksandar ; Nikodinovic-Runic, Jasmina

England: Elsevier Ltd

Searching Remote Databases, Please Wait