Anti-melanogenesis potential of a new series of Morita-Baylis-Hillman adducts in B16F10 melanoma cell line

Emna Ketata 1 Haitham Elleuch 2 Aref Neifar 1 Wafa Mihoubi 1 Wajdi Ayadi 1 Naziha Marrakchi 3 Farhat Rezgui 2 Ali Gargouri 1
1 CBS - Centre de Biotechnologie de Sfax
2 LR99ES14 - Laboratoire de Chimie Organique Structurale et Macromoléculaire
3 Laboratoire des Venins et Toxines, Institut Pasteur de Tunis
Abstract : Melanin is a natural polymer pigment which provides skin photoprotection against ultraviolet radiation. An excessive synthesis of melanin leads to hyperpigmentation disorders. Tyrosinase catalyzes the rate limiting steps on melanogenesis. Therefore, tyrosinase inhibitors have potential applications in medicine and cosmetic fields. We carried out herein the screening of a family of cyclic Morita-Baylis-Hillman adducts (MBH) to find out their effects on tyrosinase activity and on melanogenesis in murine melanoma B16F10 cell line. Kinetic analysis of tyrosinase inhibition showed that compounds 1a (2-hydroxymethyl) cyclohex-2-enone) and 3f (diethyl (1-(6-oxocyclohex-1-en-1-yl) ethyl-phosphonate) were competitive inhibitors, whereas the compound 2b (6-oxocyclohex-1-en-1-yl) ethyl acetate) was a non-competitive one. Additionally we have found that (1a, 2b and 3f) compounds had a strong melanogenesis inhibition effect in isobutylmethylxanthine (IBMX)-treated murine melanoma B16F10 cells when tested at low and non cytotoxic dose (10-50 µM), by attenuating the melanin production, intracellular tyrosinase activity and tyrosinase expression. Thus, we suggest that these compounds could be used as effective skin-whitening agents.
Keywords : Depigmentation Kinetics Melanogenesis Morita-Baylis-Hillman adducts Tyrosinase inhibition
Document type :
Journal articles
Complete list of metadatas
https://hal-riip.archives-ouvertes.fr/pasteur-01946452
Contributor : Abdelhakim Ben Hassine <>
Submitted on : Thursday, December 6, 2018 - 9:45:18 AM
Last modification on : Saturday, February 16, 2019 - 1:18:15 AM

Identifiers

Collections

RIIP | RIIP_TUNIS

Citation

Emna Ketata, Haitham Elleuch, Aref Neifar, Wafa Mihoubi, Wajdi Ayadi, et al.. Anti-melanogenesis potential of a new series of Morita-Baylis-Hillman adducts in B16F10 melanoma cell line. Bioorganic Chemistry, Elsevier, 2018, 84, pp.17-23. ⟨10.1016/j.bioorg.2018.11.028⟩. ⟨pasteur-01946452⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

15

Contact

Informations

CCSD