Izvorni znanstveni članak

https://doi.org/10.5562/cca3857

Synthesis of Arylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) Derivatives and Their Effect on Tyrosinase Activity

Elma Veljović ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
Hrvoje Rimac ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Department of Medicinal Chemistry, Ante Kovačića 1, 10000 Zagreb, Croatia
Mirsada Salihović orcid.org/0000-0001-7497-4084 ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
Selma Špirtović-Halilović ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
Amar Osmanović ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
Nejra Kovač ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71000 Sarajevo, Bosnia and Herzegovina
Elizabeta Kiršek ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Department of Medicinal Chemistry, Ante Kovačića 1, 10000 Zagreb, Croatia
Enida Članjak-Kudra ; University of Sarajevo, Veterinary Faculty, Zmaja od Bosne 90, 71000 Sarajevo, Bosnia and Herzegovina
Dijana Špirtović ; Clinical Centre of the University of Sarajevo, Department of Clinical Pathology, Cytology and Human Genetics, Bolnička 25, 71000 Sarajevo, Bosnia and Herzegovina
Mirza Bojić ; University of Zagreb, Faculty of Pharmacy and Biochemistry, Department of Medicinal Chemistry, Ante Kovačića 1, 10000 Zagreb, Croatia

Sažetak

The objective of this study was to test the inhibitory effect of five newly synthesized arylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) derivatives. The structural characterization and stereochemistry of synthesized compounds were deduced from analyses of experimental FT-IR, 1H, 13C NMR spectra and theoretical methodology of DFT study based on the global chemical reactivity indices calculated using the 6-31G** level of theory.
To predict the stability of the newly synthesized compounds, the reactivity descriptors obtained at B3LYP level (Egap, dipole moment, μ, η, ω) were computed. The docking study and the selected quantum chemical descriptors computed for compounds 1−5 exhibit a good agreement. The strongest inhibitors showed 25 to 30 % inhibition of tyrosinase activity. Results were supported by docking studies of the binding of the strongest inhibitors to the enzyme. The results suggest that tetraketones of this type, due to their tyrosinase inhibitory effect, represent potential agents in the treatment of various types of melanomas and skin hyperpigmentation.

Ključne riječi

solubility prediction; NADES; mediterranean herbs; COSMO-RS; choline chloride; eutectic; extraction

Hrčak ID:

275614

URI

https://hrcak.srce.hr/275614

Datum izdavanja:

26.4.2022.

Posjeta: 1.523 *