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The Natural-Based Optimization of Kojic Acid Conjugated to Different Thio-Quinazolinones As Potential Anti-Melanogenesis Agents With Tyrosinase Inhibitory Activity Publisher Pubmed



Sepehri N1 ; Iraji A2, 3 ; Yavari A4 ; Asgari MS5 ; Zamani S6 ; Hosseini S7 ; Bahadorikhalili S4 ; Pirhadi S2 ; Larijani B4 ; Khoshneviszadeh M2 ; Hamedifar H8 ; Mahdavi M4 ; Khoshneviszadeh M2
Authors

Source: Bioorganic and Medicinal Chemistry Published:2021


Abstract

Melanin pigment and melanogenesis are a two-edged sword. Melanin has a radioprotection role while melanogenesis has undesirable effects. Targeting the melanogenesis pathway, a series of kojyl thioether conjugated to different quinazolinone derivatives were designed, synthesized, and evaluated for their inhibitory activity against mushroom tyrosinase. All the synthesized compounds were screened for their anti-tyrosinase activity and all derivatives displayed better potency than kojic acid as the positive control. In this regard, 5j and 5h as the most active compounds showed an IC50 value of 0.46 and 0.50 µM, respectively. In kinetic evaluation against tyrosinase, 5j depicted an uncompetitive inhibition pattern. Designed compounds also exhibited mild antioxidant capacity. Moreover, 5j and 5h achieved good potency against the B16F10 cell line to reduce the melanin content, whilst showing limited toxicity against malignant cells. The proposed binding mode of new inhibitors evaluated through molecular docking was consistent with the results of structure–activity relationship analysis. © 2021 Elsevier Ltd
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