Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors

Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors Publisher

Rezapour Niri D¹ ; Sayahi MH² ; Behrouz S¹ ; Moazzam A³ ; Rasekh F⁷ ; Tanideh N⁴ ; Irajie C⁵ ; Seif Nezhad M⁴ ; Larijani B³ ; Iraji A^{4, 6} ; Mahdavi M³

Show Affiliations

1. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shiraz University of Technology, Shiraz, Iran
2. Department of Chemistry, Payame Noor University (PNU), Tehran, Iran
3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran, Iran
4. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
5. Department of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran
6. Research Center for Traditional Medicine and History of Medicine, Department of Persian Medicine, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
7. Department of Biology, Payame Noor University (PNU), Tehran, Iran

Source: Heliyon Published:2023

Abstract

In the present study, novel series of kojic acid derivatives conjugated to amino pyridine moiety were designed and synthesized to explore their inhibitory activity against tyrosinase. To this end, the structure of all derivatives was characterized by 1H NMR, 13C NMR, FT-IR, and elemental analysis. Next, all derivatives were evaluated against tyrosinase compared to the kojic acid as positive control and exhibited different inhibitory potencies. Furthermore, the antioxidant potential of all derivatives was determined. The kinetic analysis of the most active agent revealed that 3-hydroxy-6-(hydroxymethyl)-2-((3-nitrophenyl)(pyridin-2-ylamino)methyl)-4H-pyran-4-one (4h) binds to the enzyme in the uncompetitive mode of action. The docking analysis and molecular dynamic simulations showed considerable binding affinity and significant interactions with tyrosinase enzyme to target the melanogenesis pathway, proposing them as potent candidates to control hyperpigmentation in the future. © The Authors

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Mohammad Mahdavi (10)

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Style	Citing Format
MLA	Rezapour Niri D, et al.. "Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors." Heliyon, vol. 9, no. 11, 2023, pp. -.
APA	Rezapour Niri D, Sayahi MH, Behrouz S, Moazzam A, Rasekh F, Tanideh N, Irajie C, Seif Nezhad M, Larijani B, Iraji A, Mahdavi M (2023). Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors. Heliyon, 9(11), -.
Chicago	Rezapour Niri D, Sayahi MH, Behrouz S, Moazzam A, Rasekh F, Tanideh N, Irajie C, et al.. "Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors." Heliyon 9, no. 11 (2023): -.
Harvard	Rezapour Niri D et al. (2023) 'Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors', Heliyon, 9(11), pp. -.
Vancouver	Rezapour Niri D, Sayahi MH, Behrouz S, Moazzam A, Rasekh F, Tanideh N, et al.. Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors. Heliyon. 2023;9(11):-.
BibTex	@article{ author = {Rezapour Niri D and Sayahi MH and Behrouz S and Moazzam A and Rasekh F and Tanideh N and Irajie C and Seif Nezhad M and Larijani B and Iraji A and Mahdavi M}, title = {Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors}, journal = {Heliyon}, volume = {9}, number = {11}, pages = {-}, year = {2023} }
RIS	TY - JOUR AU - Rezapour Niri D AU - Sayahi MH AU - Behrouz S AU - Moazzam A AU - Rasekh F AU - Tanideh N AU - Irajie C AU - Seif Nezhad M AU - Larijani B AU - Iraji A AU - Mahdavi M TI - Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors JO - Heliyon VL - 9 IS - 11 SP - EP - PY - 2023 ER -

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