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靛红-1,4-萘醌类化合物作为有效的蘑菇酪氨酸酶抑制剂：构效关系研究。

Anilino-1,4-naphthoquinones as potent mushroom tyrosinase inhibitors: and studies.

机构信息

Department of Biochemistry, Center for Translational Medicine, Faculty of Medicine, Khon Kaen University, Khon Kaen, Thailand.

Program in Bioinformatics and Computational Biology, Graduate School, Chulalongkorn University, Bangkok, Thailand.

出版信息

J Enzyme Inhib Med Chem. 2024 Dec;39(1):2357174. doi: 10.1080/14756366.2024.2357174. Epub 2024 May 30.

DOI:10.1080/14756366.2024.2357174
PMID:38814149
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11141316/
Abstract

Tyrosinase, a pivotal enzyme in melanin synthesis, is a primary target for the development of depigmenting agents. In this work, and techniques were employed to identify novel tyrosinase inhibitors from a set of 12 anilino-1,4-naphthoquinone derivatives. Results from the mushroom tyrosinase activity assay indicated that, among the 12 derivatives, three compounds (, , and ) demonstrated the most significant inhibitory activity against mushroom tyrosinase, surpassing the effectiveness of the kojic acid. Molecular docking revealed that all studied derivatives interacted with copper ions and amino acid residues at the enzyme active site. Molecular dynamics simulations provided insights into the stability of enzyme-inhibitor complexes, in which compounds , , and particularly displayed greater stability, atomic contacts, and structural compactness than kojic acid. Drug likeness prediction further strengthens the potential of anilino-1,4-naphthoquinones as promising candidates for the development of novel tyrosinase inhibitors for the treatment of hyperpigmentation disorders.

摘要

酪氨酸酶是黑色素合成中的关键酶，是开发美白剂的主要靶标。在这项工作中，采用和技术从一组 12 种苯胺基-1,4-萘醌衍生物中鉴定新型酪氨酸酶抑制剂。蘑菇酪氨酸酶活性测定结果表明，在 12 种衍生物中，有 3 种化合物（、和）对蘑菇酪氨酸酶表现出最强的抑制活性，超过了曲酸的效果。分子对接表明，所有研究的衍生物都与铜离子和酶活性部位的氨基酸残基相互作用。分子动力学模拟提供了对酶-抑制剂复合物稳定性的深入了解，其中化合物、和特别是表现出比曲酸更高的稳定性、原子接触和结构紧凑性。药物相似性预测进一步加强了苯胺基-1,4-萘醌作为开发新型酪氨酸酶抑制剂治疗色素沉着障碍的有前途的候选药物的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/c7dc514b7188/IENZ_A_2357174_F0008_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/ff7869a56dca/IENZ_A_2357174_UF0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/004cf77fb660/IENZ_A_2357174_F0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/597cb82c79c6/IENZ_A_2357174_F0002_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/cc5a75d0d7e4/IENZ_A_2357174_F0003_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/a478e880fb42/IENZ_A_2357174_F0004_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/2628cd5d09fa/IENZ_A_2357174_F0005_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/9227fbe35899/IENZ_A_2357174_F0006_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/45e880a56fdc/IENZ_A_2357174_F0007_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/c7dc514b7188/IENZ_A_2357174_F0008_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/ff7869a56dca/IENZ_A_2357174_UF0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/004cf77fb660/IENZ_A_2357174_F0001_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/597cb82c79c6/IENZ_A_2357174_F0002_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/cc5a75d0d7e4/IENZ_A_2357174_F0003_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/a478e880fb42/IENZ_A_2357174_F0004_B.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/2628cd5d09fa/IENZ_A_2357174_F0005_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/9227fbe35899/IENZ_A_2357174_F0006_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/45e880a56fdc/IENZ_A_2357174_F0007_C.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6f41/11141316/c7dc514b7188/IENZ_A_2357174_F0008_C.jpg

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