1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors : Design, synthesis and biological evaluation
Copyright © 2018 Elsevier Inc. All rights reserved..
A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC50s = 0.06-6.80 µM), being superior to reference drug, kojic acid. In particular, the naphthyloxy analogs 6o and 6p were found to be 31-155 times more potent than kojic acid. The metal-binding study of selected compound 6o revealed that the prototype compound possesses metal-chelating ability, particularly with Cu2+ ions. The promising compounds 6o and 6p had acceptable safety profile as demonstrated by cytotoxicity assay against melanoma (B16) cell line and Human Foreskin Fibroblast (HFF) cells.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:82 |
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| Enthalten in: |
Bioorganic chemistry - 82(2019) vom: 01. Feb., Seite 414-422 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Ashooriha, Morteza [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 30.08.2019 Date Revised 30.08.2019 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bioorg.2018.10.069 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM290606888 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2018 Elsevier Inc. All rights reserved. | ||
| 520 | |a A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All compounds showed very potent anti-tyrosinase activity (IC50s = 0.06-6.80 µM), being superior to reference drug, kojic acid. In particular, the naphthyloxy analogs 6o and 6p were found to be 31-155 times more potent than kojic acid. The metal-binding study of selected compound 6o revealed that the prototype compound possesses metal-chelating ability, particularly with Cu2+ ions. The promising compounds 6o and 6p had acceptable safety profile as demonstrated by cytotoxicity assay against melanoma (B16) cell line and Human Foreskin Fibroblast (HFF) cells | ||
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| 650 | 4 | |a 1,2,3-Triazole | |
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| 650 | 4 | |a Hyperpigmentation | |
| 650 | 4 | |a Kojic acid | |
| 650 | 4 | |a Tyrosinase inhibitor | |
| 650 | 7 | |a Chelating Agents |2 NLM | |
| 650 | 7 | |a Enzyme Inhibitors |2 NLM | |
| 650 | 7 | |a Metals |2 NLM | |
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| 700 | 1 | |a Khoshneviszadeh, Mahsima |e verfasserin |4 aut | |
| 700 | 1 | |a Moradi, Seyed Ershad |e verfasserin |4 aut | |
| 700 | 1 | |a Rafiei, Alireza |e verfasserin |4 aut | |
| 700 | 1 | |a Kardan, Mostafa |e verfasserin |4 aut | |
| 700 | 1 | |a Emami, Saeed |e verfasserin |4 aut | |
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