ArticleInternational journal of molecular sciences2018
Structure-Activity Relationships of Thiazolyl Resorcinols, Potent and Selective Inhibitors of Human Tyrosinase.
Article in International journal of molecular sciences, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 65 citations in OpenAlex.
- Thiamidol containing treatment regimens in facial hyperpigmentation: An international multi-centre approach consisting of a double-blind, controlled, split-face study and of an open-label, real-world study.International journal of cosmetic science · 2020Trial
- Design, synthesis, biological activity and in silico evaluation of phenylthiazole derivatives as multifunctional skin-whitening agents.Molecular diversity · 2026Article
- Efficacy and Tolerability of 0.2% Thiamidol Cream for Facial Hyperpigmentation: A Randomized, Double-Blind, and Vehicle-Controlled Study.Dermatology and therapy · 2026Article
- Mechanistic profiling and optimized production of Altenusin, a fungal carboxy-biphenyl scaffold for tyrosinase inhibition.RSC advances · 2026Article
- Visible light induces skin darkening in vivo: comparative pilot studies reveal enhanced susceptibility in melasma and its mitigation by a human tyrosinase inhibitor.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Targeting Melanin Production: The Safety of Tyrosinase Inhibition.International journal of molecular sciences · 2025Review
- 2,5-Dihydroxyphenylethanone: an anti-melanogenic bioactive compound isolated fromJournal of enzyme inhibition and medicinal chemistry · 2025Article
- Design and synthesis of 4-(2,4-dihydroxyphenyl)thiazole-2-carboxamide derivatives as novel tyrosinase inhibitors:RSC medicinal chemistry · 2025Article
- Tyrosinase Inhibition and Antimelanogenic Effects of Resorcinol-Containing Compounds.ChemMedChem · 2024Review
- Molecular Design of Cyclic Peptides with Cell Membrane Permeability and Development of MDMX-p53 Inhibitor.ACS medicinal chemistry letters · 2023Article
- Molecular docking Study of Nuciferine as a Tyrosinase Inhibitor and Its Therapeutic Potential for Hyperpigmentation.Genomics & informatics · 2023Article
- Heterocyclic Compounds as Synthetic Tyrosinase Inhibitors: Recent Advances.International journal of molecular sciences · 2023Review
- Theoretical Studies of Cyanophycin Dipeptides as Inhibitors of Tyrosinases.International journal of molecular sciences · 2022Article
- Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects andComputational and structural biotechnology journal · 2022Article
- Evaluation of 4-(4-Fluorobenzyl)piperazin-1-yl]-Based Compounds as Competitive Tyrosinase Inhibitors Endowed with Antimelanogenic Effects.ChemMedChem · 2021Article
- Review
- Evaluation of Anti-Melanogenesis Activity of EnrichedInternational journal of molecular sciences · 2021Article
- Effective reduction of post-inflammatory hyperpigmentation with the tyrosinase inhibitor isobutylamido-thiazolyl-resorcinol (Thiamidol).International journal of cosmetic science · 2021Article
- Urolithin and Reduced Urolithin Derivatives as Potent Inhibitors of Tyrosinase and Melanogenesis: Importance of the 4-Substituted Resorcinol Moiety.International journal of molecular sciences · 2021Article
- Protocatechuic Aldehyde Inhibits α-MSH-Induced Melanogenesis in B16F10 Melanoma Cells via PKA/CREB-Associated MITF Downregulation.International journal of molecular sciences · 2021Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Tyrosinase inhibitors are of great clinical interest as agents for the treatment of hyperpigmentary disorders; however, most compounds described in the literature lack clinical efficiency due to insufficient inhibitory activity against human tyrosinase (hTyr). Recently, we reported that thiazolyl resorcinols (4-resorcinylthiazol-2-amines and -amides) are both selective and efficacious inhibitors of hTyr in vitro and in vivo. Here, we measured dose-activity profiles of a large number of thiazolyl resorcinols and analogous compounds to better understand the molecular basis of their interaction with hTyr. We show that both the resorcinyl moiety and the thiazole ring must be intact to allow efficient inhibition of hTyr, while the substituents at the thiazole 2-amino group confer additional inhibitory activity, depending on their size and polarity. The results of molecular docking simulations were in excellent agreement with the experimental data, affording a rationale for the structural importance of either ring. We further propose that a special type of interaction between the thiazole sulfur and a conserved asparagine residue is partially responsible for the superior inhibitory activity of thiazolyl resorcinols against hTyr.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.