Research paperDihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-Cysteaminylphenol and 4-S-Cysteaminylcatechol☆,☆☆
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A cell-based evaluation of human tyrosinase-mediated metabolic activation of leukoderma-inducing phenolic compounds
2022, Journal of Dermatological ScienceCitation Excerpt :Western blot analysis (Supplementary Fig. 1A) and tyrosinase activity assays (Supplementary Fig. 1B) showed that catalytically active tyrosinase was expressed in those cells 24 h after transfection. To optimize the tyrosinase expression level for the efficient production of o-quinone metabolites, the 293T cells were transfected with different amounts of the plasmid pTYR for 24 h and were then exposed to 4SCAP, which produces highly toxic metabolites [15]. After 24 h of treatment, the cell viability decreased with increasing doses of 4SCAP or amounts of pTYR (Fig. 2A).
I<inf>2</inf>/K<inf>2</inf>S<inf>2</inf>O<inf>8</inf>-Promoted ring-opening cyclizations of benzothiazoles and 3-oxo-3-arylpropanenitriles
2022, Molecular CatalysisCitation Excerpt :Jiang et.al described a novel Pd-catalyzed coupling reaction for the synthesis of substituted 1,4-benzothiazines by using stable Na2S2O3 salt as sulfurating reagent instead of foul-smelling thiols (Scheme 1b) [11]. Furthermore, the copper-catalyzed ring-opening reactions between 2-aminobenzothiazole and terminal alkynes or alkynyl carboxylic acids for the construction of 1,4-benzothiazines was achieved (Scheme 1c) [12–15]. In addition, Zhang et.al reported a copper-catalyzed three-component reaction of 2-iodo/bromophenyl isothiocyanates, terminal alkynes, and aqueous ammonia to access 1,4-benzothiazines (Scheme 1d) [16].
Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of 1,4-Benzothiazines
2016, Journal of Organic ChemistryMechanism of putative neo-antigen formation from N-propionyl-4-S- cysteaminylphenol, a tyrosinase substrate, in melanoma models
2012, Biochemical PharmacologyCitation Excerpt :In the present study, we did not examine the production of ROS from tyrosinase-mediated oxidation products of NPrCAP. However, we can expect the production of NPrCAC through redox exchange in melanoma cells and the subsequent production of ROS from this catechol, because the closely related catechol, 4-S-cysteaminylcatechol, was shown to produce superoxide radicals (which are rapidly converted to hydrogen peroxide) through autoxidation [32]. The thiol adduct RS-NPrCAC, as a catechol, may also contribute to the production of ROS.
N-propionyl-4-S-cysteaminylphenol induces apoptosis in B16F1 cells and mediates tumor-specific T-cell immune responses in a mouse melanoma model
2012, Journal of Dermatological ScienceCitation Excerpt :NPr-4-S-CAP exerts strong cytotoxicity toward melanoma cells, in which melanin synthesis is highly elevated [8,9,11]. When phenolic amine compounds are oxidized by tyrosinase, melanin intermediates inhibit the activity of SH enzymes such as thymidylate synthase, alcohol dehydrogenase and DNA polymerase by covalent binding through their cysteine residues, resulting in melanoma-specific cytotoxicity [23–25]. In the present study, NPr-4-S-CAP suppressed growth of cultured melanoma cells and induced apoptotic cell death accompanied by ROS generation.
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This paper is dedicated to the late Professor Keisuke Fujita who died on June 11, 1995.
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This study has been supported, in part, by Grants-in-Aid for Cancer Research from the Ministry of Health and Welfare of Japan.