• Login
    View Item 
    •   Home
    • The Manchester Institute Cancer Research UK
    • All Paterson Institute for Cancer Research
    • View Item
    •   Home
    • The Manchester Institute Cancer Research UK
    • All Paterson Institute for Cancer Research
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of ChristieCommunitiesTitleAuthorsIssue DateSubmit DateSubjectsThis CollectionTitleAuthorsIssue DateSubmit DateSubjectsProfilesView

    My Account

    LoginRegister

    Local Links

    The Christie WebsiteChristie Library and Knowledge Service

    Statistics

    Display statistics

    Tyrosinase-mediated cytotoxicity of 4-substituted phenols: quantitative structure-thiol-reactivity relationships of the derived o-quinones.

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Authors
    Cooksey, C J
    Land, Edward J
    Ramsden, C A
    Riley, P A
    Affiliation
    Department of Chemistry, University College London, UK.
    Issue Date
    1995-03
    
    Metadata
    Show full item record
    Abstract
    Rate constants have been determined for reactions between biologically significant thiols, represented by cysteine and glutathione, and a series of 10 4-substituted o-quinones, and unsubstituted o-quinone itself, generated by rapid disproportionation of the semiquinones formed from the corresponding catechols by pulse radiolysis. The quantitative structure-reactivity relationships were investigated by examining the correlation between the rate constants and various Hammett and other parameters characterizing the electronic nature of the substituents. From these relationships, it can be concluded that the o-quinone reactivity with thiols increases with the electron-withdrawing capacity of the substituent groups and that this effect is principally due to resonance effects. Such relationships allow the prediction of likely reactivities with cellular thiols of further o-quinones whose 4-substituents have known electronic parameters. These reactivities are likely to be one of the critical factors determining overall cytotoxicity, assisting in the choice of improved melanogenesis-targeted anti-melanoma drugs.
    Citation
    Tyrosinase-mediated cytotoxicity of 4-substituted phenols: quantitative structure-thiol-reactivity relationships of the derived o-quinones. 1995, 10 (2):119-29 Anticancer Drug Des.
    Journal
    Anti-Cancer Drug Design
    URI
    http://hdl.handle.net/10541/97498
    PubMed ID
    7710634
    Type
    Article
    Language
    en
    ISSN
    0266-9536
    Collections
    All Paterson Institute for Cancer Research

    entitlement

    Related articles

    • Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: differences between alkylthio- and alkoxy-substituents.
    • Authors: Cooksey CJ, Jimbow K, Land EJ, Riley PA
    • Issue date: 1992 Dec
    • Chemical Reactivities of ortho-Quinones Produced in Living Organisms: Fate of Quinonoid Products Formed by Tyrosinase and Phenoloxidase Action on Phenols and Catechols.
    • Authors: Ito S, Sugumaran M, Wakamatsu K
    • Issue date: 2020 Aug 24
    • Melanogenesis-targeted anti-melanoma pro-drug development: effect of side-chain variations on the cytotoxicity of tyrosinase-generated ortho-quinones in a model screening system.
    • Authors: Riley PA, Cooksey CJ, Johnson CI, Land EJ, Latter AM, Ramsden CA
    • Issue date: 1997 Jan
    • Quinone chemistry and melanogenesis.
    • Authors: Land EJ, Ramsden CA, Riley PA
    • Issue date: 2004
    • The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkylcatechol-induced toxicity in human melanoma cells.
    • Authors: Bolton JL, Pisha E, Shen L, Krol ES, Iverson SL, Huang Z, van Breemen RB, Pezzuto JM
    • Issue date: 1997 Sep 12
    DSpace software (copyright © 2002 - 2025)  DuraSpace
    Quick Guide | Contact Us
    Open Repository is a service operated by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.