Biochemical and Biological Effects of Organotins

Covalent Interactions of Organotins with Nuclear Receptors

Author(s): Felix Grun

Pp: 53-69 (17)

DOI: 10.2174/978160805265311201010053

* (Excluding Mailing and Handling)

Abstract

Organotins are widely distributed environmental contaminants with potent toxicity phenotypes and established endocrine disrupting properties in diverse species and ecosystems. Of particular interest has been the recent discovery of direct high affinity interactions between trialkyltins, such as tributyltin chloride (TBT), and the family of nuclear hormone receptors (NRs) which function as ligand dependent transcription factors for a diverse set of lipophilic endocrine hormones in vertebrates and invertebrates. Perturbed NR activity can provide a direct molecular link between environmental organotin exposure and their endocrine disrupting effects. The ability of organotins to activate NRs is surprising since they share neither structural characteristics with the endogenous steroidal or lipophilic hormone ligands nor classical modes of binding. Instead, crystallographic and mass spectroscopic data for the retinoid X receptor alpha (RXRα) shows a covalent interaction between TBT or TPhT and a critical receptor cysteine residue (C432) at the entrance to the ligand binding pocket. Therefore, covalent interactions between organotins and reactive cysteines residues, as also observed with stannin and predicted for aromatase, appears to be an emerging theme for modifying protein function in eliciting organotin toxicity. The stoichiometric modification of nuclear receptor activity, especially of RXRs that heterodimerize with a broad subset of NRs, has profound implications for assessment of organotin toxicity in organismal physiology particularly with respect to invertebrate imposex phenotypes and vertebrate metabolic integration of energy homeostasis. It is likely that additional nuclear receptors and proteins will be identified that are sensitive to organotin covalent modification.


Keywords: Nuclear receptors - RXR-PPARγ - tributyltin - covalent modification - reactive cysteines -obesogen.

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      • 11. app/Models/ContentAccess.php:647
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      • 13. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
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      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1518
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Trial Access" as access_base_text, CASE j.type WHEN 111 THEN true ELSE false END as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_trail` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 314566706 and j.to_ip >=314566706 )) and ((j.from_date <= 1740676191 and j.to_date >= 1740676191 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 51) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Subscribed" as access_base_text, false as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_corporate` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 314566706 and j.to_ip >=314566706 )) and ((j.from_date <= 1740676191 and j.to_date >= 1740676191 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 51) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Token Based Access" as access_base_text, false as terms_popup, "R" as content_download_type, j.uc_id as restricted_user_access_key, "v" as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_token` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 314566706 and j.to_ip >=314566706 )) and ((j.from_date <= 1740676191 and j.to_date >= 1740676191 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 51)
      720μsalphaeurekaselec_live_10_06_2022UserAccess.php#1266
      Backtrace
      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1549
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select b.banner_link, b.banner_name, b.banner_script, b.banner_remarks, b.banner_file_name, b.banner_placement, bd.content_type, bd.content_id from `tbl_banner` as `b` inner join `tbl_banner_detail` as `bd` on `bd`.`banner_id` = `b`.`banner_id` inner join `users` as `u` on `u`.`id` = `b`.`updated_by` where `b`.`banner_ebook` = 1 and `bd`.`content_type` = 'B' and `bd`.`content_id` = 797 and `b`.`banner_from_date` <= 1740676191 and `b`.`banner_to_date` >= 1740676191 and `b`.`banner_status` = 'A' order by `b`.`banner_id` desc
      1.1msalphaeurekaselec_live_10_06_2022Banner.php#95
      Bindings
      • 0: 1
      • 1: B
      • 2: 797
      • 3: 1740676191
      • 4: 1740676191
      • 5: A
      Backtrace
      • 13. app/Models/Banner.php:95
      • 14. app/Http/helpers.php:404
      • 17. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 18. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    • select count(*) as aggregate from `uc_cart_products` where cart_id='d92900108e25a74a0769037ff7f333c1'
      270μsalphaeurekaselec_live_10_06_2022Cart.php#271
      Backtrace
      • 15. app/Models/Cart.php:271
      • 16. view::layouts._header:260
      • 18. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 20. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    App\Models\Chapter
    1Chapter.php#?
    App\Models\Keywords
    1Keywords.php#?
    App\Models\Ebook
    1Ebook.php#?
        _token
        fCyoO7JIgRqq3sKAoXaR7nGzMq7H4MhUSFhN7txZ
        uc_cart_id
        d92900108e25a74a0769037ff7f333c1
        _previous
        array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/51" ]
        _flash
        array:2 [ "old" => [] "new" => [] ]
        PHPDEBUGBAR_STACK_DATA
        []
        path_info
        /chapter/51
        status_code
        200
        
        status_text
        OK
        format
        html
        content_type
        text/html; charset=UTF-8
        request_query
        []
        
        request_request
        []
        
        request_headers
        0 of 0
        array:16 [ "x-https" => array:1 [ 0 => "1" ] "host" => array:1 [ 0 => "alpha.eurekaselect.com" ] "priority" => array:1 [ 0 => "u=0, i" ] "accept-encoding" => array:1 [ 0 => "gzip, deflate, br, zstd" ] "sec-fetch-dest" => array:1 [ 0 => "document" ] "sec-fetch-user" => array:1 [ 0 => "?1" ] "sec-fetch-mode" => array:1 [ 0 => "navigate" ] "sec-fetch-site" => array:1 [ 0 => "none" ] "accept" => array:1 [ 0 => "text/html,application/xhtml+xml,application/xml;q=0.9,image/avif,image/webp,image/apng,*/*;q=0.8,application/signed-exchange;v=b3;q=0.7" ] "user-agent" => array:1 [ 0 => "Mozilla/5.0 AppleWebKit/537.36 (KHTML, like Gecko; compatible; ClaudeBot/1.0; +claudebot@anthropic.com)" ] "upgrade-insecure-requests" => array:1 [ 0 => "1" ] "sec-ch-ua-platform" => array:1 [ 0 => ""Windows"" ] "sec-ch-ua-mobile" => array:1 [ 0 => "?0" ] "sec-ch-ua" => array:1 [ 0 => ""HeadlessChrome";v="129", "Not=A?Brand";v="8", "Chromium";v="129"" ] "cache-control" => array:1 [ 0 => "no-cache" ] "pragma" => array:1 [ 0 => "no-cache" ] ]
        request_cookies
        []
        
        response_headers
        0 of 0
        array:5 [ "content-type" => array:1 [ 0 => "text/html; charset=UTF-8" ] "cache-control" => array:1 [ 0 => "no-cache, private" ] "date" => array:1 [ 0 => "Thu, 27 Feb 2025 17:09:51 GMT" ] "set-cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IkJkZmxDa0xmMzZxaHFiODFxZ1JVdmc9PSIsInZhbHVlIjoiMHBGUFZVL1dMN29mY1p6RHJ5dHpGeWhDL3NrTnhvaFBibzRWd2VQdmt1eTI4WU01cDVaenE3TllkdjVOeENxdkR3bzFhblBkYWhrc1RkMHBWcUxzM2N0RENHelE3R2dZQVZpR3ZTeFk2ZW54NlY4blJaZWJrekRMVVB0ZkNRSkkiLCJtYWMiOiI2YmQxMGVhODdkNjRiYjNlZDA4NzhkYzcyOGM3MWVjYTIxNzBjZjdjZDc0OGEzY2UyOWIxY2QxMTE5OGFkNDljIiwidGFnIjoiIn0%3D; expires=Sun, 02 Mar 2025 05:09:51 GMT; Max-Age=216000; path=/; secure; samesite=laxXSRF-TOKEN=eyJpdiI6IkJkZmxDa0xmMzZxaHFiODFxZ1JVdmc9PSIsInZhbHVlIjoiMHBGUFZVL1dMN29mY1p6RHJ5dHpGeWhDL3NrTnhvaFBibzRWd2VQdmt1eTI4WU01cDVaenE3TllkdjVOeENxdkR3bzFhb" 1 => "alphaeurekaselectnet_session=eyJpdiI6InZQZVRvWlZoTHpSNUdJZHZiUVkyalE9PSIsInZhbHVlIjoiZWZRQ04rc2hvc0IrcGJCOG1CMXlKc0Z4OE9iUHZsOGxUOFhlbE5FVldrdUlZeEJzdU1iOTBmZU90N0VNcmxkNXlzNlJhMlR6empWNGdmWG1INGM0VEkvbTJXQmR3NDdnRGJoVGNwT2l3MG9tVXo3N09kS21jc0YrM3ZuUHhNaXoiLCJtYWMiOiIyYWRmZjYzY2M4M2M1ZjRmMDdhNmYzOWZjMDE4NGRjM2E4ZTcwZDZiMjIxOWRiZWRiMWExZDQ1NTI5ZmI3YWU0IiwidGFnIjoiIn0%3D; path=/; secure; httponly; samesite=laxalphaeurekaselectnet_session=eyJpdiI6InZQZVRvWlZoTHpSNUdJZHZiUVkyalE9PSIsInZhbHVlIjoiZWZRQ04rc2hvc0IrcGJCOG1CMXlKc0Z4OE9iUHZsOGxUOFhlbE5FVldrdUlZeEJzdU1iOTBmZU9" ] "Set-Cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IkJkZmxDa0xmMzZxaHFiODFxZ1JVdmc9PSIsInZhbHVlIjoiMHBGUFZVL1dMN29mY1p6RHJ5dHpGeWhDL3NrTnhvaFBibzRWd2VQdmt1eTI4WU01cDVaenE3TllkdjVOeENxdkR3bzFhblBkYWhrc1RkMHBWcUxzM2N0RENHelE3R2dZQVZpR3ZTeFk2ZW54NlY4blJaZWJrekRMVVB0ZkNRSkkiLCJtYWMiOiI2YmQxMGVhODdkNjRiYjNlZDA4NzhkYzcyOGM3MWVjYTIxNzBjZjdjZDc0OGEzY2UyOWIxY2QxMTE5OGFkNDljIiwidGFnIjoiIn0%3D; expires=Sun, 02-Mar-2025 05:09:51 GMT; path=/; secureXSRF-TOKEN=eyJpdiI6IkJkZmxDa0xmMzZxaHFiODFxZ1JVdmc9PSIsInZhbHVlIjoiMHBGUFZVL1dMN29mY1p6RHJ5dHpGeWhDL3NrTnhvaFBibzRWd2VQdmt1eTI4WU01cDVaenE3TllkdjVOeENxdkR3bzFhb" 1 => "alphaeurekaselectnet_session=eyJpdiI6InZQZVRvWlZoTHpSNUdJZHZiUVkyalE9PSIsInZhbHVlIjoiZWZRQ04rc2hvc0IrcGJCOG1CMXlKc0Z4OE9iUHZsOGxUOFhlbE5FVldrdUlZeEJzdU1iOTBmZU90N0VNcmxkNXlzNlJhMlR6empWNGdmWG1INGM0VEkvbTJXQmR3NDdnRGJoVGNwT2l3MG9tVXo3N09kS21jc0YrM3ZuUHhNaXoiLCJtYWMiOiIyYWRmZjYzY2M4M2M1ZjRmMDdhNmYzOWZjMDE4NGRjM2E4ZTcwZDZiMjIxOWRiZWRiMWExZDQ1NTI5ZmI3YWU0IiwidGFnIjoiIn0%3D; path=/; secure; httponlyalphaeurekaselectnet_session=eyJpdiI6InZQZVRvWlZoTHpSNUdJZHZiUVkyalE9PSIsInZhbHVlIjoiZWZRQ04rc2hvc0IrcGJCOG1CMXlKc0Z4OE9iUHZsOGxUOFhlbE5FVldrdUlZeEJzdU1iOTBmZU9" ] ]
        session_attributes
        0 of 0
        array:5 [ "_token" => "fCyoO7JIgRqq3sKAoXaR7nGzMq7H4MhUSFhN7txZ" "uc_cart_id" => "d92900108e25a74a0769037ff7f333c1" "_previous" => array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/51" ] "_flash" => array:2 [ "old" => [] "new" => [] ] "PHPDEBUGBAR_STACK_DATA" => [] ]
        ClearShow all
        Date ↕MethodURLData
        #12025-02-27 17:09:51GET/chapter/51112193