Biochemical and Biological Effects of Organotins

Organotins as Mitochondrial Toxins

Author(s): Sabrina Manente, Alessandra Iero and Marcantonio Bragadin

Pp: 112-124 (13)

DOI: 10.2174/978160805265311201010112

* (Excluding Mailing and Handling)

Abstract

In vitro toxicity, molecular study of the toxicity mechanisms, which should account for the observed in vivo effects of toxic compounds, is a complicate issue. The study of organotin compounds is particularly complicate, since organotins, being chemically versatile, are able to bind covalently and non-covalently to many biomolecules; also organotins are soluble in lipophilic environments and can affect a wide variety of biological functions. Therefore, it is difficult to identify the biological mechanism and the molecular target inhibited by the lowest effective dose. In the interactions of organotin compounds with mitochondria, the problem is “simplified” since many organotins cause in vivo acute toxicity. Being mitochondria the energy source of the cell, mitochondrial impairment induces cell damage; therefore, in many cases, mitochondria are the molecular target responsible for the in vivo acute toxicity. On these bases, ATP synthesis mechanism in mitochondria should be carefully analysed, in order to individuate the step(s) inhibited by the toxic compounds. Many organotin effects on the mitochondrial functions are correlated with the ATP synthesis inhibition. In isolated mitochondria, the (alkyl)3-Sn- compounds inhibit all the steps involved in the ATP synthesis mechanism, but experiments performed in isolated cells suggest that the mitochondrial ATP synthesis inhibition is probably related to the opening of the membrane permeability transition pore. In addition, also triphenyltin opens the permeability transition pore and triggers apoptosis. Other putative and proven mechanisms of organotin action in mitochondria are considered in detail.


Keywords: Organotin - mitochondria - membrane permeability transition pore (MPTP) - protonophores - ATP synthesis inhibition - mitochondrial respiratory chain (MRC).

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      • 13. app/Models/UserAccess/UserAccess.php:1266
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      • 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 <= 59857113 and j.to_ip >=59857113 )) and ((j.from_date <= 1740676952 and j.to_date >= 1740676952 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 56) 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 <= 59857113 and j.to_ip >=59857113 )) and ((j.from_date <= 1740676952 and j.to_date >= 1740676952 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 56) 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 <= 59857113 and j.to_ip >=59857113 )) and ((j.from_date <= 1740676952 and j.to_date >= 1740676952 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 56)
      530μsalphaeurekaselec_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` <= 1740676952 and `b`.`banner_to_date` >= 1740676952 and `b`.`banner_status` = 'A' order by `b`.`banner_id` desc
      1.03msalphaeurekaselec_live_10_06_2022Banner.php#95
      Bindings
      • 0: 1
      • 1: B
      • 2: 797
      • 3: 1740676952
      • 4: 1740676952
      • 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='6f3bd19d4c142abfe45cff0bd48ca6f7'
      210μsalphaeurekaselec_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
        LNNLQMlbUZZifQuiPKBTkXgd7sxVvRz5KwwdQlmG
        uc_cart_id
        6f3bd19d4c142abfe45cff0bd48ca6f7
        _previous
        array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/56" ]
        _flash
        array:2 [ "old" => [] "new" => [] ]
        PHPDEBUGBAR_STACK_DATA
        []
        path_info
        /chapter/56
        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:17 [ "x-https" => array:1 [ 0 => "1" ] "host" => array:1 [ 0 => "alpha.eurekaselect.com" ] "priority" => array:1 [ 0 => "u=0, i" ] "cookie" => array:1 [ 0 => "wayfindertarget=eyJpdiI6InZnUUZGeHczRDlQdXNJQVc2cXZRZ1E9PSIsInZhbHVlIjoiaGcxUGFEdUJESjdCQ0JuYW1xMnl2bmdHeTVSc25ycU4wTDJIVFpRclZBYz0iLCJtYWMiOiI3NGQzODZkODViMDIwYjg2NTYxYThhZDg4ZTkxNDVmYmYyYWM0YjFhMWM1MDg3MmY0MmQ5YTMwM2FiOGVmZTJhIiwidGFnIjoiIn0%3Dwayfindertarget=eyJpdiI6InZnUUZGeHczRDlQdXNJQVc2cXZRZ1E9PSIsInZhbHVlIjoiaGcxUGFEdUJESjdCQ0JuYW1xMnl2bmdHeTVSc25ycU4wTDJIVFpRclZBYz0iLCJtYWMiOiI3NGQzODZkODViMDIw" ] "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
        0 of 0
        array:1 [ "wayfindertarget" => null ]
        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 17:22:32 GMT" ] "set-cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IjhSdHdRVEZxZUg2NlZpWjhmK3lSVnc9PSIsInZhbHVlIjoiQWthSE9KbFhOQy91RDlmUFgyb3NkT0tsZXMxU21kTWY1WUd5WUQ2NXo0aFcxakFRcVlMZlZKcnF6bjdPWnFUVC9kTStCZ2lrQWJHK1M1TEcvcXFHc0psSU1rRnVZa1pvQXdyeEMveWxreGFJd1ZhTXQ5VlI5eHVyQ2dOSWg0UTYiLCJtYWMiOiIyYTY3NTQ3N2I1Yzc4NDRlMjMyZTUzNzI4MDI2NmQzNmNhZDg2NTUxNDUyNTZlODk3ZWMzMGIxMjU2M2JlZDhkIiwidGFnIjoiIn0%3D; expires=Sun, 02 Mar 2025 05:22:32 GMT; Max-Age=216000; path=/; secure; samesite=laxXSRF-TOKEN=eyJpdiI6IjhSdHdRVEZxZUg2NlZpWjhmK3lSVnc9PSIsInZhbHVlIjoiQWthSE9KbFhOQy91RDlmUFgyb3NkT0tsZXMxU21kTWY1WUd5WUQ2NXo0aFcxakFRcVlMZlZKcnF6bjdPWnFUVC9kTStCZ" 1 => "alphaeurekaselectnet_session=eyJpdiI6IjhHeFJhZStQSWU4ek4xbGgxb01lcUE9PSIsInZhbHVlIjoiL2FWTE5vUHRBSlIwVUlTMEdGNXJSOVRuZkdoMEdFekdrR0pQMDR3eHhzWjJ2cndjQzdkM1UzbzhINHVOTzBXeGxCbTRFNi93bkN0ajJIM04wcXFMS3pHQzBQeG84NE9rSnN4SUtDUWE1NXA5aktsdnEyaDI0TERMUGFmcHFTK2IiLCJtYWMiOiI0OGQ5YWZhODBhNGRmMjY1ZmVjZjg0Mzc0ZTgxZmM2YjQzMDAwNTNlMmU0OGU1MDdhNjc0NzRmZWM5ZjllODI1IiwidGFnIjoiIn0%3D; path=/; secure; httponly; samesite=laxalphaeurekaselectnet_session=eyJpdiI6IjhHeFJhZStQSWU4ek4xbGgxb01lcUE9PSIsInZhbHVlIjoiL2FWTE5vUHRBSlIwVUlTMEdGNXJSOVRuZkdoMEdFekdrR0pQMDR3eHhzWjJ2cndjQzdkM1Uzbzh" ] "Set-Cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6IjhSdHdRVEZxZUg2NlZpWjhmK3lSVnc9PSIsInZhbHVlIjoiQWthSE9KbFhOQy91RDlmUFgyb3NkT0tsZXMxU21kTWY1WUd5WUQ2NXo0aFcxakFRcVlMZlZKcnF6bjdPWnFUVC9kTStCZ2lrQWJHK1M1TEcvcXFHc0psSU1rRnVZa1pvQXdyeEMveWxreGFJd1ZhTXQ5VlI5eHVyQ2dOSWg0UTYiLCJtYWMiOiIyYTY3NTQ3N2I1Yzc4NDRlMjMyZTUzNzI4MDI2NmQzNmNhZDg2NTUxNDUyNTZlODk3ZWMzMGIxMjU2M2JlZDhkIiwidGFnIjoiIn0%3D; expires=Sun, 02-Mar-2025 05:22:32 GMT; path=/; secureXSRF-TOKEN=eyJpdiI6IjhSdHdRVEZxZUg2NlZpWjhmK3lSVnc9PSIsInZhbHVlIjoiQWthSE9KbFhOQy91RDlmUFgyb3NkT0tsZXMxU21kTWY1WUd5WUQ2NXo0aFcxakFRcVlMZlZKcnF6bjdPWnFUVC9kTStCZ" 1 => "alphaeurekaselectnet_session=eyJpdiI6IjhHeFJhZStQSWU4ek4xbGgxb01lcUE9PSIsInZhbHVlIjoiL2FWTE5vUHRBSlIwVUlTMEdGNXJSOVRuZkdoMEdFekdrR0pQMDR3eHhzWjJ2cndjQzdkM1UzbzhINHVOTzBXeGxCbTRFNi93bkN0ajJIM04wcXFMS3pHQzBQeG84NE9rSnN4SUtDUWE1NXA5aktsdnEyaDI0TERMUGFmcHFTK2IiLCJtYWMiOiI0OGQ5YWZhODBhNGRmMjY1ZmVjZjg0Mzc0ZTgxZmM2YjQzMDAwNTNlMmU0OGU1MDdhNjc0NzRmZWM5ZjllODI1IiwidGFnIjoiIn0%3D; path=/; secure; httponlyalphaeurekaselectnet_session=eyJpdiI6IjhHeFJhZStQSWU4ek4xbGgxb01lcUE9PSIsInZhbHVlIjoiL2FWTE5vUHRBSlIwVUlTMEdGNXJSOVRuZkdoMEdFekdrR0pQMDR3eHhzWjJ2cndjQzdkM1Uzbzh" ] ]
        session_attributes
        0 of 0
        array:5 [ "_token" => "LNNLQMlbUZZifQuiPKBTkXgd7sxVvRz5KwwdQlmG" "uc_cart_id" => "6f3bd19d4c142abfe45cff0bd48ca6f7" "_previous" => array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/56" ] "_flash" => array:2 [ "old" => [] "new" => [] ] "PHPDEBUGBAR_STACK_DATA" => [] ]
        ClearShow all
        Date ↕MethodURLData
        #12025-02-27 17:22:32GET/chapter/56112193