Biochemical and Biological Effects of Organotins


by

Alessandra Pagliarani, Fabiana Trombetti, Vittoria Ventrella

DOI: 10.2174/97816080526531120101
eISBN: 978-1-60805-265-3, 2012
ISBN: 978-1-60805-367-4



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Indexed in: Chemical Abstracts, Scopus

Organotins are widespread contaminants especially of water environments. Their chemically versatile structure makes organotin compound...[view complete introduction]

Table of Contents

Foreword

- Pp. i

Giorgio Lenaz

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Preface

- Pp. ii-iii (2)

Alessandra Pagliarani, Fabiana Trombetti and Vittoria Ventrella

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List of Contributors

- Pp. iv-vi (3)

Alessandra Pagliarani, Fabiana Trombetti and Vittoria Ventrella

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Abbreviations of Organotin Compounds

- Pp. vii-viii (2)

Alessandra Pagliarani, Fabiana Trombetti and Vittoria Ventrella

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Ecotoxicological Impacts of Organotins: An Overview

- Pp. 3-24 (22)

Toshihiro Horiguchi

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Biological Activity of Organotin(IV) Compounds: Structural and Chemical Aspects

- Pp. 25-52 (28)

Laszlo Nagy, Claudia Pellerito and Lorenzo Pellerito

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Covalent Interactions of Organotins with Nuclear Receptors

- Pp. 53-69 (17)

Felix Grun

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Biomembrane Perturbation Induced by Organotin in Model and Biological Membranes

- Pp. 70-74 (5)

Giancarlo Falcioni

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Organotins as Endocrine Disruptors: An Examination of Tributyltin-Induced Imposex in Neogastropods

- Pp. 75-82 (8)

Robin M Sternberg

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Lipid Homeostasis Perturbation by Organotins: Effects on Vertebrates and Invertebrates

- Pp. 83-96 (14)

Miguel Machado Santos, Maria Armanda Reis-Henriques and Luis Filipe Costa Castro

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Genotoxicity and Immunotoxicity of Organotins

- Pp. 97-111 (15)

Francesca Cima and Loriano Ballarin

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Organotins as Mitochondrial Toxins

- Pp. 112-124 (13)

Sabrina Manente, Alessandra Iero and Marcantonio Bragadin

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Organotins and Hydromineral Homeostasis in Aquatic Animals

- Pp. 125-148 (24)

Mark G.J. Hartl

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Mechanisms of Organotin-Induced Apoptosis

- Pp. 149-163 (15)

Zeljko Jaksic

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Organotins and Humans: Threat and Risk

- Pp. 164-173 (10)

Asha Giriyan and Sangeeta Sonak

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Organotin Effects in Different Phyla: Discrepancies and Similarities

- Pp. 174-196 (23)

Alessandra Pagliarani, Salvatore Nesci, Fabiana Trombetti and Vittoria Ventrella

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Index

- Pp. 197-204 (8)

Alessandra Pagliarani, Fabiana Trombetti and Vittoria Ventrella

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Foreword

The book “Biochemical and biological effects of organotins” represents a due contribution and fills a gap in the scientific literature on environmental contaminants. Organotins are widespread contaminants, especially of water environments. Their chemically versatile structures make organotin compounds able to bind to a variety of biomolecules, thus widely affecting biological functions. Especially trisubstituted species, namely tributyltin and triphenyltin, widely employed in the past, in antifouling paints and still employed as plastic stabilizers, display unwanted harmful effects. Even if increasingly banned by European and non-European governments, due to their persistency and bioaccumulation, organotins still represent a global threat of unpredictable duration. The lipophilicity of the organic moiety not only favours organotin bioaccumulation in animal tissues but also facilitates their crossing plasma membranes and entering the cytoplasm. Once embedded in membrane lipid bilayers, organotins can act both at the plasma-membrane level and intracellularly by disrupting processes depending on compartmentalization. In its 12 chapters written by experts in their respective fields, this book unravels the chemical properties and the biological and biochemical effects of organotins by a careful analysis of the most recent findings, with special focus on contaminant action mechanisms at cellular and molecular level in a variety of different organisms, including humans. The various hypothesized mechanisms at the cellular and molecular level are deeply reviewed in order to provide a quite exhaustive pattern of organotin toxicity as well as of their potential beneficial or therapeutic use. Such a comprehensive review on organotins was deeply needed: besides furnishing an up-dated and excellent overview of organotin effects, the book provides a intriguing insight into the molecular mechanism involved, thus representing a unique tool to biochemists, biologists, ecotoxicologists and life science students and researchers.

Giorgio Lenaz, MD
Professor of Biochemistry
University of Bologna, Italy


Preface

From the synthesis of the first organotin, in mid nineteenth century, and the amazing discovery of a wide spectrum of exploitations and industrial uses of these man-made chemicals in the subsequent century, the dark side of organotins increasingly came out in the second half of the twentieth century. Organotins now represent a matter of environmental concerns, for the toxic effects displayed on a wide spectrum of organisms, from bacteria to humans, and for the global contamination, especially of water basins which act as reservoirs. Unfortunately, but realistically, contamination and worries are fated to persist, due to the environmental persistency and high bioaccumulation potential of these pollutants. In spite of the wealth of studies, the intimate mechanisms of the toxic action of organotin compounds are not entirely established and our knowledge needs to be continuously reviewed and updated. This e-book aims at gathering the emerging data on organotin effects on animals, with special focus on their biochemical interactions with biomolecules, on which toxicity mechanisms are often founded. Chapter by chapter, the biological and biochemical effects of organotins are unravelled by a careful analysis of the most recent findings, paying special attention to the contaminant action mechanisms at cellular and molecular level.

In the first chapter, the legislation on organotin-based antifouling paints and organotin contamination levels of aquatic environments are carefully reviewed. Special attention is paid to the most known toxic effect, namely imposex, which is a irreversible superimposition of male-type genitalia in female gastropod mollusks. Imposex mirrors environmental concentrations of the most toxic organotins.

The structural and chemical properties of toxic organotin compounds are carefully examined in Chapter 2, with special focus on their biological and pharmacological activities.

In Chapter 3 the recent discovery of direct high affinity interactions between trialkyltins and the family of nuclear hormone receptors which function as ligand dependent transcription factors for lipophilic endocrine hormones in vertebrates and invertebrates is presented.

Studies on the interactions of organotins with model and natural biological membranes are reported in Chapter 4.

The ability of organotins to act as endocrine-disrupting chemicals is considered in Chapter 5, focusing on TBT- induced imposex in neogastropods.

Chapter 6 embraces the most recent knowledge on the molecular and biochemical mechanisms involved in lipid homeostasis disruption within several metazoan phyla, from mollusks to amphibians, teleosts and mammals.

In Chapter 7 the organotin-driven genotoxicity and immunotoxicity, which among toxic effects are the most important in affecting survival, are reviewed in mammals, fish and aquatic invertebrates.

Effects on mitochondria, one of the main targets of organotins are considered in Chapter 8. The impairment of mitochondrial functions and the consequent ATP synthesis depletion may play a crucial role as molecular basis of several toxic effects of organotins.

Chapter 9 reviews the impact of organotin exposure on fresh- and seawater organisms of various phyla by examining the histophathological, physiological and molecular interactions of organotin compounds with relevant enzymes, membranes, the endocrine system, and the consequential ramifications for individuals, populations and community structure in aquatic ecosystems.

Recent research on the mechanisms of organotin-induced apoptosis is reviewed in Chapter 10. The modulation of apoptosis, involved in ontogenesis, development and cell turnover, is a critical step of cellular toxicity.

Chapter 11 reviews the impacts of organotins on humans and presents major applications of organotins, their entry in the food chain, human exposure and effects of organotins.

Once overviewed the broad susceptibility to organotins in literature data, Chapter 12 underlines the astonishing analogies of the toxic action of these chemicals in animal kingdom on one hand and on the other, the variegated toxicity displayed in different cells, tissues and species.

The long work to combine different competences as well as the complementary approach to intersecting topics mirror different standpoints and skills and provide an updated knowledge on organotin toxicity mechanisms, other than a significant contribution to detect the directions in which current research on organotins is moving. We want to dedicate this e-book in the memory of our unforgotten biochemist Prof. Romano Viviani, who taught us that biochemistry can be a helpful tool to understand biological phoenomena. Preparing this e-book was a sort of collective adventure which gave us the opportunity to increase our reciprocal knowledge. We are most grateful to all contributors for their competent efforts and patience in the editing process. We would like to thank Prof Giorgio Lenaz for writing the foreword, and, last but not least, Bentham Science Publishers, particularly the Assistant Manager Asma Ahmed, for the continuous assistance and support.

List of Contributors

Editor(s):
Alessandra Pagliarani
Department of Veterinary Medical Sciences
University of Bologna
Italy


Fabiana Trombetti
Department of Veterinary Medical Sciences
University of Bologna
Italy


Vittoria Ventrella
Department of Veterinary Medical Sciences
University of Bologna
Italy




Contributor(s):
Ballarin Loriano
Department of Biology
University of Padova
Via U.Bassi 58/ B
Padova, 35121
Italy


Bragadin Marcantonio
Department of Environmental Sciences
Cà Foscari University
Calle Larga S. Marta 2137
Dorsoduro
Venice, 30123
Italy


Costa Castro Luis Filipe
Interdisciplinary Centre of Marine and Environmental Research
University of Porto
Rua dos Bragas 289
Porto, 4050-123
Portugal


Cima Francesca
Department of Biology
University of Padova
Via U.Bassi 58/ B
Padova, 35121
Italy


Falcioni Giancarlo
School of Pharmacy and Health Products
University of Camerino
Camerino
MC, 62032
Italy


Giriyan Asha
The Energy and Resources Institute (TERI)
Western Regional Centre
Bambolim – Goa
India


Grün Felix
Center for Complex Biological Systems
University of California
Irvine
California, 92697-2300
US


Hartl Mark
Centre for Marine Biodiversity and Biotechnology
School of Life Sciences
Heriot-Watt University Riccarton
EH14 4AS Edinburgh
Scotland
UK


Horiguchi Toshihiro
Center for Environmental Risk Research
National Institute for Environmental Studies 16-2
Onogawa
Tsukuba
Ibaraki, 305-8506
Japan


Iero Alessandra
Institute of Applied Ecology
Health Science and Design
University of Camberra
Bruce
ACT, 2601
Australia


Jakšić Željko
Ruđer Bošković Institute
Center for Marine Research G. Paliage 5
Rovinj, 52210
Croati


Manente Sabrina
Department of Environmental Sciences
Cà Foscari University
Calle Larga S. Marta 2137
Dorsoduro
Venezia, 30123
Italy


Nagy László
Department of Inorganic and Analytical Chemistry
University of Szeged
H-6701, P.O. Box 440
Szeged
Hungary


Nesci Salvatore
Department of Biochemistry “G. Moruzzi”
University of Bologna
via Tolara di Sopra 50
Ozzano Emilia
BO, 40064
Italy


Pagliarani Alessandra
Department of Veterinary Medical Sciences
University of Bologna
via Tolara di Sopra 50
Ozzano Emilia
BO, 40064
Italy


Pellerito Claudia
Department of Analytic and Inorganic Chemistry "Stanislao Cannizzaro"
University of Palermo
Viale delle Scienze
Parco d’, Orleans, 90128
Italy


Pellerito Lorenzo
Department of Analytic and Inorganic Chemistry "Stanislao Cannizzaro"
University of Palermo
Viale delle Scienze
Parco d’Orleans
Palermo, 90128
Italy


Reis-Henriques Maria Armanda
CIMAR/CIIMAR, Interdisciplinary Centre of Marine and Environmental Research
University of Porto
Rua dos Bragas 289
Porto, 4050-123
Portugal


Sonak Sangeeta
Centre for Natural Resource Management, Srujan
A-G/26, Kamat Arcade
Caranzalem
Goa, 403002
India


Santos Miguel Machado
CIMAR/CIIMAR, Interdisciplinary Centre of Marine and Environmental Research
Laboratory of Environmental Toxicology, University of Porto
Rua dos Bragas 289
Porto, 4050-123
Portugal


Sternberg Robin Michelle
United States Environmental Protection Agency
Office of Chemical Safety and Pollution Prevention Office of Science Coordination and Policy
1200 Pennsylvania Ave. NW (7203M)
Washington, DC, 20460



Trombetti Fabiana
Department of Veterinary Medical Sciences
University of Bologna
via Tolara di Sopra 50
Ozzano Emilia
BO, 40064
Italy


Ventrella Vittoria
Department of Veterinary Medical Sciences
University of Bologna
via Tolara di Sopra 50
Ozzano Emilia
BO, 40064
Italy




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