Abstract
Dithiocarbamates are highly versatile mono-anionic chelating ligands which form stable complexes with all the transition elements and also the majority of main group, lanthanide and actinide elements. They are easily prepared from primary or secondary amines and depending upon the nature of the cation can show good solubility in water or organic solvents. They are related to the thiuram disulfides by a one-electron redox process (followed by dimerisation via sulfursulfur bond formation) which is easily carried out upon addition of iodide or ferric salts. Dithiocarbamates are lipophilic and generally bind to metals in a symmetrical chelate fashion but examples of other coordination modes are known, the monodentate and anisobidentate modes being most prevalent. They are planar sterically non-demanding ligands which can be electronically tuned by judicious choice of substituents. They stabilize metals in a wide range of oxidation states, this being attributed to the existence of soft dithiocarbamate and hard thioureide resonance forms, the latter formally resulting from delocalization of the nitrogen lone pair onto the sulfurs, and consequently their complexes tend to have a rich electrochemistry. Tetraethyl thiuramdisulfide (disulfiram or antabuse) has been used as a drug since the 1950s but it is only recently that dithiocarbamate complexes have been explored within the medicinal domain. Over the past two decades anti-cancer activity has been noted for gold and copper complexes, technetium and copper complexes have been used in PET-imaging, dithiocarbamates have been used to treat acute cadmium poisoning and copper complexes also have been investigated as SOD inhibitors.
Keywords: Anti-cancer, chelator, dithiocarbamate, metal complexes, thioureide, lipophilic.
Mini-Reviews in Medicinal Chemistry
Title:Metal-dithiocarbamate complexes: chemistry and biological activity
Volume: 12 Issue: 12
Author(s): Graeme Hogarth
Affiliation:
Keywords: Anti-cancer, chelator, dithiocarbamate, metal complexes, thioureide, lipophilic.
Abstract: Dithiocarbamates are highly versatile mono-anionic chelating ligands which form stable complexes with all the transition elements and also the majority of main group, lanthanide and actinide elements. They are easily prepared from primary or secondary amines and depending upon the nature of the cation can show good solubility in water or organic solvents. They are related to the thiuram disulfides by a one-electron redox process (followed by dimerisation via sulfursulfur bond formation) which is easily carried out upon addition of iodide or ferric salts. Dithiocarbamates are lipophilic and generally bind to metals in a symmetrical chelate fashion but examples of other coordination modes are known, the monodentate and anisobidentate modes being most prevalent. They are planar sterically non-demanding ligands which can be electronically tuned by judicious choice of substituents. They stabilize metals in a wide range of oxidation states, this being attributed to the existence of soft dithiocarbamate and hard thioureide resonance forms, the latter formally resulting from delocalization of the nitrogen lone pair onto the sulfurs, and consequently their complexes tend to have a rich electrochemistry. Tetraethyl thiuramdisulfide (disulfiram or antabuse) has been used as a drug since the 1950s but it is only recently that dithiocarbamate complexes have been explored within the medicinal domain. Over the past two decades anti-cancer activity has been noted for gold and copper complexes, technetium and copper complexes have been used in PET-imaging, dithiocarbamates have been used to treat acute cadmium poisoning and copper complexes also have been investigated as SOD inhibitors.
Export Options
About this article
Cite this article as:
Hogarth Graeme, Metal-dithiocarbamate complexes: chemistry and biological activity, Mini-Reviews in Medicinal Chemistry 2012; 12 (12) . https://dx.doi.org/10.2174/138955712802762095
DOI https://dx.doi.org/10.2174/138955712802762095 |
Print ISSN 1389-5575 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5607 |
Call for Papers in Thematic Issues
Bioprospecting of Natural Products as Sources of New Multitarget Therapies
According to the Convention on Biological Diversity, bioprospecting is the exploration of biodiversity and indigenous knowledge to develop commercially valuable products for pharmaceutical and other applications. Bioprospecting involves searching for useful organic compounds in plants, fungi, marine organisms, and microorganisms. Natural products traditionally constituted the primary source of more than ...read more
Computational Frontiers in Medicinal Chemistry
The thematic issue "Computational Frontiers in Medicinal Chemistry" provides a robust platform for delving into state-of-the-art computational methodologies and technologies that significantly propel advancements in medicinal chemistry. This edition seeks to amalgamate top-tier reviews spotlighting the latest trends and breakthroughs in the fusion of computational approaches, including artificial intelligence (AI) ...read more
Natural Products and Dietary Supplements in Alleviation of Metabolic, Cardiovascular, and Neurological Disorders
Metabolic disorders like diabetes, obesity, inflammation, oxidative stress, cancer etc, cardiovascular disorders like angina, myocardial infarction, congestive heart failure etc as well as neurological disorders like Alzheimer?s, Parkinson?s, Epilepsy, Depression, etc are the global burden. They covered the major segment of the diseases and disorders from which the human community ...read more
Natural Products in Drug Discovery
Natural products have always been one of the important ways of drug discovery due to their novel skeleton and diverse functional group characteristics. According to statistics, between 1981 and 2019, the FDA approved a total of 1,394 small molecule drugs for marketing, of which 930 marketed drugs originated from the ...read more
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Hepcidin: Biological Activity, Analytical Methods in Biological Fluids, Clinical Applications and Antagonists. A Short Review
Current Pharmaceutical Analysis Role of the Receptor Tyrosine Kinase Axl and its Targeting in Cancer Cells
Current Medicinal Chemistry Pharmacogenetics of Irinotecan Disposition and Toxicity: A Review
Current Clinical Pharmacology Histone Deacetylase Inhibitors: Recent Insights from Basic to Clinical Knowledge & Patenting of Anti-Cancer Actions
Recent Patents on Anti-Cancer Drug Discovery Dual-target Inhibitors Based on BRD4: Novel Therapeutic Approaches for Cancer
Current Medicinal Chemistry Importance of Kier-Hall Topological Indices in the QSAR of Anticancer Drug Design
Current Computer-Aided Drug Design Facile Synthesis and Biological Evaluation of Novel Symmetrical Biphenyls as Antitumor Agents
Medicinal Chemistry Multiple Roles of Transient Receptor Potential (TRP) Channels in Inflammatory Conditions and Current Status of Drug Development
Current Topics in Medicinal Chemistry BRCA Mutational Status is a Promising Predictive Biomarker for Platinum- based Chemotherapy in Triple-Negative Breast Cancer
Current Drug Targets Nitrogen Containing Privileged Structures and their Solid Phase Combinatorial Synthesis
Combinatorial Chemistry & High Throughput Screening Clinico-Pathologic Function of Cerebral ABC Transporters – Implications for the Pathogenesis of Alzheimers Disease
Current Alzheimer Research Nanocarriers Conjugated with Cell Penetrating Peptides: New Trojan Horses by Modern Ulysses
Current Pharmaceutical Biotechnology Modulation of Gene Transcription by Natural Products - A Viable Anticancer Strategy
Current Pharmaceutical Design Genomic Instability and Carcinogenesis: An Update
Current Genomics Possible Protecting Role of TNF-α in Kainic Acid-induced Neurotoxicity Via Down-Regulation of NFκB Signaling Pathway
Current Alzheimer Research Helical Tomotherapy versus Conventional Technique for Post Mastectomy Left Sided Breast Cancer; Dosimetric Study
Reviews on Recent Clinical Trials Two Branched Polar Groups and Polar Linker Moieties of Thiophene Amide Derivatives Are Essential for MRP2/ABCC2 Recognition
Drug Metabolism Letters Cadherins: The Superfamily Critically Involved in Breast Cancer
Current Pharmaceutical Design Inflammation in Neurodegenerative Disorders: Friend or Foe?
Current Aging Science Smart Mesoporous Silica Nanocarriers for Antitumoral Therapy
Current Topics in Medicinal Chemistry