Ruthenium Complexes
Photochemical and Biomedical Applications
Inbunden, Engelska, 2018
Av Alvin A. Holder, Lothar Lilge, Wesley R. Browne, Mark A.W. Lawrence, Jimmie L. Bullock, The Netherlands) Browne, Wesley R. (University of Groningen
1 919 kr
Produktinformation
- Utgivningsdatum2018-01-10
- Mått175 x 249 x 20 mm
- Vikt816 g
- FormatInbunden
- SpråkEngelska
- Antal sidor344
- FörlagWiley-VCH Verlag GmbH
- ISBN9783527339570
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Alvin A. Holder is an associate professor at Old Dominion University in Norfolk, USA. He graduated from the University of the West Indies (UWI), Mona Campus, Jamaica, with a B.Sc. (special chemistry) in 1989 and acquired his Ph.D. in inorganic chemistry in 1994 with Prof. Tara P. Dasgupta. He was a faculty member at the University of the West Indies, Cave Hill Campus, Barbados, and an assistant professor in chemistry at the University of Southern Mississippi, USA. His current research involves transition metal chemistry and he has published more than 65 articles and several textbooks and book chapters. In 2012, he was awarded a NSF Career Award.Lothar Lilge is a senior scientist at the Princess Margaret Cancer Centre and holds a professorship at the University of Toronto, Canada. He obtained his Diploma in physics from the Johann Wolfgang Goethe University in Frankfurt, Germany, and his Ph.D. degree in biophysics from the Westfaehlische Wilhelms University in Muenster, Germany. Additional training was provided through the Wellman Laboratories of Photomedicine at Massachusetts General Hospital, Boston, USA, and during a post-doc at McMaster University in Hamilton, Canada. His work is focused on photodynamic therapy including the use of ruthenium-based photosensitizers and optical spectroscopy for diagnostic and risk assessment among a range of other biophotonic application in medicine.Wesley R. Browne is an associate professor at Stratingh Institute for Chemistry at the University of Groningen, The Netherlands, since 2013. He completed his Ph.D. degree at Dublin City University, Ireland, with Prof. J. G. Vos in 2002, followed by a postdoc under the joint guidance of Prof. J. G. Vos and Prof. J. J. McGarvey, Queens University Belfast, UK. Between 2003 and 2007 he was a postdoctoral research fellow in the group of Prof. B. L. Feringa at the University of Groningen. He was appointed assistant professor in 2008. His current research interests include transition metal based oxidation catalysis, electrochromic materials and responsive surfaces. He is an advisory board member for the European Journal of Inorganic Chemistry, Particle & Particle Characterization (both Wiley) and Chemical Communications (RSC). He has (co-)authored over 150 research papers, reviews and book chapters.Mark A. W. Lawrence was a post-doctoral fellow at Old Dominion University in Norfolk, USA, in the group of Prof. A. Holder. He received his B.Sc. degree in 2006 and his Ph.D. degree in inorganic-physical chemistry in 2011 from the University of the West Indies (UWI), Mona Campus, Jamaica, with Prof. Tara P. Dasgupta. His research interests include synthesis of hydrazones and functionalized pyridyl benzothiazoles, their transition metal complexes and application to catalysis and biological processes.Jimmie L. Bullock Jr. is a Ph.D. student at the University of Kentucky in Lexington, USA, in the department of Chemistry. He received his B.Sc. degree from Longwood University, Farmville, USA, and his M.S. degree in biological inorganic chemistry from Old Dominion University, Norfolk, USA, in 2013 and 2016, respectively. His research interests include studying activation of signaling pathways induced by non-platinum based chemotherapeutic agents and synthesis of lanthanide sensor molecules.
- About the Editors xvPreface xviiAcknowledgments xixSection I Introduction 11 Karen J. Brewer (1961–2014): A Bright Star that Burned Out Far Too Soon 3Seth C. Rasmussen1.1 Introduction 31.2 Early Years 41.3 Graduate Studies and Clemson University 61.4 Postdoctoral Research and the University of California, Berkeley 111.5 Washington State University: Beginning an Independent Career 131.6 Move to Virginia Tech 151.7 Collaboration with BrendaWinkel and the Study of Metal-DNA Interactions 161.8 A Return to Where It All Started: Photochemical H2 Production 181.9 A Career Cut Tragically Short 191.10 Karen’s Legacy 20Acknowledgments 20References 202 Basic Coordination Chemistry of Ruthenium 25Mark A.W. Lawrence, Jimmie L. Bullock, and Alvin A. Holder2.1 Coordination Chemistry of Ruthenium 252.1.1 The Element 252.1.2 Stereochemistry and Common Oxidation States 262.1.2.1 Ruthenium in Low Oxidation States 272.1.2.2 Chemistry of Ruthenium(II) and (III) 312.1.2.3 Higher Oxidation States of Ruthenium 362.1.3 Conclusion 37References 37Section II Artificial Photosynthesis 433 Water Oxidation Catalysis with Ruthenium 45Andrea Sartorel3.1 Introduction 453.1.1 Energy Issue and Energy from the Sun 453.1.2 Photosynthesis and Solar Fuels 463.1.3 Water Oxidation 483.1.4 ArtificialWater Oxidation 493.2 Ruthenium inWater Oxidation Catalyst 503.2.1 Ruthenium Oxide 503.2.2 Molecular Ruthenium WOC 523.2.2.1 Meyer’s Blue Dimer 533.2.2.2 The Ru-Hbpp Catalyst 543.2.2.3 Single-Site Ru-WOCs 553.2.2.4 Heptacoordinated Ru Intermediates 563.2.3 Polyoxometalates: The Bridge Between Metal Oxides and Coordination Complexes 573.3 Conclusions and Perspectives 60References 614 Ruthenium- and Cobalt-Containing Complexes and Hydrogenases for Hydrogen Production 67Michael J. Celestine, Raj K. Gurung, and Alvin A. Holder4.1 Introduction 674.2 (A) Ruthenium- and Cobalt-Containing Complexes for Hydrogen Production 684.2.1 Nonbridged Systems 684.2.2 Bridged Systems 704.3 (B) Ruthenium(II)-Containing Complexes and Hydrogenases for Hydrogen Generation in Aqueous Solution 774.3.1 Hydrogenases 774.3.2 Hydrogenases with Ruthenium(II) Complexes 784.4 Conclusions 84References 85Section III Applications in Medicine 895 Ligand Photosubstitution Reactions with Ruthenium Compounds: Applications in Chemical Biology and Medicinal Chemistry 91Samantha L. Hopkins and Sylvestre Bonnet5.1 Introduction 915.2 Caging and Uncaging Biologically Active Ligands with a Nontoxic Ruthenium Complex 925.3 Caging Cytotoxic Ruthenium Complexes with Organic Ligands 965.4 Low-Energy Photosubstitution 1005.4.1 Introduction 1005.4.2 Modulating Ru Photophysics by Ligand Modulation 1005.4.3 Upconversion (UC) 1055.4.3.1 Triplet–Triplet Annihilation Upconversion 1055.4.3.2 Upconverting Nanoparticles (UCNPs) 1065.4.3.3 Two-Photon Absorption (TPA) Photosubstitution 1095.5 Conclusions 110References 1116 Use of Ruthenium Complexes as Photosensitizers in Photodynamic Therapy 117Lothar Lilge6.1 Introduction 1176.2 The Basics of PhotodynamicTherapy 1186.2.1 Singlet Oxygen Production 1206.2.2 Other Radical Production 1206.2.3 PDT Dose Definition 1206.2.3.1 PDT Dosimetry In Vitro 1226.2.3.2 PDT Dosimetry In Vivo 1246.2.3.3 Oxygen Consumption Model 1256.2.3.4 In Vivo Tissue Response Models 1256.2.4 PDT and Immunology 1266.3 Status of Ru Photosensitizing Complexes 1266.3.1 Photostability for Ru-PS Complexes 1286.3.2 LongWavelength Activation of Ru(II)-PS Complexes 1286.4 Issues to Be Considered to Further Develop Ru-Based Photosensitizers 1296.4.1 Subcellular Localization 1306.4.2 Ruthenium Complex Photosensitizers and the Immune Response 1316.5 Future Directions for Ru-PS Research 1316.6 Conclusion 132References 1327 Photodynamic Therapy in Medicine with Mixed-Metal/Supramolecular Complexes 139Jimmie L. Bullock and Alvin A. Holder7.1 Introduction 1397.2 Platinum and Rhodium Centers as Bioactive Sites 1407.2.1 Platinum(II)-Based Chemotherapeutics 1407.2.2 Rhodium(III) as a Bioactive Site 1417.3 Supramolecular Complexes as DNA Photomodification Agents 1427.4 Mixed-Metal Complexes as PhotodynamicTherapeutic Agents 1437.4.1 Photosensitizers with a Ru(II)Metal Center Coupled to Pt(II) Bioactive Sites 1437.4.1.1 Binuclear Complexes with Ru(II) and Pt(II)Metal Centers with Bidentate Ligands 1437.4.1.2 Binuclear and Trinuclear Complexes with Ru, Pt with Tridentate Ligands 1467.4.2 Photosensitizers with a Ru(II) Metal Center Coupled to Rh(III) Bioactive Sites 1477.4.2.1 Trinuclear Complexes with Ru(II), Rh(III), and Ru(II) Metal Centers 1477.4.2.2 Binuclear Complexes with Ru(II) and Rh(III) Metal Centers 1497.4.3 Photosensitizers with a Ru(II) Metal Cenetr Coupled to Other Bioactive Sites 1507.4.3.1 Binuclear Complexes with Ru(II) and Cu 1507.4.3.2 Binuclear Complexes with Ru(II) and Co(III) Metal Centers 1517.4.3.3 Binuclear Complexes with Ru (II) and V(IV) Metal Centers 1517.4.3.4 Applications of Ru(II) Metal Centers in Nanomedicine 1527.5 Summary and Conclusions 155Abbreviations 156References 1578 Ruthenium Anticancer Agents En Route to the Tumor: From Plasma Protein Binding Agents to Targeted Delivery 161Muhammad Hanif and Christian G. Hartinger8.1 Introduction 1618.2 Protein Binding RuIII Anticancer Drug Candidates 1638.2.1 RuIII Anticancer Drug Candidates Targeting Primary Tumors 1638.2.2 Antimetastatic RuIII Compounds 1658.3 Functionalization of Macromolecular Carrier Systems with Ru Anticancer Agents 1668.3.1 Proteins as Delivery Vectors for Organometallic Compounds 1668.3.2 Polymers and Liposomes as Delivery Systems for Bioactive Ruthenium Complexes 1688.3.3 Dendrimers 1698.4 Hormones, Vitamins, and Sugars: Ruthenium Complexes Targeting Small Molecule Receptors 1698.5 Peptides as Transporters for Ruthenium Complexes into Tumor Cells and Cell Compartments 1738.6 Polynuclear Ruthenium Complexes for the Delivery of a Cytotoxic Payload 1748.7 Summary and Conclusions 175Acknowledgments 175References 1769 Design Aspects of Ruthenium Complexes as DNA Probes and Therapeutic Agents 181Madeleine De Beer and Shawn Swavey9.1 Introduction 1819.2 Physical Interaction to Disrupt DNA Structure 1819.2.1 Irreversible Covalent Binding 1829.2.2 Intercalation 1849.2.3 Additional Noncovalent Binding Interactions 1859.3 Biological Consequences of Ru-Complex/DNA Interactions 1869.4 Effects of Ru Complexes on Topoisomerases and Telomerase 1919.5 Summary and Conclusions 196References 19710 Ruthenium-Based Anticancer Compounds: Insights into Their Cellular Targeting andMechanism of Action 201AntónioMatos, FilipaMendes, Andreia Valente, Tânia Morais, Ana Isabel Tomaz, Philippe Zinck, Maria Helena Garcia, Manuel Bicho, and Fernanda Marques10.1 Introduction 20110.2 Cellular Uptake 20410.3 DNA and DNA-Related Cellular Targets 20510.4 Targeting Signaling Pathways 20710.5 Targeting Enzymes of Specific Cell Functions 20710.6 Targeting Glycolytic Pathways 20910.7 Macromolecular Ruthenium Conjugates: A New Approach to Targeting 21110.8 Conclusions 214References 21511 Targeting cellular DNA with Luminescent Ruthenium(II) Polypyridyl Complexes 221Martin R. Gill and Jim A. Thomas11.1 Introduction 22111.1.1 DNA-Binding Modes of Small Molecules 22211.1.2 Metal Complexes and DNA 22311.2 [Ru(bpy)2(dppz)]2+ and the DNA “Light-Switch” Effect 22411.3 Cellular Uptake of RPCs and Application as DNA-Imaging Agents 22611.3.1 Mononuclear Complexes 22611.3.2 Dinuclear Complexes 22811.3.3 Cyclometalated Systems 22811.4 Alternative Techniques to Assess Cellular Uptake and Localization 23111.5 TowardTheranostics: luminescent RPCs as Anticancer Therapeutics 23211.6 Summary and Conclusions 234References 23512 Biological Activity of Ruthenium ComplexesWith Quinoline Antibacterial and Antimalarial Drugs 239Jakob Kljun and Iztok Turel12.1 Introduction 23912.2 Antibacterial (Fluoro)quinolones 24012.2.1 Quinolones and Their Interactions with Metal Ions 24112.2.2 Ruthenium and Quinolones 24112.2.3 Ruthenium and HIV Integrase Inhibitor Elvitegravir 24512.3 Antibacterial 8-Hydroxyquinolines 24612.3.1 Mode of Action of 8-Hydroxyquinoline Agents 24612.3.2 Ruthenium and 8-Hydroxyquinolines 24712.4 Antimalarial 4-Aminoquinolines 24812.4.1 Mechanism of Action of Antimalarial Quinoline Agents 24812.5 Metallocene Analogues of Chloroquine 24912.6 Conclusions 252References 25213 Ruthenium Complexes as NO Donors: Perspectives and Photobiological Applications 257Loyanne C.B. Ramos, Juliana C. Biazzotto, Juliana A. Uzuelli, Renata G. de Lima, and Roberto S. da Silva13.1 Introduction 25713.2 Photochemical Processes of Some Nitrogen Oxide Derivative–Ruthenium Complexes 25813.2.1 Metal-Ligand Charge-Transfer Photolysis of {Ru-NO}6 25813.2.2 Nitrosyl Ruthenium Complexes: Visible-Light Stimulation 26113.3 Photobiological Applications of Nitrogen Oxide Compounds 26513.3.1 Photovasorelaxation 265References 26814 Trends and Perspectives of Ruthenium Anticancer Compounds (Non-PDT) 271Michael A. Jakupec,Wolfgang Kandioller, Beatrix Schoenhacker-Alte, Robert Trondl,Walter Berger, and Bernhard K. Keppler14.1 Introduction 27114.2 Ruthenium(III) Compounds 27214.2.1 NAMI-A 27314.2.1.1 Biotransformation 27314.2.1.2 Antimetastatic Activity 27414.2.1.3 Mode of Action 27414.2.1.4 Clinical Studies and Perspectives 27514.2.2 KP1019/NKP-1339 27614.2.2.1 Tumor TargetingMediated by Plasma Proteins 27614.2.2.2 Activation by Reduction 27714.2.2.3 Mode of Action 27814.2.2.4 Clinical Studies and Perspectives 28114.3 Organoruthenium(II) Compounds 28214.3.1 Ruthenium(II)–Arene Compounds in Preclinical Development 28214.3.1.1 Organoruthenium Complexes Bearing Bioactive Ligand Scaffolds 28414.3.1.2 Cytotoxic Organoruthenium Complexes without Activation by Aquation 285References 28615 Ruthenium Complexes as Antifungal Agents 293Claudio L. Donnici,Maria H. Araujo, and Maria A. R. Stoianoff15.1 Introduction 29315.2 Antifungal Activity Investigations of Ruthenium Complexes 30415.2.1 Ruthenium Complexes with Activity against Several Pathogenic Fungi Species: Dinuclear, Trinuclear, and Tetranuclear ruthenium Polydentate Polypyridil ligands, Heterotrimetallic di-Ruthenium-Mono-Palladium Complexes, Dinuclearbis-β-Diketones and Pentadithiocarbamate Ligands 30415.2.2 Aromatic and Heteroaromatic Ligands in Ru Monometallic Centers (Pyridine, Phenantroline, Terpyridine, Quinoline, and Phenazine) 30515.2.3 Schiff bases, Thiosemicarbazones, and Chalcones 30715.2.3.1 Schiff bases (Tetradentate Salen Like, Tridentate, and bidentate) 30715.2.3.2 Thiosemicarbazones 30915.2.3.3 Chalcone Derivatives 31015.2.4 Other ligands (Dithio-Naphtyl-Benzamide, Arylazo, Catecholamine, Organophosphorated, Hydridotris(pyrazolyl)borate and Bioactive Azole Ligands) 31015.3 Conclusion 312References 313Index 319