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Extending the use of nitroxides as probes into more complex systems such as viable cells and whole animals requires greater knowledge of their interactions in functioning biological systems and appropriate model systems. Nitroxide Spin Labels: Reactions in Biology and Chemistry presents information essential for research in this area. Nitroxide research offers the promise of important new ways of measuring metabolism and will be useful in the diagnosis of important disease categories such as cancer, inflammation, and ischemia.
Table of Contents
Introduction General Considerations Use of Nitroxides as Contrast Agents for Nuclear Magnetic Resonance Imaging and Spectroscopy EPR Imaging and In Vivo EPR Techniques Measurements of the Concentration of Oxygen Measurement of Diffusion Measurement of Viability Measurement of Temperature Summary and Plan of the Book Terminology, Classification, and Distribution of the Nitroxides in Cells General Analysis and Terminology Classification Distribution of Nitroxides in Cells General Considerations Distributions of Neutral Nitroxides Location of Charged Nitroxides in Cells Location of Doxyl Strearates and Related Lipophilic Nitroxides Location of Phospholipids Labeled with Nitroxides Chemical Reactivity of Nitroxides General Aspects Stability of Pure Solutions Electrochemical Reactions Reduction Mechanisms of Chemical Reduction Reduction of f-Phenylenediamine Reduction by Metal Ions Reduction of Nitroxides by Ascorbic Acid and Flavins Reoxidation of Hydroxylamines and Amines to Nitroxides Interconversion of Hydroxylamines and Nitroxides Reduction of Nitroxides by SH-Containing Substances Reactions of Free Radicals with Nitroxides Photochemical Reactions Nitroxides as Redox Probes of Melanin Interactions with Singlet Oxygen Radiation-Induced Reactions Reduction Reactions Oxidation Reactions Radiosensitization by Nitroxides Inhibition of Lipid Peroxidation Reactions of Superoxide with Nitroxides Nitroxides as Catalysts of Radical Reactions Spin Trapping Challenges for Chemists and Biochemists Applications of Reactions of Nitroxides in Biophysics General Considerations The Kinetics and Mechanism of Reduction of Nitroxides by Ascorbic Acid Investigations of Model and Biological Membranes Transport of Ascorbate The Kinetics of Reductions in Membranes Reduction of Spin-Labeled Lipids Dynamics of Lipids Membrane Permeability and Transport of Nitroxides Protein Mobility Nitroxide Reduction with para-Phenylenediamine in Suspensions of Membranes The Use of the Kinetics of Reduction to Study Disease Oximetry with Nitroxides Biochemical Basis of Reduction of Nitroxides in Membranes General Aspects of Reactions of Nitroxides in Membranes Reduction of Nitroxides with Components of Biological Membranes Reactions with Sulfhydryl Groups Reactions with Mitochondrial or Other Membranes Having Respiratory Chains Kinetics of the Reduction of Nitroxides by the Electron Transport Chain Microsomal Membranes Nitroxide Binding to Cytochrome P-450 Reoxidation with the Respiratory Chain and Superoxide Hydrophobicity and Biological Activity of Membrane-Active Substances Conclusions Metabolism of Nitroxides and Their Products in Cells Scheme of Chapter and General Overview of Metabolism of Nitroxides and Hydroxylamines Detailed Considerations of Reduction of Nitroxides in Mammalian Cells Factors that Affect the Rate of Reduction of Nitroxides Mechanisms of Reduction of Nitroxides in Cells Location of Reduction of Nitroxides Cellular Oxidation of Hydroxylamines Metabolism and Distribution of Nitroxides in Specific Types of Cells Use of Rates of Reduction of Nitroxides to Detect Differences in Cells, Including Malignant Changes Erythrocytes, Plasma, and Whole Blood Macrophages Other Cellular Systems Metabolism and Distribution of Nitroxides in Tissues and Organs Homogenized Tissues Isolated and/or Perfused Tissues Nerves Other Specialized Tissues Metabolism and Distribution of Nitroxides In Vivo General Considerations on Distribution and Metabolism of Nitroxides In Vivo Principles of Metabolism and Distribution of Nitroxides In Vivo Assay Methods Used to Measure Levels of Nitroxides in Blood and Tissues Blood and Tissue Levels of Nitroxides and Hydroxylamines Single Administration Repeated Administration Metabolism In Vivo Types of Reactions Influence of Oxygen on the Reactions In Vivo Roles of Intracellular and Extracellular Reduction Metabolism in Organ Systems Physical Elimination of Nitroxides and Hydroxylamines Distribution In Vivo Conversions to Other Derivatives In Vivo Toxicity and the Use of Nitroxides as Bioactive Drugs General Aspects of Toxicity of Nitroxides Data on Toxicity from In Vitro Systems Data from Model Systems Data from Subcellular and Cellular Systems Toxicity in In Vivo Systems General Considerations LD50 and Other Measures of Lethal Effects of Nitroxides Nonlethal Acute Effects Chronic Effects Toxic Effects Involving the Non-Nitroxide Parts of the Spin Labels Effects due to Physical Interactions and/or Localization on the basis of Physical-Chemical Properties of the Nitroxides Effects Due to Chemical Reactions of the Non-Nitroxide Portion of the Molecule Summary on Toxicity Metabolism, Toxicity, and Distribution of Spin Traps Introduction Stability of Spin Traps in Cells and Tissues General Principles and Information on Stability of Adducts of Spin Traps DMPO PBN and Related Spin Traps Other Spin Traps Spin Traps and Erythrocytes Conclusions on Stability of Spin Traps and Spin Adducts in Functional Biological Systems Stability In Vivo Toxicity of Spin Traps Summary and Conclusions Introduction Principles of Metabolism of Nitroxides Potential Limitations of the Use of Nitroxides in Viable Biological Systems and Approaches to Overcome Them Bioreduction Toxicity Sensitivity Applications of Nitroxides in Viable Biological Systems which are Likely to be Affected by the Biological and Chemical Interactions of Nitroxides Assessment of the Future for Nitroxides References
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