Nitroxide Spin Labels: Reactions in Biology and Chemistry, 1st Edition (Hardback) book cover

Nitroxide Spin Labels

Reactions in Biology and Chemistry, 1st Edition

By Nickolai Kocherginsky, Harold M. Swartz

CRC Press

288 pages

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Hardback: 9780849342042
pub: 1995-05-11
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Description

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

Subject Categories

BISAC Subject Codes/Headings:
SCI049000
SCIENCE / Life Sciences / Biology / Molecular Biology
SCI086000
SCIENCE / Life Sciences / General