Lipoic Acid Energy Production Antioxidant Activity and Health Effects Oxidative Stress and Disease 1st Edition by Mulchand S Patel, Lester Packer ISBN 1420045377 9781420045376

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ISBN 10: 1420045377 
ISBN 13: 9781420045376
Author: Mulchand S Patel, Lester Packer

Lipoic Acid Energy Production Antioxidant Activity and Health Effects Oxidative Stress and Disease 1st Table of contents:

Section I Discovery and Molecular Structure
Chapter 1 A Trail of Research on Lipoic Acid
References
Chapter 2 Lipoic Acid Biosynthesis
Lipoic Acid and Lipoyl Carrier Proteins
Lipoic Acid Biosynthesis: Early Metabolic Feeding Studies
Pathways of Protein Lipoylation
Cloning of Escherichia coli lipA and lipB Genes
Cloning of the Escherichia coli lplA Gene
Role of the Acyl Carrier Protein in Lipoic Acid Biosynthesis
Characterization of Lipoate Protein Ligase A
Characterization of Octanoyl-[Acyl Carrier Protein]-Protein Transferase
Characterization of Lipoyl Synthase
Radical SAM Superfamily of Enzymes
Isolation and Characterization of Lipoyl Synthase from Escherichia coli
E. coli LipA Contains Two [4Fe–4S] Clusters per Polypeptide in Its Active Form
Mechanistic Characterization of the LipA Reaction
Similarities Between Lipoyl Synthase and Biotin Synthase
Conclusion
Acknowledgments
References
Chapter 3 The Search for Potent Alpha-Lipoic Acid Derivatives: Chemical and Pharmacological Aspects
Introduction
Pharmacokinetics of α-Lipoic Acid
α-Lipoic Acid-Based Derivatives and Pro-Drugs
Seleno-α-Lipoic Acid Derivatives
Amide and Ester Derivatives of Bis-α-Lipoic Acid
Morpholine-α-Lipoic Acid Derivative
Fluorinated Amphiphilic-α-Lipoic Acid Derivative
Indole-α-Lipoic Acid Derivatives
LA-Plus: N,N-Dimethyl, N’-2-Amidoethyl-Lipoate
Lipoamide
α-Lipoic Acid in Co-Drugs
Trolox/α-Lipoic Acid Co-Drug
Tacrine/α-Lipoic Acid Co-Drug (Lipocrine)
L-DOPA/α-Lipoic Acid Co-Drug
NOS Inhibitor/α-Lipoic Acid Co-Drug
Thiazolidinedione/α-Lipoic Acid Co-Drug
γ-Linoleic Acid/α-Lipoic Acid Co-Drug
Chlorambucil- and Cromolyn/α-Lipoic Acid Co-Drugs
Other α-Lipoic Acid-Based Co-Drugs
Summary
Acknowledgments
References
Chapter 4 Novel Indole Lipoic Acid Derivatives: Synthesis and Their Antioxidant Effects
Introduction
Chemistry and Results
Synthesis of Compounds I-4 (a-h) Comprising the First Group
Synthesis of Compounds II-3 (a-e) Comprising the Second Group
Synthesis of Compounds III-5 (a-b) Comprising the Third Group
Conclusion
References
Section II Metabolic Aspects
Chapter 5 Alpha-Keto Acid Dehydrogenase Complexes and Glycine Cleavage System: Their Regulation and Involvement in Pathways of Carbohydrate, Protein, and Fat Metabolism
Reactions Catalyzed by Mitochondrial Enzymes That Require Lipoic Acid
α-Ketoglutarate Dehydrogenase Complex
Pyruvate Dehydrogenase Complex
Branched-Chain α-Keto Acid Dehydrogenase Complex
A Hypothetical α-Ketoadipate Dehydrogenase Complex
Glycine Cleavage System
Regulation of Mitochondrial Enzymes that Require Lipoic Acid
α-Ketoglutarate Dehydrogenase Complex
Pyruvate Dehydrogenase Complex
Branched-Chain α-Keto Acid Dehydrogenase Complex
A Hypothetical α-Ketoadipate Dehydrogenase Complex
Glycine Cleavage System
Physiological Roles of Mitochondrial Enzymes that Require Lipoic Acid
α-Ketoglutarate Dehydrogenase Complex
Pyruvate Dehydrogenase Complex
Branched-Chain α-Keto Acid Dehydrogenase Complex
Glycine Cleavage System
Acknowledgments
References
Chapter 6 Pyruvate Dehydrogenase Complex Regulation and Lipoic Acid
Introduction
Structure and Catalytic Mechanism of Pyruvate Dehydrogenase Complex
Regulation of PDC by Phosphorylation/Dephosphorylation
Mechanism of Phosphorylation/Dephosphorylation of PDC
Regulation of Phosphorylation=Dephosphorylation of PDC
Effect of Lipoic Acid On Glucose Metabolism and Pdc
Effect of Lipoic Acid on Glucose Uptake
Effect of Lipoic Acid on PDC Components
Concluding Remarks
References
Chapter 7 Role of Lipoyl Domains in the Function and Regulation of Mammalian Pyruvate Dehydrogenase Complex
Introduction
Organization of Mammalian Pyruvate Dehydrogenase Complex
E2 and E3BP Domains and E1 and E3 Binding
Inner Framework and Stoichiometry of E3BP to E3 Dimers
Specificity in the Use of Lipoyl Prosthetic Group and Lipoyl Domains in Component Reactions
E1 Specificity
E2 and E3 Specificity
Relative Use of Different Lipoyl Domains in Overall PDC and E3 Reactions
Regulatory Enzymes
Kinase Isoforms and Isoform Focus
PDK2 Structure
PDP Isoforms, PDP1 Subunits, and Focus
Roles of Lipoyl Domains in the Regulation of Mammalian PDC
Enhanced PDK and PDP1 Function
E2 Constructs
Regulatory Properties of PDK
Regulated PDK2 Interaction with L2
Effector Modification of PDK2 Activity and Structure
Specific Nature of PDK3 Interaction With L2
Tight PDK3-L2 Complex
Critical L2 Domain Structure for Binding and Activation of PDK3
L2 Prosthetic Group Structure for Binding and Activation of PDK3
Effects of Free Lipoyl Group Structures on PDK3 Activity and L2 Binding
Requirements For L2 Binding to PDP1
Metal Requirements for PDP1 and PDP1c Binding to L2 Domain
L2 Domain Structure Needed for Binding PDP1c
Conclusions
Acknowledgment
References
Chapter 8 Inactivation and Inhibition of Alphα-Ketoglutarate Dehydrogenase: Oxidative Modification of Lipoic Acid
Mitochondria: A Source of Reactive Oxygen Species
Lipid Peroxidation and Formation of 4-Hydroxy-2-Nonenal
Reactivity of 4-Hydroxy-2-Nonenal With Protein
Inhibition of Mitochondrial Respiration By 4-Hydroxy-2-Nonenal
Lipoic Acid as a Target of 4-Hydroxy-2-Nonenal Modification
Detection of 4-Hydroxy-2-Nonenal-Modified Lipoic Acid
Fate of Lipoic Acid 4-Hydroxy-2-Nonenal Conjugate
Reversible Oxidative Inhibition of α-Ketoglutarate Dehydrogenase
Glutathionylation of α-Ketoglutarate Dehydrogenase
Glutathionylation of α-Ketoglutarate Dehydrogenase as an Antioxidant Response
Conclusion
References
Chapter 9 Lipoate-Protein Ligase A: Structure and Function
Introduction
Properties and Structure of E. Coli Lipoate-Protein Ligase A
Properties of E. coli LplA
Overall Structure of E. coli LplA
Lipoic Acid-Binding Site
Structure of T. Acidophilum Lipoate-Protein Ligase A
Overall Fold of the T. acidophilum LplA Molecule
Substrate-Binding Site
Predicted Catalytic Mechanism of LplA
References
Chapter 10 An Evaluation of the Stability and Pharmacokinetics of R-Lipoic Acid and R-Dihydrolipoic Acid Dosage Forms in Human Plasma from Healthy Subjects
Introduction: Structure, Stereochemistry, and Mechanisms of Action of Alpha Lipoic Acid
Structure, Physical Properties, Stability, and Stereochemistry of Alpha Lipoic Acid and Dihydrolipoic Acid
Stability of Dihydrolipoic Acid in Vitro and During Sample Preparation
Baseline Levels of R-Dihydrolipoic Acid in Human Plasma
Enzymatic Reduction of Alpha Lipoic Acid: Is Dihydrolipoic Acid an in Vivo Plasma Metabolite of Alpha Lipoic Acid?
Animal and Human Plasma Pharmacokinetics of RAC-Dihydrolipoic Acid
Plasma Pharmacokinetics of R-(þ)-A Lipoic Acid In Humans
Materials
Analytical Equipment and Methods
Plasma Collection and Comparison of Anticoagulants
Comparisons of High-Performance Liquid Chromatography Methods of Analysis
Results and Discussion: A Reevaluation of the Stability of R-Dihydrolipoic Acid
Pharmacokinetics of Na-Rla Versus R-(+)-A Lipoic Acid and R-Dihydrolipoic Acid
Abbreviations
References
Chapter 11 Pharmacokinetics, Metabolism, and Renal Excretion of Alpha-Lipoic Acid and Its Metabolites in Humans
Introduction
Metabolic Pathways of α-Lipoic Acid
Pharmacokinetic Properties of α-Lipoic Acid and its Metabolites in Healthy Volunteers
Single-Dose Trials
Multiple-Dose Trials
Summary
Pharmacokinetic Properties of α-Lipoic Acid and Its Metabolites in Patients with Renal Impairment
Patients with Severe Renal Dysfunction
Patients with End-Stage Renal Disease
Summary
Conclusions
References
Chapter 12 Modulation of Cellular Redox and Metabolic Status by Lipoic Acid
Introduction
Redox Status of Cells and the Extracellular Environment
Cellular Redox Status
Extracellular Redox Status
Effect of Lipoic Acid on Cellular and Extracellular Redox Status
Lipoic Acid Transport into Cells and Perturbation of the Cellular Redox Status
Lipoic Acid Reduction to DHLA and Redox Changes Caused by DHLA
DHLA Release into the Extracellular Cellular Environment and Consequent Redox Changes
Overview of Lipoic Acid Redox Cycling in Cells
Modulation of Cellular Energy Status by Lipoic Acid
Lipoic Acid and Mitochondrial Functionality
Perspective
Abbreviations
References
Chapter 13 Redoxin Connection of Lipoic Acid of Lipoic Acid
Introduction
Oxidative Stress and Thiol–Disulfide Homeostasis
Sources of Reducing Power For Defensive Purposes in Mitochondria
Enzyme-Bound Lipoic Acid as an Actor in Thiol Redox Homeostasis Scene
Mitochondrial Redoxin Proteins and Other Thiolic Systems
Glutaredoxins
Thioredoxins
Peroxiredoxins
Glutathione
Connection of Lipoamide with Glutathione via Glutaredoxin
Connection of Lipoamide with Thioredoxin
Interaction of Lipoamide with Peroxiredoxin
Concluding Remarks
Abbreviations
References
Chapter 14 Lipoic Acid as an Inducer of Phase II Detoxification Enzymes through Activation of Nrf2-Dependent Gene Expression
Introduction
Phase Ii Gene Induction: Role of Nrf2 Nuclear Translocation and its Binding to the Antioxidant Response Element
Keap-1 and its Role in NRF2-Mediated Gene Expression
Stress Signaling Pathways that Induce NRF2 Nuclear Translocation
Theoretical Evidence of α-Lipoic Acid as an Inducer of Phase II Detoxification
Experimental Evidence for α-Lipoic Acid as an Inducer of NRF2
Future Directions for Research on Lipoic Acid and the NRF2-Keap-1 System
References
Section III Clinical Aspects
Chapter 15 Deficiency Disorders of Components of PDH Complex: E2, E3, and E3BP Deficiencies
Introduction
Clinical Deficiency of PDHc
E2 (Dihydrolipoamide Transacetylase)
Structure of E2 Protein
Genetic Mutations Causing E2 Deficiency
Effect of E2 Mutations on PDHc Structure and Function
E3 (Dihydrolipoamide Dehydrogenase)
Structure of E3 Protein
Genetic Mutations Causing E3 Deficiency
Clinical Outcome of E3 Deficiency
Genetic Heterogeneity in E3-Deficient Patients
Mutations in FAD Domain (Amino Acids 35–184)
Mutations in NAD Domain (Amino Acids 185–317)
Mutations in Central Domain (Amino Acids 318–385)
Mutations in Homodimer Interface Domain (Amino Acids 386–509)
Mutations Creating Null Alleles
Clinical Consequences for Heterozygote Carrier Parents
Therapy for E3 Deficiency
E3-Binding Protein
Structure of E3BP Protein
Genetic Mutations Causing E3BP Deficiency
Nature of Genetic Mutations Causing E3BP Deficiency
E3BP Deficiency Leads to Reduced mRNA Transcripts and Loss of Protein Product
Parental Carrier Status Shows Variable Clinical Phenotypes
Clinical Symptoms of E3BP Deficiency
Conclusion
Abbreviations
References
Chapter 16 Relationship between Primary Biliary Cirrhosis and Lipoic Acid
Introduction
Epidemiology of Primary Biliary Cirrhosis
Serological Features of Primary Biliary Cirrhosis
Immunobiology of the Intrahepatic Biliary Epithelium
Lipoic Acid and Primary Biliary Cirrhosis
Antibodies to Lipoic Acid in the Absence of Protein Carrier
Significance of Reactivity to Lipoic Acid
Acknowledgments
References
Chapter 17 Effects of Lipoic Acid on Insulin Action in Animal Models of Insulin Resistance
Regulation and Dysregulation of Whole-Body Glucose Homeostasis
Normal Regulation of Glucose Homeostasis
Dysregulation of Glucose Homeostasis
Brief Overview of α-Lipoic Acid and its Role as an Antioxidant
Beneficial Metabolic Effects of α-Lipoic Acid in Animal Models of Insulin Resistance
Genetic Models of Insulin Resistance
Nutritional Intervention Models of Insulin Resistance
Models of Type-1 Diabetes
Effects of α-Lipoic Acid Conjugates and Derivatives on Metabolic Regulation
Summary and Perspectives
References
Chapter 18 Activation of Cytoprotective Signaling Pathways by Alpha-Lipoic Acid
α-Lipoic Acid as an Endogenous Antioxidant
La as an Anti-Inflammatory Agent
Anti-Atherosclerotic Action of La
Protection from Apoptotic and Necrotic Cell Death by La
α-Lipoic Acid Mimics and Amplifies Insulin Signaling
Conclusion
References
Chapter 19 Selenotrisulfide Derivatives of Alpha-Lipoic Acid: Potential Use as a Novel Topical Antioxidant
Introduction
α-Lipoic Acid: Use as an Antioxidant
Selenotrisulfides and their Role in Selenoprotein Synthesis
Chemistry of Selenotrisulfides
Selenoprotein Synthesis
Selenotrisulfides as Intermediates in Selenium Metabolism
Effect of Selenotrisulfides on Cellular Targets
Uptake of Selenotrisulfides and Identification In Vivo
Selenotrisulfide Derivative of α-Lipoic Acid
Synthesis and Initial Characterization
Rationale for Topical Application of Selenium
Efficiency of Selenium Utilization and Delivery from LASe
Conclusions and Future Directions
Abbreviations
References
Chapter 20 Alpha-Lipoic Acid: A Potent Mitochondria) Nutrient for Improving Memory Deficit, Oxidative Stress, and Mitochondria) Dysfunction
Introduction
α-Lipoic Acid: a Mitochondrial Nutrient?
Mitochondrial Dysfunction: A Consequence of Aging?
Age-Associated Cognitive Dysfunction and Neurodegenerative Diseases: Prevention and Amelioration by La?
Improving Mitochondrial Function and Reducing Oxidative Damage: Possible Mechanisms of La on Cognition?
Combination of La and Other Mitochondrial Nutrients or Compounds: More Effective than La Alone in Improving Cognitive Function?
La Derivatives: More Potent than La for Treating Neurodegenerative Diseases?
Conclusion
Acknowledgments
References
Chapter 21 Effects of Alpha-Lipoic Acid on AMP-Activated Protein Kinase in Different Tissues: Therapeutic Implications for the Metabolic Syndrome
Introduction
Role of Skeletal Muscle Fatty Acid Metabolism in the Genesis of Insulin Resistance
Glucose–Fatty Acid Cycle
Increased Intramyocellular Triglyceride Accumulation
Decreased Skeletal Muscle Lipolysis in Insulin Resistance
Impaired Mitochondrial Function in Insulin Resistance
Adenosine Monophosphate-Activated Protein Kinase
AMPK: Structure, Regulation, and Functions
AMPK and Metabolic Syndrome
Roles of AMPK in Peripheral Tissues
Skeletal Muscle
Liver
Vascular Endothelial Cell
Pancreatic Islet b-Cells
Role of AMPK in the Hypothalamus
Nutrient Sensing in the Hypothalamus and Feeding Regulation
Role of Hypothalamic AMPK in Regulating Food Intake and Energy Expenditure
La and Metabolic Syndrome
Beneficial Effect of LA in Metabolic Syndrome
Effect of LA on AMPK in Peripheral Tissues
Skeletal Muscle
Pancreatic Islet b-Cells
Vascular Endothelial Cell
ALA, AMPK, and Antioxidant Action
Effect of LA on AMPK in the Hypothalamus

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