2-Deoxy-D-Glucose : Chemistry and Biology.

Format:

Book

Author/Creator:

Singh, Raman.

Contributor:

Kumar, Antresh.

Singh, Kuldeep.

Language:

English

Physical Description:

1 online resource (0 pages)

Edition:

1st ed.

Place of Publication:

Sharjah : Bentham Science Publishers, 2024.

Summary:

2-Deoxy-D-Glucose: Chemistry and Biology extensively examine 2-deoxy-D-glucose (2DG), a glucose analog with profound biomedical and therapeutic potential. This detailed resource covers 2DG's chemical structure, methods of synthesis, and its pivotal roles in diagnostics and therapeutics. This book provides a comprehensive overview of the compound's multifaceted uses, from antiviral applications to its emerging role in cancer treatment. Key Features:- Comprehensive coverage of 2DG synthesis, structure, and characterization.- Insights into 2DG's diagnostic and therapeutic potential, including cancer and antiviral applications.- Exploration of its role in the Warburg effect and glycosylation inhibition.- Discussion on 2DG's clinical applications, including COVID-19 treatments. Readership: Organic and medicinal chemists, oncologists, virologists, pharmaceutical researchers, and graduate students.

Contents:

Intro

Title

Copyright

End User License Agreement

Contents

Foreword

Preface

List of Contributors

2-Deoxy-D-Glucose: Chemical Structure and Properties

Raman Singh1 and Kuldeep Singh1,*

1. INTRODUCTION

1.2. Nomenclature

2. DEOXY-GLUCOSE

3. 2-DEOXY-D-GLUCOSE (2DG)

4. PHYSICAL PROPERTIES

5. ANALYTICAL CHARACTERIZATION

5.1. Spectral Characterization

5.1.1. UV-VIS Spectrum

5.1.2. Mass Spectrum

5.1.3. IR and Raman Spectrum

5.1.4. NMR

6. ANALYSIS OF 2-DEOXY-D-GLUCOSE

7. DRUGABILITY OF 2DG

8. TOXICOLOGY AND HANDLING OF 2DG

CONCLUSION

LIST OF ABBREVIATIONS

ACKNOWLEDGEMENTS

REFERENCES

Methods and Procedures for the Synthesis of 2-Deoxy-D-Glucose

Raman Singh1, Vidushi Gupta2 and Kuldeep Singh1,*

2. SYNTHETIC METHODS

2.1. From Glucal and its Derivatives

2.2. Preparation of 2DG from D-glucose

2.3. Preparation of 2DG from Phenylhydrazone of D-Mannose

2.4. Preparation of 2DG from D-arabinose

2.5. Synthesis of 2DG by Ozonolysis of Tetrols

2.6. Synthesis of Labelled 2DG

2.7. Preparation of 2-deoxyglucoses from γ-lactones

2.8. Preparation of 2DG from 6,8-Dioxabicyclo[3.2.1]oct-2-ene

3. MODERN METHODS TO IMPROVE YIELDS AND REDUCE PROCEDURAL COMPLEXITIES

3.1. Enzymatic Syntheses of 2DG

Characterization of 2-Deoxy-D-glucose

Ramji Lal Yadav1,*, Neeru Singh1, S. N. Karaiya1, Rahul Dev1 and Anil Kumar1

2. EXPERIMENTAL

2.1. Chemicals and Reagents

2.2. Instrumentation and Methodology

2.2.1. Sulphated ash Content

2.2.2. Water Content

2.2.3. Specific Optical Rotation

2.2.4. UV-VIS Spectroscopy

2.2.5. FTIR

2.2.6. Nuclear Magnetic Resonance

2.2.7. Mass Spectrometry

2.2.8. Related Substances and Assay (By HPLC).

2.2.9. Gas Chromatography

3. RESULTS AND DISCUSSION

3.1. UV-VIS Spectroscopy

3.2. IR spectroscopic Analysis

3.3. Confirmation of Structure by NMR

3.4. Mass Spectrum

3.5. HPLC (RS/Assay)

3.5.1. Method Validation

3.5.2. Degradation Study

3.6. GC-HS

[18F]Fluoro Analogue of D-Glucose: A Chemistry Perspective

Mohd Faheem1, Vaibhav Pandey1 and Manish Dixit1,*

1.1. Definition and Background of 2-Fluoro-D-Glucose (2-FDG)

1.2. Biological Importance of [18F]FDG

2. HISTORY OF [18F]FDG

3. ELECTROPHILIC FLUORINATION

3.1. Fluorination of Carbohydrate by Electrophile

4. NUCLEOPHILIC FLUORINATION

4.1. Production of Radionuclide [18F-ion] as Nucleophile

4.2. Trapping and Separation of Nucleophiles (18F-ion)

4.3. Generation of Nucleophile for the Reaction

4.4. Nucleophilic Reaction on D-Mannose Triflate

4.5. Hydrolysis

4.6. Purification

4.7. Quality Assurance

Antiviral Potential of 2-DG Used in Different Viral Infections

Shaurya Prakash1, Minakshi1, Hemlata Kumari1 and Antresh Kumar1,*

2. HOST GLYCOSYLATION: A NECESSITY FOR VIRAL REPLICATION

3. 2-DG: BIOLOGICAL EFFECTS AND ACTION MECHANISM

4. ANTIVIRAL POTENTIAL OF 2-DG

5. SHORTCOMINGS OF 2-DG TREATMENT

6. ANTIVIRAL ACTIVITY OF 2-DG DERIVATIVES

2-Deoxy-D-Glucose and its Derivatives: Dual Role in Diagnostics and Therapeutics

Anil Kumar1,* and Krishnendu Barik1

2. THE WARBURG EFFECT

3. 2-DG IN CANCER DIAGNOSTICS

4. DISEASES TARGETED BY 2-DG

4.1. Cancer

4.1.1. Inhibition of Hexokinase (HK)

4.1.2. Inhibition of Pentose Phosphate Pathway (PPP).

4.1.3. Inhibition of Hexosamine Biosynthesis Pathway (HBP)

4.1.4. Inhibition of Proliferation and Metastasis

4.2. Coronavirus Disease (COVID-19)

4.3. Inflammation

4.4. Viral Infections

4.5. Autosomal Dominant Polycystic Kidney Disease (ADPKD)

4.6. Epilepsy

5. NOVEL 2-DG DERIVATIVES

2-Deoxy-D-Glucose as a Potential Antiviral and Anti-COVID-19 Drug

Pandeeswaran Santhoshkumar1, Arunagiri Sivanesan Aruna Poorani1, Mohamed Ibrahim Mohamed Ismail1 and Palaniswamy Suresh1,*

2. BIOLOGICAL EFFECTS OF 2-DG

3. 2-DG IN VIRAL REPLICATION

4. COVID-19

4.1. Structure of COVID-19

4.2. Metabolically, SARS-CoV-2 Affected Cells are Similar to Cancer Cells

4.3. Association between Blood Glucose and Viral Infection

4.4. 2-DG in COVID-19

4.4.1. Metabolic Insights and Therapeutic in COVID-19: 2-DG Clinical Trials

4.4.2. Clinical Trial of 2-DG in COVID-19

4.4.3. Mechanistic Insight into the Inhibition of Viral Replication by 2DG

FUNDING INFORMATION

Prospects for Cancer Diagnosis, Treatment, and Surveillance: [18F]FDG PET/CT and Innovative Molecular Imaging to Direct Immunotherapy in Cancer

Juhi Rais1, Manish Ora1 and Manish Dixit1,*

2. CURRENT STATUS OF [18F]FDG AND ITS MECHANISM OF ACTION IN VARIOUS DISEASES

2.1. Neurology

2.2. Cardiology

2.3. Inflammatory Disorders

2.4. Oncology

2.5. Planning and Treatment Strategy

3. BIOCHEMISTRY OF ACCUMULATION OF [18F]FDG

4. THE SIGNALING PATHWAYS AND [18F]FDG ACCUMULATION IN CANCER CELLS

5. IMMUNE CYCLE OF CANCER IN BRIEF

6. [18F]FDGPET/CT AND ITS STANDARD THERAPEUTIC ASSESSMENT SCALES

7. [18F]FDG PET/CT FOR IMMUNOTHERAPY AGAINST CANCER.

8. FUNCTION OF [18F]FDG PET/CT AS AN INDICATOR OF PROGNOSIS

9. ROLE OF[18F]FDG PET/CT IN EVALUATING TOXICITY

ABBREVIATIONS

ACKNOWLEDGMENTS

2-Deoxy-D-Glucose as an Emerging Chemotherapeutic Agent in Cancer Management

Ashutosh Singh1, Ravinsh Kumar1 and Amrita Srivastava1,*

2. GLUCOSE METABOLISM IN CANCER CELLS

3. 2-DEOXY-D-GLUCOSE

3.1. Structure and Properties

3.2. A Brief Historical Perspective of 2DG

4. THERAPEUTIC APPLICATIONS OF 2DG

5. IMPLICATIONS OF 2DG IN CANCER

5.1. Effects on Angiogenesis

5.2. Effects on Metastasis

5.3. Influence of 2DG on Autophagic Cell Death

5.4. Influence of 2DG on Apoptotic Cell Death

5.5. Effect of 2DG on Virus-Induced Oncogenesis

2-Deoxy-D-Glucose: A Glycolysis Inhibitor in the Treatment of Cancer

Arunagiri Sivanesan Aruna Poorani1, Mohamed Ibrahim Mohamed Ismail1, Pandeeswaran Santhoshkumar1 and Palaniswamy Suresh1,*

2. WARBURG EFFECT: ENERGY METABOLISM IN CANCER CELLS

2.1. Causes for the Warburg Effect

3. GLUCOSE IN CANCER GLYCOLYSIS

4. 2-DG AS A GLUCOSE MIMIC

4.1. 2-DG in Cancer Glycolysis

4.2. Effect of 2-DG in Cancer Inhibition

4.2.1. Effect of Diminished ATP

4.2.2. Effect of HK Inhibition

4.2.3. Effect of down-regulation of Matrix metalloprotease (MMP)

4.2.4. Effect of Reactive Oxygen Species (ROS) Upregulation

4.2.5. Effect of Inhibition of PPP

4.2.6. Effect of Downregulation of FLICE-like Inhibitory Protein (c-FLIP)

5. 2-DG AS A MANNOSE MIMIC

5.1. N-Linked Glycosylation and 2-DG Participation

5.2. Impact of 2-DG in the N-linked Glycosylation

5.3. ER Stress-Induced Autophagy (self-eating)

6. 2-DG: IS IT A POTENT ANTICANCER DRUG?.

6.1. Associated Risk, Dose-Response Study and Combination Therapy

6.1.1. 2-DG in Combination with Adezmapimod (SB203580)

6.1.2. 2-DG in Combination with PD98059

6.1.3. 2-DG in Combination with LY294002 and 10058-F4

6.1.4. 2-DG in Combination with Erlotinib

6.1.5. 2-DG in Combination with Mibefradil

7. 2-DG IN CANCER CELL IMAGING

7.1. NIR Optical Imaging Probe

7.2. Radioactive Diagnostic Agent in PET

8. 2-DG RESISTANCE

Dual Role of 2-Deoxy-D-Glucose in Seizure Modulation

Shaurya Prakash1, Kuldeep Singh2 and Antresh Kumar1,*

2. ROLE OF 2-DG IN EPILEPSY

3. ANTICONVULSANT EFFECTS

3.1. Evidence from 6-Hz Seizure Threshold Test

3.2. Evidence from Kindling Models

4. PROCONVULSANT EFFECTS

4.1. Evidence from MEST, PTZ, and KA Models

4.2. Related Evidence from 3-methylglucose

5. 2-DG MECHANISMS INVOLVED IN THE EPILEPSY TREATMENT

5.1. Inhibition of Glycolysis

5.2. Shunting of Glucose Metabolism Through Pentose Phosphate Pathway

Lipinski's Rule of Five

2. LIPINSKI'S RULE OF FIVE

3. ROLE OF LIPINSKI'S RULE OF FIVE IN DETERMINATION OF DRUG-LIKENESS

4. EXCEPTIONS OF THE RULE OF FIVE

ACKNOWLEDGEMENT

Subject Index.

Notes:

Description based on publisher supplied metadata and other sources.

ISBN:

9789815305159

9815305158

OCLC:

1477220182