Cover

Title Page

Copyright Page

Dedications

Table of contents

Contributors

Preface

References

Acknowledgments

Chapter 1 - Non-endocannabinoid N-Acylethanolamines and Monoacylglycerols: Old Molecules New Targets

1.1 - Introduction

1.2 - Formation and degradation of N-acylethanolamines

1.3 - Biological roles and drug targets of non-endocannabinoid N-acylethanolamines

1.4 - Formation and degradation of non-endocannabinoid 2-monoacylglycerols

1.5 - Biological roles and drug targets of non-endocannabinoid 2-monoacylglycerols

1.6 - Conclusion

Acknowledgment

References

Chapter 2 - Omega-3 Polyunsaturated N-Acylethanolamines: A Link Between Diet and Cellular Biology

Abbreviations

2.1 - Introduction

2.2 - Modulation of the endocannabinoidome by dietary fatty acids – biochemical aspects

2.3 - Effects of diet – animal studies

2.4 - Effects of diet – human data

2.5 - In vitro formation of n-3 fatty acid derived amides

2.6 - Biological effects of n-3 fatty acid derived NAEs and other amides

2.6.1 - Receptor Interaction

2.6.2 - Effects in Inflammation

2.6.3 - Effects on COX-2

2.6.4 - Potential Roles of DHEA and EPEA as Endogenous Mediators of Inflammation

2.6.5 - Effects in Tumor Cell Lines

2.6.6 - Role in Neuroprotection and Neurogenesis

2.7 - Conclusions and future perspectives

References

Chapter 3 - N-Acyl Amides: Ubiquitous Endogenous Cannabimimetic Lipids That Are in the Right Place at the Right Time

3.1 - N-acyl amides: all in the family

3.1.1 - How do the Broader Family of N-Acyl Amides Relate to Phytocannabinoids?

3.2 - GPR18

3.3 - N-acyl amides/endogenous cannabinoids that activate TRP receptors

3.3.1 - Activators of other TRP channels

3.3.2 - Enzymes of the eCB System: A Common Link Between Cannabimimetic Endogenous Lipids

3.3.3 - Effects of N-Acyl Amides on Additional Cannabinoid-Activated Proteins

3.3.3.1 - CaV3

3.3.3.2 - VDAC1

3.4 - N-acyl amide/eCBs with not yet identified phytocannabinoid ligands

3.5 - Nowhere to go but up

References

Chapter 4 - Oxidative Metabolites of Endocannabinoids Formed by Cyclooxygenase-2

4.1 - COX-2 metabolism of endocannabinoids

4.2 - Analysis of ECs and their COX-2 metabolites

4.2.1 - AEA and AG

4.2.2 - Lipoaminoacids

4.2.3 - Prostaglandin Glyceryl Ester (PG-G)

4.2.4 - Prostaglandin Ethanolamides (PG-EAs or Prostamides)

4.3 - Tools to study PG-G and PG-EA functions

4.4 - Biological effects of PG-Gs and PG-EAs

4.5 - Perspective

References

Chapter 5 - N-Acyldopamines and N-Acylserotonins: From Synthetic Pharmacological Tools to Endogenous Multitarget Mediators

5.1 - Introduction

5.2 - N-acyldopamines

5.2.1 - Synthesis, Discovery as Endogenous Mediators and Metabolic Pathways

5.2.2 - Molecular Targets

5.2.2.1 - TRPV1- and/or CB1-Mediated Actions

5.2.2.2 - Non-TRPV1-, non-CB1-Mediated Actions

5.2.3 - N-Acyldopamine Signaling: Conclusions

5.3 - N-acylserotonins

5.3.1 - Synthesis as FAAH Inhibitors and Recent Discovery as Endogenous Mediators

5.3.2 - Molecular Targets Other than FAAH and TRPV1

5.3.3 - N-Acyl-Serotonins: Conclusions

5.4 - Conclusions

References

Chapter 6 - The Pharmacology of Prostaglandin F2α Ethanolamide and Bimatoprost Reveals a Unique Feedback Mechanism on Endocanna...

6.1 - Introduction

6.2 - Pharmacology

6.3 - Endogenous prostamide PGF2α

6.4 - Prostamide receptor detection

6.5 - Biological function and therapeutics

Acknowledgment

References

Chapter 7 - Prostamide F2α Biosynthesizing Enzymes

7.1 - Introduction

7.2  PGF synthases belonging to the aldo-keto reductase superfamily: molecular structure and properties

7.3 - Prostamide/PGF synthase: properties

7.4 - AKR1C3 and related PGF synthases and prostamide/PGF synthase: substrates and inhibitors

7.5 - Comparative distribution of AKR1C3 and related AKR enzymes with prostamide/PGF synthase

7.6 - Prostamide/PGF synthase AKR1C3 and related PGF synthases and their relation to biological function and therapeutics

References

Chapter 8 - Metabolic Enzymes for Endocannabinoids and Endocannabinoid-Like Mediators

8.1 - Introduction

8.2 - Enzymes for the biosynthesis of N-acylethanolamines

8.3 - Enzymes for the degradation of N-acylethanolamines

8.4 - Enzymes for the biosynthesis of 2-AG

8.5 - Enzymes for the degradation of 2-AG

8.6 - Perspectives

References

Chapter 9 - Endocannabinoidomics: “Omics” Approaches Applied to Endocannabinoids and Endocannabinoid-Like Mediators

9.1 - Introduction

9.2 - Biochemistry and pharmacology of endocannabinoids and endocannabinoid-related compounds

9.3 - Lipidomics in “endocannabinoidomics”: mass-spectrometric approaches for endocannabinoid and endocannabinoid-like mol...

9.3.1 - Analytical Approaches Available for Small Molecules of the Endocannabinoidome

9.3.2 - High Resolution Ion-Trap/Time-of-Flight LC/MS for the Unequivocal Identification of New EC-Like Molecules and EC B...

9.3.3 - From Lipidomics of the Endocannabinoidome to Endocannabinoidomics

9.4 - New frontiers

9.5 - Conclusions

References

Chapter 10 - Common Receptors for Endocannabinoid-Like Mediators and Plant Cannabinoids

10.1 - Introduction

10.2 - CB1 and CB2 receptors

10.2.1 - Agonist-Evoked Signaling

10.2.2 - Constitutive Activity and Inverse Agonism

10.2.3 - CB Cannabinoid Receptor Function In Vitro and In Vivo

10.3 - Beyond CB1 and CB2 receptors: cannabinoid receptor-like GPCR

10.4 - Ligand- and voltage-gated ion channels

10.5 - Nuclear hormone receptors

10.5.1 - The Classical View of PPARs

10.5.2 - The Pharmacology of PPARs

10.5.3 - PPAR Activation by Phytocannabinoids and Endocannabinoids

10.6 - Amplification of endocannabinoid tone

10.7 - Concluding remarks

References

Index