Abstract
Sphingolipids (SLs) are ubiquitous membrane constituents that have emerged as essential lipid mediators involved in signal transduction and cancer development. Due to the implication of SLs in the alteration of cell proliferation, adhesion or migration, their metabolism has been targeted in search for novel anti-cancer therapeutic approaches. In this context, much attention has been directed towards SLs analogues interfering with these complex signalization pathways as well as the immune system.
A general structural modulation of the basic sphingosine backbone of SLs concerns its cyclisation into various types of conformationally constrained derivatives. Different series of both natural and synthetic compounds can be considered according to this common structural feature. The present review article lists these naturally occuring sphingolipids cyclic derivatives including anhydrophytosphingosine-type marine products pachastrissamine (jaspine B), penaresidine/penazetidine, broussonetine, prosopine/prosopinine/prosophylline derivatives, as well as conceptually related synthetic products. A brief statement of their biological activity is presented. Detailed informations concerning the organic synthetic aspects are given with emphasize on the natural azetidine, pyrrolidine and all the synthetic analogues that had never been reviewed before.
Keywords: Ceramide, broussonetine, jaspine, penaresidine, prosophylline, sphingosine, sphingolipids (SLs), palmitoyl CoA, sphingomyelin, stereochemistry, pyrrolidine, piperidine, prosafrinine, melanoma cells, β-glucosidase, β-galactosidase, β-mannosidase
Current Organic Chemistry
Title: Sphingolipids Cyclic Derivatives: Occurrence, Biological Relevance and Synthetic Approaches
Volume: 15 Issue: 7
Author(s): Stephanie Ballereau, Michel Baltas and Yves Genisson
Affiliation:
Keywords: Ceramide, broussonetine, jaspine, penaresidine, prosophylline, sphingosine, sphingolipids (SLs), palmitoyl CoA, sphingomyelin, stereochemistry, pyrrolidine, piperidine, prosafrinine, melanoma cells, β-glucosidase, β-galactosidase, β-mannosidase
Abstract: Sphingolipids (SLs) are ubiquitous membrane constituents that have emerged as essential lipid mediators involved in signal transduction and cancer development. Due to the implication of SLs in the alteration of cell proliferation, adhesion or migration, their metabolism has been targeted in search for novel anti-cancer therapeutic approaches. In this context, much attention has been directed towards SLs analogues interfering with these complex signalization pathways as well as the immune system.
A general structural modulation of the basic sphingosine backbone of SLs concerns its cyclisation into various types of conformationally constrained derivatives. Different series of both natural and synthetic compounds can be considered according to this common structural feature. The present review article lists these naturally occuring sphingolipids cyclic derivatives including anhydrophytosphingosine-type marine products pachastrissamine (jaspine B), penaresidine/penazetidine, broussonetine, prosopine/prosopinine/prosophylline derivatives, as well as conceptually related synthetic products. A brief statement of their biological activity is presented. Detailed informations concerning the organic synthetic aspects are given with emphasize on the natural azetidine, pyrrolidine and all the synthetic analogues that had never been reviewed before.
Export Options
About this article
Cite this article as:
Ballereau Stephanie, Baltas Michel and Genisson Yves, Sphingolipids Cyclic Derivatives: Occurrence, Biological Relevance and Synthetic Approaches, Current Organic Chemistry 2011; 15 (7) . https://dx.doi.org/10.2174/138527211794785127
DOI https://dx.doi.org/10.2174/138527211794785127 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Cellular and Subcellular Imaging in Live Mice Using Fluorescent Proteins
Current Pharmaceutical Biotechnology In vivo behavior and Safety of Lapatinib-Incorporated Lipid Nanoparticles
Current Pharmaceutical Biotechnology Low Molecular Weight and Oligomeric Chitosans and Their Bioactivities
Current Topics in Medicinal Chemistry Process Variables and Design of Experiments in Liposome and Nanoliposome Research
Mini-Reviews in Medicinal Chemistry New, Substituted Derivatives of Dicarboximides and their Cytotoxic Properties
Anti-Cancer Agents in Medicinal Chemistry The Molecular Targets of Cannabinoids in the Treatment of Cancer and Inflammation
Current Pharmaceutical Design Dietary Phytochemicals in Chemoprevention of Cancer: An Update
Immunology, Endocrine & Metabolic Agents in Medicinal Chemistry (Discontinued) 68Ga/64Cu PSMA Bio-Distribution in Prostate Cancer Patients: Potential Pitfalls for Different Tracers
Current Radiopharmaceuticals Heparan Sulphate as a Regulator of Leukocyte Recruitment in Inflammation
Current Protein & Peptide Science Preclinical Development of Novel Anti-Glioma Drugs Targeting the Endoplasmic Reticulum Stress Response
Current Pharmaceutical Design The Role of Radiopharmaceuticals in Amiodarone-Induced Thyroid Pathology
Current Radiopharmaceuticals Gene Transfer and Drug Delivery with Electric Pulse Generators
Current Drug Metabolism Luminescent Silica Nanoparticles for Cancer Diagnosis
Current Medicinal Chemistry Do We have the Evidence to Repurpose Levamisole for Treatment of COVID 19?
Current Drug Therapy Comprehensive Analysis Reveals GPRIN1 is a Potential Biomarker for Non-sm all Cell Lung Cancer
Current Bioinformatics Potential of Alphavirus Vectors in the Treatment of Advanced Solid Tumors
Recent Patents on Anti-Cancer Drug Discovery Current Trends in Pseudogene Detection and Characterization
Current Bioinformatics The Development of Copper Radiopharmaceuticals for Imaging and Therapy
Medicinal Chemistry Smad-Signaling in Mammary Gland Development and Tumorigenesis
Current Signal Transduction Therapy Etiopathogenesis, Classical Immunotherapy and Innovative Nanotherapeutics for Inflammatory Neurological Disorders
Current Nanoscience