Synthesis of Amphiphilic Compounds and Applications

Dear Colleagues,

Amphiphiles are compounds possessing a hydrophilic polar head group link to a hydrophobic nonpolar region by a spacer. Regarding their molecular scaffold, amphiphilic compounds can be classified into three main classes: conventional mono- or bicatenar amphiphiles (with one or two alkyl chains), bipolar amphiphiles (bolaamphiphiles or bolalipids), and gemini amphiphiles. A fourth class can be considered comprising amphiphilic polymers (for example, diblock or triblock polymers). For almost all classes, “nature” is a great source of inspiration for the design of synthetic or semisynthetic analogues. Amphiphilic compounds have an ambivalent character which gives them the property to self-assemble in aqueous media to form a large variety of supramolecular aggregates (micelles, liposomes, nanotubes, nanofibers) at nanometric scale. This polymorphism has been intensively investigated in recent years, broadening the use of such compounds in many fields of research and their applications in cosmetic or food industries (surfactants, emulsifiers, additives), biology and medicine (imaging, sensing, therapy) to nanobiotechnologies (biosensing, nanoreactors). More recently, the development of stimuli-responsive supramolecular amphiphilic assemblies has paved the way to new applications, one of the most common examples being drugs delivery technology for gene delivery or cancer therapeutics.

From a structural point of view, amphiphilic compounds show a broad diversity in their nature regarding the modulation of their polar head group (amino acids, carbohydrates, nucleobases, peptides, cyclodextrins, etc.), their charge (anionic, cationic, zwitterionic or neutral), and/or their hydrophobic domain (nature, size and number of alkyl chains or carbocycle). Furthermore, the nature of the spacer can also be modulated to bring new properties or biodegradability to amphiphiles and thus cover new fields of applications (pH sensitive, redox sensitive, light or thermosensitive compounds, etc.).

One of the main challenges in the manufacturing of amphiphilic compounds is their synthesis and purification especially at large scale (gram or kilograms). Many synthetic strategies have been reported in the past, for example, for the synthesis of phospholipids which include either chemical or chemoenzymatic approaches. Recently, the increasing interest in “click reaction” and the search for “greener” synthetic approaches have led to the development of new amphiphilic compounds synthesized by copper-catalysed Huisgen cycloaddition, thiol-ene or thiol-yne click reactions. Despite continuous efforts in the fields, the development of new synthetic routes to new amphiphilic compounds, interest in their physicochemical behavior, and studies of structure–properties relationship and applications is still of great importance either for research and industrial fields. 

Therefore, the scope of this Special Issue is to bring together original research articles, short communications or reviews related to the design and synthesis (or hemi-syntheses) of «amphiphilic compounds». All the classes of amphiphilic compounds may be discussed, as well as their synthesis and also their aggregation properties and their physicochemistry. Low-molecular-weight amphiphiles or polymers can be described. Although the main purpose of this issue is the synthesis of amphiphilic compounds, illustration of their applications in biology, medicine or biotechnologies would also be appreciate. Authors who would like to submit a review are kindly asked to provide in advance to the guest editor a brief outline of the subject matter of their work.

Dr. Mathieu Berchel
Guest Editor

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