Biomedically Relevant Applications of Bolaamphiphiles and Bolaamphiphile-Containing Materials

Abstract

Bolaamphiphiles (BAs) are structurally segmented molecules with rich assembly characteristics and diverse physical properties. Interest in BAs as standalone active agents or as constituents of more complex therapeutic formulations has increased substantially in recent years. The preorganized amphiphilicity of BAs allows for a range of biological activities including applications that rely on multivalency. This review summarizes BA-related research in biomedically relevant areas. In particular, we review BA-related literature in four areas: gene delivery, antimicrobial materials, hydrogels, and prodrugs. We also discuss several distinguishing characteristics of BAs that impact their utility as biomedically relevant compounds.

Spiropyran/Merocyanine Amphiphile in Various Solvents: A Joint Experimental–Theoretical Approach to Photophysical Properties and Self-Assembly

“…For the first group mentioned in the classification, where SP/MC is the head of the surfactant, both UV stimulus and/or insertion into water will turn a nonpolar molecule into a classical surfactant structure. For the amphiphiles with SP placed in a tail, the aforementioned triggers transform a classical surfactant with a positively [ 18 , 19 , 20 , 22 , 37 ] or negatively [ 14 , 37 , 45 , 46 ] charged head group, i.e.,–N(CH ) or –SO , respectively, and a hydrophobic SP-containing a tail into a structure resembling a bolaamphiphile, i.e., an amphiphilic molecule that has hydrophilic groups at both ends of a sufficiently long hydrophobic hydrocarbon chain [ 18 , 47 ]. Consequently, the length of the alkyl could be another important parameter of the surface activity.…”

A two-site reactive platform in the synthesis of amino-functionalized amphiphilic molecules via sulfenic acids

“…4 Synthetic BAs have attracted the attention of researchers for their unique property of self-assembling both at interfaces, such as air/water or liquid/solid, and in solution, forming well defined structures, such as micelles, lamellae vesicles, nanotubes, nanorods, and nanosheets. For this reason, since the nineties, several synthetic methodologies have been developed to obtain BAs and their applications have been extensively studied, including drug delivery, 5 gene delivery, 6 medical imaging, 7 and nanoelectronics. 8 In recent years, supra-amphiphiles 9 and bola-type supra-amphiphiles 10 have been obtained also by the self-assembly of components bearing both hydrophilic and hydrophobic segments held together by noncovalent interactions.…”

Spiropyran/Merocyanine Amphiphile in Various Solvents: A Joint Experimental–Theoretical Approach to Photophysical Properties and Self-Assembly

“…For the amphiphiles with SP placed in a tail, the aforementioned triggers transform a classical surfactant with a positively [26][27][28]30,45] or negatively [21,45,53,54] charged head group, i.e.-N(CH 3 ) 3 + or -SO 3 2− , respectively, and a hydrophobic SP-containing tail into a structure resembling bolaamphiphile, i.e. an amphiphilic molecule that has hydrophilic groups at both ends of a sufficiently long hydrophobic hydrocarbon chain [26,55]. Consequently, the length of the alkyl could be another important parameter of the surface activity.…”