Heterocyclic Cationic Gemini Surfactants: A Comparative Overview of Their Synthesis, Self‐assembling, Physicochemical, and Biological Properties

Abstract

Gemini surfactants (GS) are presently receiving substantial attention due to their special self-assembling properties and unique interfacial activity. This comprehensive review is focused on positively charged heterocyclic GS, presenting their major synthetic access routes and examining the impact of structural elements on physicochemical and aggregation properties of this class of amphiphiles. Interaction of geminis surfactants with cells and their biological properties as novel transfection agents are emphasized through a detailed structure-activity relationship analysis. Throughout the review we have also presented the properties of selected ammonium GS, simple surfactants and lipid congeners, in order to emphasize the advantages conferred by using heterocyclic polar heads in GS design.

A facile route to form self-carried redox-responsive vorinostat nanodrug for effective solid tumor therapy

“…The increase in the hydrophobic tail than its comparator should promote the self-assembling process. 37 Third and most importantly, as is known to all, disulfide bond plays an important role in guiding the precise folding of a protein into its native conformation and stabilizing its tertiary and quaternary structures. 38 As shown in Figure 4B, the disulfide bond showed a preference for dihedral angles approaching 90°, and SAHA-S-S-VE molecules could fold at the disulfide bond position, which synergistically favored the former two aspects to generate a stable conformation.…”

Synthesis, Physicochemical Characterization, and Interaction with DNA of Long‐Alkyl‐Chain Gemini Pyridinium Surfactants

“…The purpose of this study is also to define and optimize structure/biological activity relationships (i.e.,t he determination of the chain length to be used). [9] Pyridinium geminis urfactants, which are structurally different from the compounds presented here (they have as pacer that bridges the heteroaromatic nitrogen atoms), have been recently proposed in the literature for transfection purposes. [20] Results and Discussion…”

“…[13,[36][37][38][39][40][41][42][43] Ar ecent review evidenced the great potentialo f these nonviral vectors, in particular the gemini surfactants, owing to tunability of their molecular moieties:h ydrophobic chains and hydrophilic head group, spacer,a nd counterion. [9] However,e fficient nonviral delivery systems must still be realized.…”

“…[48] Thep yridinium group should account for better interaction with the DNA phosphate group owing to higherc harge dispersion with respect to ammonium head groups;c hloride counterion is normally used since it is nontoxic. [9] In this study we describe the synthesis of pyridinium counterpartst hat bear hexadecyl chains and the study of their aggregative properties by conductivity,s urface tension, and fluorescence measurements. In general, the use of long alkyl chains improvest he complexation and transfection ability of DNA.…”

“…[9] Firstly,t he critical micelle concentration (CMC), defined as the concentration at which as urfactants tarts to form aggregates as micelles, has to be determined.…”