Self-assembling and biological properties of single-chain dicationic pyridinium-based surfactants

Kashapov, Ruslan R.; Razuvayeva, Yuliya; Ziganshinа, Albina Y.; Mukhitova, Rezeda K.; Sapunova, Аnastasiia S.; Voloshina, Alexandra D.; Zakharova, L. Ya.

doi:10.1016/j.colsurfb.2018.12.010

Cited by 27 publications

(12 citation statements)

References 28 publications

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“…The LaS molecules form small micelles of 2–3 nm at the concentration above the critical micelle concentration (CMC) of 0.33 mM and large aggregates with a size of 50 nm below the CMC point (Figure ). It is known that conventional surfactants can form vesicles in a solution below the CMC. , The formation of vesicles in the studied solutions of the lanthanum-containing surfactant at concentrations of 0.03 mM is obviously caused by its geminal structure. The DLS data confirm the formation of aggregates in USR – LaS systems.…”

Section: Resultssupporting

confidence: 79%

Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential

et al. 2020

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Metallic amphiphiles are used as building blocks in the construction of nanoscale superstructures, where the hydrophobic effects induce the self-assembly of the nanoparticles of interest. However, the influence of synergizing multiple chemical interactions on an effective design of these structures mostly remains an open question. In this regard, supraamphiphilic systems based on flexible surfactant molecules and rigid macrocycles are being actively developed, but there are few works on the interaction between metallosurfactants and macrocycles. In the present work, the self-assembly and biological properties of a metallosurfactant with calixarene were studied for the first time. The metallosurfactant, a complex between lanthanum nitrate and two 4-aza-1-hexadecylazoniabicyclo[2.2.2]octane bromide units, and calix[4]resorcinol containing sulfonate groups on the upper rim were used to form a novel supraamphiphilic composition. The system formed was studied using a variety of physicochemical methods, including spectrophotometry, NMR, XRF, and dynamic and electrophoretic light scattering. It was found that the most optimal tetraanionic calix[4]resorcinol to dicationic metallosurfactant molar ratio, leading to mixed aggregation upon ion pair complexation, is 2:3. The mixed aggregates formed in the pentamolar concentration range were able to encapsulate hydrophilic substrates, including the anticancer drug cisplatin, the pure form of which is more cytotoxic toward healthy cells than toward diseased cells. Interestingly, the drug loaded into the macrocycle–metallosurfactant particles was less cytotoxic to a healthy Chang liver cell line and more cytotoxic to tumor M-HeLa cells. This selectivity depends on the amount of cisplatin added. The more drug is added to the macrocycle–metallosurfactant composition, the greater the biological activity against cancer cells. Taking into account that the appearance of resistance of cancer cells to drugs, especially to cisplatin, is one of the most important problems in treatment, the results of this work envisage the potential application of a mixed macrocycle–metallosurfactant system for the design of therapeutic cisplatin compositions.

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Section: Resultssupporting

confidence: 79%

Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential

et al. 2020

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“…However, these surfactants are mainly effective against Gram-positive bacteria and fungi, while most Gram-negative bacteria are resistant. Some examples of such compounds are: (i) a hexameric surfactant with amide moieties shown to be effective against E. coli [ 8 ], (ii) an amide gemini cationic surfactant 12 (AGS12) with incorporated silver nanoparticles shown to limit the growth of Bacillus subtilis, Staphylococcus aureus, E. coli, P. aeruginosa, C. albicans and Aspergillus niger [ 9 ], (iii) V-16 and VBP-16 (two dicationic surfactants containing viologen, vinylbipyridinium moieties and hexadecyl chains) exhibiting inhibitory properties against S. aureus 209P, B. cereus 8052 and C. albicans 855-653 [ 10 ] and (iv) lysine-derived mono-catenary or gemini surfactants with anti- S. aureus, Staphylococcus epidermidis and B. subtilis activity [ 11 ]. Other surfactants and surfactant emulsions rely on their hydrophobic moieties for their anti-microbial activity.…”

Section: Anti-microbial Propertiesmentioning

confidence: 99%

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

et al. 2020

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Surface active agents (SAAs) are molecules with the capacity to adsorb to solid surfaces and/or fluid interfaces, a property that allows them to act as multifunctional ingredients (e.g., wetting and dispersion agents, emulsifiers, foaming and anti-foaming agents, lubricants, etc.) in a widerange of the consumer products of various industrial sectors (e.g., pharmaceuticals, cosmetics, personal care, detergents, food, etc.). Given their widespread utilization, there is a continuously growing interest to explore their role in consumer products (relevant to promoting human health) and how such information can be utilized in order to synthesize better chemical derivatives. In this review article, weaimed to provide updated information on synthetic and biological (biosurfactants) SAAs and their health-promoting properties (e.g., anti-microbial, anti-oxidant, anti-viral, anti-inflammatory, anti-cancer and anti-aging) in an attempt to better define some of the underlying mechanism(s) by which they exert such properties.

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“…Though the approach here proposed is based on the use of a similar surfactant using chloride as counterion, the major ion of the human body, named cetyltrimethylammonium chloride (CTAC), which has also been demonstrated to possess an antimicrobial effect (Figure 1 shows the chemical analogy between CTAC and CTAB). The medical regulatory agency FDA (U.S. Food and Drug Administration) has approved CTAC for topicals [23], and has reported this ingredient as being commonly found in lotions at 0.2% w/w, so indicating its safeness at this concentration [24][25][26]. Besides, to note that in previous work it was demonstrated that cationic surfactants nanostructured in the nanovesicles broadly reduced their potential irritation effect [8].…”

Section: Development Of Delos Nanovesicle Suspensions With Different ...mentioning

confidence: 99%

DELOS Nanovesicles-Based Hydrogels: An Advanced Formulation for Topical Use

et al. 2022

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Topical delivery has received great attention due to its localized drug delivery, its patient compliance, and its low risk for side effects. Recent developments have focused on studying new drug delivery systems as a strategy for addressing the challenges of current topical treatments. Here we describe the advances on an innovative drug delivery platform called DELOS nanovesicles for topical drug delivery. Previously, the production of DELOS nanovesicles demonstrated potentiality for the topical treatment of complex wounds, achieving well-tolerated liquid dispersions by this route. Here, research efforts have been focused on designing these nanocarriers with the best skin tolerability to be applied even to damaged skin, and on exploring the feasibility of adapting the colloidal dispersions to a more suitable dosage form for topical application. Accordingly, these drug delivery systems have been efficiently evolved to a hydrogel using MethocelTM K4M, presenting proper stability and rheological properties. Further, the integrity of these nanocarriers when being gellified has been confirmed by cryo-transmission electron microscopy and by Förster resonance energy transfer analysis with fluorescent-labeled DELOS nanovesicles, which is a crucial characterization not widely reported in the literature. Additionally, in vitro experiments have shown that recombinant human Epidermal Growth Factor (rhEGF) protein integrated into gellified DELOS nanovesicles exhibits an enhanced bioactivity compared to the liquid form. Therefore, these studies suggest that such a drug delivery system is maintained unaltered when hydrogellified, becoming the DELOS nanovesicles-based hydrogels, an advanced formulation for topical use.

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Self-assembling and biological properties of single-chain dicationic pyridinium-based surfactants

Cited by 27 publications

References 28 publications

Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential

Supraamphiphilic Systems Based on Metallosurfactant and Calix[4]resorcinol: Self-Assembly and Drug Delivery Potential

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

DELOS Nanovesicles-Based Hydrogels: An Advanced Formulation for Topical Use

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