Synthesis and Evaluation of Surface Activity of Gemini Borate Surfactants Based on Glucose Moiety

Emara, Mostafa M.; Abdel-Salam, Fatma H.; Ali, R. A.; Turky, Amal S.; Elghayish, Mahmoud M.

doi:10.1080/01932691.2015.1060487

Cited by 3 publications

(4 citation statements)

References 31 publications

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“…Alternatively, cationic QA gemini surfactants may also contain a natural moiety [47,48,49]). Examples are: (i) glucose moieties containing gemini surfactant ( 1c ), where the spacer links the monomers at hydroxyl group of glucose moiety [49], as shown in Figure 1 and (ii) serine-based cationic gemini surfactant ( 1d ), where the spacer links two serine nitrogen atoms, quaternarized by substitution with a long alkyl chain [48], Figure 1.…”

Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

115

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The development of biotechnological protocols based on cationic surfactants is a modern trend focusing on the fabrication of antimicrobial and bioimaging agents, supramolecular catalysts, stabilizers of nanoparticles, and especially drug and gene nanocarriers. The main emphasis given to the design of novel ecologically friendly and biocompatible cationic surfactants makes it possible to avoid the drawbacks of nanoformulations preventing their entry to clinical trials. To solve the problem of toxicity various ways are proposed, including the use of mixed composition with nontoxic nonionic surfactants and/or hydrotropic agents, design of amphiphilic compounds bearing natural or cleavable fragments. Essential advantages of cationic surfactants are the structural diversity of their head groups allowing of chemical modification and introduction of desirable moiety to answer the green chemistry criteria. The latter can be exemplified by the design of novel families of ecological friendly cleavable surfactants, with improved biodegradability, amphiphiles with natural fragments, and geminis with low aggregation threshold. Importantly, the development of amphiphilic nanocarriers for drug delivery allows understanding the correlation between the chemical structure of surfactants, their aggregation behavior, and their functional activity. This review focuses on several aspects related to the synthesis of innovative cationic surfactants and their broad biological applications including antimicrobial activity, solubilization of hydrophobic drugs, complexation with DNA, and catalytic effect toward important biochemical reaction.

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Section: Structural Diversity Of Biocompatible and Ecologically Frmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

115

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“…The efforts of scientists resulted in obtaining gemini surfactants with different head groups that can be anionic (e.g., alkylbenzene sulfonate, phosphate, dicarboxylate) [ 16 , 17 , 18 ], cationic (e.g., quaternary ammonium, arginine, lysine, serine, imidazolium, morpholinium, pyridinium, piperidinium, pyrrolidinium) [ 19 , 20 , 21 , 22 , 23 , 24 , 25 ], zwitterionic (e.g., betaine, heterogemini surfactants) [ 26 , 27 ], and non-ionic (e.g., 3-deoxy-D-glucitol, lactobionic acid residues) [ 28 , 29 ]. Moreover, plenty of different spacers were used such as hydrocarbons (saturated and unsaturated), stilbene units, p-xylenes, cyclohexane derivatives, disulfides, lysine esters, triazines, or even borates [ 30 , 31 , 32 , 33 , 34 , 35 ]. Formally, geminis that are asymmetric (e.g., those with a lysine spacer) are classified as geminoid or gemini-like surfactans [ 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Neubauer

Jaśkiewicz

Bauer

et al. 2021

IJMS

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Ultrashort cationic lipopeptides (USCLs) and gemini cationic surfactants are classes of potent antimicrobials. Our recent study has shown that the branching and shortening of the fatty acids chains with the simultaneous addition of a hydrophobic N-terminal amino acid in USCLs result in compounds with enhanced selectivity. Here, this approach was introduced into arginine-rich gemini cationic surfactants. l-cystine diamide and l-lysine amide linkers were used as spacers. Antimicrobial activity against planktonic and biofilm cultures of ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) strains and Candida sp. as well as hemolytic and cytotoxic activities were examined. Moreover, antimicrobial activity in the presence of human serum and the ability to form micelles were evaluated. Membrane permeabilization study, serum stability assay, and molecular dynamics were performed. Generally, critical aggregation concentration was linearly correlated with hydrophobicity. Gemini surfactants were more active than the parent USCLs, and they turned out to be selective antimicrobial agents with relatively low hemolytic and cytotoxic activities. Geminis with the l-cystine diamide spacer seem to be less cytotoxic than their l-lysine amide counterparts, but they exhibited lower antibiofilm and antimicrobial activities in serum. In some cases, geminis with branched fatty acid chains and N-terminal hydrophobic amino acid resides exhibited enhanced selectivity to pathogens over human cells.

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“…Gemini borate surfactants based on glucose moiety were synthesized [80] through a reaction involving four steps as shown in Scheme 19. The first step is the synthesis of fatty chloride which was carried out by the reaction of fatty alcohol such as lauryl, cetyl, and stearyl alcohols with thionyl chloride.…”

Section: Synthetic Approach For Different Types Of Gemini Surfactantsmentioning

confidence: 99%

“…ΔS mic (kJ mol À 1 K À 1 ) SDDO 0.605 [78] 1.930 [79] 0.352 [79] 0.311 [79] 25 25 [80] 0.250 [80] 0.235 [80] 25 25 [81] 0.562 [81] [82] 25 Tensiometry -----À 43.26 -13.13 0.090 3 C 10 -DS 0.410 [83] 25 Tensiometry 27.60 -2.53 1.66 1.01 ----18-3-18 16-3-16 14-3-14 0.438 [84] 0.466 [84] 0.499 [84] 25. ChemistrySelect amine diacetate.…”

Section: Anionic Gemini Surfactantsmentioning

confidence: 99%

Research Progress on the Synthesis of Different Types of Gemini Surfactants with a Functionalized Hydrophobic Moiety and Spacer

2022

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Gemini surfactants are advantageous over conventional surfactants as they find applications as antimicrobial agents, corrosion inhibitors, enhanced oil recovery, capping agents for nanoparticle synthesis, drug delivery agents, etc. This article provides a detailed overview of synthetic procedures for various types of geminis and the fundamental physicochemical parameters of these systems. This includes a discussion on the cationic geminis based on various groups such as biphenyl, amide (with/without alkane tail), binol, quaternary ammonium (with/without hydroxyl group as a spacer), morpholinium, pyridinium, amide (with/without alkane tail), ester quaternary ammonium, and imidazolium (spacer with/without hydroxyl group and thioether/ester) types. Further, it is focused on anionic geminis with carboxylate, borate, and sulfonate head groups. Zwitterionic geminis such as betaine surfactants, cocogem surfactants based on dodecylisopropylol amine and dicarboxylic acid, diester type, sulphobetaine gemini based on S‐triazine, zwitterionic hetero gemini containing ammonium and carboxylate head groups, zwitterionic gemini containing quaternary ammonium and a sulfate group, gemini containing phosphodiester anion and quaternary ammonium salt are also reviewed. Lastly, synthesis of nonionic geminis from sunflower oil, amide‐based nonionic, sulfonamide nonionic, N,N’‐diethylaminedialkyldiamide nonionic gemini, sugar‐based gemini, and nonionic gemini with sulfonate spacer have been discussed.

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Synthesis and Evaluation of Surface Activity of Gemini Borate Surfactants Based on Glucose Moiety

Cited by 3 publications

References 31 publications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Research Progress on the Synthesis of Different Types of Gemini Surfactants with a Functionalized Hydrophobic Moiety and Spacer

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