Self‐Assembly of Chiral Propeller‐like Supermolecules with Unusual “Sergeants‐and‐Soldiers” and “Majority‐Rules” Effects

Nie, Bo; Zhan, Tian‐Guang; Zhou, Tian; Xiao, Zeyun; Jiang, Guo‐Fang; Zhao, Xin

doi:10.1002/asia.201301522

Cited by 19 publications

(14 citation statements)

References 48 publications

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“…The organic phase was collected and then dehydrated with anhydrous sodium sulfate. After filtration and solvent evaporation under vacuum, the compound was obtained as an oil [15,16].…”

Section: Methodsmentioning

confidence: 99%

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

et al. 2019

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Quaternary ammonium amphiphiles are a class of compounds with a wide range of commercial and industrial uses. In the pharmaceutical field, the most common quaternary ammonium surfactant is benzalkonium chloride (BAC), which is employed as a preservative in several topical formulations for ocular, skin, or nasal application. Despite the broad antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as fungi and small enveloped viruses, safety concerns regarding its irritant and cytotoxic effect on epithelial cells still remain. In this work, quaternary ammonium derivatives of leucine esters (C10, C12 and C14) were synthesised as BAC analogues. These cationic surfactants were characterised in terms of critical micelle concentration (CMC, by tensiometry), cytotoxicity (MTS and LDH assays on the Caco-2 and Calu-3 cell lines) and antimicrobial activity on the bacterial species Staphylococcus aureus and Enterococcus faecalis among the Gram-positives, Escherichia coli and Pseudomonas aeruginosa among the Gram-negatives and the yeast Candida albicans. They showed satisfactory surface-active properties, and a cytotoxic effect that was dependent on the length of the hydrophobic chain. Lower minimum inhibiting concentration (MIC) values were calculated for C14-derivatives, which were comparable to those calculated for BAC toward Gram-positive bacteria and slightly higher for Gram-negative bacteria and C. albicans. Thus, the synthesised leucine-based quaternary ammonium cationic surfactants can potentially find application as promising surface-active compounds with antimicrobial activity.

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“…The organic phase was collected and then dehydrated with anhydrous sodium sulfate. After filtration and solvent evaporation under vacuum, the compound was obtained as an oil [15,16].…”

Section: Methodsmentioning

confidence: 99%

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

et al. 2019

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“…Another extraordinary finding has been reported, in which four-component supramolecular, propeller-like architectures were constructed through co-assembly of an achiral disk-shaped molecule and chiral amino acid derivatives driven by intermolecular hydrogen bonding. Chiral amplification in this system was shown to be explainable by both the "sergeants-and-soldiers" principle and "majority-rules" effect [198].…”

Section: Majority-rules Principle and Related Approachesmentioning

confidence: 87%

Functional Chirality: From Small Molecules to Supramolecular Assemblies

Adawy

2022

Symmetry

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Many structures in nature look symmetric, but this is not completely accurate, because absolute symmetry is close to death. Chirality (handedness) is one form of living asymmetry. Chirality has been extensively investigated at different levels. Many rules were coined in attempts made for many decades to have control over the selection of handedness that seems to easily occur in nature. It is certain that if good control is realized on chirality, the roads will be ultimately open towards numerous developments in pharmaceutical, technological, and industrial applications. This tutorial review presents a report on chirality from single molecules to supramolecular assemblies. The realized functions are still in their infancy and have been scarcely converted into actual applications. This review provides an overview for starters in the chirality field of research on concepts, common methodologies, and outstanding accomplishments. It starts with an introductory section on the definitions and classifications of chirality at the different levels of molecular complexity, followed by highlighting the importance of chirality in biological systems and the different means of realizing chirality and its inversion in solid and solution-based systems at molecular and supramolecular levels. Chirality-relevant important findings and (bio-)technological applications are also reported accordingly.

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“…The oil was dissolved in ethyl acetate and the excess of p-toluenesulfonic acid was extracted using Na 2 CO 3 . The organic phase was collected and then dehydrated with anhydrous sodium sulfate, followed by evaporation under vacuum, obtaining the compound as an oil [24,25].…”

Section: Synthesis Of O-acyl Leu and O-acyl Met Derivativesmentioning

confidence: 99%

Quaternary ammonium surfactants derived from leucine and methionine: Novel challenging surface active molecules with antimicrobial activity

Perinelli

Petrelli

Vitali

et al. 2019

Journal of Molecular Liquids

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Self‐Assembly of Chiral Propeller‐like Supermolecules with Unusual “Sergeants‐and‐Soldiers” and “Majority‐Rules” Effects

Cited by 19 publications

References 48 publications

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

Functional Chirality: From Small Molecules to Supramolecular Assemblies

Quaternary ammonium surfactants derived from leucine and methionine: Novel challenging surface active molecules with antimicrobial activity

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