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Gemini Surfactants for Medical and Non-medical Applications
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Gemini Surfactants for Medical and Non-medical Applications

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Macromolecular Chemistry".

Deadline for manuscript submissions: 31 December 2024 | Viewed by 5878

Special Issue Editor

Prof. Dr. Bogumil E. Brycki

E-Mail Website
Guest Editor
Department of Bioactive Compounds, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznan, Poland
Interests: organic synthesis; molecular interactions; surface chemistry; microbiocide chemistry; smart materials; corrosion inhibition; environmental chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Gemini surfactants consist of two cationic monomers of a surfactant linked together with a spacer. The specific structure of a cationic gemini surfactant is the reason for both their high surface activity and their ability to decrease the surface tension of water. The high surface activity and unique structure of gemini surfactants result in outstanding properties, including antibacterial and antifungal activity, anticorrosion properties, unique aggregation behaviour, the ability to form various structures reversibly in response to environmental conditions, and interactions with biomacromolecules such as DNA and proteins. These properties can be tailored by selecting the optimal structure of a gemini surfactant in terms of the nature and length of its alkyl substituents, spacer, and head group. Additionally, regarding their properties, comparison with their monomeric counterparts demonstrates that gemini surfactants have higher performance efficacy at lower concentrations. Hence, less material is needed, and the toxicity is lower. However, there are some limitations regarding their biocompatibility that have led researchers to develop amino-acid-based and sugar-based gemini surfactants. Owing to their remarkable properties, cationic gemini surfactants are promising candidates for both medical and nonmedical applications.

Prof. Dr. Bogumil E. Brycki
Guest Editor

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Keywords

  • gemini surfactants
  • antimicrobials
  • corrosion inhibitors
  • biocorrosion
  • bio-application
  • drug delivery
  • gene therapy
  • biomaterial surface modification

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Published Papers (3 papers)

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Research

25 pages, 3952 KiB  
Article
Arginine Gemini-Based Surfactants for Antimicrobial and Antibiofilm Applications: Molecular Interactions, Skin-Related Anti-Enzymatic Activity and Cytotoxicity
by Francisco Fábio Oliveira de Sousa, Aurora Pinazo, Zakaria Hafidi, María Teresa García, Elena Bautista, Maria del Carmen Moran and Lourdes Pérez
Molecules 2023, 28(18), 6570; https://doi.org/10.3390/molecules28186570 - 11 Sep 2023
Cited by 1 | Viewed by 1880
Abstract
The antimicrobial and antibiofilm properties of arginine-based surfactants have been evaluated. These two biological properties depend on both the alkyl chain length and the spacer chain nature. These gemini surfactants exhibit good activity against a wide range of bacteria, including some problematic resistant [...] Read more.
The antimicrobial and antibiofilm properties of arginine-based surfactants have been evaluated. These two biological properties depend on both the alkyl chain length and the spacer chain nature. These gemini surfactants exhibit good activity against a wide range of bacteria, including some problematic resistant microorganisms such us methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Moreover, surfactants with a C10 alkyl chain and C3 spacer inhibit the (MRSA) and Pseudomonas aeruginosa biofilm formation at concentrations as low as 8 µg/mL and are able to eradicate established biofilms of these two bacteria at 32 µg/mL. The inhibitory activities of the surfactants over key enzymes enrolled in the skin repairing processes (collagenase, elastase and hyaluronidase) were evaluated. They exhibited moderate anti-collagenase activity while the activity of hyaluronidase was boosted by the presence of these surfactants. These biological properties render these gemini arginine-based surfactants as perfect promising candidates for pharmaceutical and biological properties. Full article
(This article belongs to the Special Issue Gemini Surfactants for Medical and Non-medical Applications)
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12 pages, 1145 KiB  
Article
Self-Aggregation, Antimicrobial Activity and Cytotoxicity of Ester-Bonded Gemini Quaternary Ammonium Salts: The Role of the Spacer
by Yaqin Liang, Hui Li, Jiahui Ji, Jiayu Wang and Yujie Ji
Molecules 2023, 28(14), 5469; https://doi.org/10.3390/molecules28145469 - 17 Jul 2023
Cited by 2 | Viewed by 1250
Abstract
Five ester-bonded gemini quaternary ammonium surfactants C12-En-C12 (n = 2, 4, 6), with a flexible spacer group, and C12-Bm-C12 (m = 1, 2), with rigid benzene spacers, were synthesized via a two-step reaction [...] Read more.
Five ester-bonded gemini quaternary ammonium surfactants C12-En-C12 (n = 2, 4, 6), with a flexible spacer group, and C12-Bm-C12 (m = 1, 2), with rigid benzene spacers, were synthesized via a two-step reaction and analyzed. Furthermore, the effects of the spacer structure, spacer length and polymerization degree on the self-aggregation, antimicrobial activity and cytotoxicity of C12-En-C12 and C12-Bm-C12 and their corresponding monomer N-dodecyl-N,N,N-trimethyl ammonium chloride DTAC were investigated. The results showed that C12-En-C12 and C12-Bm-C12 had markedly lower critical micellar concentration (CMC) values and lower surface tension than DTAC. Moreover, the CMC values of C12-En-C12 and C12-Bm-C12 decreased with increasing spacer length. In the case of equivalent chain length, the rigidity and steric hindrance of phenylene and 1,4-benzenediyl resulted in larger CMC values for C12-Bm-C12 than for C12-En-C12. The antibacterial ability of C12-En-C12 and C12-Bm-C12 was assessed using Escherichia coli (E. coli) and Staphylococcus albus (S. aureus) based on minimum inhibitory concentrations (MICs). Furthermore, C12-En-C12 and C12-Bm-C12 exhibited higher antimicrobial activity than DTAC and had stronger function toward S. aureus than E. coli. The antimicrobial activity was enhanced by increasing the spacer chain length and decreased with the increased rigidity of the spacers. The cytotoxic effects of C12-En-C12 and C12-Bm-C12 in cultured Hela cells were evaluated by the standard CCK8 method based on half-maximal inhibitory concentration (IC50). The cytotoxicity of C12-En-C12 and C12-Bm-C12 was significantly lower than alkanediyl-α,ω-bis(dimethyldodecylammonium) bromide surfactants and DTAC. The spacer structure and the spacer length could induce significant cytotoxic effects on Hela cells. These findings indicate that the five ester-bonded GQASs have stronger antibacterial activity and lower toxicity profile, and thus can be used in the pharmaceutical industry. Full article
(This article belongs to the Special Issue Gemini Surfactants for Medical and Non-medical Applications)
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15 pages, 4610 KiB  
Article
Promoting Efficacy and Environmental Safety of Pesticide Synergists via Non-Ionic Gemini Surfactants with Short Fluorocarbon Chains
by Ruiguo Wang, Xinxin Xu, Xiaodi Shi, Junjie Kou, Hongjian Song, Yuxiu Liu, Jingjing Zhang and Qingmin Wang
Molecules 2022, 27(19), 6753; https://doi.org/10.3390/molecules27196753 - 10 Oct 2022
Cited by 8 | Viewed by 2119
Abstract
Improving the utilization rate of pesticides is key to achieve a reduction and synergism, and adding appropriate surfactant to pesticide preparation is an effective way to improve pesticide utilization. Fluorinated surfactants have excellent surface activity, thermal and chemical stability, but long-chain linear perfluoroalkyl [...] Read more.
Improving the utilization rate of pesticides is key to achieve a reduction and synergism, and adding appropriate surfactant to pesticide preparation is an effective way to improve pesticide utilization. Fluorinated surfactants have excellent surface activity, thermal and chemical stability, but long-chain linear perfluoroalkyl derivatives are highly toxic, obvious persistence and high bioaccumulation in the environment. Therefore, new strategies for designing fluorinated surfactants which combine excellent surface activity and environmental safety would be useful. In this study, four non-ionic gemini surfactants with short fluorocarbon chains were synthesized. The surface activities of the resulting surfactants were assessed on the basis of equilibrium surface tension, dynamic surface tension, and contact angle. Compared with their monomeric counterparts, the gemini surfactants had markedly lower critical micelle concentrations and higher diffusivities, as well as better wetting abilities. We selected a single-chain surfactant and a gemini surfactant with good surface activities as synergists for the glyphosate water agent. Both surfactants clearly improved the efficacy of the herbicide, but the gemini surfactant had a significantly greater effect than the single-chain surfactant. An acute toxicity test indicated that the gemini surfactant showed slight toxicity to rats. Full article
(This article belongs to the Special Issue Gemini Surfactants for Medical and Non-medical Applications)
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