Gemini surfactant-based systems for drug and gene delivery

Makhlouf, Amal; Hajdu, István; Badea, Ildikó

doi:10.1016/b978-0-12-813663-8.00013-0

Cited by 14 publications

(13 citation statements)

References 77 publications

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“…Gemini surfactants have been attracting increased attention from the end of the last century, due to their enhanced surface properties (increased surface activity, low critical micelle concentration (cmc), useful viscoelastic properties) with respect to the monomeric counterparts [ 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. Taking advantage of these properties, they have been proposed as components of new drug delivery systems and as non-viral vectors for gene delivery [ 29 ]. Their multiple cationic character allows the binding and compacting of DNA into soft nanoparticles of tunable size, able to protect the DNA from enzymatic degradation and to prevent rapid leakage into blood capillary but small enough to escape macrophages of the reticuloendothelial system [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

“…Biomedical and biopharmaceutical applications of cationic amphiphiles as gene delivery vectors, together with their chemico-physical and aggregation properties, have been collected in a very interesting book [ 28 ]. Gemini surfactants with heterocyclic polar heads and their use as nonviral vectors have been extensively reviewed [ 29 , 31 ]. The use of gemini surfactants as candidates for gene delivery and the effect on the efficiency of transfection of the chemical structure of the surfactant (variations in the alkyl tail length and spacer/head group) and of the resulting physicochemical properties of the lipoplexes was also emphasized [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

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Gene-Delivery Ability of New Hydrogenated and Partially Fluorinated Gemini bispyridinium Surfactants with Six Methylene Spacers

Massa

Rivara

Donofrío

et al. 2022

IJMS

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The pandemic emergency determined by the spreading worldwide of the SARS-CoV-2 virus has focused the scientific and economic efforts of the pharmaceutical industry and governments on the possibility to fight the virus by genetic immunization. The genetic material must be delivered inside the cells by means of vectors. Due to the risk of adverse or immunogenic reaction or replication connected with the more efficient viral vectors, non-viral vectors are in many cases considered as a preferred strategy for gene delivery into eukaryotic cells. This paper is devoted to the evaluation of the gene delivery ability of new synthesized gemini bis-pyridinium surfactants with six methylene spacers, both hydrogenated and fluorinated, in comparison with compounds with spacers of different lengths, previously studied. Results from MTT proliferation assay, electrophoresis mobility shift assay (EMSA), transient transfection assay tests and atomic force microscopy (AFM) imaging confirm that pyridinium gemini surfactants could be a valuable tool for gene delivery purposes, but their performance is highly dependent on the spacer length and strictly related to their structure in solution. All the fluorinated compounds are unable to transfect RD-4 cells, if used alone, but they are all able to deliver a plasmid carrying an enhanced green fluorescent protein (EGFP) expression cassette, when co-formulated with 1,2-dioleyl-sn-glycero-3-phosphoethanolamine (DOPE) in a 1:2 ratio. The fluorinated compounds with spacers formed by six (FGP6) and eight carbon atoms (FGP8) give rise to a very interesting gene delivery activity, greater to that of the commercial reagent, when formulated with DOPE. The hydrogenated compound GP16_6 is unable to sufficiently compact the DNA, as shown by AFM images.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Gene-Delivery Ability of New Hydrogenated and Partially Fluorinated Gemini bispyridinium Surfactants with Six Methylene Spacers

Massa

Rivara

Donofrío

et al. 2022

IJMS

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“…The word gemini means dimeric, an amphiphilic molecule, earlier it used to be synthesized by joining the two discrete surfactant molecules by a rigid spacer. It contains two terminal hydrocarbon tails (short or long); two polar head groups (cationic, anionic, or nonionic); and a spacer (short or long, flexible or rigid) [4]. The gemini surfactant has an efficiency of self-assembling at low concentration.…”

Section: Introductionmentioning

confidence: 99%

Gemini Imidazolinium Surfactants: A Versatile Class of Molecules

Bhati¹,

Tripathy²,

Gupta³

2021

Colloids - Types, Preparation and Applications

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Gemini imidazolinium surfactants fascinated the researchers and many industries towards it due to their distinct molecular structure. It belongs to the cationic surfactant group. The variation in the physicochemical properties of the gemini surfactant can be achieved by changing the characteristics in the structure. There are several applications of imidazolinium such as antistatic agents, fabric softener that makes it a demanding surfactant in detergent industries as well as in the laundry industries due to the immense number of properties like dispersibility, viscosity, desirable storage stability, emulsification, critical micelle concentration and fabric conditioning etc. This book chapter discussed about the Gemini imidazolinium surfactants and its various properties, synthesis methods and applications in various fields.

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“…3,4 Indeed, the hydrophilic head groups of the sugar-based surfactants consist of monosaccharides, disaccharides, other oligosaccharides, and even carbohydrate derivatives, which retain the advantages of the nonionic surfactants. 5,6 So far, they showed a number of excellent properties such as low/no toxicity, 6 nonirritation, solubility, surface activity, 7 biocompatibility, and biodegradability besides utilizing the abundant renewable resources and reducing the high rate of the global petroleum consumption. With the advantage of renewable/ rich/cheap plant-derived carbohydrates, sugar-based surfactants including the well-known glycolipid are inevitably engaged in the dedicated conventional application fields such as hand dishwashing liquids, 8 oil recovery, industrial cleaners, 9 agriculture, food, and soil remediation.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, with the in-depth study of glycolipid surfactants, they are used in special areas such as membrane protein extraction 10 and pharmaceuticals 11 and for wetting, dispersing, and emulsifying properties. They, as detergents, biological reagents, drug and gene delivery systems, 5 new materials, and so on, should have been rapidly broadened because their exhaustive research should have theoretical value and trigger probably the potential industrial production and commercial developments after careful assessment involving raw materials, environmental protection, ecology, polyorientation, investment, technical difficulty, production scale, application field, favor degree, and market share. 2,12 From an overall view of the current situation and the development trend of the surfactant family, it can be demonstrated that there are naturally a number of different nonionic surfactants used in large amounts such as fatty alcohol ethoxylate, 13 coconut oil monoethanolamide, 14 Triton X-100, alkylphenol ethoxylate (APE), 15 amine.…”

Section: Introductionmentioning

confidence: 99%

Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

Fan

Chen

et al. 2020

J. Agric. Food Chem.

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Dioxyethene fragment (−(OCH2CH2)2−) was introduced into traditional alkyl β-d-glucopyranosides to ameliorate the water solubility, and eight nonionic surfactants, that is, alkoxy ethoxyethyl β-d-glucopyranosides with alkyl chain lengths (n = 6–16), were synthesized and characterized. Their hydrophilic and lipophilic balance number, water solubility, critical micelle concentration (cmc), γcmc, Γmax, and hygroscopic rate decreased with an increase in the alkyl chain length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and n-octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides (n = 6–12) exhibited excellent surface activity. In addition, for the binary mixture of alkoxy ethoxyethyl β-d-glucopyranosides (n = 8, 10, 12) and sodium dodecyl sulfate or cetyl trimethyl ammonium chloride, their cmc values were lower than the pure β-d-glucopyranosides, indicating that they had synergistic interactions. The fan focal conic textures of alkoxy ethoxyethyl β-d-glucopyranosides (n = 7–16) were observed during the cooling process under a polarizing optical microscope. Alkoxy ethoxyethyl β-d-glucopyranosides (n = 14, 16) had the related melting points and the clear points with differential scanning calorimetry. With β-d-glucopyranosides (n = 6–16) and n-butanol as the surfactant and cosurfactant, respectively, and with cyclohexane as the oil phase, the related microemulsion areas in their pseudoternary phase diagram system were investigated with the visual observation at 25 °C. Along with the slashing requirements of petroleum consumption, environmental protection, and green and sustainable development, nonionic sugar-based alkoxy ethoxyethyl β-d-glucopyranosides should be expected to have their potential practical application because of their strengthened hydrophilicity, improved water solubility, and enhanced surface activity.

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Gemini surfactant-based systems for drug and gene delivery

Cited by 14 publications

References 77 publications

Gene-Delivery Ability of New Hydrogenated and Partially Fluorinated Gemini bispyridinium Surfactants with Six Methylene Spacers

Gene-Delivery Ability of New Hydrogenated and Partially Fluorinated Gemini bispyridinium Surfactants with Six Methylene Spacers

Gemini Imidazolinium Surfactants: A Versatile Class of Molecules

Surface Activity of Alkoxy Ethoxyethyl β-d-Glucopyranosides

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