Amino acid-based cationic gemini surfactant–protein interactions

Branco, Mafalda A.; Pinheiro, Lídia; Faustino, Célia

doi:10.1016/j.colsurfa.2014.12.022

Cited by 52 publications

(29 citation statements)

References 73 publications

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“…Some of them like lipoaminoacids were investigated to be good drug carrier . Amphipathic Gemini surfactants are highly efficient in all respect in comparison to conventional surfactants due to its low CMC, high surface activity, more solubilizing power . So, it is very useful in formulation of personal care products.…”

Section: Application Of Surfactantsmentioning

confidence: 99%

Novel Amphiphiles and Their Applications for Different Purposes with Special Emphasis on Polymeric Surfactants

et al. 2019

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Amphiphiles or surfactants are widely known for its reducing power of interfacial tension and extraordinary rheological properties. Among the various classes of surfactants gemini surfactants, biosurfactants and polymeric surfactants are remarkable and distinguishable among the others for their structural diversity and profitable usefulness. Primarily, the performance of any surfactant can be determined by HLB (Hydrophile Lipophile Balance) value, an empirical parameter. This review attempts to clarify some of the terminology used in literature by providing illustration of classification, features and diverse applications of different surfactants.

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Section: Application Of Surfactantsmentioning

confidence: 99%

Novel Amphiphiles and Their Applications for Different Purposes with Special Emphasis on Polymeric Surfactants

et al. 2019

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“…Cationic surfactant-DNA interactions have been extensively debated regarding their biological significance and potential biomedical relevance. Experimental and theoretical studies suggest that, at low surfactant concentrations, far below the critical micelle concentration (CMC) of the surfactant, the surfactant monomers bind DNA through electrostatic interactions between the positively charged headgroups of the cationic surfactant and the negatively charged phosphate groups of the DNA backbone [61,[67][68][69]. A further increase in surfactant concentration leads to cooperative binding due to hydrophobic interaction between the alkyl chains of neighboring surfactant molecules with the formation of micelle-like clusters along the polynucleotide chain once critical aggregation concentration (CAC) is reached.…”

Section: Cationic Lipoaminoacid-dna Interactionsmentioning

confidence: 99%

Lipoaminoacids Enzyme-Based Production and Application as Gene Delivery Vectors

et al. 2019

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Biosurfactant compounds have been studied in many applications, including biomedical, food, cosmetic, agriculture, and bioremediation areas, mainly due to their low toxicity, high biodegradability, and multifunctionality. Among biosurfactants, the lipoplexes of lipoaminoacids play a key role in medical and pharmaceutical fields. Lipoaminoacids (LAAs) are amino acid-based surfactants that are obtained from the condensation reaction of natural origin amino acids with fatty acids or fatty acid derivatives. LAA can be produced by biocatalysis as an alternative to chemical synthesis and thus become very attractive from both the biomedical and the environmental perspectives. Gemini LAAs, which are made of two hydrophobic chains and two amino acid head groups per molecule and linked by a spacer at the level of the amino acid residues, are promising candidates as both drug and gene delivery and protein disassembly agents. Gemini LAA usually show lower critical micelle concentration, interact more efficiently with proteins, and are better solubilising agents for hydrophobic drugs when compared to their monomeric counterparts due to their dimeric structure. A clinically relevant human gene therapy vector must overcome or avoid detect and silence foreign or misplaced DNA whilst delivering sustained levels of therapeutic gene product. Many non-viral DNA vectors trigger these defence mechanisms, being subsequently destroyed or rendered silent. The development of safe and persistently expressing DNA vectors is a crucial prerequisite for a successful clinical application, and it one of the main strategic tasks of non-viral gene therapy research.

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“…Gemini surfactants can be used in traditional surfactant applications as solubilizers, surface tension reducers, and wetting agents 4 .In recent years, Gemini surfactants have been utilized in nanotechnology applications as stabilizers of carbon nanotubes 5 and silica spheres 6 . Considerable attention has also been focused on the interaction of Gemini surfactants with proteins, DNA, and biomembranes [7][8][9][10] .Topical cutaneous interferon gamma gene delivery using Gemini surfactant-based nanoparticles is safe and leads to increased gene expression in the skin 11 .When Gemini surfactants were applied to a paclitaxel delivery system, they promoted cellular drug uptake and showed good biocompatibility 12 .Because Gemini surfactants are positively charged, we speculated that they could be used as bioadhesive materials to improve the bioavailability of oral drugs through interaction with the negatively charged gastrointestinal mucosa. To our knowledge, there is no related report on the utilization of Gemini surfactants as bioadhesives thus far.…”

Section: Introductionmentioning

confidence: 99%

The 12-3-12 cationic gemini surfactant as a novel gastrointestinal bioadhesive material for improving the oral bioavailability of coenzyme Q10 naked nanocrystals

Song

Han

Feng

et al. 2016

Drug Development and Industrial Pharmacy

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To improve the oral bioavailability of nanocrystalline drug preparations, the cationic 12-3-12 quaternary ammonium surfactant gemini was introduced into nanocrystals as a novel gastrointestinal bioadhesive material. Coenzyme Q10 (CoQ10), a typical Biopharmaceutics Classification System (BCS) class II drug, was used as a model drug. The 12-3-12 gemini surfactant was added to the preparation at a low concentration and imbued the particles with abundant positive charges. In vitro and in vivo gastrointestinal adhesion tests confirmed that the gemini-modified nanocrystals were prone to adhere to the upper gastrointestinal tract (GIT), thereby prolonging retention time in the GIT and enhancing absorption. In the distribution study in rats, the use of nanocrystals modified with gemini led to greater drug distribution to the heart and the liver than that achieved with the naked nanocrystals. A pharmacokinetic study in beagle dogs showed that the gemini-modified CoQ10 nanocrystals improved the oral bioavailability of CoQ10 in a dose-dependent manner, and the smaller size produced a much better effect with the same gemini modification. These results demonstrate that the cationic surfactant gemini is a promising oral bioadhesive material with applications in nanoscale drug delivery systems.

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Amino acid-based cationic gemini surfactant–protein interactions

Cited by 52 publications

References 73 publications

Novel Amphiphiles and Their Applications for Different Purposes with Special Emphasis on Polymeric Surfactants

Novel Amphiphiles and Their Applications for Different Purposes with Special Emphasis on Polymeric Surfactants

Lipoaminoacids Enzyme-Based Production and Application as Gene Delivery Vectors

The 12-3-12 cationic gemini surfactant as a novel gastrointestinal bioadhesive material for improving the oral bioavailability of coenzyme Q10 naked nanocrystals

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