Solution Properties and Emulsification Properties of Amino Acid-Based Gemini Surfactants Derived from Cysteine

Yoshimura, Tomokazu; Sakato, Ayako; Esumi, Kunio

doi:10.5650/jos.62.579

Cited by 14 publications

(10 citation statements)

References 17 publications

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“…Structurally, they comprise two aliphatic chains (called "tails") and two hydrophilic groups (called "heads") linked together by a linker, which may be either rigid or more susceptible to deformation. [1][2][3] The most commonly used linkers are disulde bridges, amides or straight alkyl chains. Furthermore, recent studies revealed that their structure affects both surface activity as well as biodegradability of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Bis(ammonium) ionic liquids with herbicidal anions

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Bis(ammonium) ionic liquids with herbicidal anions

et al. 2015

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“…The CAC represents the ability of the lipopeptide to form micelles and to associate in complexes with other compounds, such as proteins or nucleic acids. The lower the CAC value, the better the performance of the carrier [12]. We demonstrate here that cationic lipopeptides may be used in subunit vaccine formulations and that they can enhance the humoral immune response induced by a protein antigen.…”

mentioning

confidence: 77%

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confidence: 99%

Gemini lipopeptides as vaccine adjuvants: a new role for these versatile carriers

Grippo

Reidel

García

et al. 2020

Clin Exp Vaccine Res

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Brief communication Vaccines are one of the most significant interventions of medicine, and showed important progress from empirical formulations to rational designs, along the time. Nevertheless, adjuvant development did not experience similar progress [1]. Oligonucleotides containing non-methylated CpG sequences (CpG-ODN) are immunostimulant molecules that are added in vaccine formulations as adjuvants, mostly as phosphorothioate modified ODN (PS-CpG-ODN). These types of bonds give resistance to nucleases leading to a longer in vivo persistence than natural phosphodiester ODN (PO-CpG-ODN). However, the cost of production of PS-CpG-ODN is higher than PO-CpG-ODN, and it has been reported that the long-term use of modified ODN may be associated with adverse side effects in mice, and primates [2]. Those are important factors to consider when developing vaccine systems. Nevertheless, PO-CpG-ODN can be used as adjuvant if complexed with an adequate vehicle, as liposomes [3,4]. Gemini compounds are amphipathic molecules formed by a hydrophobic moiety containing two hydrocarbon chains of variable length, and two hydrophilic portions that can be peptides, among other low molecular weight groups [5]. We developed a series of monomeric lipopeptides that function as DNA and protein carriers, called [AGn-Cm]2, where AGn is the peptidic polar head group and Cm is the non-polar region, attached to the peptide N-terminus [5]. A cysteine in the peptide can form a disulphide bridge with another monomer and generates the gemini lipopeptide by dimerization at physiological pH. Based on their ability to form complexes with negatively charged DNA, some of them are transfection reagents with high efficiency [5,6]. However, the use of these molecules in adjuvant formulations has not been described. In this study, we developed formulations based on cationic gemini lipopeptides and

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“…The gemini surfactant was less efficient in surface tension reduction than its monomeric counterpart, which was attributed to the film formation by the hydrocarbon chains of the former at the air/water interface so that they cannot adsorb effectively at the interface, an unusual phenomenon also found for other gemini surfactants from cystine with the same alkyl chain lenght [43]. Chirality was found to influence the surface active properties of the gemini AAS and their interaction with chiral biomacromolecules but not their micellar properties in solution since similar CMC values and Gibbs energy of micellization were obtained for gemini AAS derived from L-and D-cystine, and their racemate [40,41].…”

Section: Gemini Surfactantsmentioning

confidence: 93%

Amino Acid-Based Surfactants for Biomedical Applications

Pinheiro¹,

Faustino²

2017

Application and Characterization of Surfactants

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The growing demand for surfactants worldwide has a profound impact on the environment and public health. The quest for environmentally friendly "green" surfactants has driven research toward bio-based surfactants from renewable sources with improved performances and low toxicity. Amino acid-based surfactants (AAS) are a promising class of biocompatible and biodegradable surfactants for biomedical applications due to their improved safety profiles that meet the requirements of both physiological and ecological compatibility. Natural amino acids are chiral compounds and important raw materials for production of AAS. The amino acid pool allows the synthesis of multifunctional surfactants with chiral properties that can be tailored for specific technological and/or biomedical applications. The nature of the amino acid residue, the chirality, and the ability for hydrogen bond formation strongly influences the surface active properties and self-assembly behavior of AAS. This review summarizes recent developments in AAS structure-property relationships providing valuable information for modulation of the surface active and biological properties of AAS to meet specific biomedical applications. The interaction of AAS with biointerfaces and biological molecules is also addressed concerning cellular toxicity and potential therapeutic applications of AAS as antimicrobial agents, drug delivery vehicles, and a promising alternative to viral vectors in gene therapy.

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Solution Properties and Emulsification Properties of Amino Acid-Based Gemini Surfactants Derived from Cysteine

Cited by 14 publications

References 17 publications

Bis(ammonium) ionic liquids with herbicidal anions

Bis(ammonium) ionic liquids with herbicidal anions

Gemini lipopeptides as vaccine adjuvants: a new role for these versatile carriers

Amino Acid-Based Surfactants for Biomedical Applications

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