Cationic Gemini Surfactants Based on Tartaric Acid: Synthesis, Aggregation, Monolayer Behaviour, and Interaction with DNA

Buijnsters, Peter; Rodrı́guez, Cristina; Willighagen, Egon; Sommerdijk, Nico A. J. M.; Kremer, Andreas; Camilleri, Patrick; Feiters, Martinus C.; Nolte, Roeland J. M.; Zwanenburg, B.

doi:10.1002/1099-0690(200204)2002:8<1397::aid-ejoc1397>3.0.co;2-6

Cited by 39 publications

(25 citation statements)

References 36 publications

(28 reference statements)

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“…The formation of the condensed -phase in gemini surfactant-DNA systems has also been observed for a series of diastereomers of the gemini surfactant 2,3-dimethoxy-1,4-bis(N-hexadecyl-N,N-dimethylammonium)-butane dibromide, as well as for 1,4-bis(N-hexadecyl-N,Ndimethylammonium)butane dibromide (16-4-16) [28,29]. Non-ionic tartaric acid-based gemini surfactants were not observed to induce substantial changes in the structure of -phage DNA; observed decreases in ellipticity at 278 nm were attributed to changes in the hydration state of the DNA [30].…”

Section: Interactions With Dnamentioning

confidence: 89%

Gemini Surfactants: A New Family of Building Blocks for Non-Viral Gene Delivery Systems

Wettig

Verrall²,

Földvári³

2008

CGT

139

112

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Gemini surfactants provide a significant opportunity in the development of new non-viral delivery systems designed for gene therapy applications. This review summarizes the wide range of gemini surfactant structures that have been employed for DNA transfection in vitro. A general observation is that those structures capable of inducing a wide variety of polymorphic structures (lamellar, hexagonal, or cubic phases) demonstrate higher transfection efficiencies. Those compounds whose structures result in pH-dependent changes in aggregate structure similarly show higher levels of transfection. In vivo transfection using gemini surfactants has been demonstrated in only three cases, and in a recent study the transfection was linked to a specific therapeutic response.

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Section: Interactions With Dnamentioning

confidence: 89%

Gemini Surfactants: A New Family of Building Blocks for Non-Viral Gene Delivery Systems

Wettig

Verrall²,

Földvári³

2008

CGT

139

112

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“…In the case of the IMI_Gly_n2_C12 surfactant (Figure a), the presence of the amphiphile in solution is expressed as a loss of the intensity of all observed CD bands. This is usually attributed to changes in the hydration shell near the phosphate groups and ribose rings, as a result of ion exchange and the binding of surfactant molecules to DNA . With increasing surfactant content, the loss of the CD signal becomes more pronounced.…”

Section: Resultsmentioning

confidence: 99%

Dicationic Surfactants with Glycine Counter Ions for Oligonucleotide Transportation

2016

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Gemini surfactants are good candidates to bind, protect, and deliver nucleic acids. Herein, the concept of amino acids (namely glycine) as counter ions of gemini surfactants for gene therapy application was explored. This study was conducted on DNA and RNA oligomers and two quaternary bis-imidazolium salts, having 2,5-dioxahexane and 2,8-dioxanonane spacer groups. The toxicity level of surfactants was assessed by an MTT assay, and their ability to bind nucleic acids was tested through electrophoresis. The nucleic acid conformation was established based on circular dichroism and infrared spectroscopic analyses. The structures of the formed complexes were characterized by small-angle scattering of synchrotron radiation. Both studied surfactants appear to be suitable for gene therapy; however, although they vary by only three methylene groups in the spacer, they differ in binding ability and toxicity. The tested oligonucleotides maintained their native conformations upon surfactant addition and the studied lipoplexes formed a variety of structures. In systems based on a 2,5-dioxahexane spacer, a hexagonal phase was observed for DNA-surfactant complexes and a micellar phase was dominant with RNA. For the surfactant with a 2,8-dioxanonane spacer group, the primitive cubic phase prevailed.

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“…Reduced sugar geminis linked through their tertiary amino head groups through four or six carbons or alkyl spacers and with differing unsaturated chains have the capability of transferring Chinese hamster ovary (CHO) cell line. [77] Buijnsters et al [78] reported novel cationic type gemini surfactants based on tartaric acid linked with biocompatible palmitoyl tails and with lysine or the assorted lysineethylenediamine head groups. These surfactants show activity in luciferase gene-transfection assay, but this was accompanied by a considerable toxicity.…”

Section: Gene Therapy Techniquesmentioning

confidence: 99%

Industrial Applications of Dimeric Surfactants: A Review

Kumar

Tyagi

2014

Journal of Dispersion Science and Technology

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Dimeric surfactants also known as gemini surfactants have received lots of attention for high performance formulations in the various scientific and commercial products. Due to the greater amount of hydrocarbon per molecule, the critical micelle concentrations (CMC) of dimeric are typically one order of magnitude lower than the corresponding monomeric surfactant. They are ten to hundred times more efficient at reducing the surface tension of water and the interfacial tension of the oil-water interface than conventional surfactants. Besides, the Krafft temperatures of gemini surfactants with hydrophilic spacers are generally very low giving these surfactants the capacity to be used in cold water. These surfactants display a range of interesting properties, including elevated surface activity, extremely low CMC and extraordinary rheology and selfassimilation aspect. As a consequence of these properties, they have many potential applications include detergents and cleaning agents, cosmetics, textile, and dyeing, dispersion stabilization and emulsion polymerization, genetics science, pharmaceutical, and biological applications.

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Cationic Gemini Surfactants Based on Tartaric Acid: Synthesis, Aggregation, Monolayer Behaviour, and Interaction with DNA

Cited by 39 publications

References 36 publications

Gemini Surfactants: A New Family of Building Blocks for Non-Viral Gene Delivery Systems

Gemini Surfactants: A New Family of Building Blocks for Non-Viral Gene Delivery Systems

Dicationic Surfactants with Glycine Counter Ions for Oligonucleotide Transportation

Industrial Applications of Dimeric Surfactants: A Review

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