Specific Anion Binding to Sulfobetaine Micelles and Kinetics of Nucleophilic Reactions

Marte, Luisa; Beber, Rosane Costa; Farrukh, Muhammad Akhyar; Micke, Gustavo Amadeu; Costa, Ana Carolina Oliveira; Gillitt, Nicholas D.; Bunton, Clifford A.; Profio, Pietro Di; Savelli, Gianfranco; Nome, Faruk

doi:10.1021/jp0727897

Cited by 35 publications

(88 citation statements)

References 20 publications

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“…In the presence of salt, the otherwise neutrally charged micelles gain an overall negative charge. 10,11 Marte 11 reports that anions bind to the interface in the following order OH À o Cl À o Br À o ClO 4 À , which parallels the Hofmeister series. 12 Hydration of a dried film of the SB lipids in 150 mM NaCl at a temperature above the T m of the lipid did not lead to the formation of liposomes.…”

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confidence: 88%

Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties

Perttu¹,

Szoka²

2011

Chem. Commun.

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We describe a class of zwitterionic sulfobetaine (SB) lipids with fascinating salt-dependent properties. SB lipids are zwitter-neutral across a broad pH range; however they have negative surface potentials in the presence of anions and two salt-dependent transition temperatures. These new SB lipids provide insight on the role of charge orientation at the membrane interface and may be useful components in drug delivery systems.

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confidence: 88%

Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties

Perttu¹,

Szoka²

2011

Chem. Commun.

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“…This lipid collection has elucidated the influence of headgroup properties such as hydrogen bonding capability, size, and charge on superstructure formation and molecular interactions (Langner and Kubica, 1999; Chemin et al, 2008). For instance, zwitterionic surfactants interact with ions with higher affinity than do surfactants with a nonionic headgroup (Marte et al, 2007). However, there are a number of lipid headgroup architectures that have not been well characterized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of betaine-like diacyl lipids: zwitterionic lipids with the cationic amine at the bilayer interface

Kohli

Walsh

Szoka

2012

Chemistry and Physics of Lipids

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We synthesized and characterized a series of zwitterionic, acetate-terminated, quaternized amine diacyl lipids (AQ). These lipids have an inverted headgroup orientation as compared to naturally occurring phosphatidylcholine (PC) lipids; the cationic group is anchored at the membrane interface, while the anionic group extends into the aqueous phase. AQ lipids preferentially interact with highly polarizable anions (ClO4−) over less polarizable ions (Cl−), in accord with the Hofmeister series, as measured by the change in zeta potential of AQ liposomes. Conversely, AQ lipids have a weaker association with calcium than do PC lipids. The transition temperatures (Tm) of the AQ lipids are similar to the Tm observed with phosphatidylethanolamine (PE) lipids of the same chain length. AQ lipids form large lipid sheets after heating and sonication; however, in the presence of cholesterol, (Chol) these lipids form stable liposomes that encapsulate carboxyfluorescein. The AQ:Chol liposomes retain their contents in the presence of serum at 37 °C, and when injected intravenously into mice, their organ biodistribution is similar to that observed with PC:Chol liposomes. AQ lipids demonstrate that modulating the headgroup charge orientation significantly alters the biophysical properties of liposomes. For the drug carrier field, these new materials provide a non-phosphate containing zwitterlipid for the production of lipid vesicles.

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“…However, this broad trend is often surfactant specific. Interestingly, the effect of temperature in the range 6-60 C over CMC of aqueous solution of zwitterionic alkyl betaine has found a steady decrease in CMC (Marte et al, 2007).…”

Section: Temperature Dependence Of the Cmcmentioning

confidence: 99%

“…On the basis of the nature of the head group, surfactants are often classified as neutral, ionic (anionic, cationic), and zwitterionic. Zwitterionic surfactants have no net charge, but their micelles still have binding affinity for anions, and if suitable conditions are provided, they can also interact with cations (Iso & Okada, 2000;Marte et al, 2007;Priebe et al, 2008;Tondo et al, 2007Tondo et al, , 2010.…”

Section: Introductionmentioning

confidence: 99%

Interfacial activity and micellar morphology of an imidazolium ring containing zwitterionic surfactants

Ali

Khan

Ahmad

et al. 2022

J Surfact & Detergents

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Zwitterionic surfactants based on 3-(1-alkyl-3-imidazolio) propane-sulfonate where R is octyl or dodecyl) is an emerging and important class of amphiphile due to their relevance as nano reactors for the synthesis of metallic nanoparticles and accelerated acid hydrolysis. The physicochemical properties of such synthesized imidazolium ring-containing zwitterionic surfactants have been characterized by surface tension and small-angle neutron scattering (SANS) techniques. Surface tension measurements were used to calculate several thermodynamic parameters over a range of concentrations and temperatures (298-313 K). The results obtained showed a weak signature representing the critical micelle concentration (CMC) for ImS3-8, however, by increasing the alkyl length of the hydrophobic group to dodecyl, that is, ImS3-8 to ImS3-12, the signature of the CMC was much more evident. As expected, the CMC for ImS3-12 shifted to a lower concentration. An increase in temperature increased the surface activity and decreased the CMC of both zwitterionic surfactants, although the changes were small. Compared to classical surfactants, that is, sodium dodecyl sulfate and dodecyl trimethylammonium bromide, the CMC of ImS3-12 is much lower. Modeling of SANS data demonstrated that the morphology of the micelles formed by these amphiphiles may be described by the "classical" model, a central hydrophobic core, with a shell of hydrated headgroups. Due to their widespread applications in colloidal and interfacial science, the present study adds new insight to the fundamental understanding of these interesting imidazolium-based surface-active ionic liquids (ImS3-R).

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Specific Anion Binding to Sulfobetaine Micelles and Kinetics of Nucleophilic Reactions

Cited by 35 publications

References 20 publications

Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties

Zwitterionic sulfobetaine lipids that form vesicles with salt-dependent thermotropic properties

Synthesis and characterization of betaine-like diacyl lipids: zwitterionic lipids with the cationic amine at the bilayer interface

Interfacial activity and micellar morphology of an imidazolium ring containing zwitterionic surfactants

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