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

Perttu, Emily K.; Szoka, Francis C.

doi:10.1039/c1cc15804j

Cited by 40 publications

(52 citation statements)

References 21 publications

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“…Zwitterionic sulfobetaine liposomes (Perttu and Szoka, 2011) bind to anions in aqueous solutions to a greater extent than do phosphatidylcholines. To investigate if this binding preference is a general phenomenon associated with the inverted headgroup, we measured the zeta potential of DMAQ:Chol liposomes in the presence of various anions and compared it to the zeta potential of DMPC:Chol liposomes measured under the same conditions.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, our group has synthesized zwitterionic sulfobetaine diacyllipids and zwitterionic choline phosphate diacyl lipids with interesting salt-dependant thermotropic properties (Perttu and Szoka, 2011; Perttu and Szoka, unpublished data). These diacyllipids have a cationic amine adjacent to the membrane interface and an anionic group (sulfonate, phosphate or ethylphosphate) that extends away from the membrane.…”

Section: Introductionmentioning

confidence: 99%

“…Conversely, at low salt concentrations, these lipids exhibit elevated Tm similar to those observed in phosphatidylethanolamine (PE) lipids of the same chain length. We propose that the change in Tm is driven by interactions of anions with the cationic amine at the membrane interface (Perttu and Szoka, 2011; Perttu and Szoka, unpublished data).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…Divalent cations, especially Ca 2+ , are of particular interest because they are ubiquitous in biological systems and can interact with lipid headgroups to cause membrane destabilization via aggregation, fusion, or alteration of surface charge [142]. CP, CPe, AQ and SB liposomes do not aggregate in the presence of physiological levels of Ca 2+ , and IZ liposomes interact with Ca 2+ less than PC liposomes [143–145]. Reduced divalent cation interactions make IZ liposomes interesting candidates to investigate as in vivo delivery systems.…”

Section: Lipids That Direct Membrane Biophysics and Payload Releasementioning

confidence: 99%

Designer lipids for drug delivery: From heads to tails

Kohli

Kierstead

Venditto

et al. 2014

Journal of Controlled Release

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136

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For four decades, liposomes composed of both naturally occurring and synthetic lipids have been investigated as delivery vehicles for low molecular weight and macromolecular drugs. These studies paved the way for the clinical and commercial success of a number of liposomal drugs, each of which required a tailored formulation; one liposome size does not fit all drugs! Instead, the physicochemical properties of the liposome must be matched to the pharmacology of the drug. An extensive biophysical literature demonstrates that varying lipid composition can influence the size, membrane stability, in vivo interactions, and drug release properties of a liposome. In this review we focus on recently described synthetic lipid headgroups, linkers and hydrophobic domains that can provide control over the intermolecular forces, phase preference, and macroscopic behavior of liposomes. These synthetic lipids further our understanding of lipid biophysics, promote targeted drug delivery, and improve liposome stability. We further highlight the immune reactivity of novel synthetic headgroups as a key design consideration. For instance it was originally thought that synthetic PEGylated lipids were immunologically inert; however, it’s been observed that under certain conditions PEGylated lipids induce humoral immunity. Such immune activation may be a limitation to the use of other engineered lipid headgroups for drug delivery. In addition to the potential immunogenicity of engineered lipids, future investigations on liposome drugs in vivo should pay particular attention to the location and dynamics of payload release.

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“…S3D). Although, good solubility of the zwitterionic compound in water (Table S2), existing with aggregation form mainly and the opposite charge (the positive and negative charges) carried by the compound, which means that the substitutes of the Pc is apt to form inner-salt because of electrostatic attraction [26,27]. Then ZS-ZnPc compound shows extreme photostability upon the irradiation.…”

mentioning

confidence: 96%

Zwitterionic phthalocyanine zinc (II) synthesis, and photodynamic activity comparison with nonionic and cationic phthalocyanine

Gui

Zhang

Wang

et al. 2017

Inorganic Chemistry Communications

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

Cited by 40 publications

References 21 publications

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

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

Designer lipids for drug delivery: From heads to tails

Zwitterionic phthalocyanine zinc (II) synthesis, and photodynamic activity comparison with nonionic and cationic phthalocyanine

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