Tetraether bolaform amphiphiles as models of archaebacterial membrane lipids: Raman spectroscopy, phosphorus-31 NMR, x-ray scattering, and electron microscopy

Thompson, David H.; Wong, Kim F.; Humphry‐Baker, Robin; Wheeler, Jeffery J.; Kim, Jong Mok; Rananavare, Shankar B.

doi:10.1021/ja00049a040

Cited by 76 publications

(51 citation statements)

References 4 publications

(7 reference statements)

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“…Synthetic tetraether bolaform amphiphiles were shown to form large unilamellar and multilamellar vesicles in particular conditions of temperature and /or pH. Experimental data indicate that these molecules span a monolayer-type membrane with minimal contribution from bend molecules (12). Such result is in agreement with our analysis of the molecular packing of bipolar lipids.…”

Section: Resultssupporting

confidence: 87%

Bipolar Lipid Vesicles: A Model for Archaeobacteria Membranes

Gliozzi

Mirghani²,

Relini

1993

Journal of Liposome Research

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Section: Resultssupporting

confidence: 87%

Bipolar Lipid Vesicles: A Model for Archaeobacteria Membranes

Gliozzi

Mirghani²,

Relini

1993

Journal of Liposome Research

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“…Permeability in lipid membranes is related to the packing of the hydrocarbon chains. In the case of bolaamphiphiles, it was found that the permeability of the bolalipid layer is reduced compared with that of a monopolar lipid bilayer 187. Bilayer membranes can easily undergo delamination, since they are weakly bonded at the bilayer midplan, resulting in low mechanical stability 188.…”

Section: Bolaamphiphiles and Nano-structures For Drug Deliverymentioning

confidence: 99%

Lipid-Based Nanoparticles as Pharmaceutical Drug Carriers: From Concepts to Clinic

Puri

Loomis

Smith

et al. 2009

Crit Rev Ther Drug Carrier Syst

859

559

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In recent years, various nanotechnology platforms in the area of medical biology, including both diagnostics and therapy, have gained remarkable attention. Moreover, research and development of engineered multifunctional nanoparticles as pharmaceutical drug carriers have spurred exponential growth in applications to medicine in the last decade. Design principles of these nanoparticles, including nano-emulsions, dendrimers, nano-gold, liposomes, drug-carrier conjugates, antibody-drug complexes, and magnetic nanoparticles, are primarily based on unique assemblies of synthetic, natural, or biological components, including but not limited to synthetic polymers, metal ions, oils, and lipids as their building blocks. However, the potential success of these particles in the clinic relies on consideration of important parameters such as nanoparticle fabrication strategies, their physical properties, drug loading efficiencies, drug release potential, and, most importantly, minimum toxicity of the carrier itself. Among these, lipid-based nanoparticles bear the advantage of being the least toxic for in vivo applications, and significant progress has been made in the area of DNA/RNA and drug delivery using lipid-based nanoassemblies. In this review, we will primarily focus on the recent advances and updates on lipid-based nanoparticles for their projected applications in drug delivery. We begin with a review of current activities in the field of liposomes (the so-called honorary nanoparticles), and challenging issues of targeting and triggering will be discussed in detail. We will further describe nanoparticles derived from a novel class of amphipathic lipids called bolaamphiphiles with unique lipid assembly features that have been recently examined as drug/DNA delivery vehicles. Finally, an overview of an emerging novel class of particles (based on lipid components other than phospholipids), solid lipid nanoparticles and nanostructured lipid carriers will be presented. We conclude with a few examples of clinically successful formulations of currently available lipid-based nanoparticles.

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“…A number of acyclic, macrocyclic and hemimacrocyclic tetraether lipids have been synthesized (Benvegnu et al, , 2005Brard et al, 2004Brard et al, , 2007Eguchi et al, 1998;Kim and Thompson, 1992;Nakamura et al, 2007;Thompson et al, 1992) (for a recent review, see Benvegnu et al, 2008;Jacquemet et al, 2009). Synthetic methods have been developed to incorporate cyclopentane rings into the isoprenoid chain, diacetylenic groups into the polymethylene units, and various polar headgroups to the synthetic tetraether lipid cores Brard et al, 2004Brard et al, , 2007Eguchi et al, 1998;Patwardhan and Thompson, 2000) and to create varying alkyl chain lengths in the hydrocarbon core region (Nakamura et al, 2007).…”

Section: Chemical Synthesis and Modification Of Btlmentioning

confidence: 99%