Self-assembly of synthetic glycolipid/water systems

Hato, Masakatsu; Minamikawa, Hiroyuki; Tamada, Kaoru; Baba, Teruhiko; Tanabe, Yukito

doi:10.1016/s0001-8686(98)00085-2

Cited by 105 publications

(87 citation statements)

References 92 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Surfactants based on maltooligosaccharides show a reduction in their Krafft point upon increasing the number of glucose units of the saccharide. The opposite trend has been noticed for cellooligosaccharides, possibly because the intramolecular hydrogen bonding of the headgroup in the latter case inhibits its extensive hydration (39).…”

Section: Discussionmentioning

confidence: 86%

“…For instance, intramolecular hydrogen bonds may be formed that reduce the number of possible hydrogen bonds with solvent molecules and increase the rigidity of the sugar (36)(37)(38). The importance of the sugar stereochemistry in this respect is obvious in the example of the different structures adopted by homopolysaccharides: cellulose assumes an extended ribbon conformation whereas amylose assumes a flexible helix structure (39). By extrapolating this in the case of sugar surfactants one could expect to see a significant variability in their properties depending on the exact headgroup structure.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Surface Activity and Critical Aggregation Concentration of Pure Sugar Esters with Different Sugar Headgroups

Garofalakis

Murray

Sarney³

2000

Journal of Colloid and Interface Science

132

View full text Add to dashboard Cite

Section: Discussionmentioning

confidence: 86%

Section: Discussionmentioning

confidence: 99%

Surface Activity and Critical Aggregation Concentration of Pure Sugar Esters with Different Sugar Headgroups

Garofalakis

Murray

Sarney³

2000

Journal of Colloid and Interface Science

132

View full text Add to dashboard Cite

“…They carry hydrophobic moieties and hydrophilic carbohydrate head groups like glucose, sucrose or glycoside. Sugar surfactants with two or more hydrophobic chains are usually referred to as glycolipids (Hato et al, 1999;Stubenrauch, 2001). Naturally occurring sugar-based surfactants have obtained increased attention for drug solubilization because of their interesting characteristics like high-surface activity, biodegradability and lower toxicity.…”

Section: Introductionmentioning

confidence: 99%

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

et al. 2016

View full text Add to dashboard Cite

Context: Vesicular systems have attracted great attention in drug delivery because of their amphiphilicity, biodegradability, non-toxicity and potential for increasing drug bioavailability. Objective: A novel sugar-based double-tailed surfactant containing renewable block was synthesized for preparing niosomal vesicles that could be exploited for Levofloxacin encapsulation, aiming to increase its oral bioavailability. Materials and methods: The surfactant was characterized by 1 H NMR, mass spectroscopy and Fourier transform infrared spectroscopy (FT-IR). Its biocompatibility was studied against cell cultures and human blood hemolysis. In vivo acute toxicity was evaluated in mice. The vesicle morphology, size, drug-excipients interaction and entrapment efficiency (EE) were examined using atomic force microscope (AFM), dynamic light scattering (DLS), FT-IR and HPLC. Oral bioavailability studies of Levofloxacin in surfactant-based niosomal formulation were carried out using rabbits and plasma samples were analyzed using HPLC. Results and discussion: Vesicles were spherical in shape and the size was 190.31 ± 4.51 nm with a polydispersity index (PDI) of 0.29 ± 0.03. The drug EE in niosomes was 68.28 ± 3.45%. When applied on cell lines, high cell viability was observed even after prolonged exposure at high concentrations. It caused 5.77 ± 1.34% hemolysis at 1000 mg/mL and was found to be safe up to 2000 mg/kg. Elevated Levofloxacin plasma concentration was achieved when delivered with novel vesicles. Conclusion:The surfactant was demonstrated to be safe and effective as carrier of Levofloxacin. The study suggests that this sugar-based double-tailed nonionic surfactant could be promising nano-vesicular system for delivery and enhancing oral bioavailability of the hydrophobic Levofloxacin.

show abstract

“…According to the packing parameter theory, a single-tailed surfactant tends to form spherical micelles, while a double-tailed surfactant leads to a bilayer structure in aqueous solution. Generally, a systematical examination of the effect of the surfactant head group on the molecular aggregates has some difficulties compared with that of the hydrophobic tail group, except for some nonionic surfactants with polyethylene or polysaccharide units [3][4][5][6][7][8][9][10][11][12][13][14]. Another exception is the amino acid-type surfactant system [15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Effect of the side chain of N-acyl amino acid surfactants on micelle formation: An isothermal titration calorimetry study

Ohta

Toda

Morimoto

et al. 2008

Colloids and Surfaces A: Physicochemical and Engineering Aspect

View full text Add to dashboard Cite

The enthalpy of micelle formation, critical micelle concentration (CMC), and aggregation number of micelles for seven amino acid type surfactants, sodium-L-glutaminate (C12Gln), and -L-threoninate (C12Thr), were obtained at three temperatures ranging from 288.15 to 308.15 K by isothermal titration calorimetry. The enthalpies of micelle formation for these surfactants were positive at 288.15 K and decreased with increasing temperature to ultimately become negative above 308.15 K. The CMC of the amino acid surfactants decreased monotonously with increasing hydrophobicity of the amino acid residue without exception, while with the exception of the C12Phe system, the enthalpy of micelle formation increased. The micellization behavior of C12Phe also deviated from that of other amino acid systems in terms of the heat capacity and the aggregation number. These results suggest the presence of a strong intra-micelle interaction between the side chains of phenylalanine.

show abstract

Self-assembly of synthetic glycolipid/water systems

Cited by 105 publications

References 92 publications

Surface Activity and Critical Aggregation Concentration of Pure Sugar Esters with Different Sugar Headgroups

Surface Activity and Critical Aggregation Concentration of Pure Sugar Esters with Different Sugar Headgroups

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

Effect of the side chain of N-acyl amino acid surfactants on micelle formation: An isothermal titration calorimetry study

Contact Info

Product

Resources

About