Displaying all 5 publications

  1. Salman AA, Tabandeh M, Heidelberg T, Duali Hussen RS
    Carbohydr Res, 2015 Apr 10;406:41-5.
    PMID: 25658065 DOI: 10.1016/j.carres.2014.12.015
    A series of glycolipid crown ether analogs was prepared by bis-propargylation of lauryl glycoside followed by subsequent click-coupling with ethylene glycol-based diazides. The triazole-linked macrocycles were obtained in remarkable high yields. While the surfactant assembly was affected by presence of sodium ions, suggesting the formation of complexes, no ion-selectivity was observed for the macrocylic ligands. Computational studies suggest a low but significant cation-binding activity of the macrocycle, involving coordination at both oxygen and nitrogen atoms.
  2. Goh EW, Heidelberg T, Duali Hussen RS, Salman AA
    ACS Omega, 2019 Oct 15;4(16):17039-17047.
    PMID: 31646251 DOI: 10.1021/acsomega.9b02809
    Aiming for glycolipid-based vesicles for targeted drug delivery, cationic Guerbet glycosides with spacered click functionality were designed and synthesized. The cationic charge promoted the distribution of the glycolipids during the formulation, thereby leading to homogeneously small vesicles. The positive surface charge of the vesicles stabilizes them against unwanted fusion and promotes interactions of the drug carriers with typical negative charge-dominated target cells. High bioconjugation potential of the functionalized glycolipids based on the copper-catalyzed azide alkyne cycloaddition makes them highly valuable components for targeted drug delivery systems.
  3. Salman AA, Tabandeh M, Heidelberg T, Hussen RS, Ali HM
    Carbohydr Res, 2015 Aug 14;412:28-33.
    PMID: 26000863 DOI: 10.1016/j.carres.2015.04.022
    A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.
  4. Tabandeh M, Goh EW, Salman AA, Heidelberg T, Duali Hussen RS
    Carbohydr Res, 2018 Nov;469:14-22.
    PMID: 30196011 DOI: 10.1016/j.carres.2018.08.016
    Two azide-terminated oligoethylene oxide spacered glycolipids have been synthesized, and their assembly behavior has been studied in comparison to the corresponding base surfactants. The results suggest potential of the Guerbet lactoside-based compound for targeted drug delivery, while a coiling of the ethylene oxide linker disfavors the application of the glucoside.
  5. Tabandeh M, Salman AA, Goh EW, Heidelberg T, Hussen RSD
    Chem Phys Lipids, 2018 05;212:111-119.
    PMID: 29409839 DOI: 10.1016/j.chemphyslip.2018.01.011
    A new synthesis approach towards biantennary lipids of Guerbet glycoside type was developed based on oleic acid as sustainable resource. Functionalization of the double bond provided access to primary alcohols with α-branched C19-skeleton. Formulation studies with corresponding lactosides indicated formation of vesicles with high assembly stability. A relatively narrow bimodal size distribution of the latter, which turns into a narrow unimodal distribution of small vesicles upon addition of an ionic cosurfactant, suggests potential for a vesicular drug delivery system.
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