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. 2019 Sep 30;4(16):17039-17047.
doi: 10.1021/acsomega.9b02809. eCollection 2019 Oct 15.

Imidazolium-Linked Azido-Functionalized Guerbet Glycosides: Multifunctional Surfactants for Biofunctionalization of Vesicles

Ean Wai Goh  1 , Thorsten Heidelberg  1 , Rusnah Syahila Duali Hussen  1 , Abbas Abdulameer Salman  1
Affiliations

Imidazolium-Linked Azido-Functionalized Guerbet Glycosides: Multifunctional Surfactants for Biofunctionalization of Vesicles

Ean Wai Goh et al. ACS Omega. .

Abstract

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Conceptual design for targeted biofunctionalized vesicles.
Figure 2
Figure 2
Structural design of the glycolipid core surfactant (A) and the functionalized bioconjugation anchor (B) for vesicular drug carriers.
Scheme 1
Scheme 1. Synthetic Scheme for the Functionalized Anchor Glycolipid
Figure 3
Figure 3
IR spectra for model click coupling.
Figure 4
Figure 4
1H NMR analysis of the aromatic region for model click coupling.
Scheme 2
Scheme 2. Model Click Coupling on a Surfactant Micelle
See this image and copyright information in PMC

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