Synthesis, Characterization, and Drug Delivery Application of Self-assembling Amphiphilic Cyclodextrin

Mayank R. Patel, Dimitrios A. Lamprou, Pradeep R. Vavia

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The main aim of the research was to synthesize amphiphilic cyclodextrin (AMCD) by substituting C12 alkyl chain to a β-cyclodextrin (βCD) in a single step and to study its self-assembly in an aqueous medium. The drug delivery application of the AMCD was also evaluated by encapsulating tamoxifen citrate as a model hydrophobic drug. AMCD was able to self-assemble in aqueous media; forming nanovesicles of size <200 nm, capable of encapsulating Tamoxifen Citrate (TMX). Molecular docking and MD simulation studies revealed the interaction between TMX and AMCD which formed a stable complex. TEM and AFM studies showed that nanovesicles were perfectly spherical having a smooth surface and a theoretical AMCD bilayer thickness of ~7.2 nm as observed from SANS studies. XRD and DSC studies revealed that TMX was amorphized and molecularly dispersed in AMCD bilayer which was released slowly following Fickian diffusion. AMCD has excellent hemocompatibility as opposed to βCD and no genotoxicity. IC50 of TMX against MCF-7 cell lines was significantly reduced from 11.43 µg/ml to 7.96 µg/ml after encapsulation in nanovesicle because of nanovesicles being endocytosed by the MCF-7 cells.  AMCD was well tolerated by IV route at a dose >2000 mg/kg in rats. Pharmacokinetic profile of TMX after encapsulation was improved giving 3-fold higher AUC; extended mean residence time is improving chances of nanovesicle to extravasate in tumor via EPR effect.

Original languageEnglish
Article number11
Number of pages16
JournalAAPS PharmSciTech
Publication statusPublished - 05 Dec 2019


  • Amphiphilic cyclodextrin
  • Molecular modelling
  • nanovesicles
  • bilayer
  • Cytotoxicity


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