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Synthesis and biocompatibility of self-assembling multi-tailed resorcinarene-based supramolecular amphiphile

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Abstract

Nano-vesicles of multi-tailed macrocycle molecules have demonstrated a great ability to enhance the bioavailability of hydrophobic drugs. In this study, amphiphilic multi-tailed resorcinarene (MTR) derivative was synthesised in two steps reaction by O-alkylation of 4-hydroxybenzaldehyde and then condensation with resorcinol. The synthesised amphiphilic macrocycle was characterized by 1H-NMR, FT-IR and mass spectrometry. Self-assembly and aggregation behaviour of amphiphilic macrocycle was studied in aqueous medium and vesicles were characterised for morphology, critical micelle concentration (CMC), size and surface potential and cellular biocompatibility. The self-assembling ability of MTR was used for one-step loading of hydrophobic drug, i.e. clarithromycin. MTR presented a low CMC value, i.e. 0.055 mM and formed niosomal vesicles with a mean diameter of 210 ± 2 nm, narrow size distribution and 65.12 ± 3.31% drug entrapment efficiency. MTR vesicles showed sustained in vitro drug release while maximum drug release was achieved at 8 h. Biocompatibility of MTR was investigated with blood haemolysis and cytotoxicity assays. The results indicated suitability of MRT as amphiphilic macromolecular surfactant.

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Authors and Affiliations

  1. H.E.J. Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, Karachi University, Karachi, 74200, Pakistan

    Imdad Ali, Salim Saifullah, Muhammed Imran & Muhammad Raza Shah

  2. National Centre of Excellence in Physical Chemistry, University of Peshawar, Peshawar, 25120, Pakistan

    Jan Nisar

  3. ARC Centre of Excellence in Convergent Bio-Nano Science and Technology, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC, 3052, Australia

    Ibrahim Javed

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  1. Imdad Ali
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  2. Salim Saifullah
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  3. Muhammed Imran
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  4. Jan Nisar
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  5. Ibrahim Javed
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  6. Muhammad Raza Shah
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Correspondence to Ibrahim Javed or Muhammad Raza Shah.

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Ali, I., Saifullah, S., Imran, M. et al. Synthesis and biocompatibility of self-assembling multi-tailed resorcinarene-based supramolecular amphiphile. Colloid Polym Sci 298, 331–339 (2020). https://doi.org/10.1007/s00396-020-04610-x

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  • DOI: https://doi.org/10.1007/s00396-020-04610-x

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