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Evaluation of EDTA Dianhydride Versus Diphenyl Carbonate Nanosponges for Curcumin

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Abstract

Cyclodextrin-based nanosponges are widely investigated for several applications and are considered potential drug carriers. The method of nanosponges preparation involves the use of chemical cross-linking agents where the properties of Nanosponges can be affected. This study compared the resulting differences in the final nanosponges’ properties using carbonate and dianhydride crosslinkers. Diphenyl carbonate and EDTA dianhydride were used for the synthesis of nanosponges. Both types of nanosponges were loaded with curcumin as a model drug. Physicochemical characterizations, including PXRD, DSC, FTIR, scanning electron microscopy, AFM, particle size, zeta potential, and surface area analysis, were carried out for the prepared nanosponges. Curcumin release and drug content were also evaluated. Nanosponges prepared by Diphenyl carbonate crosslinker resulted in an amorphous form compared to crystalline EDTA-nanosponges. This study reported the successful inclusion and complexation of curcumin inside carbonate cross-linked cyclodextrin-based nanosponges and suggested the physical entrapment of crystalline curcumin in EDTA dianhydride. These findings were further investigated and supported by computational modeling.

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Funding

The authors acknowledge the Deanship of Research at Jordan University of Science and Technology for funding this project with Fund number 312/2021.

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Authors and Affiliations

  1. Department of Pharmaceutical Technology, Faculty of Pharmacy, Jordan University of Science and Technology, Ar-Ramtha, Jordan

    Hadeia Mashaqbeh & Rana Obaidat

  2. Department of Medicinal Chemistry, Faculty of Pharmacy, Jordan University of Science and Technology, Ar-Ramtha, Jordan

    Nizar A. Al-shar’i

Authors
  1. Hadeia Mashaqbeh
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  2. Rana Obaidat
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  3. Nizar A. Al-shar’i
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Contributions

Conceptualization RO and HM, Supervision and project administration RO, Conduct the experimental work HM, Methodology HM and NA, Write the first draft HM and NA, Writing/editing RO, HM and NA, Data analysis RO, HM and NA, Computational investigations and software analysis NA.

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Correspondence to Rana Obaidat.

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Supplementary Information

Figure S1

PXRD pattern of raw cyclodextrin. (PNG 274 kb)

High resolution (TIF 86 kb)

Figure S2

FTIR spectra of raw β-cyclodextrin polymer, Plain EDTA Dianhydride cross-linked nanosponge, and plain DPC cross-linked nanosponge. (PNG 788 kb)

High resolution (TIF 1316 kb)

βCD-DPC NS model. Color codes: C in grey, O in red, and H in white. Hydrogen bond donor (magenta) and acceptor (green). (AVI 26534 kb)

βCD-EDTA NS model. Color codes: C in grey, O in red, and H in white. Hydrogen bond donor (magenta) and acceptor (green). (AVI 12649 kb)

Curcumin inclusion complex in βCD-DPC NS animation (WEBM 5157 kb)

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Mashaqbeh, H., Obaidat, R. & Al-shar’i, N.A. Evaluation of EDTA Dianhydride Versus Diphenyl Carbonate Nanosponges for Curcumin. AAPS PharmSciTech 23, 229 (2022). https://doi.org/10.1208/s12249-022-02372-z

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