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. 2022 Sep 5;12(39):25123-25132.
doi: 10.1039/d2ra04530c.

Synthesis and characterization of a new reusable calix[4]arene-bonded silica gel sorbent for antidiabetic drugs

Fahimeh Hokmabadi  1 , Reza Zadmard  1 , Mohammad Reza Jalali  1 , M Saeed Abaee  1
Affiliations

Synthesis and characterization of a new reusable calix[4]arene-bonded silica gel sorbent for antidiabetic drugs

Fahimeh Hokmabadi et al. RSC Adv. .

Abstract

A novel calix[4]arene-bonded silica gel (C4BS) is prepared by covalent attachment of a calix[4]arene derivative to silica gel through a thiol-ene process. The structure and properties of C4BS were studied by Fourier Transform Infra-Red (FTIR) spectroscopy, thermal gravimetric analysis (TGA), elemental analysis (CHN), scanning electron microscopy (SEM), and surface area analysis (BET). In addition, the binding affinity of some antidiabetic drugs towards C4BS was investigated, by quantitative measurement of the drugs in aqueous solution using UV-visible spectroscopy. Results showed that C4BS has higher affinities than plain silica gel for binding to empagliflozin, dapagliflozin and linagliptin at neutral pH, while metformin hydrochloride was not adsorbed efficiently using either C4BS or plain silica gel. Thus, C4BS can be introduced as a promising binder for selective adsorption of the quoted antidiabetic drugs in pharmaceutical effluents, while being reusable by aqueous/acetonitrile (1 : 1) extraction.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Chemical structures of EMPA, DAPA, LINA and MET.
Scheme 1
Scheme 1. Synthesis of precursor 5.
Scheme 2
Scheme 2. Synthetic pathway of C4BS.
Fig. 2
Fig. 2. Calibration curves of MET, DAPA, EMPA and LINA.
Fig. 3
Fig. 3. Drugs adsorption percentages onto C4BS in comparison with that of thiolated and pure silica gel.
Fig. 4
Fig. 4. FT-IR spectra of (A) silica gel, (B) compound 5 and (C) C4BS.
Fig. 5
Fig. 5. The SEM of (A) silica gel (B) C4BS.
Fig. 6
Fig. 6. N2 adsorption–desorption curves of silica gel and C4BS.
Fig. 7
Fig. 7. Pore size distribution curves of silica gel and C4BS.
Fig. 8
Fig. 8. Thermogravimetric curves of bare silica gel, thiolated silica gel and C4BS.
Fig. 9
Fig. 9. Effect of the amounts of C4BS in the adsorption process.
Fig. 10
Fig. 10. Effect of the amounts of silica gel in the adsorption process.
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