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Olsalazine-Based Metal–Organic Frameworks as Biocompatible Platforms for H2 Adsorption and Drug Delivery

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    Olsalazine-Based Metal–Organic Frameworks as Biocompatible Platforms for H2 Adsorption and Drug Delivery
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    † ‡ †Department of Chemistry and ‡Department of Chemical and Biomolecular Engineering, University of California, Berkeley, Berkeley, California 94720, United States
    § Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States
    ∥ Department of Physics and Astronomy, Oberlin College, Oberlin, Ohio 44074, United States
    *E-mail: [email protected] (J.R.L.).
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2016, 138, 32, 10143–10150
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    https://doi.org/10.1021/jacs.6b03523
    Published August 3, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    The drug olsalazine (H4olz) was employed as a ligand to synthesize a new series of mesoporous metal–organic frameworks that are expanded analogues of the well-known M2(dobdc) materials (dobdc4– = 2,5-dioxido-1,4-benzenedicarboxylate; M-MOF-74). The M2(olz) frameworks (M = Mg, Fe, Co, Ni, and Zn) exhibit high surface areas with large hexagonal pore apertures that are approximately 27 Å in diameter. Variable temperature H2 adsorption isotherms revealed strong adsorption at the open metal sites, and in situ infrared spectroscopy experiments on Mg2(olz) and Ni2(olz) were used to determine site-specific H2 binding enthalpies. In addition to its capabilities for gas sorption, the highly biocompatible Mg2(olz) framework was also evaluated as a platform for the delivery of olsalazine and other encapsulated therapeutics. The Mg2(olz) material (86 wt % olsalazine) was shown to release the therapeutic linker through dissolution of the framework under simulated physiological conditions. Furthermore, Mg2(olz) was used to encapsulate phenethylamine (PEA), a model drug for a broad class of bioactive compounds. Under simulated physiological conditions, Mg2(olz)(PEA)2 disassembled to release PEA from the pores and olsalazine from the framework itself, demonstrating that multiple therapeutic components can be delivered together at different rates. The low toxicity, high surface areas, and coordinatively unsaturated metal sites make these M2(olz) materials promising for a range of potential applications, including drug delivery in the treatment of gastrointestinal diseases.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.6b03523.

    • Synthesis of olsalazine, scanning electron microscopy, comparison of M2(olz) to M2(dobdc) and M2(dobpdc), structural model of M2(olz), Rietveld refinement, unit cell parameters and Pawley fits, 77 K N2 adsorption isotherms, linear BET plots, thermogravimetric analysis, 77 and 87 K H2 adsorption isotherms and fit parameters, IR spectra of H2 binding to M2(olz) and M2(dobdc), release of olsalazine from Mg2(olz) in PBS at 37 °C, examples of bioactive phenethylamine derivatives, NMR spectra of phenethylamine and N-methylphenethylamine loaded in Mg2(olz), IR spectra of Mg2(olz)(PEA)2 and components (PDF)

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