Synthesis and Functionalization of Porous Zr-Diaminostilbenedicarboxylate Metal–Organic Framework for Storage and Stable Delivery of Ibuprofen

Abstract

A stable porous metal–organic framework (MOF), Zr-diaminostilbenedicarboxylate (Zr-DASDCA), was synthesized and modified with oxalyl chloride (OC) or terephthaloyl chloride (TC) to introduce various functional groups onto the Zr-DASDCA. Both pristine and functionalized Zr-DASDCAs, together with activated carbon, were used as a potential carrier for ibuprofen (IBU) storage and delivery. Zr-DASDCAs, especially the modified ones (OC-Zr-DASDCA and TC-Zr-DASDCA), showed competitive results in IBU delivery. Specifically, the release rate in phosphate-buffered saline solution at pH 7.4 was nearly constant ( R 2 ≈ 0.98) for up to 10 days, which would be very effective in IBU dosing to the human body. Moreover, the release rate could be controlled by changing the pH of the releasing solution. The rate of IBU release from both pristine and modified Zr-DASDCAs at pH 7.4 and 3.0 was also explained with a few interactions such as H-bonding and electrostatic repulsion, together with the relative pore size of the Zr-DASDCAs. Therefore, the results suggested that functionalization of MOFs via postsynthetic modification, especially with OC and TC, to introduce various functional groups onto MOFs is an effective approach to not only reducing the release rate of IBU but also inducing a constant release of IBU for as long as 10 days.

Anti-inflammatory and antioxidant effects of nanoformulations composed of metal-organic frameworks delivering rutin and/or piperine natural agents

“…As such, mixed release patterns are likely the result of having no burst in the first stage, with a slight increase in Ru or Pip release at the second stage. The observation of a two-stage pattern is in agreement with previous reports, including release of ibuprofen from various MOFs (Silva et al, 2016 ; Rojas et al, 2018 ; Sarker et al, 2019 ; Pham et al, 2020 ), 5-fluorouracil from Mg-MOFs (Hu et al, 2020 ), caffeine from ZrMOFs (Sarker & Jhung, 2019 ), and DOX from a zeolitic imidazolate MOF (Bi et al, 2018 ).…”

“…This shift is connected to the decomposition/volatilization of both natural agents used. Of note, the shifted peaks in the nanoformulations appeared to correspond to those for free Ru and Pip, confirming the successful loading process for either single or double drug loading (Cunha et al, 2013a , b ; Sarker & Jhung, 2019 ; Sarker et al, 2019 ).…”

“…The DTG patterns ( Figure 5(B) ) of the modified MOFs were characterized by three stages of mass loss associated with adsorbed water removal (centered at ∼90 °C), decomposition of the organic content (centered at ∼220 °C), and destruction of MOF structure (centered at ∼580 °C for ZrMOF and 420 °C for TiMOF) (Sarker et al, 2019 ). Apart from modified materials, in nanoformulations, there was an increment in weight loss observed, verifying the success of loading to both MOFs.…”

Metal‐organic framework‐based biomaterials for biomedical applications

“…However, this method has several stringent requirements to ensure the stability of the MOFs. Sarker et al [25] synthesised a stable, porous MOF named Zr-diaminostyrene dicarboxylic acid (Zr-DASDCA). The MOF was modified with oxaloyl chloride (OC) or p-benzoyl chloride (TC) after its synthesis to introduce different functional groups into Zr-DASDCA.…”

The novel composite material MOF‐[Mg3(BTC)2]/GO/Fe3O4 and its use in slow‐release ibuprofen

“…For example, a Zr‐MOF modified with oxalyl chloride or terephthaloyl chloride (i.e., OC‐Zr‐DASDCA and TC‐Zr‐DASDCA, respectively) resulted in nearly 100% release of ibuprofen in phosphate‐buffered saline (PBS) at pH 7.4 for 10 days and 45% at pH 3.0. [ 26 ] Lestari et al used a [Zn 3 (BTC) 2 ]‐based matrix, and their results showed the presence of the matrix reduced the rate of ibuprofen release by 33.4%. Other MOFs that have been developed for ibuprofen encapsulation are [Zn 2 (bdc) 2 (dabco)], which was synthesized in situ and has a drug release capability up to 80% after 12 days, [ 27 ] and MIL‐53(Fe), which was studied by Horcajada et al and had an adsorption ability of 0.21 g of ibuprofen in 1 g of MOF in simulated body fluid at 37°C for 3 weeks.…”