Kinetics and degradation pathways of photolytic and photocatalytic oxidation of the anthelmintic drug praziquantel

Čizmić, Mirta; Ljubas, Davor; Ćurković, Lidija; Škorić, Irena; Babić, Sandra

doi:10.1016/j.jhazmat.2016.04.065

Cited by 32 publications

(13 citation statements)

References 44 publications

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“…The plausible structure of DP neither belongs to the type of degradation products reported by Cizmić and coworkers [22] nor to those we have seen before in our research [18]. By NMR and MS anal- yses the different mechanism of degradation with Syloid was found in comparison to povidone and crospovidone [18].…”

Section: Resultscontrasting

confidence: 46%

“…Our previous studies conducted on the same drug testified to a peculiar propensity to chemical degradation when neat ground in the presence of pharmaceutical excipients [17], while, in an unexpected way, PZQ is not prone to degradation when ground by itself [18][19][20]. Further studies also attested that degradation products are dependent upon the type of polymer used during milling [21], and these compounds are different from those documented for PZQ in different stressing conditions [22,23]. To highlight differences due to the grinding process in the presence of this specific mesoporous excipient both physical and chemical characterizations (DSC, PXRD, ESEM, HPLC-UV, UPLC-MS and 1 H NMR) are carried out on the simple physical mixture and on mechanochemically activated samples.…”

Section: Introductionmentioning

confidence: 87%

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Impact of mesoporous silica on the chemical degradation of Praziquantel upon grinding

Šagud¹,

Zanolla²,

Zingone³

et al. 2021

Comptes Rendus. Chimie

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Praziquantel and Syloid 244 FP (amorphous silicon dioxide) were ground in a vibrational mill in standard conditions (15 or 30 at 25 Hz). Amorphous solid dispersions were obtained in a very short grinding time (15 min), as testified by DSC, PXRD and ESEM analyses. Samples ground at 15 and 30 showed the presence of the same degradation product, as was evident from UPLC, MS and NMR analyses. This short paper brings to light the tremendous lattice de-structuration ability of Syloid 244 FP upon grinding toward Praziquantel as well as its detrimental influence on promoting chemical degradation through ring opening and oxidation.

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Section: Resultscontrasting

confidence: 46%

Section: Introductionmentioning

confidence: 87%

Impact of mesoporous silica on the chemical degradation of Praziquantel upon grinding

Šagud¹,

Zanolla²,

Zingone³

et al. 2021

Comptes Rendus. Chimie

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“…Among the degradation products observed, several were previously reported in the literature with fragment ions at m / z 345 (IV), 273 (VII), 329 (VIII), and 311 (X), detected at relative retention times (RRT) 0.77, 0.90, 1.10, and 1.17, respectively. 36 − 39 The degradation product at RRT 0.77 ( m / z 345) corresponding to dihydroxypraziquantel was detected in all three PZQ/CD complexes. The MS spectrum displayed fragment m / z 327, while fragment m / z 309 was absent.…”

Section: Resultsmentioning

confidence: 98%

Investigation of Praziquantel/Cyclodextrin Inclusion Complexation by NMR and LC-HRMS/MS: Mechanism, Solubility, Chemical Stability, and Degradation Products

et al. 2021

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Praziquantel (PZQ) is a biopharmaceutical classification system (BCS) class II anthelmintic drug characterized by poor solubility and a bitter taste, both of which can be addressed by inclusion complexation with cyclodextrins (CD). In this work, a comprehensive investigation of praziquantel/cyclodextrin (PZQ/CD) complexes was conducted by means of UV–vis spectroscopy, spectrofluorimetry, NMR spectroscopy, liquid chromatography-high-resolution mass spectrometry (LC-HRMS/MS), and molecular modeling. Phase solubility studies revealed that among four CDs tested, the randomly methylated β-CD (RMβCD) and the sulfobutylether sodium salt β-CD (SBEβCD) resulted in the highest increase in PZQ solubility (approximately 16-fold). The formation of 1:1 inclusion complexes was confirmed by HRMS, NMR, and molecular modeling. Both cyclohexane and the central pyrazino ring, as well as an aromatic part of PZQ are included in the CD central cavity through several different binding modes, which exist simultaneously. Furthermore, the influence of CDs on PZQ stability was investigated in solution (HCl, NaOH, H 2 O 2 ) and in the solid state (accelerated degradation, photostability) by ultra-high-performance liquid chromatography–diode array detection–tandem mass spectrometry (UPLC-DAD/MS). CD complexation promoted new degradation pathways of the drug. In addition to three already known PZQ degradants, seven new degradation products were identified ( m / z 148, 215, 217, 301, 327, 343, and 378) and their structures were proposed based on HRMS/MS data. Solid complexes were prepared by mechanochemical activation, a solvent-free and ecologically acceptable method.

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“…Generally, two types of photocatalytic reactors can be found in literature: slurry photoreactors (suspended photocatalyst particles) and fixed-bed photoreactors (immobilized photocatalyst particles or films on a surface of adequate planar substrates such as glass, quartz, stainless steel, polymers, or porous substrates such as pumice stone, clay, ceramics, polymeric materials, zeolites, carbon nanotubes, graphene oxide, fibers, etc.) [28][29][30][31]. In practice, immobilized catalyst photoreactors are preferred for advanced wastewater treatment as they avoid the complex separation step which is needed in the case of slurry photoreactors.…”

Section: Advanced Deposition Methods Include Chemical Vapor Depositiomentioning

confidence: 99%

“…Therefore, the applicability of TiO 2 in the form of a suspension is not optimal for the applications in real systems. These disadvantages of the application of TiO 2 nanoparticles in the suspension form may be eliminated by the immobilization of TiO 2 on different substrates in the form of a stable nanostructured film [29][30][31]48], which was applied in this work. The most widely used method for producing the TiO 2 film is the sol-gel synthesis process [24,49].…”

Section: Photocatalytic Degradation Of Memantine On Tio 2 -Coated Al mentioning

confidence: 99%

Titania-Coated Alumina Foam Photocatalyst for Memantine Degradation Derived by Replica Method and Sol-Gel Reaction

et al. 2020

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In the present work, alumina (Al2O3) foam was prepared by the replica method where a polyurethane (PU) foam (30 pores per inch (ppi)) template was impregnated with a 60 wt.% Al2O3 suspension. Sintered Al2O3 foam was used as substrate for the deposition of sol-gel derived titania (TiO2) film using dip coating. For the preparation of TiO2 sol, titanium(IV) isopropoxide (Ti-iPrOH) was used as the precursor. The common problem of qualification and quantification of a crystalline coating on a highly porous 3D substrate with an uneven surface was addressed using a combination of different structural characterization methods. Using Powder X-ray Diffraction (PXRD) and synchrotron Grazing Incidence X-ray Diffraction (GIXRD) on bulk and powdered Al2O3 foam and TiO2-coated Al2O3 foam samples, it was determined Al2O3 foam crystallizes to corundum and coating to anatase, which was also confirmed by Fourier Transformed Infrared Spectroscopy (FTIR). Scanning Electron Microscopy with Energy Dispersive X-ray Spectroscopy (SEM/EDS) revealed the structural and microstructural properties of the substrate and coating. Differential Thermal Analysis (DTA) and Thermogravimetric Analysis (TGA) were used to clarify the evolution of the porous microstructure. The Al2O3-TiO2 composite was evaluated as a photocatalyst candidate for the degradation of the micropollutant medication memantine. The degradation rate was monitored using a light-emitting diode (LED) lamp operating at electromagnetic (EM) wavelength of 365 nm. The photocatalytic activity of sol-gel-derived TiO2 film immobilized on the Al2O3 foam was compared with commercially available TiO2 nanoparticles, P25-Degussa, in the form of a suspension. The levels of memantine were monitored by High-Performance Liquid Chromatography–Tandem Mass Spectrometry (HPLC–MS/MS). The efficiency and rate of the memantine photodegradation by suspended TiO2 nanoparticles is higher than the TiO2-coated Al2O3 foam. But, from the practical point of view, TiO2-coated Al2O3 foam is more appropriate as a valuable photocatalytic composite material.

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Kinetics and degradation pathways of photolytic and photocatalytic oxidation of the anthelmintic drug praziquantel

Cited by 32 publications

References 44 publications

Impact of mesoporous silica on the chemical degradation of Praziquantel upon grinding

Impact of mesoporous silica on the chemical degradation of Praziquantel upon grinding

Investigation of Praziquantel/Cyclodextrin Inclusion Complexation by NMR and LC-HRMS/MS: Mechanism, Solubility, Chemical Stability, and Degradation Products

Titania-Coated Alumina Foam Photocatalyst for Memantine Degradation Derived by Replica Method and Sol-Gel Reaction

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