Qualitative Profiling of Polyglucose Degradation Products in Peritoneal Dialysis Fluids

Abstract

Heat sterilization of peritoneal dialysis (PD) fluids leads to partial degradation of the osmotic agent to form reactive carbonyl structures, which significantly reduce the biocompatibility of PD fluids and impair long-term PD therapy. Hence, it is important to know the exact composition of the degradation products to improve biocompatibility of PD fluids. Our study conducted targeted screening for degradation products in polyglucose (icodextrin)-containing PD fluids (pGDPs) by applying o-phenylenediamine (OPD) to form stable derivatives, which were analyzed by ultrahigh-performance liquid chromatography with hyphenated diode array tandem mass spectrometry (UHPLC–DAD–MS/MS). For the first time, specific degradation products of polyglucose, namely, 4-deoxyglucosone (4-DG) and 3,4-dideoxypentosone (3,4-DDPS), could be identified in PD fluids. Further, a reaction product of 5-hydroxymethylfurfural (5-HMF) and OPD could be characterized to be (5-(1H-benzo­[d]­imidazol-2-yl)­furan-2-yl)­methanol. Additionally, 3-deoxyglucosone (3-DG) and 3-deoxygalactosone (3-DGal), both known to be present in glucose-based PD fluids, were also detected in polyglucose-containing fluids. Trapping a hitherto unknown degradation product with OPD yielded 1,4-bis­(1H-benzo­[d]­imidazol-2-yl)-3,4-dihydroxybutan-1-one, which was present in heat- as well as filter-sterilized PD fluids.

Evaluation of Fructo-, Inulin-, and Galacto-Oligosaccharides on the Maillard Reaction Products in Model Systems with Whey Protein

“…Nine α-dicarbonyls were detected in these samples; however, 3-DG was not detected in the galactobiose sample. Although the peak showing the molecular protonated ion of m / z 235 equal to 3-DG-quinoxaline was detected at the retention time of 11.8 min, its product ion spectrum was very similar to that of 4-deoxyglucosone (4-DG)-quinoxaline reported by Gensberger et al Therefore, it was identified as 4-DH. Our results showed that β-1 → 4 glycosidic linkages between galactoses were not directly attributed to the marked increase in 3-DG observed in the GOS model.…”

“…Our results showed that β-1 → 4 glycosidic linkages between galactoses were not directly attributed to the marked increase in 3-DG observed in the GOS model. So far, 4-DG has been detected in a heated solution of lactose, 16 maltose, 31 and icodextrin, 30 which contain 1,4-glycosidic linkages. 4-DH might be formed in GOS models, which mainly contain 4′-GL and 4′-diGL; however, it was not detected with or without whey protein in our experiments.…”

Degradation and de novo formation of nine major glucose degradation products during storage of peritoneal dialysis fluids

“…1 a) using a derivatization method that was previously optimized and validated for the analysis of the six major α-dicarbonyls in PDFs 3 . The monocarbonyl GDP 5-HMF also reacts with OPD yielding a benzimidazole derivative, which gives a signal at 316 nm and can coelute with the quinoxaline derivatives of 3-DGal or glyoxal 16 , thus limiting their accurate quantification. In order to achieve baseline separation of 5-HMF and all major α-dicarbonyls, the pH of the eluent A was set to 3.3 (Fig.…”

2-Deoxyglucosone: A New C6-α-Dicarbonyl Compound in the Maillard Reaction of d-Fructose with γ-Aminobutyric Acid

“…The NMR spectrum of this mixture consists of superimposed spectra of 2-deoxyglucosone-q, 3-deoxyglucosone-q, and 4-deoxyglucosone-q with low intensity. With application of 2D NMR spectroscopy and a comparison of the extracted spectral information to data given in the literature, the signals could be assigned to 4-deoxyglucosone-q . From the intensities of the signals in the NMR spectrum, a molar ratio between 2-deoxyglucosone, 3-deoxyglucosone, and 4-deoxyglucosone of 100:50:2.5 could be determined.…”

“…With application of 2D NMR spectroscopy and a comparison of the extracted spectral information to data given in the literature, the signals could be assigned to 4-deoxyglucosone-q. 28 From the intensities of the signals in the NMR spectrum, a molar ratio between 2-deoxyglucosone, 3-deoxyglucosone, and 4deoxyglucosone of 100:50:2.5 could be determined. Thus, when model reactions were performed with pre-derivatization, the formation of 4-deoxyglucosone could be observed in addition to 1-deoxyglucosone, 2-deoxyglucosone, 3-deoxyglucosone, and D-glucosone.…”