Kinetic study of the reaction of sulfamethoxazole and glucose under acidic conditions

Lucida, Henny; Parkin, J.E.; Sunderland, V Bruce

doi:10.1016/s0378-5173(00)00413-0

Cited by 47 publications

(23 citation statements)

References 17 publications

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“…The result supported the assumption that product I was the β glycosylamine and the product II was the α glycosylamine. The more stable form, the β glycosylamine, appeared in a higher ratio in the reaction mixture, in agreement with the observations of Sunderland and coworkers for the reaction of glucose and sulfamethoxazole (6). Figure 5 shows the expanded COSY spectrum in the region of the aromatic protons for product I.…”

Section: Identification Of Reaction Productssupporting

confidence: 89%

“…The m/z of 393 in the mass spectra for the two products corresponds to molecular ion plus sodium. Though the expected products were the glycosylamines, as has been reported for reactions of amines with sugars (6,8,26) this was further confirmed using UV and NMR spectroscopy. The two products showed similar UV spectral properties to that of kynurenine.…”

Section: Identification Of Reaction Productssupporting

confidence: 74%

“…The coupling constant (J) for the decoupled doublets was determined to be 7.98 for product I and 3.67 for product II. These coupling constants were typical to that of the β-glucose (J~8) and the α-glucose (J~4), respectively (6,30,40). The result supported the assumption that product I was the β glycosylamine and the product II was the α glycosylamine.…”

Section: Identification Of Reaction Productssupporting

confidence: 72%

“…Examples of drug instability due to the Maillard reaction include both primary and secondary amines as in the case of amphetamines, insulin, fluoxetine, sulfa drugs, procainamide, metoclopropamide, and daptomycin to name a few (4)(5)(6)(7)(8)(9). For example, Duval et al studied the browning of dextroamphetamine sulfate solutions containing lactose and found that the solution darkens on storage at 50°C with the formation of brownish precipitate (4).…”

Section: Introductionmentioning

confidence: 99%

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Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme

2009

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Abstract. The reactions of aliphatic and aromatic amines with reducing sugars are important in both drug stability and synthesis. The formation of glycosylamines in solution, the first step in the Maillard reaction, does not typically cause browning but results in decreased potency and is hence significant from the aspect of drug instability. The purpose of this research was to present (1) unreported ionic equilibria of model reactant (kynurenine), (2) the analytical methods used to characterize and measure reaction products, (3) the kinetic scheme used to measure reaction rates and (4) relevant properties of various reducing sugars that impact the reaction rate in solution. The methods used to identify the reversible formation of two products from the reaction of kynurenine and monosaccharides included LC mass spectrometry, UV spectroscopy, and 1-D and 2-D 1 H-1 H COSY NMR spectroscopy. Kinetics was studied using a stability-indicating HPLC method. The results indicated the formation of α and β glycosylamines by a pseudo first-order reversible reaction scheme in the pH range of 1-6. The forward reaction was a function of initial glucose concentration but not the reverse reaction. It was concluded that the reaction kinetics and equilibrium concentrations of the glycosylamines were pH-dependent and also a function of the acyclic content of the reacting glucose isomer.

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Section: Identification Of Reaction Productssupporting

confidence: 89%

Section: Identification Of Reaction Productssupporting

confidence: 74%

Section: Identification Of Reaction Productssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

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Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme

2009

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“…The sorption of SMX at selected pH values reflected the sorption behavior of different SMX species. SMX has two pK a (acid dissociation constant) values, 1.7 and 5.7 (Lucida et al, 2000). The cationic, neutral, and anionic species of SMX dominate at pH values of <1.7, around 3.7, and >5.7, respectively (Zhang et al, 2010a).…”

Section: Sorption Mechanism Of Smx On Rice Straw Biocharmentioning

confidence: 99%

Simultaneous removal of cadmium and sulfamethoxazole from aqueous solution by rice straw biochar

Han

Liang

et al. 2013

J. Zhejiang Univ. Sci. B

105

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Abstract:The simultaneous sorption behavior and characteristics of cadmium (Cd) and sulfamethoxazole (SMX) on rice straw biochar were investigated. Isotherms of Cd and SMX were well modeled by the Langmuir equation (R 2 >0.95). The calculated maximum adsorption parameter (Q) of Cd was similar in single and binary systems (34 129.69 and 35 919.54 mg/kg, respectively). However, the Q of SMX in a binary system (9 182.74 mg/kg) was much higher than that in a single system (1 827.82 mg/kg). The presence of Cd significantly promoted the sorption of SMX on rice straw biochar. When the pH ranged from 3 to 7.5, the sorption of Cd had the characteristics of a parabola pattern with maximum adsorption at pH 5, while the adsorption quantity of SMX decreased with increasing pH, with maximum adsorption at pH 3. The amount of SMX adsorbed on biochar was positively correlated with the surface area of the biochar, and the maximum adsorption occurred with d 250 biochar (biochar with a diameter of 150-250 μm). Scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) showed that the removal of Cd and SMX by rice straw biochar may be attributed to precipitation and the formation of surface complexes between Cd or SMX and carboxyl or hydroxyl groups. The results of this study indicate that rice straw biochar has the potential for simultaneous removal of Cd and SMX from co-contaminated water.

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Fixed‐Bed and Batch Adsorption of Pharmaceuticals from Aqueous Solutions on Ionic Liquid‐Modified Montmorillonite

Lawal

Moodley

2018

Chem Eng & Technol

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Batch and column adsorption of four pharmaceuticals, namely, tetracycline (TC), sulfamethoxazole (SMZ), nalidixic acid (NAD), and chloramphenicol (CHL) on ionic liquid modified montmorillonite (Mt‐IL) was evaluated. The effects of variation in pH and contact time were analyzed and the data were fitted to kinetics and isotherm models. The equilibrium experimental data were best explained by the Freundlich model. A pseudo second‐order kinetic model described all pharmaceuticals adsorbed on Mt‐IL. In column studies, the exchange zone depth, adsorption capacity, the required time for the pharmaceuticals to move through the height of the adsorbent in the column, and adsorption rates were investigated by the Yoon‐Nelson and the Thomas and Adams‐Bohart models.

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Kinetic study of the reaction of sulfamethoxazole and glucose under acidic conditions

Cited by 47 publications

References 17 publications

Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme

Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme

Simultaneous removal of cadmium and sulfamethoxazole from aqueous solution by rice straw biochar

Fixed‐Bed and Batch Adsorption of Pharmaceuticals from Aqueous Solutions on Ionic Liquid‐Modified Montmorillonite

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