Formation of imine derivatives between Tris(hydroxymethyl)-aminomethane and saturated 3-oxo steroids during conventional work up of biological samples dissolved in Tris-HCl buffers

Eriksson, C.-G.; Nordström, Lennart; Eneroth, P.

doi:10.1016/0022-4731(83)90417-x

Cited by 13 publications

(2 citation statements)

References 9 publications

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“…To fulfill its function, an ideal biological buffer should not only possess the correct pK a and buffer capacity but should also produce no adverse effects on biochemical reactions [1][2][3], and there may be no one ideal buffer for a given pH range. For example, TRIS [1], HEPES, and Tricine buffers have been shown to react with radicals [4][5][6][7], and TRIS has also been shown to react with aldehydes [8][9][10][11][12]. It is important to carry out measurements in more than one kind of buffer to establish which buffers cause least disturbance to the system under study, the usual criterion being that the observed reaction rates or transformations are maximal.…”

Section: Introductionmentioning

confidence: 99%

Buffer interactions: Densities and solubilities of some selected biological buffers in water and in aqueous 1,4-dioxane solutions

Taha

Lee

2009

Biochemical Engineering Journal

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Section: Introductionmentioning

confidence: 99%

Buffer interactions: Densities and solubilities of some selected biological buffers in water and in aqueous 1,4-dioxane solutions

Taha

Lee

2009

Biochemical Engineering Journal

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“…Far from ideality, many buffers have been found to be quite reactive, besides performing their normal pH-stabilizing function. For example, TRIS, HEPES, and Tricine buffers have been shown to react with radicals ( − ), and TRIS has been shown to react with aldehydes ( − ).…”

Section: Introductionmentioning

confidence: 99%

Effects of Common Buffer Systems on Drug Activity: The Case of Clerocidin

Richter

Fabris

Binaschi

et al. 2004

Chem. Res. Toxicol.

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Two widely used biological buffers [tris(hydroxymethyl)aminomethane (TRIS) and phosphate] covalently react with the topoisomerase II inhibitor clerocidin, affecting the drug's reactivity profile. Comprehensive analytical and structural analysis obtained by LC/MS, MS/MS, NMR, and IR techniques shows that these buffers form reversible and irreversible adducts through reactions with chemical groups, such as carbonyls, aldehydes, and epoxide. Analysis of the kinetic data on adducts formation suggests two parallel mechanisms for the inhibition of drug activity. The first involves modulation of the reactivity of the epoxide group obtained by elimination of the spiro system and relief of ring strain. This effect does not abolish epoxide reactivity and is more evident for the TRIS adduct, which can count on intramolecular stabilization of the form devoid of the spiro system. The second mechanism involves the slow nucleophilic attack to the epoxide ring, which results in permanent deactivation of the functional group responsible for topoisomerase II inhibition. This effect is predominant in phosphate buffer and is more evident for longer reaction times. These results provide a compelling reminder that the activity of chemically complex drugs in biological systems can be severely altered by buffer interactions, which may not be immediately predictable from the identity of the active group(s) and may require a more detailed knowledge of the subtle effects induced by vicinal groups.

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Investigation of sample handling steps for accurate heparan sulphate disaccharide analysis using HPLC–MS

Pál,

Tóth,

Turiák

2024

Electrophoresis

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Heparan sulphates (HSs), a specific class of glycosaminoglycans (GAGs), are important participants of cellular signalling. Analytical characterization of GAGs requires a complex sample preparation workflow. Although a detailed stability and recovery study is available for the chondroitin sulphate GAG class, the literature concerning HS is incomplete in this regard. Therefore, our aim was to systematically investigate various parameters that could potentially influence the stability and recovery of HS samples when performing disaccharide analysis using high‐performance liquid chromatography–mass spectrometry. First, effects concerning vacuum evaporation and freezing were investigated. Next, the storage stability of the HS disaccharides was analysed under several conditions such as temperature, pH, digestion buffers, injection solvents and storage vessels. We have identified several critical parameters influencing the stability and recovery of HS disaccharides. We concluded that major sample loss is expected when Tris–HCl is used as digestion buffer, followed by vacuum evaporation at elevated temperatures, or samples are stored under alkaline conditions. Following the practical considerations of this paper can contribute to increasing the reliability of future analytical measurements.

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Formation of imine derivatives between Tris(hydroxymethyl)-aminomethane and saturated 3-oxo steroids during conventional work up of biological samples dissolved in Tris-HCl buffers

Cited by 13 publications

References 9 publications

Buffer interactions: Densities and solubilities of some selected biological buffers in water and in aqueous 1,4-dioxane solutions

Buffer interactions: Densities and solubilities of some selected biological buffers in water and in aqueous 1,4-dioxane solutions

Effects of Common Buffer Systems on Drug Activity: The Case of Clerocidin

Investigation of sample handling steps for accurate heparan sulphate disaccharide analysis using HPLC–MS

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