Characterization of polysorbates by OH- negative ion chemical ionization mass spectrometry

Brumley, William C.; Warner, Charles R; Daniels, Daniel H.; Andrzejewski, Denis; White, Kevin D.; Zhao, Min; Chen, Jo Y. T.; Sphon, James A.

doi:10.1021/jf00063a012

Cited by 10 publications

(4 citation statements)

References 23 publications

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“…Techniques such as colorimetry (5,6), infrared spectroscopy (6), and gravimetric determination by precipitation (7,8) focus on qualitative detection of polysorbates in food products. Quantification and rudimentary characterization have been attempted using techniques such as thin-layer chromatography (5,6,9,10), gas chromatography (6,11,12), high-performance liquid chromatography (10,13), OHnegative ion chemical ionization mass spectrometry (14), and recently, an optical chemical sensor method (15). Unfortunately, none of these methods allows satisfactory separation or resolution of the individual polymer species, nor identification of the components.…”

Section: Introductionmentioning

confidence: 99%

Investigating the Molecular Heterogeneity of Polysorbate Emulsifiers by MALDI-TOF MS

Frison-Norrie

Sporns

2001

J. Agric. Food Chem.

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Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) is a new technique that can be used to determine the molecular composition of polysorbate emulsifiers, which are commonly used as food additives. This is the first study to offer such a detailed examination of these heterogeneous compounds. MALDI-TOF MS is a powerful tool that can provide a polysorbate mass profile in less than two minutes. 2',4',6'-Trihydroxyacetophenone monohydrate was chosen to be an ideal matrix, as it easily facilitated desorption and ionization, provided good resolution, and allowed for fast and simple preparation of the sample. By addition of aqueous 0.01 M potassium chloride, species were resolved exclusively as potassium adducts in the positive ion mode. MALDI-TOF MS analysis before and after saponification indicated the presence of unbound ethylene oxide polymers, as well as free and esterified sorbitan- and sorbide-based species. Some evidence for the presence of disorbitan-based species was provided. Also illustrated were the polydispersity of the oxyethylene chains, the degree of esterification, and the identity of esterified fatty acids.

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Section: Introductionmentioning

confidence: 99%

Investigating the Molecular Heterogeneity of Polysorbate Emulsifiers by MALDI-TOF MS

Frison-Norrie

Sporns

2001

J. Agric. Food Chem.

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“…This, in addition to molecular heterogeneity attributed to the existence of esters of several fatty acids with sorbitol anhydrides, makes characterization of polysorbates an analytical challenge. NMR , and several mass spectrometry methods, including OH – negative ion chemical ionization and, more recently, matrix-assisted laser desorption/ionization (MALDI) mass spectrometry − have been used for direct characterization of polysorbates and products of their degradation. These reports emphasize the molecular complexity of polysorbates and demonstrate the presence of three major polyoxyethylated components based on ethylene glycol and mono- and dianhydrides of sorbitol (sorbitan and isosorbide, respectively).…”

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confidence: 99%

Toward Understanding Molecular Heterogeneity of Polysorbates by Application of Liquid Chromatography–Mass Spectrometry with Computer-Aided Data Analysis

Borisov¹,

Ji²,

Wang³

et al. 2011

Anal. Chem.

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Polysorbates (PS) are widely used as oil-in-water emulsifiers, stabilizers, wetting agents, solubilizers, and dispersants in the agricultural, food, personal care, and pharmaceutical industries due to their cost effectiveness, biocompatibility, formulation flexibility, low toxicity, and good stabilizing and protecting properties. The polysorbates are often pictured as polyoxyethylated sorbitan monoesters of saturated and/or unsaturated fatty acids. In reality, polysorbates are complex mixtures of multiple components, as follows from the reactions involved in their production. In this work, we report a novel application of liquid chromatography-mass spectrometry (LC-MS) for the characterization of polysorbates. This method takes advantage of accurate mass measurements and information on the identity of a fatty acid from "in-source" generated characteristic dioxolanylium ions. The method allowed us to perform quick profiling of fatty acids in PS 20 and 80 which, combined with a computer-aided peak assignment algorithm, facilitated detailed characterization of their constituents. As a major finding, we determined that different samples of PS 20 varied from 0% to 15% in relative amounts of unsaturated oleic acid. Although the consequences of this difference were not fully evaluated in this work, one might expect that PS 20 with larger amounts of oleic acid will be more prone to autoxidation, thus potentially having greater impact on the oxidative degradation of the biotherapeutics it formulates.

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“…3 There are a number of characterization approaches that employ separation techniques such as gas chromatography 3 and liquid chromatography 1 but which do not employ mass spectrometry as the detection technique. Negative ion chemical ionization mass spectrometry 5 utilizing OH − has also been shown to be an effective approach in the characterization of polysorbate formulations by mass spectrometry.…”

Section: ■ Existing Approachesmentioning

confidence: 99%

Characterization of Complex Polysorbate Formulations by Means of Shape-Selective Mass Spectrometry

2012

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Complex synthetic formulations based on polysorbates can be challenging to characterize. They may be composed of many similar products including those of the same molecular weight, which cannot be readily separated by separation science approaches. Carbon number variation and ethylene oxide distribution add to the complexity. The properties of these formulations will be dependent on the chemical structure and relative concentration of formulation components. Here we describe the use of two experimental approaches based on mass spectrometry to provide enhanced characterization of these formulations. The first utilizes an atmospheric pressure solids analysis probe to rapidly determine the percentage content of individual esters in a formulation. These are shown to be in good agreement with product specification sheets. In a second approach, mobility separation has been integrated into a MALDI-MS/MS experiment to categorize major, minor, and trace ingredients. Components of identical molecular mass in the polysorbate formulations have been separated by ion mobility and then fragmented for additional characterization. The rapidity and level of structural detail provided by these experiments offers a significant opportunity to develop practical screening methods for complex formulations.

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Characterization of polysorbates by OH- negative ion chemical ionization mass spectrometry

Cited by 10 publications

References 23 publications

Investigating the Molecular Heterogeneity of Polysorbate Emulsifiers by MALDI-TOF MS

Investigating the Molecular Heterogeneity of Polysorbate Emulsifiers by MALDI-TOF MS

Toward Understanding Molecular Heterogeneity of Polysorbates by Application of Liquid Chromatography–Mass Spectrometry with Computer-Aided Data Analysis

Characterization of Complex Polysorbate Formulations by Means of Shape-Selective Mass Spectrometry

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