Accurate Quantification of <i>N</i>-Glycolylneuraminic Acid in Therapeutic Proteins Using Supramolecular Mass Spectrometry

Lee, Hyun Hee L.; Heo, Chae Eun; Seo, Nari; Yun, Seung Gyu; An, Hyun Joo; Kim, Hugh I.

doi:10.1021/jacs.8b07864

Cited by 12 publications

(13 citation statements)

References 50 publications

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“…It is worth mentioning that these techniques are not able to distinguish various types of sialic acids, such as Neu5Ac and Neu5Gc. Due to the immunogenic effects of the non-human Neu5Gc, a second complementary approach should be applied to characterize sialic acids [117,118]. This approach often includes the chemical release of sialic acid from the glycans and fluorescent labeling with DMB, prior RPLC chromatography with FD detection [119].…”

Section: Glycan Analysis and Sialic Acids Contentmentioning

confidence: 99%

Therapeutic Fc‐fusion proteins: Current analytical strategies

Duivelshof

Murisier

Camperi

et al. 2020

J of Separation Science

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Fc-Fusion proteins represent a successful class of biopharmaceutical products, with already 13 drugs approved in the European Union and United States as well as three biosimilar versions of etanercept. Fc-Fusion products combine tailored pharmacological properties of biological ligands, together with multiple functions of the fragment crystallizable domain of immunoglobulins. There is a great diversity in terms of possible biological ligands, including the extracellular domains of natural receptors, functionally active peptides, recombinant enzymes, and genetically engineered binding constructs acting as cytokine traps. Due to their highly diverse structures, the analytical characterization of Fc-Fusion proteins is far more complex than that of monoclonal antibodies and requires the use and development of additional product-specific methods over conventional generic/platform methods. This can be explained, for example, by the presence of numerous sialic acids, leading to high diversity in terms of iso-

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Section: Glycan Analysis and Sialic Acids Contentmentioning

confidence: 99%

Therapeutic Fc‐fusion proteins: Current analytical strategies

Duivelshof

Murisier

Camperi

et al. 2020

J of Separation Science

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show abstract

“…The FIDI‐MS setup is presented in Figure S1. Mass spectrometry has a notable history in the study of host–guest chemistry, and it can provide detailed, fingerprint information on the reaction products. Collectively, FIDI‐MS has proven to be an excellent means to examine oxidation chemistry at the air–water interface.…”

Section: Figurementioning

confidence: 99%

Host–Guest Complexation of Amphiphilic Molecules at the Air–Water Interface Prevents Oxidation by Hydroxyl Radicals and Singlet Oxygen

et al. 2020

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The oxidation of antioxidants by oxidizers imposes great challenges to both living organisms and the food industry. Here we show that the host–guest complexation of the carefully designed, positively charged, amphiphilic guanidinocalix[5]arene pentadodecyl ether (GC5A‐12C) and negatively charged oleic acid (OA), a well‐known cell membrane antioxidant, prevents the oxidation of the complex monolayers at the air–water interface from two potent oxidizers hydroxyl radicals (OH) and singlet delta oxygen (SDO). OH is generated from the gas phase and attacks from the top of the monolayer, while SDO is generated inside the monolayer and attacks amphiphiles from a lateral direction. Field‐induced droplet ionization mass spectrometry results have demonstrated that the host–guest complexation achieves steric shielding and prevents both types of oxidation as a result of the tight and “sleeved in” physical arrangement, rather than the chemical reactivity, of the complexes.

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“…CB[6] has been modified by substituting the locations denoted by “R” with 2-(butylamino)ethanethiol, and the resulting cucurbituril derivative disrupts the cellular membranes in a number of bacterial species . Several CB[ n ] complexes also traverse cellular membranes, making CB[ n ]s potentially useful in selective drug delivery. − CB[ n ]s have also been utilized for inducing protein dimerization; separating and quantifying sialic acid species; catalyzing oxidation, , hydrolysis, and ring formation reactions; and altering the photophysical properties of both the ground , and excited , states of guests for chemosensing experiments.…”

Section: Introductionmentioning

confidence: 99%

Barriers for Extrusion of a Guest from the Interior Binding Cavity of a Host: Gas Phase Experimental and Computational Results for Ion-Capped Decamethylcucurbit[5]uril Complexes

et al. 2018

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Factors affecting the extrusion of guests from metal ion-capped decamethylcucurbit [5]uril (mc5) molecular container complexes are investigated using both collision-induced dissociation techniques and molecular mechanics simulations. For guests without polar bonds, the extrusion barrier increases with increasing guest volume. This is likely because escape of larger guests requires more displacement of the metal ion caps and, thus, more disruption of the ion-dipole interactions between the ion caps and the electronegative rim oxygens of mc5. However, guests larger than the optimum size for encapsulation displace the ion caps prior to collision-induced dissociation, resulting in less stable complexes and lower dissociation thresholds. The extrusion barriers obtained for guests with polar bonds are smaller than those obtained for similarly sized guests without polar bonds. This is likely because the partial charges on the guest allow electrostatic interactions with the ion cap and rim oxygens of mc5 during extrusion, thus stabilizing the extrusion transition state and reducing the extrusion barrier. Results from this study demonstrate simple principles to consider for designing host−guest complexes with specific guest-loss behaviors. Similar trends are observed between the experimental and computational results, demonstrating that molecular mechanics simulations can be used to approximate the relative stability of mc5 molecular container complexes and likely those of other similar complexes.

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Accurate Quantification of N-Glycolylneuraminic Acid in Therapeutic Proteins Using Supramolecular Mass Spectrometry

Cited by 12 publications

References 50 publications

Therapeutic Fc‐fusion proteins: Current analytical strategies

Therapeutic Fc‐fusion proteins: Current analytical strategies

Host–Guest Complexation of Amphiphilic Molecules at the Air–Water Interface Prevents Oxidation by Hydroxyl Radicals and Singlet Oxygen

Barriers for Extrusion of a Guest from the Interior Binding Cavity of a Host: Gas Phase Experimental and Computational Results for Ion-Capped Decamethylcucurbit[5]uril Complexes

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