Synthesis of substituted terpyridine ligands for use in protein purification

Lin, Chih-Pei; Florio, Pas; Campi, Eva M.; Zhang, Chunfang; Fredericks, Dale Patricia; Saito, Kei; Jackson, W. Roy; Hearn, Milton Thomas William

doi:10.1016/j.tet.2014.09.074

Cited by 9 publications

(2 citation statements)

References 27 publications

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“…A set of terpyridine‐based ligands has been immobilized onto Sepharose and investigated with a humanized IgG2 monoclonal antibody for adsorption isotherms, dynamic loading, and elution properties . The synthetic protocol for the substituted terpyridine ligands and the modification of Sepharose has been published previously . One of the terpyridine‐modified Sepharose sorbent exhibited very high selectivity in terms of host cell protein clearance rivaling found for Protein A adsorbents.…”

Section: Polymeric Mixed‐mode Stationary Phasesmentioning

confidence: 99%

Recent advances in mixed‐mode chromatographic stationary phases

Sýkora

Řezanka

Záruba

et al. 2018

J of Separation Science

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Mixed‐mode phases have become very popular in the last decade, and the number of new mixed/multi‐mode sorbents is growing fast. Unlike single‐mode stationary phases, perfectly suited for the separation of the analytes possessing similar physicochemical properties, for instance reversed‐phase chromatography for hydrophobic solutes, mixed‐mode sorbents providing multimodal interactions can render better separation selectivity for complex mixtures of solutes differing significantly in their physicochemical characteristics. The most frequent modern mixed‐mode stationary phases are di/tri‐mode sorbents embracing the following interactions, hydrophobic, electrostatic (coulombic), and hydrophilic. According to their structures, it is possible to distinguish silica‐based, polymer‐based, hybrid, and monolithic mixed‐mode stationary phases. Herewith, newly synthesized mixed‐mode sorbents developed within the last two and half years are categorized, discussed, and summarized. The main attention is devoted to the description of the synthetic routes and characterization methods applied for the new stationary phases.

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Section: Polymeric Mixed‐mode Stationary Phasesmentioning

confidence: 99%

Recent advances in mixed‐mode chromatographic stationary phases

Sýkora

Řezanka

Záruba

et al. 2018

J of Separation Science

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“…Recently, we reported the synthesis of a library of synthetic heterocyclic ligands containing a 4′‐(2‐aminoethylsulfanyl)‐2,2′:6′,2″‐terpyridine (terpy) core. In associated investigations, adsorbents (known as TIGs), derived from the immobilization of these terpyridine ligands onto Sepharose 6FF gels, were shown to exhibit high binding affinities ( K a ~ 10 6 M −1 ), high loading capacities (40–70 mg IgG/ml adsorbent) and excellent host cell protein (HCP) clearance capabilities comparable to Protein A adsorbents (Mountford et al , ; Lin et al , ; Zhang et al , ). Other chromatographic studies based on high throughput screening methods with these TIGs revealed the interplay of multimodal binding mechanisms for different monoclonal IgG isotypes, with the selectivity of these adsorbents dependent on the chemical nature of the substituents introduced into the terpy core (unpublished results).…”

Section: Introductionmentioning

confidence: 99%

Studies on the binding sites of IgG2 monoclonal antibodies recognized by terpyridine‐based affinity ligands

Lin

Boysen

Campi

et al. 2016

J of Molecular Recognition

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This investigation has examined the origin of the molecular recognition associated with the interaction of monoclonal IgG2's with terpyridine-based ligands immobilized onto agarose-derived chromatographic adsorbents. Isothermal titration calorimetric (ITC) methods have been employed to acquire thermodynamic data associated with the IgG2-ligand binding. These ITC investigations have documented that different enthalpic and entropic processes are involved depending on the nature of the chemical substituents in the core structure of the terpyridinyl moiety. In addition, molecular docking studies have been carried out with IgG2 structures with the objective to identify possible ligand binding sites and key interacting amino acid residues. These molecular docking experiments with the different terpyridine-based ligands have shown that all of the examined ligands can potentially undergo favorable interactions with a site located within the Fab region of the IgG2. However, another favorable binding site was also identified from the docking poses to exist within the Fc region of the IgG2 for some, but not all, of the ligands studied. These investigations have provided a basis to elucidate the unique binding properties and chromatographic behaviors shown by several substituted terpyridine ligands in their interaction with IgGs of different isotype. Copyright © 2016 John Wiley & Sons, Ltd.

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CO₂ Conversion into Esters by Fluoride‐Mediated Carboxylation of Organosilanes and Halide Derivatives

Frogneux

Wolff

Thuéry

et al. 2016

Chemistry A European J

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A one-step conversion of CO2 into heteroaromatic esters is presented under metal-free conditions. Using fluoride anions as promoters for the C-Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO2 in the C-Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO2 into a polyester material for the first time.

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Synthesis of substituted terpyridine ligands for use in protein purification

Cited by 9 publications

References 27 publications

Recent advances in mixed‐mode chromatographic stationary phases

Recent advances in mixed‐mode chromatographic stationary phases

Studies on the binding sites of IgG2 monoclonal antibodies recognized by terpyridine‐based affinity ligands

CO₂ Conversion into Esters by Fluoride‐Mediated Carboxylation of Organosilanes and Halide Derivatives

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Synthesis of substituted terpyridine ligands for use in protein purification

Cited by 9 publications

References 27 publications

Recent advances in mixed‐mode chromatographic stationary phases

Recent advances in mixed‐mode chromatographic stationary phases

Studies on the binding sites of IgG2 monoclonal antibodies recognized by terpyridine‐based affinity ligands

CO2 Conversion into Esters by Fluoride‐Mediated Carboxylation of Organosilanes and Halide Derivatives

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Product

Resources

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CO₂ Conversion into Esters by Fluoride‐Mediated Carboxylation of Organosilanes and Halide Derivatives