Separation of polyethylene glycols and amino-terminated polyethylene glycols by high-performance liquid chromatography under near critical conditions

Wei, Y.-Z.; Zhuo, Ren‐Xi; Jiang, Xulin

doi:10.1016/j.chroma.2016.04.035

Cited by 12 publications

(4 citation statements)

References 37 publications

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“…The intersection point provides an indication of the critical solvent composition, at which the retention time of the polymer is independent of the molar mass [18]. The critical compositions for nonfunctional PEGs and bifunctional maleimidesubstituted PEGs are found to be identical at about 40% acetonitrile in water at 25ЊC, which is similar to our previous observation on Shodex C 18 column [42]. At this critical composition, nearly identical elution times for nonfunctional PEGs or bifunctional PEGs with different molar masses (2, 4, and 6k) were obtained, which indicates that the molar mass does not strongly influence the retention at the selected critical chromatographic condition.…”

Section: Effects Of Organic Solvent Composition On the Retention Of Pegssupporting

confidence: 85%

Separation of polyethylene glycols and maleimide‐terminated polyethylene glycols by reversed‐phase liquid chromatography under critical conditions

Wei

Zhuo

Jiang

2016

J of Separation Science

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The separation of polyethylene glycols and maleimide-substituted polyethylene glycol derivatives based on the number of maleimide end-groups under critical liquid chromatography conditions has been investigated on a reversed-phase column. The critical solvent compositions for nonfunctional polyethylene glycols and bifunctional maleimide-substituted polyethylene glycols were determined to be identical at about 40% acetonitrile in water on a reversed-phase octadecyl carbon chain-bonded silica column using mixtures of acetonitrile and water of varying composition as the mobile phase at 25°C. The maleimide-functionalized polyethylene glycols were successfully separated according to maleimide functionality (with zero, one, two, or three maleimide end-groups, respectively) under the critical isocratic elution conditions without obvious effect of molar mass. The separation was mainly due to the hydrophobic interaction between the maleimide end-groups and the column packing. Off-line matrix-assisted laser desorption/ionization time of flight mass spectrometry was used to identify the repeating units and, especially, the end-groups of the maleimide-substituted polyethylene glycols. Liquid chromatography analysis at critical conditions could provide useful information to optimize the synthesis of functional polyethylene glycols. To our knowledge, this is the first report of the baseline separation of maleimide-functionalized polyethylene glycols based on the functionality independent of the molar mass without derivatization by isocratic elution.

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Section: Effects Of Organic Solvent Composition On the Retention Of Pegssupporting

confidence: 85%

Separation of polyethylene glycols and maleimide‐terminated polyethylene glycols by reversed‐phase liquid chromatography under critical conditions

Wei

Zhuo

Jiang

2016

J of Separation Science

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“…Maleimide functionality is also of vital importance towards the synthesis of functional bioconjugates . On the other hand, α,ω‐bifunctional and 3‐arm PEG have been extensively utilized for hydrogel and network fabrication . We then utilized the carbamate strategy to synthesize high‐fidelity multifunctional PEG derivatives bearing one, two, and three maleimide moieties.…”

Section: Methodsmentioning

confidence: 99%

High‐Fidelity End‐Functionalization of Poly(ethylene glycol) Using Stable and Potent Carbamate Linkages

et al. 2020

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Commercial PEG‐amine is of unreliable quality, and conventional PEG functionalization relies on esterification and etherification steps, suffering from incomplete conversion, harsh reaction conditions, and functional‐group incompatibility. To solve these challenges, we propose an efficient strategy for PEG functionalization with carbamate linkages. By fine‐tuning terminal amine basicity, stable and high‐fidelity PEG‐amine with carbamate linkage was obtained, as seen from the clean MALDI‐TOF MS pattern. The carbamate strategy was further applied to the synthesis of high‐fidelity multi‐functionalized PEG with varying reactive groups. Compared to with an ester linkage, amphiphilic PEG‐PS block copolymers bearing carbamate junction linkage exhibits preferential self‐assembly tendency into vesicles. Moreover, nanoparticles of the latter demonstrate higher drug loading efficiency, encapsulation stability against enzymatic hydrolysis, and improved in vivo retention at the tumor region.

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“…Fortunately, the method of separation for PEGs and amino-terminated PEGs using HPLC under near critical conditions has been reported very recently in our group. 44 The modification efficiency and purity of LA-PEG-Ad were investigated using HPLC (Fig. S6, ESI †).…”

Section: Synthesis and Characterization Of Adamantyl Functionalized T...mentioning

confidence: 99%

A facile modular approach toward multifunctional supramolecular polyplexes for targeting gene delivery

et al. 2016

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Separation of polyethylene glycols and amino-terminated polyethylene glycols by high-performance liquid chromatography under near critical conditions

Cited by 12 publications

References 37 publications

Separation of polyethylene glycols and maleimide‐terminated polyethylene glycols by reversed‐phase liquid chromatography under critical conditions

Separation of polyethylene glycols and maleimide‐terminated polyethylene glycols by reversed‐phase liquid chromatography under critical conditions

High‐Fidelity End‐Functionalization of Poly(ethylene glycol) Using Stable and Potent Carbamate Linkages

A facile modular approach toward multifunctional supramolecular polyplexes for targeting gene delivery

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