Analytical method development for a specific assay method for monomethoxypoly(ethylene glycol)succinimido carbonate (mPEG-SC): A comparison of spectrophotometric, titrimetric and chromatographic methods

Niemczyk, Henry J.; Arnum, Susan D. Van

doi:10.1016/j.aca.2008.03.035

Cited by 8 publications

(8 citation statements)

References 21 publications

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“…Since cooling, the absorbance at 420 nm remained constant within at least 120 min so that absorbance at 420 nm can be easily measured. This property makes the new method more advantageous over the classical spectrophotometric method based on the absorbance of NHS at 260 nm after reaction with ammonia or hydroxide ion in aqueous solutions [9,11]. …”

Section: Resultsmentioning

confidence: 99%

“…The method completely followed those reported [9,11]. NHS ester was added to 0.10 mol/L aqueous ammonia and absorbance at 260 nm was measured from 5 min to 20 min since reaction initiation.…”

Section: Methodsmentioning

confidence: 99%

“…Chromatographic methods can validate NHS esters of mPEGs and quantify their molar equivalents [9,10], but are laborious and require a reference compound for each NHS ester of mPEG that is usually unavailable. Ionized NHS has an absorbance peak at 260 nm; molar equivalents of NHS esters of mPEGs can be quantified based on absorbance of NHS released by reactions of NHS esters of mPEGs with ammonia and/or hydroxide ion in alkaline aqueous solutions [9,11].…”

Section: Introductionmentioning

confidence: 99%

“…Ionized NHS has an absorbance peak at 260 nm; molar equivalents of NHS esters of mPEGs can be quantified based on absorbance of NHS released by reactions of NHS esters of mPEGs with ammonia and/or hydroxide ion in alkaline aqueous solutions [9,11]. However, NHS esters of mPEGs undergo so fast reactions with ammonia and/or hydroxide ion that pre-existed NHS from spontaneous hydrolysis can not be accurately measured.…”

Section: Introductionmentioning

confidence: 99%

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Facile spectrophotometric assay of molar equivalents of N-hydroxysuccinimide esters of monomethoxyl poly-(ethylene glycol) derivatives

Gao

Yang

Zhang

et al. 2012

Chemistry Central Journal

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BackgroundA new method is developed to quantify molar equivalents of N-hydroxysuccinimide (NHS) esters of derivatives of monomethoxyl poly-(ethylene glycol) (mPEG) in their preparations with NHS acetate ester as the reference.ResultsNHS ester of succinic monoester or carbonate of mPEG of 5,000 Da was synthesized and reacted with excessive ethanolamine in dimethylformamide at 25°C for 15 min. Residual ethanolamine was subsequently quantified by absorbance at 420 nm after reaction with 2,4,6-trinitrobenzenesulfonic acid (TNBS) at pH 9.2 for 15 min at 55°C followed by cooling with tap water. Reaction products of ethanolamine and NHS esters of mPEG caused no interference with TNBS assay of residual ethanolamine. Reaction between ethanolamine and NHS acetate ester follows 1:1 stoichiometry. By the new method, molar equivalents of NHS esters of carbonate and succinic monoester of mPEG in their preparations were about 90% and 60% of their theoretical values, respectively. During storage at 37°C in humid air, the new method detected spontaneous hydrolyses of the two NHS esters of mPEG more sensitively than the classical spectrophotometric method based on absorbance at 260 nm of NHS released by reaction with ammonia in aqueous solution.ConclusionThe new method is favorable to quantify molar equivalents of NHS esters of mPEG derivatives and thus control quality of their preparations.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Facile spectrophotometric assay of molar equivalents of N-hydroxysuccinimide esters of monomethoxyl poly-(ethylene glycol) derivatives

Gao

Yang

Zhang

et al. 2012

Chemistry Central Journal

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“…Menadione (9) was used as received from Vanetta Chemical Co and podophylotoxin (5) was obtained from Aldrich Chemical Co. HPLC analysis for PEG menadiol 11 was done on a Prosphere HP C18 300Å , 5 m, 250 mm )4.6 mm column by Alltech (19). Gradient elution was used with a mixture of water and acetonitrile and a flow rate of 1.00 mL/min.…”

Section: Resultsmentioning

confidence: 99%

A green synthetic process for the preparation of water-soluble drugs: pegylation of menadiol and podophyllotoxin

Niemczyk¹,

Arnum²

2008

Green Chemistry Letters and Reviews

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Pegylation of drugs is a frequently employed strategy used to improve the pharmacokinetics and pharmacodynamics of drugs. Despite this, the virtues of pegylation as a green synthetic approach to enhance the water solubility of drugs has not been discussed. Using two well-known active pharmaceutical ingredients, menadiol sodium diphosphate (1) and the semisynthetic natural product, etoposide phosphate (3), green metrics for the processes of pegylation versus phosphorylation are presented and discussed. Menadiol (2) was prepared by an ultrasound mediated reduction of menadione (9). In a study done by the National Cancer Institute, PEG podophyllotoxin 12 was screened for activity against 60 different human cancer cell lines and the desired anticancer properties of podophyllotoxin (5) were retained. As podophyllotoxin (5) is a natural product, the concept of ''green drugs'' is espoused.

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Simple Synthesis of Aldehyde and Carboxylic Acid Terminated Methoxypoly(ethylene glycol)

Guastavino

Vaillard

Cristaldi³

et al. 2016

Macro Chemistry & Physics

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mPEG‐aldehydes and activated mPEG‐carboxylic acids on which the polymer and the reactive functional group are separated by aliphatic chains of different lengths, are well known reagents of widespread application in PEGylation technology. The syntheses of these functional polymers are not easy and usually the preparation of each of these compounds requires a very specific set of reagents and experimental conditions. In fact, a general method for their preparation is, still nowadays, unavailable. In this work a simple synthetic method is developed for preparation of mPEG‐aldehydes and carboxylic acids with excellent yields. The key step of the method involves a substitution reaction of mPEG‐mesylate with mono‐alkoxides of symmetrical diols to afford hydroxyl‐terminated polymers, which are converted to the aldehydes and acids by mild oxidation reactions.

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Analytical method development for a specific assay method for monomethoxypoly(ethylene glycol)succinimido carbonate (mPEG-SC): A comparison of spectrophotometric, titrimetric and chromatographic methods

Cited by 8 publications

References 21 publications

Facile spectrophotometric assay of molar equivalents of N-hydroxysuccinimide esters of monomethoxyl poly-(ethylene glycol) derivatives

Facile spectrophotometric assay of molar equivalents of N-hydroxysuccinimide esters of monomethoxyl poly-(ethylene glycol) derivatives

A green synthetic process for the preparation of water-soluble drugs: pegylation of menadiol and podophyllotoxin

Simple Synthesis of Aldehyde and Carboxylic Acid Terminated Methoxypoly(ethylene glycol)

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