Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - a potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals

Corrigan, Damion K.; Whitcombe, Michael J.; McCrossen, Sean; Piletsky, Sergey A.

doi:10.1211/jpp/61.04.0017

Cited by 5 publications

(6 citation statements)

References 10 publications

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“…561 Corrigan et al used betaine 1 as a reagent for the detection of low levels of alkylating agents, such as 4-chloro-1-butanol and ethylmethanesulfonate. 562 The development of assays for the visual detection and quantification of alkylating agents is important because these compounds are potentially genotoxic impurities that may be present in pharmaceuticals. The rationale here is based on the fact that the alkylation of 1 occurs on the phenolate moiety, and the ether generated is colorless, as shown previously by Linert et al 563 in a kinetic study of the methylation of a series of pyridinium-N-phenolate betaine dyes in organic solvents.…”

Section: Chromogenic Chemosensors For Neutral Analytesmentioning

confidence: 99%

PyridiniumN-Phenolate Betaine Dyes

2014

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Introduction 10429 2. Historical Contextualization 10431 3. Synthesis of Pyridinium N-Phenolate Dyes 10433 4. Solvatochromic Properties of Pyridinium N-Phenolate Dyes 10435 4.1. X-ray Crystallographic Studies of the Molecular Structures of Pyridinium N-Phenolate Dyes 10437 4.2. Quantum Chemical Calculations Involving Pyridinium N-Phenolate Dyes 10438 4.3. The E T (30) and E T N Solvent Polarity Scale 10440 4.4. Multiparametric Approaches to the Analysis of the E T (30) and E T N Scale 10441 5. Secondary Solvatochromic Pyridinium N-Phenolate Dyes 10442 6. Investigation of the Physical Properties of Room-Temperature Ionic Liquids 10443 7. Thermosolvatochromism of Pyridinium N-Phenolate Dyes 10450 8. Halochromism of Pyridinium N-Phenolate Dyes 10451 9. Piezosolvatochromism of Pyridinium N-Phenolate Dyes 10452 10. Pyridinium N-Phenolate Dyes in the Investigation of Solvent Mixtures 10453 11. Application of Pyridinium N-Phenolate Dyes in the Construction of Chromogenic Chemosensors 10455 11.1. Chirosolvatochromism of Pyridinium N-Phenolate Dyes 10456 11.2. Chromoionophores 10456 11.3. Chromogenic Chemosensors for Anionic Species 10457 11.4. Chromogenic Chemosensors for Neutral Analytes 10458 12. Pyridinium N-Phenolate Dyes as Probes To Measure the Polarity of Solid Surfaces 10459 13. Pyridinium N-Phenolate Dyes in the Study of Microheterogeneous Systems 10460 13.1. Investigation of Surfactants in Aqueous and Organic Media 10462 13.2. Pyridinium N-Phenolate Dyes in the Investigation of Cyclodextrins in Solution 10463 13.

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Section: Chromogenic Chemosensors For Neutral Analytesmentioning

confidence: 99%

PyridiniumN-Phenolate Betaine Dyes

2014

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“…Sensor technologies have been an active area of research for a great many years with examples of the oxygen monitoring electrode for surgery and first-, second- and third-generation glucose biosensors finding widespread adoption and now routine use [1]. Sensor technologies have enabled environmental monitoring [2], improved control of industrial processes [3], given rise to purer drug formulations [4,5] and found numerous medical and biological applications, including the measurement of glucose for diabetes [6], lactate for a range of conditions [7] and the routine determination of blood clotting [8]. Sensor technologies have also been used in wild animal research since the first application of an intravascular pO 2 electrode in a diving penguin in 2005 [9], but the field of wild animal sensing lags far behind the biomedical industry.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in biomedical, biosensor and clinical measurement devices for use in humans and the potential application of these technologies for the study of physiology and disease in wild animals

MacDonald

Hawkes

Corrigan

2021

Phil. Trans. R. Soc. B

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The goal of achieving enhanced diagnosis and continuous monitoring of human health has led to a vibrant, dynamic and well-funded field of research in medical sensing and biosensor technologies. The field has many sub-disciplines which focus on different aspects of sensor science; engaging engineers, chemists, biochemists and clinicians, often in interdisciplinary teams. The trends which dominate include the efforts to develop effective point of care tests and implantable/wearable technologies for early diagnosis and continuous monitoring. This review will outline the current state of the art in a number of relevant fields, including device engineering, chemistry, nanoscience and biomolecular detection, and suggest how these advances might be employed to develop effective systems for measuring physiology, detecting infection and monitoring biomarker status in wild animals. Special consideration is also given to the emerging threat of antimicrobial resistance and in the light of the current SARS-CoV-2 outbreak, zoonotic infections. Both of these areas involve significant crossover between animal and human health and are therefore well placed to seed technological developments with applicability to both human and animal health and, more generally, the reviewed technologies have significant potential to find use in the measurement of physiology in wild animals. This article is part of the theme issue ‘Measuring physiology in free-living animals (Part II)’.

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“…Several analytical methods that use these techniques for detecting 4-chloro-1-butanol at the sub-ppm level in APIs have been reported. 11,17,18 In a previous study, we developed a GC-MS method for 4-chloro-1-butanol analysis.…”

Section: Introductionmentioning

confidence: 99%

Novel Sensitive Determination Method for a Genotoxic Alkylating Agent, 4-Chloro-1-butanol, in Active Pharmaceutical Ingredients by LC-ICP-MS Employing Iodo Derivatization

Harigaya¹,

Yaku²,

Nishi

et al. 2014

ANAL. SCI.

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An alkylating agent, 4-chloro-1-butanol, is a genotoxic impurity (GTI); it may be generated during the synthesis of active pharmaceutical ingredients (APIs). For the trace-level detection of GTIs in APIs, usually, gas chromatography-mass spectrometry (GC-MS) or liquid chromatography-mass spectrometry (LC-MS) is employed. In this study, a novel LC-inductively coupled plasma (ICP)-MS method was developed and validated. Linearity was observed over the 0.5 -50 ppm (μg/g API) range, with an R 2 value of 0.9994. The detection limit (DL) and quantitation limit (QL) were 0.2 and 0.5 ppm, respectively. The DL and QL values are well over the thresholds specified in the guidelines. The accuracy was 95.1 -114.7% for concentrations of 1 -50 ppm, and the relative standard deviation of the spiked recovery test's repeatability was 6.2%. In addition, six lots of an API were analyzed, and all results were lower than the reported threshold (1 ppm).

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Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - a potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals

Abstract: Using standard solutions and in the presence of a drug matrix, Reichardt's dye shows promise as a reagent for detection of low levels of industrially important alkylating agents.

Cited by 5 publications

References 10 publications

PyridiniumN-Phenolate Betaine Dyes

PyridiniumN-Phenolate Betaine Dyes

Recent advances in biomedical, biosensor and clinical measurement devices for use in humans and the potential application of these technologies for the study of physiology and disease in wild animals

Novel Sensitive Determination Method for a Genotoxic Alkylating Agent, 4-Chloro-1-butanol, in Active Pharmaceutical Ingredients by LC-ICP-MS Employing Iodo Derivatization

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