Adduct formation of steroids in APCI and its relation to structure identification

Honing, Maarten; Bockxmeer, E. van; Beekman, Daniel W.

doi:10.1051/analusis:2000280921

Cited by 6 publications

(4 citation statements)

References 6 publications

(10 reference statements)

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“…Adduct formation has been previously reported in analysis of steroids using both ESI and atmospheric pressure chemical ionization LC−MS interfaces. , The formation of sodium adducts has been associated with the presence of sodium in HPLC solvents stored in borosilicate containers. Their formation depends on the pH of the solvents used for LC as both the proton and sodium compete for the same substrates.…”

Section: Resultsmentioning

confidence: 95%

Methodology for Profiling the Steroid Metabolome in Animal Tissues Using Ultraperformance Liquid Chromatography−Electrospray-Time-of-Flight Mass Spectrometry

Flores-Valverde

Hill²

2008

Anal. Chem.

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The advent of mass spectrometry-based metabolite profiling techniques should allow investigations into the behavior and regulation of many of the low abundant signaling molecules present in the animal metabolome such as hormones and so aid investigations into the mechanisms of endocrine system function and disorders. Examples of their potential applications include endocrine-related diseases such as some cancers, as well as endocrine disruption in wildlife and humans caused by some environmental contaminants. In the present study, a method was developed to profile a variety of vertebrate steroids and their conjugates in fish tissues using solid phase extraction (SPE) prior to ultraperformance liquid chromatography linked to electrospray-time-of-flight mass spectrometry (UPLC-TOF MS). Analysis of tissue extracts spiked with steroids revealed that most analytes could be detected at subnanogram per gram concentrations in liver or testes, but ovarian extracts caused ion suppression of estrogens. A comparison of the steroid metabolome of the ovaries and testes using partial least-squares discrimination analysis (PLS-DA) revealed that the androgens 11-ketotestosterone, 11-hydroxyandrostenedione, androstenedione, and two unidentified cortisol-type glucocorticoids were discriminatory steroid markers in testes extracts. In contrast, cortisol was the predominant glucocorticoid marker in ovary extracts, and cortisone was abundant in extracts of both testes and ovaries. A number of other unidentified nonsteroidal metabolites were also differentially expressed between the testes and ovarian tissues. These studies reveal that metabolite profiling using UPLC-TOF MS is a promising approach to investigate steroid homeostasis in animal tissues.

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Section: Resultsmentioning

confidence: 95%

Methodology for Profiling the Steroid Metabolome in Animal Tissues Using Ultraperformance Liquid Chromatography−Electrospray-Time-of-Flight Mass Spectrometry

Flores-Valverde

Hill²

2008

Anal. Chem.

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“…We can neither confirm nor exclude either of these hypotheses because the positive and negative modes of APCI involve different processes . However, several studies have shown that APCI also produces adducts in negative ion mode, so further investigations are required to determine the mechanism of adduction. However, we observed a reproducibility of adduct formation among the different samples and even between the two technical replicates of a single sample.…”

Section: Discussionmentioning

confidence: 91%

Performance comparison of electrospray ionization and atmospheric pressure chemical ionization in untargeted and targeted liquid chromatography/mass spectrometry based metabolomics analysis of grapeberry metabolites

Commisso

Anesi

Santo

et al. 2016

Rapid Comm Mass Spectrometry

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ESI and APCI are not complementary ion sources. Indeed, ESI can be exploited to analyze moderately polar metabolites, whereas APCI can be used to investigate weakly polar/non-polar metabolites and, as demonstrated by our results, also strongly polar metabolites. ESI and APCI can be used in parallel, exploiting their strengths to cover the plant metabolome more broadly than either method alone. Copyright © 2016 John Wiley & Sons, Ltd.

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“…An in-depth knowledge of the physicochemical properties of molecules allows the tentative identification of some functional groups. As an example, intense adducts with alkali-metal ions are related to cis-dihydroxylated entities, while adducts with acetic acids would suggest the presence of proton-donating hydroxyl groups, as has been shown for an number of steroidal drug candidates [72]. Switching from the most commonly applied positive ion mode to the detection of negative ions can help to determine the presence of such hydroxyl group or carboxylic entities.…”

Section: Chemical and Photostability Testingmentioning

confidence: 98%

“…These mass spectra lack any compound-specific fragment ions as one would get in classical electron ionization mass spectra. on the other hand, polarity switching and a good sense for proton transfer reactions in "buffered" aqueous solutions or the gas phase can be used as a first stage in identifying specific functionalities in molecules [72,73]. Abundant response in the negative ion mode may indicate the presence of carboxyl groups, while, in general, aromatic hydroxyls tend to be acidic.…”

Section: The Role Of Ms In the Elucidation Of Chemical Structuresmentioning

confidence: 99%

MS Applications in Support of Medicinal Chemistry Sciences

Honing¹,

Ingelse²,

Pramanik³

2013

Mass Spectrometry for Drug Discovery and Drug Development

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In the drug discovery process, medicinal chemistry plays a crucial role in the optimal design and synthesis (production) of new chemical entities (NCEs) or new biological entities (NBEs); this is true for a single entity as well as a complete compound library. A key requirement in this field of science is the optimization of both the chemical and the biological properties of these potential drug-like compounds. Important criteria are the design of efficient synthesis routes, the balancing of the physical chemical properties with optimal in vitro and in vivo drug metabolism and pharmacokinetic (DMPK) processes, and a profound understanding of the pharmacodynamics in the appropriate pharmacological models. In the lead optimization stage, an important step is scaling up the synthesis route as needed for the execution of toxicology studies and the screening of suitable drug formulations. In summary, medicinal chemistry support includes participating in a large variety of activities and decision making processes that play a key role in the search for either a "first in class" new drug or a "best in class" new drug [1].These "drug discovery" processes are continuously under pressure, as the research and development (R&D) costs continue to increase and more data are requested before new drug candidates are taken into (pre-)clinical development. Hence, the choice of "targeted" high-throughput screening (HTS) libraries, the process of hit appraisal, and the understanding of target-ligand interactions can be considered the starting points for a new drug discovery program [2]. Next, the main focus is on the discovery of a lead compound; typically, this is a compound showing promising data regarding target affinity, reasonable efficacy in cellular models, good physical chemical parameters (i.e., a "drug-like" compound), and acceptable oral bioavailability in Mass Spectrometry for Drug Discovery and Drug Development, First Edition. Edited by Walter A. Korfmacher.

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Adduct formation of steroids in APCI and its relation to structure identification

Cited by 6 publications

References 6 publications

Methodology for Profiling the Steroid Metabolome in Animal Tissues Using Ultraperformance Liquid Chromatography−Electrospray-Time-of-Flight Mass Spectrometry

Methodology for Profiling the Steroid Metabolome in Animal Tissues Using Ultraperformance Liquid Chromatography−Electrospray-Time-of-Flight Mass Spectrometry

Performance comparison of electrospray ionization and atmospheric pressure chemical ionization in untargeted and targeted liquid chromatography/mass spectrometry based metabolomics analysis of grapeberry metabolites

MS Applications in Support of Medicinal Chemistry Sciences

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