A study of the analytical behaviour of selected synthetic and naturally occurring quinolines using electrospray ionisation ion trap mass spectrometry, liquid chromatography and gas chromatography and the construction of an appropriate database for quinoline characterisation

O'Donnell, F.R.; Ramachandran, V. N.; Smyth, W. Franklin; Hack, Catherine; Patton, Elizabeth

doi:10.1016/j.aca.2006.05.018

Cited by 13 publications

(9 citation statements)

References 6 publications

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“…ESI-MS n studies of antimalarial compounds as bisthiazolium or quinolines can be found on reports by Nicolas et al [38] or Smyth et al and O'Donnell et al [34,39], respectively. However, ESI-MS studies contributing to the development of antimalarials are scarce.…”

Section: Introductionmentioning

confidence: 99%

Characterization of primaquine imidazolidin-4-ones with antimalarial activity by electrospray ionization-ion trap mass spectrometry

Vale

Moreira

Gomes

2008

International Journal of Mass Spectrometry

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The extensive characterization by electrospray ionization-ion trap mass spectrometry (ESI-MS n ) of 20 imidazolidin-4-ones derived from the antimalarial primaquine was well obtained. These compounds are being under investigation as potential antimalarials, as they have been previously found to be active against rodent P. berghei malaria and to be highly stable under physiological conditions. Experiments by collision-induced dissociation (CID) in the nozzle-skimmer region or by tandem-MS have shown the title compounds to be remarkably stable. Mechanisms are proposed to explain the major fragmentations observed in ESI-MS n experiments. Overall, this work represents an unprecedented contribution to a deeper insight into imidazolidin-4-one antimalarials based on a classic 8-aminoquinolinic scaffold. Data herein reported and discussed may be an useful guide for future studies on therapeutically relevant molecules possessing either the 8-aminoquinoline or the imidazolidin-4-one motifs.

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Section: Introductionmentioning

confidence: 99%

Characterization of primaquine imidazolidin-4-ones with antimalarial activity by electrospray ionization-ion trap mass spectrometry

Vale

Moreira

Gomes

2008

International Journal of Mass Spectrometry

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“…Overall, this work embodies an original and valuable contribution towards a deeper insight into the molecular properties of novel antimalarials, which can be viewed as representative of both the O ver the past decade, electrospray ionization mass spectrometry (ESI-MS) has been used for the most diverse analytical purposes. This technique has provided deeper insight into the structural properties and stability of numerous compounds, from natural products [1][2][3] to synthetic drugs [4][5][6][7][8], peptides [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23], and heterocycles [24][25][26][27][28], among many others. Notwithstanding, little has been done on the application of this technique to the study of relevant antimalarials such as primaquine (PQ, 1) or related structures.…”

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confidence: 99%

Electrospray ionization-ion trap mass spectrometry study of PQAAPro and PQProAA mimetic derivatives of the antimalarial primaquine

Vale

Matos

Moreira

et al. 2008

J. Am. Soc. Mass Spectrom.

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Electrospray ionization-ion trap mass spectrometry (ESI-MS) of imidazolidin-4-one peptidemimetic derivatives of the antimalarial drug primaquine (PQ) is reported. These compounds contain the imidazolidin-4-one moiety either at the N-or the C-terminal of a dipeptide backbone, thus respectively mimicking PQ-Amino Acid-Proline (PQAAPro) and PQProAA derivatives of PQ. Both the peptidomimetics and precursors previously developed by us are promising drug candidates, as they were found to be active against rodent Plasmodium berghei malaria and Pneumocystis carinii pneumonia. Collision-induced dissociation (GD) and tandemmass spectra (MS) of the title compounds, and fragmentation pathways thereof, led to the following findings: (1) CID patterns present some parallelism with the reactivity towards hydrolysis previously found for the same or related compounds; (2) a positional shift of the imidazolidin-d-one ring is reflected on both degree and pathways of fragmentation, which makes tandem-MS a key tool for differentiation of imidazolidin-i-one isomers; (3) the major MS/MS fragmentation of PQProAA mimetics involves release of a neutral diketopiperazine (DKP), in parallel to the "diketopiperazine pathway" described in tandem-MS studies of oligopeptides; (4) the relative abundance of a major fragment in tandem-MS spectra is inversely correlated with the size of the N-terminal AA in PQProAA mimetics. Overall, this work embodies an original and valuable contribution towards a deeper insight into the molecular properties of novel antimalarials, which can be viewed as representative of both the 8-aminoquinoline and, especially, the imidazolidin-4-one structural classes. aAm Soc Mass Spectrom 2008, 19, 1476-1490 ) © 2008 American Society for Mass SpectrometryO ver the past decade, electrospray ionization mass spectrometry (ESI-MS) has been used for the most diverse analytical purposes. This technique has provided deeper insight into the structural properties and stability of numerous compounds, from natural products [1-3] to synthetic drugs [4-8], peptides [9-23], and heterocycles [24][25][26][27][28], among many others. Notwithstanding, little has been done on the application of this technique to the study of relevant antimalarials such as primaquine (PQ, 1) or related structures. Analytical methods focused on PQ or its analogues have been so far applied to pharmacokinetics studies and metabolite scrutiny [29][30][31][32][33][34][35][36][37] or isomer characterization [38,39]. Examples of mass spectrometry techniques employed to the study/analysis of PQ and related compounds include fast atom bombardment mass spectral (FAB-MS) analysis of PQ oxidation products [32] and supercritical fluid chromatography-mass Address reprint requests to Dr. P.

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“…In addition, the pyrano ring structure molecules generally show a loss of 42 Da, corresponding to CH 2 CHCH 3 from the pyrano ring. As a result, compounds 43 b were identified as N ‐methylflindersine, and agree with the literature . These fragmentation characteristics, when combined with database searching, permitted the characterisation of 10 quinoline alkaloids from T. asiatica .…”

Section: Resultsmentioning

confidence: 99%

Simultaneous qualitative and quantitative evaluation of Toddalia asiatica root by using HPLC‐DAD and UPLC‐QTOF‐MS/MS

Zhu

Wei

Peng

et al. 2018

Phytochemical Analysis

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Introduction Coumarin and alkaloids are the major bioactive constituents of Toddalia asiatica, playing an important role in various biological activities such as anti‐inflammatory, analgesic, anti‐bacterial and anti‐tumour. Objective To establish a method that will simultaneously determine the coumarins and alkaloids compounds in T. asiatica and identify their characteristic fragmentation patterns, while combining fingerprints and chemical identification with chemometrics for discrimination and quality assessment of T. asiatica samples. Methodology Qualitative characterisation of coumarins and alkaloids compounds in the methanol extracts of T. asiatica was determined by ultra‐high‐performance liquid chromatography‐quadrupole time‐of‐flight tandem mass spectrometry (UPLC‐QTOF‐MS/MS). Quantitative analysis relies on high‐performance liquid chromatography with a diode array detector (HPLC‐DAD). Results A total of 59 components were characterised by UPLC‐QTOF‐MS/MS, including 29 coumarin, 25 alkaloids, one phenolic acid and four flavonoids. While the 19 characteristic components out of 23 common peaks in the chromatographic fingerprints of T. asiatica were confirmed. Quantitative analysis of seven major compounds from 18 samples were simultaneously detected by HPLC‐DAD at wavelengths of 280 nm. The samples were classified into three groups by hierarchical clustering analysis (HCA) combined with principal component analysis (PCA), and orthogonal partial least squares discriminant analysis (OPLS‐DA) which screened out the main chemical markers responsible for the samples differences. Conclusion Fingerprints combined with chemometrics and chemical identification are a simple, rapid and effective method for the quality control of T. asiatica.

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A study of the analytical behaviour of selected synthetic and naturally occurring quinolines using electrospray ionisation ion trap mass spectrometry, liquid chromatography and gas chromatography and the construction of an appropriate database for quinoline characterisation

Cited by 13 publications

References 6 publications

Characterization of primaquine imidazolidin-4-ones with antimalarial activity by electrospray ionization-ion trap mass spectrometry

Characterization of primaquine imidazolidin-4-ones with antimalarial activity by electrospray ionization-ion trap mass spectrometry

Electrospray ionization-ion trap mass spectrometry study of PQAAPro and PQProAA mimetic derivatives of the antimalarial primaquine

Simultaneous qualitative and quantitative evaluation of Toddalia asiatica root by using HPLC‐DAD and UPLC‐QTOF‐MS/MS

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