Detection and Characterization of Natural Polyamines by High-Performance Liquid Chromatography-Atmospheric Pressure Chemical Ionization (Electrospray Ionization) Mass Spectrometry

Chesnov, Sergiy; Bigler, Laurent; Hesse, Manfred

doi:10.1255/ejms.467

Cited by 22 publications

(16 citation statements)

References 32 publications

(34 reference statements)

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“…4,6,125 These compounds have been used as challenges in synthesis, but most notably as templates for structure-activity studies at ionotropic receptors, primarily nAChRs and IGRs. Interestingly, new structures of polyamine toxins are still being discovered, particularly using various mass spectrometric analyses, [126][127][128] and these studies, together with previous seminal work 93 have revealed the intriguing combinatorial approach that spiders have used when producing polyamine toxins. In most cases large combinatorial libraries are created from distinct building blocks, leading to a plethora of systematically different polyamine toxins.…”

Section: M E D I C I N a L C H E M I S T R Ymentioning

confidence: 99%

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Strømgaard

Mellor

2004

Medicinal Research Reviews

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Alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors (AMPAR), subtype of the ionotropic glutamate receptors (IGRs), mediate fast synaptic transmission in the central nervous system (CNS), and are involved in many neurological disorders, as well as being a key player in the formation of memory. Hence, ligands affecting AMPARs are highly important for the study of the structure and function of this receptor, and in this regard polyamine-based ligands, particularly polyamine toxins, are unique as they selectively block Ca2+ -permeable AMPARs. Indeed, endogenous intracellular polyamines are known to modulate the function of these receptors in vivo. In this study, recent developments in the medicinal chemistry of polyamine-based ligands are given, particularly focusing on the use of solid-phase synthesis (SPS) as a tool for the facile generation of libraries of polyamine toxin analogues. Moreover, the recent development of highly potent and very selective AMPAR ligands is described. Additionally, we provide a detailed account on the mechanism and site of action of AMPAR blockade by polyamine-based ligands, including examples of how these ligands are used as tools to study AMPAR, and a comparison with their action on other ionotropic receptors.

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Section: M E D I C I N a L C H E M I S T R Ymentioning

confidence: 99%

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Strømgaard

Mellor

2004

Medicinal Research Reviews

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“…P olyamines and polyamine-containing alkaloids are widely found throughout the plant and animal kingdom [1,2]. Over the past decades, spider venoms, particularly their fractions containing acylpolyamine derivatives [1,3,4], have increasingly attracted the attention of scientists. With the advent of more sensitive and selective analytical methods-in particular of the modern mass spectrometric approaches-not only the major but also minor constituents of such trace toxin sources became amenable to detection and structural elucidation.…”

Section: Tandem Mass Spectrometric Investigation Of Acylpolyamines Ofmentioning

confidence: 99%

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

Tzouros

Manov

Bienz

et al. 2004

J. Am. Soc. Mass Spectrom.

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The fragmentation mechanism of the acylpentamine toxins 1-4 found in the venom of the spider Agelenopsis aperta has been investigated in detail. To identify the origin of the two doublets of unexpected fragment ions at m/z 129/112 and m/z 115/98, three synthetic 15N-labeled analogs 5-7 have been prepared and subjected to CID fragmentation on a triple quadrupole mass spectrometer. It appears that the unexpected doublet of fragment ions arises from an internal portion of the polyamine backbone after either a transaminative Zip reaction or a sequential fragmentation of the quasi-molecular ion. The second option has been proven by in-source CID experiments. The detailed knowledge of acylpentamine fragmentation mechanisms is essential for the correct characterization of isomeric compounds, particularly for coeluting compounds within complex mixtures such as spider venoms.

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“…8 In the meantime, many different spider species have been investigated by several groups and the analytical procedures have been well refined. [9][10][11][12][13][14][15][16][17][18][19][20] Today's analytical setups of choice are arrays of high-performance liquid chromatography (HPLC) and electrospray or atmospheric-pressure chemical ionization mass spectrometry (ESI-MS or APCI-MS) combined with ultraviolet diode array detection (UV-DAD). These arrangements not only allow the separation and detection of lowly abundant polyamine toxins within complex mixtures-which is the general challenge to be confronted with when working with spider venoms-but, in most cases, also the direct structural deduction of the sample molecules by MS/MS or multi-stage mass spectrometry (MS n ).…”

mentioning

confidence: 99%

A Template Approach for the Characterization of Linear Polyamines and Derivatives in Spider Venom

Tzouros

Chesnov

Bigler

et al. 2013

Eur J Mass Spectrom (Chichester)

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A combination of high-performance liquid chromatography (HPLC) and atmospheric-pressure chemical ionization mass spectrometry (APCI-MS and APCI-MS/MS) was used to detect and characterize linear polyamine derivatives in the venom of the spiders Agelenopsis aperta, Hololena curta and Paracoelotes birulai. The compounds were identified with a template approach, by which the collision-induced dissociation (CID) spectra of known compounds are directly compared and correlated with those of the analytes. To facilitate the perception of the spectra and the recognition of the structural features of the analytes, an ion nomenclature closely leaned on the accepted nomenclature for fragment ions of peptides or nucleic acids is introduced. The structure identification of polyamine derivatives by direct correlation of MS spectra is possible because such compounds show very distinctive fragmentation behavior. Of particular relevance is the fact that the signal patterns that are observed with analytes possessing different polyamine backbones are not only distinct with regard to mass distributions but also with regard to relative signal intensities, resulting in fingerprint-like signal patterns. The direct correlation of these patterns--more than the correlation of the ion distributions--was found to be of key significance. With this, the new approach is fundamentally different from the sequencing of peptides or nucleic acids, which are largely based on mass distributions. The method is more efficient and more reliable than the de novo interpretation of the MS data and it even allows the identification of polyamine portions in compounds that are analyzed within mixtures.

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Detection and Characterization of Natural Polyamines by High-Performance Liquid Chromatography-Atmospheric Pressure Chemical Ionization (Electrospray Ionization) Mass Spectrometry

Cited by 22 publications

References 32 publications

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives

A Template Approach for the Characterization of Linear Polyamines and Derivatives in Spider Venom

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Detection and Characterization of Natural Polyamines by High-Performance Liquid Chromatography-Atmospheric Pressure Chemical Ionization (Electrospray Ionization) Mass Spectrometry

Cited by 22 publications

References 32 publications

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

AMPA receptor ligands: Synthetic and pharmacological studies of polyamines and polyamine toxins

Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their 15N-labeled derivatives

A Template Approach for the Characterization of Linear Polyamines and Derivatives in Spider Venom

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Tandem mass spectrometric investigation of acylpolyamines of spider venoms and their ¹⁵N-labeled derivatives