Post-column metal complexation of quinolone antibiotics in a quadrupole ion trap

Shen, Jim X.; Brodbelt, Jennifer S.

doi:10.1002/(sici)1097-0231(19990730)13:14<1381::aid-rcm646>3.0.co;2-a

Cited by 19 publications

(27 citation statements)

References 32 publications

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“…Due to our previous studies in this area [53][54][55][56][57][58], 2,2Ј-bipyridine was selected as the first auxiliary ligand and CoBr 2 was used as the metal salt. For the flavonoids, acidic sites that may be deprotonated in solution and are adjacent to a second binding site (i.e., another oxygen atom) are the likely chelation sites for the metal ions.…”

Section: Metal Complexationmentioning

confidence: 99%

“…Although deprotonation results in more intense mass spectra in the negative ESI mode, the fragmentation patterns again frequently do not differentiate similar compounds or isomers. Metal complexation is an alternative ionization mode which has been explored in the Brodbelt group in the past [53][54][55][56][57][58]. It has been observed that metal complexation can both increase ion intensity and alter fragmentation pathways, resulting in many more structurally distinctive fragment ions.…”

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confidence: 99%

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Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry

Pikulski

Brodbelt

2003

J. Am. Soc. Mass Spectrom.

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The elucidation of flavonoid isomers is accomplished by electrospray ionization tandem mass spectrometry (ESI-MS/MS) via formation and collisional activated dissociation (CAD) of metal/flavonoid complexes containing an auxiliary ligand. Addition of a metal salt and a suitable neutral auxiliary ligand to flavonoids in solution results in the formation of [M(II) (flavonoid-H) ligand]+ complexes by ESI which, upon collisional activated dissociation, often result in more distinctive fragmentation patterns than observed for conventional protonated or deprotonated flavonoids. Previously, 2,2'-bipyridine was used as an auxiliary ligand, and now we compare and explore the use of alternative pyridyl ligands, including 4,7-diphenyl-1,10-phenanthroline. Using this technique, three groups of flavonoid glycoside isomers are differentiated, including glycosides of apigenin, quercetin, and luteolin.

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Section: Metal Complexationmentioning

confidence: 99%

mentioning

confidence: 99%

Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry

Pikulski

Brodbelt

2003

J. Am. Soc. Mass Spectrom.

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“…A number of groups have studied metal complexes by mass spectrometry and found that the fragmentation pathways of analytes can be significantly altered, allowing new opportunities for structural determination [55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71]. The Brodbelt group has shown that metal complexation combined with the use of a neutral auxiliary ligand dramatically increases sensitivity for detection of flavonoids while also providing a richer array of fragments to aid in isomer differentiation [50 -52, 72].…”

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confidence: 99%

Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry

Davis

Brodbelt

2004

J. Am. Soc. Mass Spectrom.

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Metal complexation and tandem mass spectrometry were used to differentiate C-and O-bonded flavonoid monoglucoside isomers. Electrospray ionization of solutions containing a flavonoid glycoside and a metal salt led to the generation of the key [M(II) (L) (L-H)] ϩ complexes, where M is the metal ion and L is the flavonoid glycoside. Thirteen flavonoid monoglucosides were examined in combination with Ca(II), Mg(II), Co(II), Ni(II), and Cu(II). Collisional activated dissociation (CAD) of the [M(II) (L) (L-H)] ϩ complexes resulted in diagnostic mass spectra, in contrast to the CAD mass spectra of the protonated, deprotonated, and sodium-cationized flavonoid glucosides. Five common sites of glycosylation could be predicted based on the fragmentation patterns of the flavonoid glucoside/magnesium complexes, while flavonoid glucoside/calcium complexes also were effective for location of the glycosylation site when MS 3 was employed. Cobalt, nickel and copper complexation had only limited success in this application. The metal complexation methods were also applied for characterization of a flavonoid rhamnoside, and the dissociation pathways of the metal complexes indicate that flavonoid rhamnosides have distinctive dissociation features from flavonoid glucosides. (J Am Soc Mass Spectrom 2004, 15, 1287-1299

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“…[21][22][23][24][25] In a recent paper, we focused on structural characterization of everninomicins by positive ion ESI-MS n analysis that demonstrated the usefulness of this technique. 26 The data suggested in general that a charge-remote fragmentation 27-30 mechanism predominated for sodiated molecules.…”

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Negative ion multiple-stage mass spectrometric analysis of complex oligosaccharides (everninomicins) in a quadruple ion trap: implications for charge-remote fragmentation

Ganguly¹,

Chen²,

Pramanik³

et al. 2003

Arkivoc

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Negative ion electrospray ionization (ESI) tandem mass spectrometry (MS/MS) by a quadrupole ion-trap has been utilized to characterize a class of complex oligosaccharide antibiotics (everninomicins), that includes everninomicin-D, SCH 27899, amino everninomicin (SCH 27900), and SCH 49088 containing a hydroxylamino-ether sugar. The deprotonated molecules are dominant ions in the negative ion ESI mass spectra of these compounds. The multiple-stage mass spectrometric analysis (MS n ) of these deprotonated species indicates that the negative charge resides in the deprotonated dichlorophenoxyl group in the substituted aromatic ester ring (ring 1) and the fragmentation occurs remote to this charge site in generating simple sugar sequence-specific fragment ions. One exception to this process is SCH 49088 in which the side chain of the hydroxylamino-ether sugar dominates fragmentation pathway in a charge-driven mechanism and results in less structural information.

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Post-column metal complexation of quinolone antibiotics in a quadrupole ion trap

Cited by 19 publications

References 32 publications

Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry

Differentiation of flavonoid glycoside isomers by using metal complexation and electrospray ionization mass spectrometry

Determination of the glycosylation site of flavonoid monoglucosides by metal complexation and tandem mass spectrometry

Negative ion multiple-stage mass spectrometric analysis of complex oligosaccharides (everninomicins) in a quadruple ion trap: implications for charge-remote fragmentation

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