2007
DOI: 10.1016/j.jasms.2006.09.026
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Establishment of mass spectrometric fingerprints of novel synthetic cholesteryl neoglycolipids: The presence of a unique C-glycoside species during electrospray ionization and during collision-induced dissociation tandem mass spectrometry

Abstract: In this study we evaluated the fragmentation pattern of 16 novel amphiphilic neoglycolipid cholesteryl derivatives that can be efficiently used to increase cationic liposomal stability and to enhance gene transfer ability. These neoglycolipids bear different sugar moieties, such as D-glucosamine, In addition, we observed a unique ion that could not be rationally explained by the expected fragmentation of these amphiphilic molecules. The structure of this ion was tentatively proposed with that of a C-glycoside … Show more

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Cited by 10 publications
(12 citation statements)
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(42 reference statements)
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“…Mass spectrometry combined with chromatographic techniques has become very popular owing to its sensitivity and selectivity [9]. The analysis of steroids has been carried out by gas chromatography-mass spectrometry (GC-MS) [10][11][12][13][14][15][16], liquid chromatography-mass spectrometry (LC-MS) [17][18][19], electrospray mass spectrometry (ESI-MS) [20][21][22][23][24], atmospheric pressure chemical ionization mass spectrometry (APCI-MS) [25], matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS) [26][27][28], and immunoassay [29]. Although GC-MS approaches are highly sensitive, they have some limitations due to the need for multistep derivatization procedures for these thermally-labile compounds, especially those that contain large numbers of hydroxyl groups [9,30,31].…”
mentioning
confidence: 99%
“…Mass spectrometry combined with chromatographic techniques has become very popular owing to its sensitivity and selectivity [9]. The analysis of steroids has been carried out by gas chromatography-mass spectrometry (GC-MS) [10][11][12][13][14][15][16], liquid chromatography-mass spectrometry (LC-MS) [17][18][19], electrospray mass spectrometry (ESI-MS) [20][21][22][23][24], atmospheric pressure chemical ionization mass spectrometry (APCI-MS) [25], matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS) [26][27][28], and immunoassay [29]. Although GC-MS approaches are highly sensitive, they have some limitations due to the need for multistep derivatization procedures for these thermally-labile compounds, especially those that contain large numbers of hydroxyl groups [9,30,31].…”
mentioning
confidence: 99%
“…[33] For example, using electrospray ionization (ESI), the MS=MS analysis of 18 novel cholesteryl neoglycolipids, used in liposomes-based gene delivery, resulted in the formation of specific common fingerprint fragments regardless of the nature of the sugar moiety or the spacer group that linked the carbohydrate portion to the lipid cholesteryl moiety. [34] In addition, the unknown molecular structure of lipid A, isolated from the A. salmonicida lipopolysaccharide, was established by single-stage MS and MS=MS analysis using ESI ionization and quadrupole time-of-flight (Qq-ToF) MS=MS techniques. [35,36] Similarly, the fragmentation routes of morphine antagonists were precisely determined using ESI-Qq-ToF MS=MS.…”
Section: Figurementioning
confidence: 99%
“…We have reported the electrospray ionization mass spectrometry (ESI‐MS) and low‐energy collision‐induced dissociation tandem mass spectrometry (CID‐MS/MS) of a series of synthetic neoglycolipids measured with a hybrid quadrupole‐quadrupole‐time‐of‐flight (QqTOF)‐MS instrument . The amphiphilic neoglycolipids were composed of a polar end consisting of a 2‐amino‐2‐deoxy‐ and 2‐acetamido‐2‐deoxy‐D‐glucoside linked to a polyethylene spacer which was covalently linked to a lipophilic cholesteryl moiety . We have also recently produced evidence for the in situ formation of a [C‐glycoside+H] + species, both at the electrospray interface and in the collision cell, during CID‐MS/MS measurements .…”
mentioning
confidence: 99%
“…The understanding of this unique ' in situ ' gas‐phase C ‐glycosylation should provide novel insights into new synthetic routes for these compounds . To our knowledge, the gas‐phase formation of this [C‐glycoside+H] + ion has never been reported . It is important to mention that in recent decades the therapeutic values of the C ‐glycoside analogues have been established as anticancer vaccines, treatments for melanoma metastases, and protection against malaria …”
mentioning
confidence: 99%
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