Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

Peptu, Cristian; Balan-Porcăraşu, Mihaela; Šišková, Alena Opálková; Škultéty, Ľudovít; Mosnáček, Jaroslav

doi:10.3762/bjoc.13.77

Cited by 12 publications

(14 citation statements)

References 26 publications

(51 reference statements)

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“…The 1 H NMR analysis may give information about the structure of the compounds (chemical nature), about the site of the esterification (at the OH groups from the second, third, or sixth position of the glycoside ring), about the length of the oligolactide chains, and possibly about the total number of LA monomer units attached to the CD [ 15 , 18 ].…”

Section: Resultsmentioning

confidence: 99%

“…CD modified with oligolactide chains (CD-LA) can be synthesized by bulk [ 17 , 18 ] or solution polymerization [ 19 ]. CD-LA was demonstrated to be highly degradable in a water environment and may be further used for the preparation of drug inclusion complexes.…”

Section: Introductionmentioning

confidence: 99%

“…The CD-oligoester derivatives have been characterized by MALDI MS [ 12 , 13 , 16 , 18 ] or ESI MS [ 15 , 19 , 24 , 25 ] for the structural assignment of the products. However, complex structure identification requires more than a single-stage MS measurement.…”

Section: Introductionmentioning

confidence: 99%

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Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

et al. 2018

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Cyclodextrins (CDs) were used in the present study for the ring-opening oligomerization (ROO) of l-lactide (LA) in order to synthesize biodegradable products with possible applications in pharmaceutical and medical fields. The practical importance of ROO reactions may reside in the possibility of synthesizing novel CD derivatives with high purity due to the dual role played by CDs, the role of the initiator through the hydroxylic groups, and the role of the catalyst by monomer inclusion in the CD cavity. The analyzed compounds were CDs modified with oligolactides obtained through ROO reactions of l-lactide in dimethylformamide. The resulting CD isomeric mixtures were investigated using classical characterization techniques such as gel permeation chromatography and nuclear magnetic resonance. Moreover, advanced mass spectrometry (MS) techniques were employed for the determination of the average number of monomer units attached to the cyclodextrin and the architecture of the derivatives (if the monomer units were attached as a single chain or as multiple chains). Thus, fragmentation studies effectuated on two different instruments (ESI Q-TOF and MALDI TOF) allowed us to correlate the size of the oligolactide chains attached to the CD with the observed fragmentation patterns.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

et al. 2018

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“…This is why the implementation of an accurate characterization is fundamental and a real challenge in our work. It is well-known that complex CDs derivatives mixtures lead to broad and unresolved 1 H-NMR signals [16] preventing the attribution of their inextricable spectra. In this context, NMR is of only limited help and mass spectrometry is considered as the most appropriate technique.…”

Section: Introductionmentioning

confidence: 99%

“…In this context, NMR is of only limited help and mass spectrometry is considered as the most appropriate technique. Indeed, electrospray ionization (ESI) either in direct introduction [17] or coupled with liquid chromatography (LC/ESI-MS) [18] and matrix assisted laser desorption ionization (MALDI) [16] are frequently used in that context. To go deeper in the structural analysis of cyclic oligosaccharides tandem mass spectrometry (MS/MS) [19] and more recently ion mobility spectrometry (IMS) [20] are described.…”

Section: Introductionmentioning

confidence: 99%

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

et al. 2020

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Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2017–2018

Harvey

2021

Mass Spectrometry Reviews

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This review is the tenth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization mass spectrometry (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2018. Also included are papers that describe methods appropriate to glycan and glycoprotein analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. Topics covered in the first part of the review include general aspects such as theory of the MALDI process, new methods, matrices, derivatization, MALDI imaging, fragmentation and the use of arrays. The second part of the review is devoted to applications to various structural types such as oligo‐ and poly‐saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Most of the applications are presented in tabular form. The third part of the review covers medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. The reported work shows increasing use of combined new techniques such as ion mobility and highlights the impact that MALDI imaging is having across a range of diciplines. MALDI is still an ideal technique for carbohydrate analysis and advancements in the technique and the range of applications continue steady progress.

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Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

Cited by 12 publications

References 26 publications

Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2017–2018

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