Structural characterization of biocompatible lipoic acid–oligo‐(3‐hydroxybutyrate) conjugates by electrospray ionization mass spectrometry

Maksymiak, Magdalena; Dębowska, Renata; Jelonek, Katarzyna; Kowalczuk, Marek; Adamus, Grażyna

doi:10.1002/rcm.6509

Cited by 18 publications

(36 citation statements)

References 36 publications

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“…Additionally, very low-intensity signals of crotonate end-group protons (signals 10-12 in Figure 1 and signals 12-14 in Figure 2; δ = 1.87 ppm corresponding to CH 3 -as well as signals at δ = 5.80 ppm and δ = 6.95 ppm corresponding to vinyl protons, -CH=CH-) were detected in the spectra. The content (in mol%) of minor products of oligo-3-hydroxybutyrate terminated by crotonate and carboxyl groups (estimated from the 1 H NMR spectra 15 , Figures 1 and 2) was, in both cases, less than 5 mol%. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 1 2...…”

Section: Resultsmentioning

confidence: 99%

“…Among synthetic approaches for covalently bonded biodegradable polymer bioactive conjugates the four main strategies may be outlined. In the first one (i) bioactive compound may act as initiators of polymerization and as a result the polymer end caped conjugates may be obtained on this way [8][9][10][11][12][13][14][15][16] . The second strategy 4 (ii) is focused on incorporation of bioactive moiety into the polymer backbone 17 .…”

Section: Introductionmentioning

confidence: 99%

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Designing of Biodegradable and Biocompatible Release and Delivery Systems of Selected Antioxidants Used in Cosmetology

et al. 2015

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Conjugates of antioxidants p-anisic (p-AA) and vanillic (VA) acids with nontoxic, biocompatible, and biodegradedable oligo-(R,S)-(3-hydoxybutyrate) carrier were synthesized, and their structural and biological characterization was performed. The molecular structure of the bioconjugates, in which antioxidants are covalently bonded with oligo(3-hydroxybutyrate) (OHB) chains, has been proven by mass spectrometry supported by NMR. The bioconjugate hydrolytic degradation studies allowed gaining thorough insight into the hydrolysis process and confirmed the release of p-AA and VA. In vitro studies demonstrated that all of the conjugates studied were well tolerated by KB and HaCaT cell lines, as they had no marked cytotoxicity, while conjugates with a relatively short OHB carrier are optimal to support keratinocyte function. The preliminary study of the biological activity confirmed the protective effect of VA-OHB conjugates against H2O2-induced lipid peroxidation in human keratinocytes (HaCaT). It was also demonstrated that the selected bioconjugates can penetrate all layers of the skin, which shows their functionality and opens up their potential application in cosmetology.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Designing of Biodegradable and Biocompatible Release and Delivery Systems of Selected Antioxidants Used in Cosmetology

et al. 2015

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“…18 . Novel delivery systems obtained via the elaborated synthetic strategy contain a larger loading of biologically active substances per polymer macromolecule than the respective cosmetic delivery system that we have already reported [16][17][18] . The object of further work will be to carry out preliminary studies proving the usefulness of the developed (co)oligoesters as new controlled release systems for applications in cosmetology.…”

Section: Structural Characterization Of Random (P-aa-ch 2 -Hp) M /Hb mentioning

confidence: 99%

“…These novel bioactive (co)oligoesters have a larger loading of biologically active substances (p-anisic acid, p-AA) per polymer macromolecule in comparison to the already reported conjugates of oligo(3-hydroxybutyrate) (OHB) with several selected antioxidants [16][17][18] .…”

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confidence: 98%

“…In our recent works we reported the application of ESI-MS/MS techniques for characterization at the molecular level of OHB conjugates with bioactive compounds including antioxidants used in cosmetics. The molecular structure of bioconjugates, in which antioxidants (α-lipoic, p-coumaric, p-anisic and vanillic acids) are covalently bonded to OHB chains as the end group, has also been proven by tandem mass spectrometry [16][17][18] . We have also demonstrated the utility of this technique for the analysis of individual molecules of homo-and co-polyesters obtained by anionic ring-opening copolymerization of selected β-substituted β-lactones [11][12] .…”

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confidence: 99%

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Bioactive (co)oligoesters with antioxidant properties – synthesis and structural characterization at the molecular level

et al. 2016

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ABSTRACT:A contemporary synthetic route, starting from the bioactive compound via the corresponding glycidyl ester and β-substituted β-lactone to (homo)-and (co)oligoesters with a bioactive moiety covalently linked as pendent groups along an oligomer backbone, was reported.The bioactive compounds were selected from antioxidants used in cosmetics. Two models of bioactive (homo)-and (co)oligoesters were synthesized via anionic ring-opening (co)oligomerization of p-methoxybenzoyloxymethylpropiolactone (p-AA-CH 2 -PL) initiated by p-anisic acid sodium salt. An analytical protocol was developed for a detailed structural characterization at the molecular level of these bioactive (co)oligoesters. The molecular level structure of the obtained bioactive (homo)-and (co)oligoesters was established by electrospray ionization tandem mass spectrometry (ESI-MS/MS) supported by 1 H NMR analysis.Additionally, the results presented here are important for the analysis of designed biodegradable polymeric controlled-release systems of bioactive compounds with potential applications in cosmetology.1

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Mass spectrometry for the elucidation of the subtle molecular structure of biodegradable polymers and their degradation products

Kowalczuk

Adamus

2015

Mass Spectrometry Reviews

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Contemporary reports by Polish authors on the application of mass spectrometric methods for the elucidation of the subtle molecular structure of biodegradable polymers and their degradation products will be presented. Special emphasis will be given to natural aliphatic (co)polyesters (PHA) and their synthetic analogues, formed through anionic ring-opening polymerization (ROP) of b-substituted b-lactones. Moreover, the application of MS techniques for the evaluation of the structure of biodegradable polymers obtained in ionic and coordination polymerization of cyclic ethers and esters as well as products of step-growth polymerization, in which bifunctional or multifunctional monomers react to form oligomers and eventually long chain polymers, will be discussed. Furthermore, the application of modern MS techniques for the assessment of polymer degradation products, frequently bearing characteristic end groups that can be revealed and differentiated by MS, will be discussed within the context of specific degradation pathways. Finally, recent Polish accomplishments in the area of mass spectrometry will be outlined. # 2015 Wiley Periodicals, Inc. Mass Spec Rev 35: 188-198, 2016.

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Structural characterization of biocompatible lipoic acid–oligo‐(3‐hydroxybutyrate) conjugates by electrospray ionization mass spectrometry

Cited by 18 publications

References 36 publications

Designing of Biodegradable and Biocompatible Release and Delivery Systems of Selected Antioxidants Used in Cosmetology

Designing of Biodegradable and Biocompatible Release and Delivery Systems of Selected Antioxidants Used in Cosmetology

Bioactive (co)oligoesters with antioxidant properties – synthesis and structural characterization at the molecular level

Mass spectrometry for the elucidation of the subtle molecular structure of biodegradable polymers and their degradation products

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