Synthesis and Application of Novel Fluorescent Labeling Tags
for Oligosaccharide and N-Linked Glycan Analysis

k 2023

Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis

VESELÝ, Hubert; Michal GREGUŠ; Hana PÍŽOVÁ; Denisa SMOLKOVA; Richard CMELIK et al.

Základní údaje

Originální název

Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis

Autoři

VESELÝ, Hubert; Michal GREGUŠ; Hana PÍŽOVÁ; Denisa SMOLKOVA; Richard CMELIK; Jana LAVICKA a Pavel BOBÁĽ

Vydání

57th Conference: Advances in Organic, Bioorganic and Pharmaceutical Chemistry – Liblice 2023, 2023

Další údaje

Jazyk

angličtina

Typ výsledku

Prezentace na konferencích

Obor

10401 Organic chemistry

Stát vydavatele

Česká republika

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14160/23:00139107

Organizační jednotka

Farmaceutická fakulta

Klíčová slova anglicky

BODIPY; fluorescent labeling tags; HPLC/FLD

Štítky

rivok, ÚChL

Změněno: 21. 3. 2025 10:53, Ing. Richard Heger, Ph.D.

Anotace

V originále

Monitoring glycosylation and investigating the influence of glycan structures on their function is an essential area of research, particularly in the diagnosis of disease and the study of mechanisms of pathogenesis.1 Analysis of glycans is still arduous because of their extreme structure complexity and conjugation diversity. But there are also instrumental aspects, such as the sensitivity limits of analyses.2 Therefore, glycan analysis is very often combined with fluorescence detection in addition to MS. In this work, we present the synthesis of novel fluorescent labeling tags for oligosaccharide and N-linked glycan analysis based on the hydrazide derivative of dipyrrometheneboron difluoride (BODIPY) and derivatives of 1,3-diaza-tricyclo[7.3.0.0³,⁷]dodeca-5,7,9,11-tetraene-2,4-dione. Furthermore, we present the application of a newly synthesized hydrazide derivative of BODIPY for oligosaccharide and glycan analysis by high-performance liquid chromatography with fluorescence detection (HPLC/FLD). The labeling method was optimized on maltooligosaccharide standards. The analysis provided the detection limit in the low tens of femtomole, which is at least 30 times more sensitive than the standard approach. In addition, this labeling method was used for N-linked glycan profiling of several glycoproteins by RP-HPLC and HILIC/FLD analysis.

Návaznosti

GA22-00236S, projekt VaV

Název: Vývoj nových fluorescenčních značek pro elektroforetické analýzy glykoproteinů asociovaných s rakovinou prsu (Akronym: 22-00236S)

Investor: Grantová agentura ČR, Vývoj nových fluorescenčních značek pro elektroforetické analýzy glykoproteinů asociovaných s rakovinou prsu

Citovat

VESELÝ, Hubert; Michal GREGUŠ; Hana PÍŽOVÁ; Denisa SMOLKOVA; Richard CMELIK; Jana LAVICKA a Pavel BOBÁĽ. Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis. In 57th Conference: Advances in Organic, Bioorganic and Pharmaceutical Chemistry – Liblice 2023. 2023.

@proceedings{2484971,
   author = {Veselý, Hubert and Greguš, Michal and Pížová, Hana and Smolkova, Denisa and Cmelik, Richard and Lavicka, Jana and Bobáľ, Pavel},
   booktitle = {57th Conference: Advances in Organic, Bioorganic and Pharmaceutical Chemistry – Liblice 2023},
   keywords = {BODIPY; fluorescent labeling tags; HPLC/FLD},
   language = {eng},
   title = {Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis},
   url = {http://www.liblice2023.cz/},
   year = {2023}
}

TY  - CONF
ID  - 2484971
AU  - Veselý, Hubert - Greguš, Michal - Pížová, Hana - Smolkova, Denisa - Cmelik, Richard - Lavicka, Jana - Bobáľ, Pavel
PY  - 2023
TI  - Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis
KW  - BODIPY
KW  - fluorescent labeling tags
KW  - HPLC/FLD
UR  - http://www.liblice2023.cz/
N2  - Monitoring glycosylation and investigating the influence of glycan structures on their function is an essential area of research, particularly in the diagnosis of disease and the study of mechanisms of pathogenesis.1 Analysis of glycans is still arduous because of their extreme structure complexity and conjugation diversity. But there are also instrumental aspects, such as the sensitivity limits of analyses.2 Therefore, glycan analysis is very often combined with fluorescence detection in addition to MS. In this work, we present the synthesis of novel fluorescent labeling tags for oligosaccharide and N-linked glycan analysis based on the hydrazide derivative of dipyrrometheneboron difluoride (BODIPY) and derivatives of 1,3-diaza-tricyclo[7.3.0.0³,⁷]dodeca-5,7,9,11-tetraene-2,4-dione. Furthermore, we present the application of a newly synthesized hydrazide derivative of BODIPY for oligosaccharide and glycan analysis by high-performance liquid chromatography with fluorescence detection (HPLC/FLD). The labeling method was optimized on maltooligosaccharide standards. The analysis provided the detection limit in the low tens of femtomole, which is at least 30 times more sensitive than the standard approach. In addition, this labeling method was used for N-linked glycan profiling of several glycoproteins by RP-HPLC and HILIC/FLD analysis.
ER  -

VESELÝ, Hubert; Michal GREGUŠ; Hana PÍŽOVÁ; Denisa SMOLKOVA; Richard CMELIK; Jana LAVICKA a Pavel BOBÁĽ. Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis. In \textit{57th Conference: Advances in Organic, Bioorganic and Pharmaceutical Chemistry – Liblice 2023}. 2023.

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