DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF
BIOMOLECULES

k 2023

DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES

VESELÝ, Hubert a Pavel BOBÁĽ

Základní údaje

Originální název

DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES

Autoři

VESELÝ, Hubert (203 Česká republika, domácí) a Pavel BOBÁĽ (703 Slovensko, domácí)

Vydání

Student Scientific Conference MUNI Pharm, 2023

Další údaje

Jazyk

angličtina

Typ výsledku

Prezentace na konferencích

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Česká republika

Utajení

není předmětem státního či obchodního tajemství

Kód RIV

RIV/00216224:14160/23:00130945

Organizační jednotka

Farmaceutická fakulta

ISBN

978-80-280-0324-1

Klíčová slova anglicky

fluorophore; pyrrole; glycan

Štítky

rivok, ÚChL

Změněno: 12. 6. 2023 13:08, Mgr. Hubert Veselý

Anotace

V originále

Changes in the composition of glycans correlate with the progression of many diseases, therefore they are investigated as disease markers. On the other hand, their analysis is difficult because they do not contain a chromophore or charges that would enable their electrophoretic separation. Our goal was to develop a new fluorescent marker covalently bound to glycans providing fast labeling kinetics, high quantum yield, increased detection sensitivity using MS, and at the same time carrying a charge in the structure, which will enable the studied glycans to be separated electrophoretically. The basic skeleton of this fluorophore is based on pyrrole and indolizine. The synthesis was based on two building blocks, synthon A and synthon B, which were subsequently connected. The plan was to prepare variants of the fluorophore carrying electron-donating or electron-accepting groups on synthon A. These substitutions allow for variability in the wavelength of the absorption maximum and thus the wavelength of fluorescence. The molecule also carries a trimethylammonium functional group and a propanoate chain, which is necessary for the attachment of the fluorophore to the glycan. Synthon B and synthon A were prepared without substitution at the 4-phenyl position and with methyl and methoxycarbonyl groups at this position. The methyl derivative was used for the synthesis of the fluorophore backbone. This structure showed fluorescence in the UV region of the spectrum. The substance was subsequently oxidized to an aldehyde, which will have to be further converted to a quaternary ammonium compound. Also, the side chain carrying the methyl ester function will need to be converted to a hydrazide. The prepared substances will also be characterized in cooperation with the Institute of Analytical Chemistry of the Academy of Sciences of the Czech Republic. The usability of the newly developed fluorophores will be demonstrated by profiling glycoproteins associated with breast cancer.

Návaznosti

MUNI/A/1232/2021, interní kód MU

Název: Design a syntéza nových fluoroforů pro detekci biomolekul

Investor: Masarykova univerzita, Design a syntéza nových fluoroforů pro detekci biomolekul

Citovat

VESELÝ, Hubert a Pavel BOBÁĽ. DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES. In Student Scientific Conference MUNI Pharm. 2023. ISBN 978-80-280-0324-1.

@proceedings{2290978,
   author = {Veselý, Hubert and Bobáľ, Pavel},
   booktitle = {Student Scientific Conference MUNI Pharm},
   keywords = {fluorophore; pyrrole; glycan},
   language = {eng},
   isbn = {978-80-280-0324-1},
   title = {DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES},
   year = {2023}
}

TY  - CONF
ID  - 2290978
AU  - Veselý, Hubert - Bobáľ, Pavel
PY  - 2023
TI  - DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES
SN  - 9788028003241
KW  - fluorophore
KW  - pyrrole
KW  - glycan
N2  - Changes in the composition of glycans correlate with the progression of many diseases, therefore they are investigated as disease markers. On the other hand, their analysis is difficult because they do not contain a chromophore or charges that would enable their electrophoretic separation. Our goal was to develop a new fluorescent marker covalently bound to glycans providing fast labeling kinetics, high quantum yield, increased detection sensitivity using MS, and at the same time carrying a charge in the structure, which will enable the studied glycans to be separated electrophoretically. The basic skeleton of this fluorophore is based on pyrrole and indolizine. The synthesis was based on two building blocks, synthon A and synthon B, which were subsequently connected. The plan was to prepare variants of the fluorophore carrying electron-donating or electron-accepting groups on synthon A. These substitutions allow for variability in the wavelength of the absorption maximum and thus the wavelength of fluorescence. The molecule also carries a trimethylammonium functional group and a propanoate chain, which is necessary for the attachment of the fluorophore to the glycan. Synthon B and synthon A were prepared without substitution at the 4-phenyl position and with methyl and methoxycarbonyl groups at this position. The methyl derivative was used for the synthesis of the fluorophore backbone. This structure showed fluorescence in the UV region of the spectrum. The substance was subsequently oxidized to an aldehyde, which will have to be further converted to a quaternary ammonium compound. Also, the side chain carrying the methyl ester function will need to be converted to a hydrazide. The prepared substances will also be characterized in cooperation with the Institute of Analytical Chemistry of the Academy of Sciences of the Czech Republic. The usability of the newly developed fluorophores will be demonstrated by profiling glycoproteins associated with breast cancer.
ER  -

VESELÝ, Hubert a Pavel BOBÁĽ. DESIGN AND SYNTHESIS OF NEW FLUOROPHORES FOR THE DETECTION OF BIOMOLECULES. In \textit{Student Scientific Conference MUNI Pharm}. 2023. ISBN~978-80-280-0324-1.

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