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001-es BibID:	BIBFORM122671
035-os BibID:	(Scopus)85194971433 (WoS)001249651100001
Első szerző:	Peřina, Miroslav
Cím:	Synthesis and estrogenic activity of BODIPY-labeled estradiol conjugates / Miroslav Peřina, Rita Börzsei, Henrietta Ágoston, Tamás Hlogyik, Miklós Poór,Réka Rigó, Csilla Özvegy-Laczka, Gyula Batta,Csaba Hetényi, Veronika Vojáčková, Radek Jorda,Erzsébet Mernyák
Dátum:	2024
ISSN:	0928-0987
Megjegyzések:	Novel BODIPY-estradiol conjugates have been synthesized by selecting position C-3-O for labeling. The conjugation strategy was based on Cu(I)-catalyzed azide?alkyne cycloaddition (CuAAC) or etherification. Estradiol derivatives used as azide partners bearing an ?-azidoalkyl function through C4?C8-long linkers have been prepared. CuAAC reactions of estradiol azides with BODIPY alkyne furnished fluorescent 3-O-labeled conjugates bearing the triazole ring as a coupling moiety. Williamson etherifications of 3-O-(?-bromoalkyl)-17?-estradiol derivatives with BODIPY-OH resulted in labeled conjugates connected with an ether moiety. Interactions of the conjugates with estrogen receptor (ER) were investigated using molecular docking calculations in comparison with estradiol. The conjugates occupied both the classical and alternative binding sites on human ER?, with slightly lower binding affinity to references estradiol and diethystilbestrol. All compounds have displayed reasonable estrogenic activity. They increased the proliferation of ER-positive breast cancer cell line MCF7 contrary to ER-negative SKBR-3 cell line. The most potent compound 13a induced the transcriptional activity of ER in dose-dependent manner in dual luciferase recombinant reporter model and increased progesterone receptor's expression, proving the retained estrogenic activity. The fluorescence of candidate compound 13a co-localised with the ER?. The newly synthesized labeled compounds might serve as good starting point for further development of fluorescent probes for modern biological applications. In addition to studying steroid uptake and transport in cells, e.g. in the processes of biodegradation of estrogen-hormones micropollutants, they could also be utilized in examination of estrogen-binding proteins.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban folyóiratcikk 17béta-estradiol BODIPY CuAAC Estrogenic activity Human estrogen receptor alpha
Megjelenés:	European Journal Of Pharmaceutical Sciences. - 199 (2024), p. 1-12. -
További szerzők:	Börzsei Rita Ágoston Henrietta Hlogyik Tamás Poór Miklós Rigó Réka Özvegy-Laczka Csilla Batta Gyula (1953-) (molekula-szerkezet kutató) Hetényi Csaba Vojáčková, Veronika Jorda, Radek Mernyák Erzsébet
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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