The Red Shift in Estrogen Research An Estrogen-Receptor Targeted aza-BODIPY–Estradiol Fluorescent Conjugate /
Estradiol (E2) plays an important role in cell proliferation and certain brain functions. To reveal its mechanism of action, its detectability is essential. Only a few fluorescent-labeled hormonally active E2s exist in the literature, and their mechanism of action usually remains unclear. It would b...
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2025
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| Sorozat: | INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
26 No. 15 |
| Tárgyszavak: | |
| doi: | 10.3390/ijms26157075 |
| mtmt: | 36263554 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/37607 |
| LEADER | 03054nab a2200373 i 4500 | ||
|---|---|---|---|
| 001 | publ37607 | ||
| 005 | 20250903081132.0 | ||
| 008 | 250903s2025 hu o 000 eng d | ||
| 022 | |a 1661-6596 | ||
| 024 | 7 | |a 10.3390/ijms26157075 |2 doi | |
| 024 | 7 | |a 36263554 |2 mtmt | |
| 040 | |a SZTE Publicatio Repozitórium |b hun | ||
| 041 | |a eng | ||
| 100 | 1 | |a Hlogyik Tamás | |
| 245 | 1 | 4 | |a The Red Shift in Estrogen Research |h [elektronikus dokumentum] : |b An Estrogen-Receptor Targeted aza-BODIPY–Estradiol Fluorescent Conjugate / |c Hlogyik Tamás |
| 260 | |c 2025 | ||
| 300 | |a 18 | ||
| 490 | 0 | |a INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES |v 26 No. 15 | |
| 520 | 3 | |a Estradiol (E2) plays an important role in cell proliferation and certain brain functions. To reveal its mechanism of action, its detectability is essential. Only a few fluorescent-labeled hormonally active E2s exist in the literature, and their mechanism of action usually remains unclear. It would be of particular interest to develop novel labeled estradiol derivatives with retained biological activity and improved optical properties. Due to their superior optical characteristics, aza-BODIPY dyes are frequently used labeling agents in biomedical applications. E2 was labeled with the aza-BODIPY dye at its phenolic hydroxy function via an alkyl linker and a triazole coupling moiety. The estrogenic activity of the newly synthesized fluorescent conjugate was evaluated via transcriptional luciferase assay. Docking calculations were performed for the classical and alternative binding sites (CBS and ABS) of human estrogen receptor α. The terminal alkyne function was introduced into the tetraphenyl aza-BODIPY core via selective formylation, oxidation, and subsequent amidation with propargyl amine. The conjugation was achieved via Cu(I)-catalyzed azide–alkyne click reaction of the aza-BODIPY-alkyne with the 3-O-(4-azidobut-1-yl) derivative of E2. The labeled estrogen induced a dose-dependent transcriptional activity of human estrogen receptor α with a submicromolar EC50 value. Docking calculations revealed that the steroid part has a perfect overlap with E2 in ABS. In CBS, however, a head-tail binding deviation was observed. A facile, fluorescent labeling methodology has been elaborated for the development of a novel red-emitting E2 conjugate with substantial estrogenic activity. Docking experiments uncovered the binding mode of the conjugate in both ABS and CBS. | |
| 650 | 4 | |a Általános orvostudomány | |
| 700 | 0 | 2 | |a Bózsity-Faragó Noémi |e aut |
| 700 | 0 | 2 | |a Börzsei Rita |e aut |
| 700 | 0 | 2 | |a Kovács Benjamin |e aut |
| 700 | 0 | 2 | |a Labos Péter |e aut |
| 700 | 0 | 2 | |a Hetényi Csaba |e aut |
| 700 | 0 | 2 | |a Csontné Kiricsi Mónika |e aut |
| 700 | 0 | 2 | |a Huliák Ildikó |e aut |
| 700 | 0 | 2 | |a Kele Zoltán |e aut |
| 700 | 0 | 2 | |a Poór Miklós |e aut |
| 700 | 0 | 2 | |a Erostyák János |e aut |
| 700 | 0 | 2 | |a Hunyadi Attila |e aut |
| 700 | 0 | 2 | |a Zupkó István |e aut |
| 700 | 0 | 2 | |a Mernyák Erzsébet |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/37607/1/ijms-26-07075.pdf |z Dokumentum-elérés |