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Article

Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates

1
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
2
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
3
Membrane protein research group, Institute of Enzymology, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok körútja 2, H-1117 Budapest, Hungary
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(4), 821; https://doi.org/10.3390/molecules23040821
Submission received: 6 March 2018 / Revised: 29 March 2018 / Accepted: 2 April 2018 / Published: 3 April 2018
(This article belongs to the Section Organic Chemistry)

Abstract

Novel BODIPY–estrone conjugates were synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC). Estrone-alkynes or an estrone-azide as starting compounds were synthesized via Michael addition or Sonogashira reaction as key steps. Fluorescent dyes based on BODIPY-core were provided by azide or alkyne functional groups. Fluorescent labeling of estrone was efficiently achieved at the C-2 or C-15 position. The newly-elaborated coupling procedures might have a broad applicability in the synthesis of fluorescent-labeled estrone conjugates suitable for biological assays.
Keywords: BODIPY; estrone; CuAAC; fluorescent labeling; estrone conjugates BODIPY; estrone; CuAAC; fluorescent labeling; estrone conjugates
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MDPI and ACS Style

Bacsa, I.; Konc, C.; Orosz, A.B.; Kecskeméti, G.; Rigó, R.; Özvegy-Laczka, C.; Mernyák, E. Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates. Molecules 2018, 23, 821. https://doi.org/10.3390/molecules23040821

AMA Style

Bacsa I, Konc C, Orosz AB, Kecskeméti G, Rigó R, Özvegy-Laczka C, Mernyák E. Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates. Molecules. 2018; 23(4):821. https://doi.org/10.3390/molecules23040821

Chicago/Turabian Style

Bacsa, Ildikó, Csilla Konc, Anna Boglárka Orosz, Gábor Kecskeméti, Réka Rigó, Csilla Özvegy-Laczka, and Erzsébet Mernyák. 2018. "Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates" Molecules 23, no. 4: 821. https://doi.org/10.3390/molecules23040821

APA Style

Bacsa, I., Konc, C., Orosz, A. B., Kecskeméti, G., Rigó, R., Özvegy-Laczka, C., & Mernyák, E. (2018). Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates. Molecules, 23(4), 821. https://doi.org/10.3390/molecules23040821

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