Synthesis and biological evaluation of nandrolone–bodipy conjugates

• Four fluorescent nandrolone–bodipy conjugates were synthesized.
• The subcellular localization and cytotoxicity of the nandrolone conjugates were studied.
• The conjugates colocalized with endoplasmic reticulum and/or mitochondria.
• The binding was displaceable by an excess of unlabelled androgenic steroids.

Here, we report synthesis and biological evaluation of fluorescent nandrolone-3-carboxymethyloxime derivatives conjugated with green-emitting bodipy dye via PEG linkers. All the newly-synthesized compounds were evaluated for their effect on cell proliferation in vitro in MCF-7, LNCaP, PC-3 and HEK 293T model cell lines using WST-1 assay. By means of live-cell fluorescence microscopy, the intracellular localization of nandrolone–bodipy conjugates was revealed in endoplasmic reticulum. Moreover, we performed competitive localization study with nonfluorescent nandrolone, metandrolone, boldenone, trenbolone, and testosterone.

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