New way to green biological assays fluorescent steroids replace radioisotopes

Novel BODIPY–estrone and BODIPY–estradiol conjugates have been synthesized via Cu(I)- catalyzed azide-alkyne click (CuAAC) and/or Sonogashira reactions by selecting position C3-O for labeling. The steroidal azides and/or bromides were reacted with BODIPY-based fluorescent dye bearing alkyne function. The new fluorescent estrone conjugates might replace radiolabeled compounds in certain biochemical assays

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

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