Novel BODIPY Conjugates with Myrtenol: Design, Spectral Characteristics, and Possibilities for Practical Application

The synthesis of new fluorescent probes, based on biocompatible luminophors and exhibiting various specificities, is intensively developed worldwide. Many contain a hydrophobic group that limits their application for cell staining under vital conditions. Herein, we report the two BODIPY molecules—BF2-meso-(4-butan/pentanamido-N-(((1S,5R)-6,6-dimethylbicyclo [3.1.1]hept-2-en-2-yl)methyl)-N,N-dimethylpropan-1-aminium)-3,3′,5,5′-tetramethyl-2,2′-dipyrromethene bromides—designed as 10, 11 with spacer either four or three CH2 groups in length, respectively. These molecules present conjugates (+)-myrtenol via quaternary ammonium group. Both terpene-BODIPY demonstrated high fluorescence efficiency solvents such OctOH, DMSO water, were characterized by stability at pH 1.65–9.18. fusion myrtenol, monocyclic terpene, to fluorophore meso-substituent facilitated penetration into filamentous fungi Fusarium solani, while impairing binding latter S. aureus, K. pneumoniae P. aeruginosa. additional between myrtenol moieties restored bacterial cell-staining it did not affect fungi. Finally, conjugate was able stain both Gram-positive Gram-negative bacteria its interaction wall (or membrane), well penetrating F. solani mitochondria.