N-(5-Amino-9H-benzo[a]phenoxazin-9-ylidene)propan-1-aminium chlorides as antifungal agents and NIR fluorescent probes

Abstract

The search for benzo[a]phenoxazines, Nile Blue derivatives, with high antifungal activity and cell labelling capacity based on our previously published works in this type of compounds, led us to the...

Novel Nile Blue Analogue Stains Yeast Vacuolar Membrane, Endoplasmic Reticulum, and Lipid Droplets, Inducing Cell Death through Vacuole Membrane Permeabilization

“…In previous work in our laboratory, we found that several newly synthetized fluorescent compounds derived from benzo[a]phenoxazine displayed antiproliferative activity against S. cerevisiae, used as a model eukaryotic organism, and that minor changes in substituents of the benzo[a]phenoxazine nucleus drastically influenced their activity, with MIC values ranging from 3.75 μM to over 400 μM, as well as their intracellular staining patterns [7,13,14,26,27,56]. Here, we found that one of these compounds, BaP1, induced a regulated cell death process and uncovered its mode of action to unveil its potential for pharmacological applications.…”

Design, Synthesis, and Evaluation of Near-Infrared Fluorescent Molecules Based on 4H-1-Benzopyran Core

“…M-3 exhibited long wavelength, strong red-emission, and highly efficient optical performance, due to the p•••π and CH•••N hyperconjugation effect [36]. Besides, M-3 exhibited typical properties of molecular rotors with high viscosity sensitivity in a glycerol-ethanol system and showed high environmental sensitivity [37,38] in different polar To further confirm the subcellular distribution of M-3, after uptake into tumor cells, DAPI was used, which is known to stain intact nuclei selectively and strongly. The subcellular distribution behavior of M-3 in three cells was measured by CLSM.…”

“…M-3 exhibited long wavelength, strong red-emission, and highly efficient optical performance, due to the p•••π and CH•••N hyperconjugation effect [36]. Besides, M-3 exhibited typical properties of molecular rotors with high viscosity sensitivity in a glycerol-ethanol system and showed high environmental sensitivity [37,38] in different polar solvents with a certain degree of polarity dependence. M-3 also possessed high environmental sensitivity in that the addition of gradient concentrations of BSA in PBS and elicited a significant 4-fold increase in fluorescence intensity.…”

Novel Benzo[A]Phenoxazinium Chlorides Functionalized with Sulfonamide Groups as Nir Fluorescent Probes for Vacuole, Endoplasmic Reticulum and Plasma Membrane Staining

“…Benzo [a]phenoxazinium chlorides are long-wavelength, NIR fluorescent probes that possess exceptional optical properties. They strongly absorb and emit fluorescence up to about 720 nm, with modest Stokes shifts (20-60 nm) and have high photostability, quantum yields, and molar absorption [17][18][19][20][21][22][23][24][25][26][27][28][29][30].…”

“…In addition to their outstanding optical properties, benzo[a]phenoxazine compounds have also been reported for their pharmaceutical properties. These compounds were reported for their validity as antitumor agents [33,34], antifungals [23,[35][36][37], antibacterials [38,39], antimalarials [40,41], antivirals [42], and as photo-sensitizers in photodynamic therapy [43,44]. Their compact structure, and the presence of amines in 5-and 9-positions allows benzo[a]phenoxazinium chlorides to possess different functional groups, resulting in compounds with variable behaviors.…”