Antifungal Activity of an Original Amino-Isocyanonaphthalene (ICAN) Compound Family: Promising Broad Spectrum Antifungals.

Multiple drug resistant fungi pose a serious threat to human health, therefore the development of completely new antimycotics is of paramount importance. The in vitro antifungal activity of the original, 1-amino-5-isocyanonaphthalenes (ICANs) was evaluated against reference strains of clinically important species. Structure-activity studies revealed that the naphthalene core and the isocyano- together with the amino moieties are all necessary to exert antifungal activity.

Amino-isocyanoacridines: Novel, Tunable Solvatochromic Fluorophores as Physiological pH Probes.

Amino-isocyanoacridines (ICAAcs), as first members of their class, turned out to be a novel, multifunctional acridine orange (AO) type dye family with a number of additional favorable properties. They have enhanced solvatochromic emission range, low quantum yields (Φ = 2.9-0.

Isocyanonaphthalenes as extremely low molecular weight, selective, ratiometric fluorescent probes for Mercury(II).

The specially designed chemical structure of our recently developed solvatochromic amino-isocyanonaphthalene (ICAN) dye family enables the selective detection of Hg and at the same time is able to indicate the presence of Ag. In addition to its easy preparation and nontoxic nature, ICAN is the lowest molecular weight dye reported for ratiometric fluorescent Hg detection in water, so far. The basis of this double selectivity is the reduction of the isonitrile moiety to amine by a chemical reaction with Hg resulting in a greater than 100 nm hypsochromic shift (and switch on of fluorescence) of the emission maximum relative to ICAN, whereas the complexation of Ag with the NC group yields an approximately 20 nm bathochromic shift (and quenching).

MICAN, a new fluorophore for vital and non-vital staining of human cells.

Fluorescence time-lapse microscopy is in connection with the invasive properties of fluorochrome applied, and with the toxicity of the excitation energy and wavelength of the dye itself. Experiments with the newly synthesized fluorescent dye 1-N-methylamino-5-isocyanonaphthalene (MICAN) served to test its cytotoxicity on human HaCaT keratinocyte cell cultures. Experiments related to staining capability were performed with paraformaldehyde (PFA) fixed cells and observed with fluorescence microscope.

Novel fluorochromes label tonoplast in living plant cells and reveal changes in vacuolar organization after treatment with protein phosphatase inhibitors.

The recently synthesized isocyanonaphtalene derivatives ACAIN and CACAIN are fluorochromes excitable at wavelengths of around 366 nm and bind cysteine-rich proteins with hydrophobic motifs. We show that these compounds preferentially label tonoplasts in living Arabidopsis and tobacco (Nicotiana tabacum SR1) cells. ACAIN-labeled membranes co-localized with the GFP signal in plants expressing GFP-δ-TIP (TIP2;1) (a tonoplast aquaporin) fusion protein.

Solvatochromic study of highly fluorescent alkylated isocyanonaphthalenes, their π-stacking, hydrogen-bonding complexation, and quenching with pyridine.

Mono- and dialkylated derivatives of 1-amino-5-isocyanonaphthalene (ICAN) were studied as new members of a multifunctional, easy-to-prepare fluorophore family, which showed excellent solvatochromic properties. The monoallyl derivative and the starting ICAN exhibited strong fluorescence quenching in the presence of small amounts of pyridine. The formation of a hydrogen-bonded ground-state pyridine complex was detected; however, analysis of quantum chemical calculations suggested the presence of an additional π-stacked pyridine complex.