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

Nagy, Zsolt László; Nagy, Miklós; Kiss, Alexandra; Rácz, Dávid; Barna, Beatrix; Könczöl, Péter; Bankó, Csaba; Bacsó, Zsolt; Kéki, Sándor; Bánfalvi, Gáspár; Szemán-Nagy, Gábor

doi:10.1016/j.tiv.2018.01.012

Cited by 7 publications

(8 citation statements)

References 22 publications

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“…Nevertheless, none of the ICAN derivatives prepared by us have any odor at all. On the contrary, they proved to be one of the most versatile “smart” fluorophore dye families, which found applications as nontoxic supravital stains for the investigation and characterization of both plant and animal cells [19,20], enable the selective detection of Hg 2+ , and at the same time are able to indicate the presence of Ag + , which is unprecedented among fluorescent sensors [21]. In addition, to the best of our knowledge, ICAN is the simplest and lowest molecular weight fluorophore that has ever been used for fluorescent Hg(II) detection.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores

et al. 2019

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The properties of 1,4-isocyanoaminonaphthalene (1,4-ICAN) and 2,6-isocyanoaminonaphthalene (2,6-ICAN) isomers are discussed in comparison with those of 1,5-isocyanoaminonaphthalene (1,5-ICAN), which exhibits a large positive solvatochromic shift similar to that of Prodan. In these isocyanoaminonaphthalene derivatives, the isocyano and the amine group serve as the donor and acceptor moieties, respectively. It was found that the positions of the donor and the acceptor groups in these naphthalene derivatives greatly influence the Stokes and solvatochromic shifts, which decrease in the following order: 1,5-ICAN > 2,6-ICAN > 1,4-ICAN. According to high-level quantum chemical calculations, this order is well correlated with the charge transfer character of these compounds upon excitation. Furthermore, unlike 1,5-ICAN, the 1,4-ICAN and 2,6-ICAN isomers showed relatively high quantum yields in water, that were determined to be 0.62 and 0.21, respectively. In addition, time-resolved fluorescence experiments revealed that both the radiative and non-radiative decay rates for these three ICAN isomers varied unusually with the solvent polarity parameter ET(30). The explanations of the influence of the solvent polarity on the resulting steady-state and time-resolved fluorescence emission spectra are also discussed.

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Section: Introductionmentioning

confidence: 99%

Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores

et al. 2019

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“…Recently, we developed a novel amino-isocyanonaphthalene (ICAN) based solvatochromic fluorophore family [14], which despite their very simple structure and easy preparation, still mark a white spot on the map of chemistry. Despite their relative novelty, they already found numerous and versatile use in both analytical chemistry [15][16][17] and cell-biology [18][19][20]. During our experiments to utilize ICAN derivatives as vital stains on CaCo2, OCM-1, HuLi and HaCat cell lines [20] we noticed that they are perfectly suitable for the staining of different fungi, too.…”

Section: Introductionmentioning

confidence: 91%

“…Despite their relative novelty, they already found numerous and versatile use in both analytical chemistry [15][16][17] and cell-biology [18][19][20]. During our experiments to utilize ICAN derivatives as vital stains on CaCo2, OCM-1, HuLi and HaCat cell lines [20] we noticed that they are perfectly suitable for the staining of different fungi, too. However, after testing 1-N-methylamino-5-isocyanonaphthalene (MICAN) on a commercial strain of Saccharomyces cerevisiae, a strong antimycotic effect was observed.…”

Section: Introductionmentioning

confidence: 91%

“…We previously carried out extensive studies to successfully utilize 1-N-methylamino-5isocyanonaphthalene (MICAN) as a vital cell dye on different human cell lines [20]. The compound along with ICAN and 1,1-N-dimethylamino-5-isocyanonaphthalene (DIMICAN) are well tolerated by human cell cultures, their LD 50 values (on HaCat cell line) were determined (MTT bio assay technique) to be 10 µg/mL for ICAN, 18 µg/mL for MICAN, and 13 µg/mL for DIMICAN.…”

Section: Antifungal Activity Of the Ican Derivativesmentioning

confidence: 99%

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

et al. 2020

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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 Candida species. Structure-activity studies revealed that the naphthalene core and the isocyano- together with the amino moieties are all necessary to exert antifungal activity. 1,1-N-dimethylamino-5-isocyanonaphthalene (DIMICAN), the most promising candidate, was tested further in vitro against clinical isolates of Candida species, yielding a minimum inhibitory concentration (MIC) of 0.04–1.25 µg/mL. DIMICAN was found to be effective against intrinsically fluconazole resistant Candida krusei isolates, too. In vivo experiments were performed in a severly neutropenic murine model inoculated with a clinical strain of Candida albicans. Daily administration of 5 mg/kg DIMICAN intraperitoneally resulted in 80% survival even at day 13, whereas 100% of the control group died within six days. Based on these results, ICANs may become an effective clinical lead compound family against fungal pathogens.

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“…Based on literature data, 1% (v/v) is the amount that is tolerated even without significant change in cells. However, this may vary depending on the sensitivity of the cell [51,52].…”

Section: Time-lapse Image Video-microscopy and Image Analysismentioning

confidence: 99%

Synthesis and Cytostatic Effect of 3’-deoxy-3’-C-Sulfanylmethyl Nucleoside Derivatives with d-xylo Configuration

et al. 2019

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A small library of 3’-deoxy-C3’-substituted xylofuranosyl-pyrimidine nucleoside analogues were prepared by photoinduced thiol-ene addition of various thiols, including normal and branched alkyl-, 2-hydroxyethyl, benzyl-, and sugar thiols, to 3’-exomethylene derivatives of 2’,5’-di-O-tert-butyldimethylsilyl-protected ribothymidine and uridine. The bioactivity of these derivatives was studied on tumorous SCC (mouse squamous carcinoma cell) and immortalized control HaCaT (human keratinocyte) cell lines. Several alkyl-substituted analogues elicited promising cytostatic activity in low micromolar concentrations with a slight selectivity toward tumor cells. Near-infrared live-cell imaging revealed SCC tumor cell-specific mitotic blockade via genotoxicity of analogue 10, bearing an n-butyl side chain. This analogue essentially affects the chromatin structure of SCC tumor cells, inducing a condensed nuclear material and micronuclei as also supported by fluorescent microscopy. The results highlight that thiol-ene chemistry represents an efficient strategy to discover novel nucleoside analogues with non-natural sugar structures as anticancer agents.

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

Cited by 7 publications

References 22 publications

Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores

Effect of the Substitution Position on the Electronic and Solvatochromic Properties of Isocyanoaminonaphthalene (ICAN) Fluorophores

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

Synthesis and Cytostatic Effect of 3’-deoxy-3’-C-Sulfanylmethyl Nucleoside Derivatives with d-xylo Configuration

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