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Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells in vitro and in vivo by varying counter anions.

ABSTRACT: Chemotherapeutics specifically targeting cancer cells without damaging healthy cells is the long-awaited goal of cancer treatment. In this paper, a series of nanoparticles (NanoTPES 1-4) assembled from pyridinium-substituted tetraphenylethylene salts were synthesized and investigated both in vitro and in vivo for this purpose. By changing the counter anions, NanoTPES 1-4 exhibit tunable emission colors, sizes and surface charges. NanoTPES 2 and 3 with tetraphenyl borate and tetra(4-chlorophenyl) borate as the respective anions selectively imaged and targeted mitochondria in cancer cells. Accordingly, these two nanoparticles specifically kill cancer cells with minimal effect on normal cells. Such selective cytotoxicity was attributed to the change of membrane potential and inhibition of ATP synthesis in the mitochondria of cancer cells. Furthermore, both NanoTPES 2 and 3 exhibited efficient tumor accumulation and tumor growth inhibition in vivo, with negligible systemic toxicity.

SUBMITTER: Huang Y

PROVIDER: S-EPMC5355829 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells in vitro and in vivo by varying counter anions.

Huang Yanyan Y Zhang Guanxin G Hu Fang F Jin Yulong Y Zhao Rui R Zhang Deqing D

Chemical science 20160718 12

Chemotherapeutics specifically targeting cancer cells without damaging healthy cells is the long-awaited goal of cancer treatment. In this paper, a series of nanoparticles (NanoTPES 1-4) assembled from pyridinium-substituted tetraphenylethylene salts were synthesized and investigated both in vitro and in vivo for this purpose. By changing the counter anions, NanoTPES 1-4 exhibit tunable emission colors, sizes and surface charges. NanoTPES 2 and 3 with te ...[more]

PMID: 28451137

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Project description:A series of specific task ionic liquids (ILs) based on a pyridiniumhydrazone scaffold in combination with hexafluorophosphate (PF₆-), tetrafluoroboron (BF₄-) and/or trifluoroacetate (CF₃COO-) counter anion, were designed and characterized by IR, NMR and mass spectrometry. The reactions were conducted under both conventional and green ultrasound procedures. The antifungal potential of the synthesized compounds 2-25 was investigated against 40 strains of Candida (four standard and 36 clinical isolates). Minimum inhibitory concentrations (MIC90) of the synthesized compounds were in the range of 62.5-2000 μg/mL for both standard and oral Candida isolates. MIC90 results showed that the synthesized 1-(2-(4-chlorophenyl)-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-pyridin-1-ium hexafluorophosphate (11) was found to be most effective, followed by 4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-1-(2-(4-nitrophenyl)-2-oxoethyl)-pyridin-1-ium hexafluorophosphate (14) and 1-(2-ethoxy-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)pyridin-1-ium hexafluorophosphate (8). All the Candida isolates showed marked sensitivity towards the synthesized compounds. Ergosterol content was drastically reduced by more active synthesized compounds, and agreed well with MIC90 values. Confocal scanning laser microscopy (CLSM) results showed that the red colored fluorescent dye enters the test agent treated cells, which confirms cell wall and cell membrane damage. The microscopy results obtained suggested membrane-located targets for the action of these synthesized compounds. It appears that the test compounds might be interacting with ergosterol in the fungal cell membranes, decreasing the membrane ergosterol content and ultimately leading to membrane disruption as visible in confocal results. The present study indicates that these synthesized compounds show significant antifungal activity against Candida which forms the basis to carry out further in vivo experiments before their clinical use.

Dataset Information

Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells in vitro and in vivo by varying counter anions.

Publications

Emissive nanoparticles from pyridinium-substituted tetraphenylethylene salts: imaging and selective cytotoxicity towards cancer cells <i>in vitro</i> and <i>in vivo</i> by varying counter anions.

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