perfluorophenyl 1-(1,3-dioxoisoindolin-2-yloxy)-3,6,9,12-tetraoxapentadecan-15-oate

Glyconanomaterials, an emerging class of bio-functional nanomaterials, have shown promise in detecting, imaging and targeting proteins, bacteria, and cells. In this article, we report that dynamic light scattering (DLS) can be used as an efficient tool to study glyconanoparticle (GNP)--lectin interactions. Silica and Au nanoparticles (NPs) conjugated with D-mannose (Man) and D-galactose (Gal) were treated with the lectins Concanavalin A (Con A) and Ricinus communis agglutinin (RCA(120)), and the hydrodynamic volumes of the resulting aggregates were measured by DLS. The results showed that the particle size grew with increasing lectin concentration. The limit of detection (LOD) was determined to be 2.9 nM for Con A with Man-conjugated and 6.6 nM for RCA(120) with Gal-conjugated silica NPs (35 nm), respectively. The binding affinity was also determined by DLS and the results showed 3-4 orders of magnitude higher affinity of GNPs than the free ligands with lectins. The assay sensitivity and affinity were particle size dependent and decreased with increasing particle diameter. Because the method relies on the particle size growth, it is therefore general and can be applied to nanomaterials of different compositions.

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.

A new series of sidewall modified single-walled carbon nanotubes (SWCNTs) with perfluorophenyl molecules bearing carboxylic acid or methyl ester moieties are herein reported. Pristine and functionalized SWCNTs (p-SWCNTs and f-SWCNTs, respectively) were characterized by X-ray photoelectron spectroscopy (XPS), Raman spectroscopy and scanning electron microscopy (SEM). The nitrene-based functionalization provided intact SWCNTs with methyl 4-azido-2,3,5,6-tetrafluorobenzoate (SWCNT-N-C6F4CO2CH3) and 4-azido-2,3,5,6-tetrafluorobenzoic acid (SWCNT-N-C6F4CO2H) attached every 213 and 109 carbon atoms, respectively. Notably, SWCNT-N-C6F4CO2H was sensitive in terms of the percentage of conductance variation from 5 to 40 ppm of ammonia (NH3) and trimethylamine (TMA) with a two-fold higher variation of conductance compared to p-SWCNTs at 40 ppm. The sensors are highly sensitive to NH3and TMA as they showed very low responses (0.1%) toward 200 ppm of volatile organic compounds (VOCs) containing various functional groups representative of different classes of analytes such as benzene, tetrahydrofurane (THF), hexane, ethyl acetate (AcOEt), ethanol, acetonitrile (CH3CN), acetone and chloroform (CHCl3). Our system is a promising candidate for the realization of single-use chemiresistive sensors for the detection of threshold crossing by low concentrations of gaseous NH3and TMA at room temperature.