With the aim of discerning between different sugar and sugar alcohols of biomedical relevance, such as gut permeability, arrays of 2-component probes were assembled with up to six boronic acid-appended viologens (BBVs): 4,4′-o-BBV, 3,3′-o-BBV, 3,4′-o-BBV, 4,4′-o,m-BBV, 4,7′-o-PBBV, and pBoB, each coupled to the fluorophore 8-hydroxypyrene, 1,3,6-trisulfonic acid trisodium salt (HPTS). These probes were screened for their ability to discriminate between lactulose, l-rhamnose, 3-O-methyl-d-glucose, and xylose. Binding studies of sugar alcohols mannitol, sorbitol, erythritol, adonitol, arabitol, galactitol, and xylitol revealed that diols containing threo-1,2-diol units have higher affinity for BBVs relative diols containing erythro-1,2 units. Those containing both threo-1,2- and 1,3-syn diol motifs showed high affinity for boronic acid binding. Fluorescence from the arrays were examined by principle component analysis (PCA) and linear discriminant analysis (LDA). Arrays with only three BBVs sufficed to discriminate between sugars (e.g., lactulose) and sugar alcohols (e.g., mannitol), establishing a differential probe. Compared with 4,4′-o-BBV, 2-fold reductions in lower limits of detection (LOD) and quantification (LOQ) were achieved for lactulose with 4,7-o-PBBV (LOD 41 μM, LOQ 72 μM). Using a combination of 4,4′-o-BBV, 4,7-o-PBBV, and pBoB, LDA statistically segregated lactulose/mannitol (L/M) ratios from 0.1 to 0.5, consistent with values encountered in small intestinal permeability tests. Another triad containing 3,3′-o-BBV, 4,4′-o-BBV, and 4,7-o-PBBV also discerned similar L/M ratios. This proof-of-concept demonstrates the potential for BBV arrays as an attractive alternate to HPLC to analyze mixtures of sugars and sugar alcohols in biomedical applications and sheds light on structural motifs that make this possible.
McDuff and Schlenk have recently determined exactly when a fourdimensional symplectic ellipsoid symplectically embeds into a symplectic ball. Similarly, Frenkel and Müller have recently determined exactly when a symplectic ellipsoid symplectically embeds into a symplectic cube. Symplectic embeddings of more complicated structures, however, remain mostly unexplored. We study when a symplectic ellipsoid E(a, b) symplectically embeds into a polydisc P (c, d). We prove that there exists a constant C depending only on d/c (here, d is assumed greater than c) such that if b/a is greater than C, then the only obstruction to symplectically embedding E(a, b) into P (c, d) is the volume obstruction. We also conjecture exactly when an ellipsoid embeds into a scaling of P (1, b) for b greater than or equal to 6, and conjecture about the set of (a, b) such that the only obstruction to embedding E(1, a) into a scaling of P (1, b) is the classical volume. Finally, we verify our conjecture for b = 13 2 .
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