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Multiwell Assay for the Analysis of Sugar Gut Permeability Markers: Discrimination of Sugar Alcohols with a Fluorescent Probe Array Based on Boronic Acid Appended Viologens
Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA.
Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA.
Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA.
Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA.
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2016 (English)In: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 88, no 10, 5444-5452 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2016. Vol. 88, no 10, 5444-5452 p.
Keyword [en]
organoborane, gut permeability
National Category
Medical and Health Sciences
Research subject
Medical Science; Organic Chemistry; Biochemistry
URN: urn:nbn:se:uu:diva-293552DOI: 10.1021/acs.analchem.6b00880ISI: 000376223500058PubMedID: 27116118OAI: oai:DiVA.org:uu-293552DiVA: diva2:929607
Swedish Society of Medicine, SLS-178281, SLS-249741, SLS-330891, SLS-327661, SLS-411921, SLS-503131Sven Jerring Foundation
Available from: 2016-05-19 Created: 2016-05-13 Last updated: 2016-06-29Bibliographically approved

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