S-Nitrosothiol-Impregnated Silicone Catheter for Colorimetric Sensing of Indole and E. coli: Toward On-Body Detection of Urinary Tract Infections.

Abstract

Although there are many techniques to detect pathogenic bacteria, most of them are only suited for in vitro diagnostics. We report a urinary catheter-based colorimetric sensor for potential on-body detection of E. coli, the most prevalent bacterial species in urinary tract infections associated with the use of urinary catheters. In urine, indole is secreted by E. coli and reacts with a nitrosating agent incorporated in a silicone catheter. A red dimeric product, indoxyl red, is generated within silicone rubber to allow for color-based indole sensing with high sensitivity, linearity, and specificity. This reaction is initiated by the nitrosation reaction of indole at its C-3 position via reagents like sodium nitrite or S-nitroso-N-acetyl-penicillamine under aerobic conditions. The generated 3-nitrosoindole undergoes tautomerization, dimerization, and deoximation to form indoxyl red with high absorbance at 537 nm. In contrast to other indole sensors, the presented method can be applied in real catheters to detect indole and E. coli in biofluids such as urine. The is because (1) S-nitroso-N-acetyl-penicillamine, the nitrosating agent, can be impregnated into silicone elastomers, (2) indole from urine is extracted into silicone due to its hydrophobicity, and (3) the high acidity and oxygen solubility of silicone facilitates the sensing reaction within the silicone matrix. This silicone-based colorimetric sensor clearly differentiates E. coli below and above 105 CFU/mL, which is the threshold concentration of bacteriuria. We expect that early diagnosis of urinary tract infections using the naked eye is possible by functionalizing an exposed section of urinary catheters with the proposed molecular probe.