AI Article Synopsis
- Salicylate hydroxylase (SHL) catalyzes the conversion of salicylate to catechol, producing CO2 and H2O, and has potential applications in biosensors due to its coimmobilization with dehydrogenases.
- Researchers synthesized a new fluorogenic substrate, SHLF, which generates a fluorescence signal that is specific and detectable in the near-red region (595 nm).
- The SHLF-based fluorescence assay shows enhanced sensitivity for detecting biological analytes like 3-hydroxybutyrate and cholesterol compared to existing amperometric sensors, paving the way for its use in fiber-optic fluorescence biosensors for clinical diagnostics.
Article Abstract
Salicylate hydroxylase (SHL) catalyzes the production of catechol (plus CO(2) and H(2)O) from salicylate, NADH, and O(2). Coimmobilization of SHL with a NAD(P)(+)-dependent dehydrogenase in front of a Clark-type oxygen electrode has been investigated in the development of a general type of dehydrogenase-based biosensors that can detect various biological analytes; however, currently, no fluorophores are available for these applications. We synthesized the first new long-wavelength latent fluorogenic substrate SHLF (3) for SHL. In the presence of NADH and under aerobic conditions, SHL catalyzes the decarboxylative hydroxylation of SHLF followed by a quinone-methide-type rearrangement reaction concomitant with the ejection of a fluorescence coumarin 2, which is spontaneous and irreversible at physiological temperatures in aqueous media. The fluorescence signal generated by this process is specific and, in the near red spectral region with an emission maximum at 595 nm, is suppressed by salicylic acid. The fluorescence response of SHLF is insensitive to various biological reactive oxygen species (ROS) and reductants. Furthermore, SHLF is a sensitive fluorimetric indicator for analyte determination in the SHL-coupled dehydrogenase assay in which NAD(+) is converted to NADH. This novel fluorescence assay detected 3-hydroxybutyrate and cholesterol in the nanomolar range and is more sensitive than the current SHL-dehydrogenase amperometric sensors, making it applicable to the construction of a fiber-optic fluorescence biosensor for clinical diagnostic uses.
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