Abstract
Ample evidence suggests that H2S is an important biological mediator, produced by endogenous enzymes and microbiota. So far, several techniques including colorimetric methods, electrochemical analysis and sulfide precipitation have been developed for H2S detection. These methods provide sensitive detection, however, they are destructive for tissues and require tedious sequences of preparation steps for the analyzed samples. Here, we report synthesis of a new fluorescent probe for H2S detection, 4-methyl-2-oxo-2H-chromen-7-yl 5-azidopentanoate (1). The design of 1 is based on combination of two strategies for H2S detection, i.e., reduction of an azido group to an amine in the presence of H2S and intramolecular lactamization. Finally, we measured salivary H2S concentration in healthy, 18–40-year-old volunteers immediately after obtaining specimens. The newly developed self-immolative coumarin-based fluorescence probe (C15H15N3O4) showed high sensitivity to H2S detection in both sodium phosphate buffer at physiological pH and in saliva. Salivary H2S concentration in healthy volunteers was within a range of 1.641–7.124 μM.
Highlights
Ample evidence shows that H2 S plays a role of a mediator in many biological systems.For example, H2 S has been found to contribute to the regulation of the circulatory system [1,2,3]nervous system [4,5], reproductive system [6,7,8] and energy balance [9,10]
There are at least three enzymes that are responsible for converting sulfur-containing molecules into H2 S: cystathionine β-synthase (CBS), cystathionine γ-lyase (CSE) and 3-mercaptopyruvate sulfurtransferase (MPST) [11,12]
The operation of compound 1 is based on the azide group to amine group reduction mediated by H2 S in combination with spontaneous intramolecular lactamization
Summary
Ample evidence shows that H2 S plays a role of a mediator in many biological systems.For example, H2 S has been found to contribute to the regulation of the circulatory system [1,2,3]nervous system [4,5], reproductive system [6,7,8] and energy balance [9,10]. Ample evidence shows that H2 S plays a role of a mediator in many biological systems. H2 S has been found to contribute to the regulation of the circulatory system [1,2,3]. H2 S is generated endogenously from cysteine and homocysteine. H2 S is generated in large amounts by microbiota, which is present in the intestines and in the oral cavity. Microbiota-produced H2 S seems to play a significant physiological role in cardiovascular and gastrointestinal systems [13,14,15,16,17,18,19]. The excessive bacterial production of H2 S may cause medical complaints such as halitosis, a chronic bad breath condition [20,21]
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