Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe

Department of Experimental Physiology and Pathophysiology, Laboratory of the Centre for Preclinical Research, Medical University of Warsaw, 02-097 Warsaw, Poland

Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

Authors to whom correspondence should be addressed.

Molecules 2018, 23(9), 2241; https://doi.org/10.3390/molecules23092241

Received: 22 July 2018 / Revised: 27 August 2018 / Accepted: 28 August 2018 / Published: 3 September 2018

(This article belongs to the Section Medicinal Chemistry)

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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. View Full-Text

Keywords: fluorescent probe; hydrogen sulfide; azide; assay; Ellman’s Reagent; biological systems; saliva; halitosis

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MDPI and ACS Style

Zaorska, E.; Konop, M.; Ostaszewski, R.; Koszelewski, D.; Ufnal, M. Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe. Molecules 2018, 23, 2241. https://doi.org/10.3390/molecules23092241

AMA Style

Zaorska E, Konop M, Ostaszewski R, Koszelewski D, Ufnal M. Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe. Molecules. 2018; 23(9):2241. https://doi.org/10.3390/molecules23092241

Chicago/Turabian Style

Zaorska, Ewelina, Marek Konop, Ryszard Ostaszewski, Dominik Koszelewski, and Marcin Ufnal. 2018. "Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe" Molecules 23, no. 9: 2241. https://doi.org/10.3390/molecules23092241

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Salivary Hydrogen Sulfide Measured with a New Highly Sensitive Self-Immolative Coumarin-Based Fluorescent Probe

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