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Biosensors
Volume 15
Issue 3
10.3390/bios15030174
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Article

Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications

by
Trevor Dvorak
1,
Haley Hernandez-Sandoval
1,
Sunayn Cheku
2,
Marijose Mora Valencia González
3,
Linus Borer
1,
Riley Grieser
1,
Kimberly A. Carlson
2 and
Haishi Cao
1,*
1
Department of Chemistry, University of Nebraska at Kearney, 2504 9th Ave, Kearney, NE 68849, USA
2
Department of Biology, University of Nebraska at Kearney, 2504 9th Ave, Kearney, NE 68849, USA
3
Facultad de Medicina Región Veracruz, Universidad Veracruzana, C. Agustín de Iturbide S/N, Zona Centro, Veracruz 91700, Mexico
*
Author to whom correspondence should be addressed.
Biosensors 2025, 15(3), 174; https://doi.org/10.3390/bios15030174
Submission received: 2 February 2025 / Revised: 20 February 2025 / Accepted: 26 February 2025 / Published: 7 March 2025
(This article belongs to the Special Issue Fluorescent Materials with Excellent Biocompatibility and Their Application in Bio-Sensing, Bio-Imaging (Volume II))
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Abstract

Hydrogen sulfide (H2S) is an important signaling molecule involved in various physiological and pathological processes, making its accurate detection in biological systems highly desirable. In this study, two fluorescent probes (M1 and M2) based on 1,8-naphthalimide were developed for H2S detection via a nucleophilic aromatic substitution. M1 demonstrated high sensitivity and selectivity for H2S in aqueous media, with a detection limit of 0.64 µM and a strong linear fluorescence response in the range of 0–22 µM of NaHS. The reaction kinetics revealed a rapid response, with a reaction rate constant of 7.56 × 102 M−1 s−1, and M1 was most effective in the pH range of 6–10. Mechanism studies using 1H NMR titration confirmed the formation of 4-hydroxyphenyl-1,8-naphthalimide as the product of H2S-triggered nucleophilic substitution. M1 was applied in MDA-MB-231 cells for cell imaging, in which M1 provided significant fluorescence enhancement upon NaHS treatment, confirming its applicability for detecting H2S in biological environments. In comparison, M2, designed with extended conjugation for red-shifted emission, exhibited weaker sensitivity due to the reduced stability of its naphtholate product and lower solubility. These results demonstrate that M1 is a highly effective and selective fluorescent probe for detecting H2S, providing a valuable resource for investigating the biological roles of H2S in health and disease.
Keywords: 1,8-naphthalimide; H2S; probes 1,8-naphthalimide; H2S; probes
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MDPI and ACS Style

Dvorak, T.; Hernandez-Sandoval, H.; Cheku, S.; Mora Valencia González, M.; Borer, L.; Grieser, R.; Carlson, K.A.; Cao, H. Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications. Biosensors 2025, 15, 174. https://doi.org/10.3390/bios15030174

AMA Style

Dvorak T, Hernandez-Sandoval H, Cheku S, Mora Valencia González M, Borer L, Grieser R, Carlson KA, Cao H. Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications. Biosensors. 2025; 15(3):174. https://doi.org/10.3390/bios15030174

Chicago/Turabian Style

Dvorak, Trevor, Haley Hernandez-Sandoval, Sunayn Cheku, Marijose Mora Valencia González, Linus Borer, Riley Grieser, Kimberly A. Carlson, and Haishi Cao. 2025. "Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications" Biosensors 15, no. 3: 174. https://doi.org/10.3390/bios15030174

APA Style

Dvorak, T., Hernandez-Sandoval, H., Cheku, S., Mora Valencia González, M., Borer, L., Grieser, R., Carlson, K. A., & Cao, H. (2025). Development of a Rapid-Response Fluorescent Probe for H2S: Mechanism Elucidation and Biological Applications. Biosensors, 15(3), 174. https://doi.org/10.3390/bios15030174

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