Lyso‐H2S: A Mycophenolic Acid‐Derived Probe for Ultra‐Low Toxicity, Intracellular H2S Detection, and Zebrafish Model Validation

Author:

Jain Neha1,An Jongkeol1,Roychaudhury Arkaprava2,Park Sujeong3,Sonawane Prasad M.1,Punyamung Pheeranat1,Aartsen Lars1,Nimse Satish Balasaheb3,Kim Cheol‐Hee2,Churchill David G.1ORCID

Affiliation:

1. Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST) Daejeon 34141 Republic of Korea

2. Department of Biology Chungnam National University Daejeon 34134 Republic of Korea

3. Department of Chemistry Hallym University Chuncheon 24252 Republic of Korea

Abstract

AbstractIn several biological processes, H2S is known to function as an endogenous gaseous agent. It is very necessary to monitor H2S and relevant physiological processes in vivo. Herein, a new type of fluorophore with a reliable leaving group allows for excited‐state intramolecular transfer characteristics (ESIPT), inspired by mycophenolic acid. A morpholine ring was connected at the maleimide position of the probe to target the lysosome. Subsequently, the dinitrophenyl group known for a photoinduced electron transfer (PET) effect, was connected to allow for an effective “turn‐on” probe Lyso‐H2S. Lyso‐H2S demonstrated strong selectivity towards H2S, a large Stokes shift (111 nm), and an incredibly low detection limit (41.8 nM). The imaging of endogenous and exogenous H2S in living cells (A549 cell line) was successfully achieved because of the specificity and ultra‐low toxicity (100 % cell viability at 50 μM concentration of Lyso‐H2S.) Additionally, Lyso‐H2S was also employed to visualize the activity of H2S in the gallbladder and intestine in a living zebrafish model. This is the first report of a fluorescent probe to track H2S sensing in specific organ systems to our knowledge.

Funder

Ministry of Oceans and Fisheries

Publisher

Wiley

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