Nucleophilic Ring-Opening of N -Benzoylaziridine Combined with Spirolactamization of Rhodol Enables Ratiometric Fluorescence Imaging of Hydropersulfides in Arabidopsis thaliana .

Abstract

Hydropersulfides (RSSH) are an important class of reactive sulfur species (RSS) involved in a variety of physiological processes in biological systems. However, selective detection of RSSH is challenging since the persulfide group (-SSH) exhibits reactivity akin to biologically abundant biothiols. To address this issue, we designed CRBA as a ratiometric fluorescent probe for RSSH by integrating the nucleophilic ring-opening of an N -benzoylaziridine and spirolactamization of a rhodol. The ratiometric sensing of RSSH is realized by modulating Förster resonance energy transfer (FRET) in the coumarin-rhodol dyad. Nucleophilic attack of the N -benzoylaziridine moiety in CRBA by RSSH affords the corresponding secondary amide ring-opened product, which subsequently undergoes a spontaneous intramolecular spirolactamization to disrupt the π-conjugation structure of the rhodol. The tandem reaction decreases the intramolecular FRET efficiency within the probe and causes a clear dual-emission signal change. Probe CRBA possesses outstanding selectivity toward RSSH over biothiols and H 2 S, and is capable of tracking RSSH levels in Arabidopsis thaliana roots. Moreover, we observed the upregulation of RSSH levels in heavy metal (HM)-induced stress of A. thaliana with probe CRBA , and revealed the correlation between S -persulfidation and H 2 S levels in living plants.

Plant phenotyping relevance

植物体内のRSSH（過硫化水素）を定量的に可視化する蛍光プローブを開発・検証し、Arabidopsisの根および重金属ストレス下の生理状態を測定しているため、植物フェノタイピング手法が中心です。

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