A rhodol-based fluorescent chemosensor for hydrazine and its application in live cell bioimaging

Khomsan Tiensomjitr; Rattha Noorat; Kanokorn Wechakorn; Samran Prabpai; Kanoknetr Suksen; Phongthon Kanjanasirirat; Yongyut Pewkliang; Suparerk Borwornpinyo; Palangpon Kongsaeree

doi:10.1016/j.saa.2017.05.058

A rhodol-based fluorescent chemosensor for hydrazine and its application in live cell bioimaging

Spectrochim Acta A Mol Biomol Spectrosc. 2017 Oct 5:185:228-233. doi: 10.1016/j.saa.2017.05.058. Epub 2017 May 29.

Authors

Khomsan Tiensomjitr¹, Rattha Noorat¹, Kanokorn Wechakorn¹, Samran Prabpai¹, Kanoknetr Suksen², Phongthon Kanjanasirirat³, Yongyut Pewkliang³, Suparerk Borwornpinyo⁴, Palangpon Kongsaeree⁵

Affiliations

¹ Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand; Center for Excellence in Protein and Enzyme Technology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
² Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
³ Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
⁴ Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok 10400, Thailand; Department of Biotechnology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
⁵ Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand; Center for Excellence in Protein and Enzyme Technology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. Electronic address: [email protected].

PMID: 28582724
DOI: 10.1016/j.saa.2017.05.058

Abstract

A rhodol cinnamate fluorescent chemosensor (RC) has been developed for selective detection of hydrazine (N₂H₄). In aqueous medium, the rhodol-based probe exhibited high selectivity for hydrazine among other molecules. The addition of hydrazine triggered a fluorescence emission with 48-fold enhancement based on hydrazinolysis and a subsequent ring-opening process. The chemical probe also displayed a selective colorimetric response toward N₂H₄ from colorless solution to pink, readily observed by the naked eye. The detection limit of RC for hydrazine was calculated to be 300nM (9.6ppb). RC is membrane permeable and was successfully demonstrated to detect hydrazine in live HepG2 cells by confocal fluorescence microscopy.

Keywords: Bioimaging; Fluorescent detection; Hydrazine-selective chemosensor; Rhodol.

MeSH terms

Cytological Techniques / methods*
Fluorescent Dyes / chemistry*
Hep G2 Cells
Humans
Hydrazines / analysis*
Spectrometry, Fluorescence / methods*
Xanthones / chemistry*

Substances

Fluorescent Dyes
Hydrazines
Xanthones
rhodol