A Novel Benzimidazole-Based Fluorescence Probe for Detecting Zinc Ion in Aqueous Solution and Zebrafish

• Published in: Bulletin of the Chemical Society of Japan Vol. 92; no. 5; pp. 961 - 966
• Main Authors: Yun, Jin Yeong, Kim, Ahran, Hwang, Suh Mi, Yun, Dongju, Lee, Hyojin, Kim, Ki-Tae, Kim, Cheal
• Format: Journal Article
• Language: English
• Published: TOKYO The Chemical Society of Japan 2019; Chemical Soc Japan; Chemical Society of Japan
• Subjects: Aqueous solutions; Chemical sensors; Chemistry; Chemistry, Multidisciplinary; Chemoreceptors; Cosmetics industry; Ethylenediaminetetraacetic acids; Fluorescent indicators; Ionization; Ions; NMR; Nuclear magnetic resonance; Organic chemistry; Physical Sciences; Science & Technology; Titration; Zebrafish; Zinc; Zinc sensor; Zebrafish imaging; DFT-calculations; RECOGNITION; SENSOR; SENSITIVE DETECTION; CHEMOSENSOR; SEQUENTIAL DETECTION; PYROPHOSPHATE; SELECTIVE DETECTION; LIVING CELLS; ZN2; WATER
• ISSN: 0009-2673; 1348-0634
• DOI: 10.1246/bcsj.20180390

A novel selective and sensitive chemosensor, (E)-1-(((1H-benzo[d]imidazol-2-yl)methyl)imino)methyl)naphthalen-2-ol (BIN), was developed for fluorescence detection of Zn2+. The compound BIN acts as a fluorescent “turn-on” detector for Zn2+. The limit of detection (2.26 µM) for zinc ion is well below the WHO standard (76.0 µM). Probe BIN can be chemically reversible with ethylenediaminetetraacetic acid (EDTA). The binding mechanism of BIN with zinc ion was demonstrated by fluorescence, UV-visible, electrospray ionization mass spectroscopy, 1H NMR titration and calculations. Importantly, probe BIN could be applied to determine zinc ion in water samples and living zebrafish.