Next Article in Journal
Leftover Kiwi Fruit Peel-Derived Carbon Dots as a Highly Selective Fluorescent Sensor for Detection of Ferric Ion
Next Article in Special Issue
A Novel Dialkylamino GFP Chromophore as an Environment-Polarity Sensor Reveals the Role of Twisted Intramolecular Charge Transfer
Previous Article in Journal
Novel Colour-Based, Prototype Indicator for Use in High-Pressure Processing (HPP)
Previous Article in Special Issue
Bicyclic 1,3a,6a-Triazapentalene Chromophores: Synthesis, Spectroscopy and Their Use as Fluorescent Sensors and Probes
 
 
Article

BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application

1
National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Khlong Nueng 12120, Thailand
2
School of Liberal Arts, King Mongkut’s University of Technology Thonburi, Bangkok 10140, Thailand
3
Integrated Applied Chemistry Research Unit, King Mongkut’s Institute of Technology Ladkrabang, School of Science, Bangkok 10520, Thailand
4
Institute of Science, School of Chemistry, Suranaree University of Technology, Nakhon Ratchasima 30000, Thailand
5
Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Ladyao, Chatuchak, Bangkok 10900, Thailand
6
Synchrotron Light Research Institute, 111 University Avenue, Suranaree, Muang, Nakhon Ratchasima 30000, Thailand
7
Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
8
Research Network of Nanotec-CU on Nanotechnology for Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
*
Author to whom correspondence should be addressed.
Academic Editor: Yinyin Bao
Chemosensors 2021, 9(7), 165; https://doi.org/10.3390/chemosensors9070165
Received: 29 May 2021 / Revised: 24 June 2021 / Accepted: 27 June 2021 / Published: 2 July 2021
(This article belongs to the Special Issue Organic Fluorescent Materials as Chemical Sensors)
A novel pyridylhydrazone-tethered BODIPY (BODIPY-PH) was synthesized, fully characterized via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopic (FTIR), and single-crystal X-ray diffraction (SC-XRD) techniques, and developed for the selective detection of Fe3+ through fluorescent enhancement process. This derivative showed 1:1 binding with Fe3+ in an acetonitrile-water mixture (1:9 v/v) with the binding constant (K) of 5.4 × 104 M−1 and the limit of detection of 0.58 µM. The Fe3+ complexation reaction has been proved to be a reversible process and could be effectively repeated up to three cycles. The electronic properties of BODIPY-PH and its Fe3+ complex modeled by the density functional theory (DFT) method suggested the presence of chelation-enhanced fluorescence (CHEF) effect in the Fe3+ binding reaction. The X-ray absorption spectroscopy (XAS) probed at Fe K-edge confirmed the complex formation between BODIPY-PH and the Fe3+ in an octahedral geometry. Finally, bioimaging against human embryonic kidney (Hek293) cell, through confocal fluorescence microscopic technique indicated that the BODIPY-PH displayed good permeability and low toxicity toward the tested cell lines and showed enhanced fluorescent signal in the cells incubated with Fe3+ proving its capability for Fe3+ analysis in cellular matrix. View Full-Text
Keywords: BODIPY; ferric ions; fluorescence; bioimaging; pyridyl group BODIPY; ferric ions; fluorescence; bioimaging; pyridyl group
Show Figures

Figure 1

MDPI and ACS Style

Nootem, J.; Sattayanon, C.; Daengngern, R.; Kamkaew, A.; Wattanathana, W.; Wannapaiboon, S.; Rashatasakhon, P.; Chansaenpak, K. BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application. Chemosensors 2021, 9, 165. https://doi.org/10.3390/chemosensors9070165

AMA Style

Nootem J, Sattayanon C, Daengngern R, Kamkaew A, Wattanathana W, Wannapaiboon S, Rashatasakhon P, Chansaenpak K. BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application. Chemosensors. 2021; 9(7):165. https://doi.org/10.3390/chemosensors9070165

Chicago/Turabian Style

Nootem, Jukkrit, Chanchai Sattayanon, Rathawat Daengngern, Anyanee Kamkaew, Worawat Wattanathana, Suttipong Wannapaiboon, Paitoon Rashatasakhon, and Kantapat Chansaenpak. 2021. "BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application" Chemosensors 9, no. 7: 165. https://doi.org/10.3390/chemosensors9070165

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop