Signal turn-on probe for nucleic acid detection based on 19F nuclear magnetic resonance

Shimoyama, Takashi; Shimizu, Yuki; Sasaki, Jun; Hayakawa, Hikaru; Fujimoto, Kenzo

doi:10.1016/j.bmcl.2010.11.013

Cited by 22 publications

(92 citation statements)

References 9 publications

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“… Responsive fluorinated probes whose signals are modulated by the paramagnetic relaxation enhancement effect of Gd III ( 24 , Mizukami et al, 2008 ; 25 , Mizukami et al, 2009 ; 26 , Mizukami et al, 2011 ; 27 , Keliris et al, 2012 ; 28 , Matsushita et al, 2012 ; 29 , Yue et al, 2014 , 2017 ; 30 , Sakamoto et al, 2011 ). …”

Section: Exploiting the Metal Ion To Design Responsive Fluorine Probementioning

confidence: 99%

“…Similar responses can be obtained with an analyte-induced conformational changes that either increase (turn on) or decrease (turn off) the 19 F–Gd distance (Figure 5B,C , respectively). Fujimoto and coworkers used this approach to the PRE effect to extend the traditional molecular beacon motif commonly used to detect DNA (or RNA) by luminescence to that by 19 F NMR ( 30 , Figure 6 ) (Sakamoto et al, 2011 ). Hybridization with the target nucleotide sequence causes the stem loop of the probe to unfold, thereby increasing d and thus also the T 2 and signal intensity of the 19 F nuclei.…”

Section: Exploiting the Metal Ion To Design Responsive Fluorine Probementioning

confidence: 99%

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Fluorinated Paramagnetic Complexes: Sensitive and Responsive Probes for Magnetic Resonance Spectroscopy and Imaging

2018

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Fluorine magnetic resonance spectroscopy (MRS) and magnetic resonance imaging (MRI) of chemical and physiological processes is becoming more widespread. The strength of this technique comes from the negligible background signal in in vivo 19F MRI and the large chemical shift window of 19F that enables it to image concomitantly more than one marker. These same advantages have also been successfully exploited in the design of responsive 19F probes. Part of the recent growth of this technique can be attributed to novel designs of 19F probes with improved imaging parameters due to the incorporation of paramagnetic metal ions. In this review, we provide a description of the theories and strategies that have been employed successfully to improve the sensitivity of 19F probes with paramagnetic metal ions. The Bloch-Wangsness-Redfield theory accurately predicts how molecular parameters such as internuclear distance, geometry, rotational correlation times, as well as the nature, oxidation state, and spin state of the metal ion affect the sensitivity of the fluorine-based probes. The principles governing the design of responsive 19F probes are subsequently described in a “how to” guide format. Examples of such probes and their advantages and disadvantages are highlighted through a synopsis of the literature.

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Section: Exploiting the Metal Ion To Design Responsive Fluorine Probementioning

confidence: 99%

Section: Exploiting the Metal Ion To Design Responsive Fluorine Probementioning

confidence: 99%

Fluorinated Paramagnetic Complexes: Sensitive and Responsive Probes for Magnetic Resonance Spectroscopy and Imaging

2018

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“…Fujimoto and colleagues reported a PRE-based DNA probe that detects a complementary oligonucleotide using 19 F NMR. 38) This probe showed molecular beacon-like structural changes in the presence and absence of target DNA and induced 19 F NMR peak enhancement according to the distance between the trifluoromethyl groups and a Gd F MRI detection probe for a hypoxia environment using the CSI technique. 39) Another approach is to utilize the mobility of fluorine atoms.…”

Section: F Mri Detection Of Gene Expressionmentioning

confidence: 99%

Development of Molecular Imaging Tools to Investigate Protein Functions by Chemical Probe Design

Mizukami

2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Molecular imaging technologies, which enable the visualization of the behaviors or functions of biomolecules in living systems, have received considerable attention from life scientists. Novel imaging technologies that overcome the limitations of current imaging techniques are desired. In this review, two independent technologies that were recently developed by the authors are described. The first technology is for smart 19 F magnetic resonance imaging (MRI) probes that were developed for in vivo applications. These probes were developed by exploiting paramagnetic relaxation enhancement in order to detect hydrolase activity. With respect to cellular applications, gene expression in cells was visualized using one of the 19 F MRI probes. It was confirmed that this probe design principle is effective for various hydrolases, and broad applications are expected. The second technology is for practical protein labeling. This labeling method is based on a mutant b b -lactamase and its specific labeling probes. Since the probe is fluorescence resonance energy transfer (FRET)-based, this labeling method achieves both specific and fluorogenic labeling of target proteins. In addition, derivatization of the probe enabled the labeling of intracellular proteins and the modification of various functional molecules.

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“…Enzyme induced molecular cleavage separates the fluorine moiety from the relaxing center producing enhanced 19 F signal and consequently revealing activity as demonstrated for caspase, β-gal [187, 326], and β-lactamase [327]. A gene reporter has been suggested using a stem-loop structured oligodeoxyribonucleotide based on a sequence for point mutated K-ras mRNA [328]. A bis(trifluoromethyl)benzene moiety experiences strong line broadening from associated Gd-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid until the loop separates upon binding the target complementary mRNA.…”

Section: Proteomicsmentioning

confidence: 99%

New frontiers and developing applications in 19F NMR

Jian

Hallac

Chiguru

et al. 2013

Progress in Nuclear Magnetic Resonance Spectroscopy

175

161

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Signal turn-on probe for nucleic acid detection based on 19F nuclear magnetic resonance

Cited by 22 publications

References 9 publications

Fluorinated Paramagnetic Complexes: Sensitive and Responsive Probes for Magnetic Resonance Spectroscopy and Imaging

Fluorinated Paramagnetic Complexes: Sensitive and Responsive Probes for Magnetic Resonance Spectroscopy and Imaging

Development of Molecular Imaging Tools to Investigate Protein Functions by Chemical Probe Design

New frontiers and developing applications in 19F NMR

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