Rhodamine-aminopyridine based fluorescent sensors for Fe3+ in water: Synthesis, quantum chemical interpretation and living cell application

Yan, Fanyong; Zheng, Tancheng; Shi, Dechao; Zou, Yu; Ya, Wang; Fu, Manman; Chen, Li; Fu, Weigui

doi:10.1016/j.snb.2015.03.096

Cited by 64 publications

(18 citation statements)

References 61 publications

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“…In the case of RD-1 developed by Ji et al ( 47 ) , a pyridylmethylaminomethylcarbonyl group was introduced as an iron receptor that allowed use of this probe in aqueous system and imaging study. Yan and coworkers ( 48 ) attached a 1,2,3-triazine structure bearing a 2-pyridylamino substituent on the spirolactum to improve water compatibility affording RC2P. RC2P worked in pure aqueous solutions (without organic co-solvent) and successfully detected Fe 3+ in living HL7702 cells by fluorescence imaging.…”

Section: Fluorescent Probesmentioning

confidence: 99%

Chemical tools for detecting Fe ions

Hirayama

Nagasawa

2017

J. Clin. Biochem. Nutr.

122

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Owing to its distinctive electrochemical properties with interconvertible multiple oxidation states, iron plays a significant role in various physiologically important functions such as respiration, oxygen transport, energy production, and enzymatic reactions. This redox activity can also potentially produce cellular damage and death, and numerous diseases are related to iron overload resulting from the dysfunction of the iron regulatory system. In this case, “free iron” or “labile iron,” which refers to iron ion weakly bound or not bound to proteins, causes aberrant production of reactive oxygen species. With the aim of elucidating the variation of labile iron involved in pathological processes, some chemical tools that can qualitatively and/or quantitatively monitor iron have been utilized to investigate the distribution, accumulation, and flux of biological iron species. Since iron ions show unique reactivity depending on its redox state, i.e., Fe2+ or Fe3+ (or transiently higher oxidative states), methods for the separate detection of iron species with different redox states are preferred to understand its physiological and pathological roles more in detail. The scope of this review article covers from classical chromogenic to newly emerging chemical tools for the detection of Fe ions. In particular, chemical tools applicable to biological studies will be presented.

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Section: Fluorescent Probesmentioning

confidence: 99%

Chemical tools for detecting Fe ions

Hirayama

Nagasawa

2017

J. Clin. Biochem. Nutr.

122

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“…Chemical probes of Fe 3+ based on rhodamine B possess noteworthy absorbance change to realize “naked eye” detection. Meanwhile, they also reveal miraculously fluorescence intensity changes . As shown in Figure , the maximum absorption band of rhodamine B group R1 in the mixture of water and acetonitrile was at ∼390 nm; upon addition of 10 μM of Fe 3+ , the solution of R1 changed from light yellow to red and the maximum absorption band red shifted remarkably to 580 nm.…”

Section: Resultsmentioning

confidence: 93%

Fe³⁺‐Responsive Micelle Based on an Amphiphilic Polymer and a Rhodamine B‐Containing Amphiphile in Aqueous Media

Yan

Wang

et al. 2018

ChemistrySelect

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Fe 3 + -responsive micelle in aqueous media was achieved based on an amphiphilic polymer and a rhodamine B-containing amphiphile. This self-assembly micelle displayed highly selective and sensitive response to Fe 3 + . After addition of Fe 3 + , the micelle was destroyed along with the significant color variance of the solution from light yellow to red and an "Off-On" fluorescence phenomenon.[a] Dr.

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“…The LANL2TZ basis set was used for Hg and the 6‐311G(d) basis set was used for nonmetal atoms such as H, C, N, and O . All calculations were performed using the Gaussian 09 package, and the results of the calculation were visualized using the GaussView 5.0 program …”

Section: Methodsmentioning

confidence: 99%

A triazole‐based fluorescence probe for detecting Hg²⁺ ions and its biological application

Liu

Ding

et al. 2019

Luminescence

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A new compound, ethyl 5-phenyl-2-(p-tolyl)-2H-1,2,3-triazole-4-carboxylate was successfully introduced and synthesized as a novel rhodamine B derivative named REPPC, and characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high resolution mass spectrometry (HRMS). It showed an obvious fluorescence and UV-visible light absorption enhancement towards Hg 2+ ion without interference from common metal ions in N,N-dimethylformamide-H 2 O (pH 7.4). The spirolactam ring moiety of rhodamine in REPPC was converted to the open-ring form generating a 1:1 complex with the intervention of a mercury ion, verified by electrospray ionization-mass spectroscopy testing and density functional theory calculation.REPPC was used to visualize the level of mercury ions in living HeLa cells with encouraging results. KEYWORDSbinding mechanism, bio-imaging, ethyl 5-phenyl-2-(p-tolyl)-2H-1,2,3-triazole-4-carboxylate, mercury ion As shown in Scheme 1, first rhodamine B hydrazide 1 was synthesized according to a reported procedure. [15] Next, 20 ml of ethanol was used SCHEME 1 Synthesis route of REPPC. 130LIU ET AL. 0 3 shows the corresponding colour photograph for REPPC in the presence of different metal ions. There was a 615-fold increase in fluorescence signal at 577 nm for the REPPC-Hg 2+ system; this result suggested that REPPC can be used as a sensor to detect Hg 2+ using FIGURE 1 Effect of pH on the fluorescence signal of REPPC and the REPPC-mercury complex 132 LIU ET AL.

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Rhodamine-aminopyridine based fluorescent sensors for Fe3+ in water: Synthesis, quantum chemical interpretation and living cell application

Cited by 64 publications

References 61 publications

Chemical tools for detecting Fe ions

Chemical tools for detecting Fe ions

Fe³⁺‐Responsive Micelle Based on an Amphiphilic Polymer and a Rhodamine B‐Containing Amphiphile in Aqueous Media

A triazole‐based fluorescence probe for detecting Hg²⁺ ions and its biological application

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Rhodamine-aminopyridine based fluorescent sensors for Fe3+ in water: Synthesis, quantum chemical interpretation and living cell application

Cited by 64 publications

References 61 publications

Chemical tools for detecting Fe ions

Chemical tools for detecting Fe ions

Fe3+‐Responsive Micelle Based on an Amphiphilic Polymer and a Rhodamine B‐Containing Amphiphile in Aqueous Media

A triazole‐based fluorescence probe for detecting Hg2+ ions and its biological application

Contact Info

Product

Resources

About

Fe³⁺‐Responsive Micelle Based on an Amphiphilic Polymer and a Rhodamine B‐Containing Amphiphile in Aqueous Media

A triazole‐based fluorescence probe for detecting Hg²⁺ ions and its biological application