One-step synthesis of rhodamine-based Fe3+ fluorescent probes via Mannich reaction and its application in living cell imaging

Zhang, Mengyao; Shen, Chuanchuan; Jia, Ting; Qiu, Jian‐Wen; Zhu, Hongmin; Gao, Yong

doi:10.1016/j.saa.2020.118105

Cited by 23 publications

(7 citation statements)

References 35 publications

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“…To date, many colorimetric fluorescent probes consisted of large π-conjugated system such as fluorescein ( 36 ), rhodamine ( 37 ), coumarin ( 38 , 39 ), anthracene ( 40 ), and BODIPY ( 41 , 42 ) with obvious spectra absorption or strong fluorescence have been successfully synthesized ( 43 ). Among those probes, the fluorescein family dyes have excellent spectroscopic properties, such as long absorption and emission wavelengths, high extinction coefficients, high quantum yields, and excellent photostability, which are always introduced to construct optical sensors for metal ions ( 44 ).…”

Section: Introductionmentioning

confidence: 99%

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

Leng

She²,

Jin³

et al. 2022

Front. Nutr.

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Copper is a vital trace metal in human body, which plays the significant roles in amounts of physiological and pathological processes. The application of copper-selective probe has attracted great interests from environmental tests to life process research, yet a few of sensitive Cu2+ tests based on on-site analysis have been reported. In this paper, a novel fluorescein-based fluorescent probe N4 was designed, synthesized, and characterized, which exhibited high selectivity and sensitivity to Cu2+ comparing with other metal ions in ethanol–water (1/1, v/v) solution. The probe N4 bonded with Cu2+ to facilitate the ring-opening, and an obvious new band at 525 nm in the fluorescence spectroscopy appeared, which could be used for naked-eye detection of Cu2+ within a broad pH range of 6–9. Meanwhile, a good linearity between the fluorescence intensity and the concentrations of Cu2+ ranged 0.1–1.5 eq. was observed, and the limit of detection of N4 to Cu2+ was calculated to be as low as 1.20 μm. In addition, the interaction mode between N4 and Cu2+ was found to be 1:1 by the Job's plot and mass experiment. Biological experiments showed that the probe N4 exhibited low biological toxicity and could be applied for Cu2+ imaging in living cells. The significant color shift associated with the production of the N4-Cu2+ complex at low micromolar concentrations under UV light endows N4 with a promising probe for field testing of trace Cu2+ ions.

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Section: Introductionmentioning

confidence: 99%

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

Leng

She²,

Jin³

et al. 2022

Front. Nutr.

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“…However, their disadvantages including low specificity, complicated sample preparation, and expensive instruments hindered their wide applications. − Recently, increasingly more attention has been paid to the fluorescence method for the detection of Fe 3+ because of its ability to detect Fe 3+ rapidly, sensitively, and selectively. And it could not cause any damage to cell. − To date, many fluorescent probes for Fe 3+ have been synthesized successfully, which included coumarin, , anthracene, BODIPY, , cyanine, and rhodamines . Among these probes, rhodamine 6G has many advantages over other derivatives, including high extinction coefficients, high quantum yields, excellent photostability, and emission wavelengths. − However, most rhodamine derivatives were obtained through CN, but a few compounds linked by amide have been reported. − It was clear that the amide-modified rhodamine 6G derivatives have more potential coordination sites to bind metal ions than CN .…”

Section: Introductionmentioning

confidence: 99%

“…14−18 To date, many fluorescent probes for Fe 3+ have been synthesized successfully, which included coumarin, 19,20 anthracene, 21 BODIPY, 22,23 cyanine, 24 and rhodamines. 25 Among these probes, rhodamine 6G has many advantages over other derivatives, including high extinction coefficients, high quantum yields, excellent photostability, and emission wavelengths. 26−31 However, most rhodamine derivatives were obtained through CN, but a few compounds linked by amide have been reported.…”

Section: ■ Introductionmentioning

confidence: 99%

Novel Fluorescent Probe toward Fe³⁺ Based on Rhodamine 6G Derivatives and Its Bioimaging in Adult Mice, Caenorhabditis elegans, and Plant Tissues

Zhang

Chen

et al. 2021

ACS Omega

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A new fluorescent probe LXY based on the rhodamine 6G platforms has been designed, synthesized, and characterized, which could recognize Fe3+ effectively in HEPES buffer (10 mM, pH = 7.4)/CH3CN (2:3, v/v). And the distinct color change and the rapid emergence of fluorescence emission at 550 nm achieved “naked eye” detection of Fe3+. The interaction mode between them was achieved by Job’s plot, MS, SEM, and X-ray single-crystal diffraction. Importantly, the crystal structures proved that Fe3+ could induce the rhodamine moiety transform the closed-cycle form to the open-cycle form. But it is interesting that Fe3+ did not appear in the crystal structures. Meanwhile, the limit of detection (LOD) of LXY to Fe3+ was calculated to be 3.47 × 10–9. In addition, the RGB experiment, test papers, and silica gel plates all indicated that the probe LXY could be used to distinguish Fe3+ quantitatively and qualitatively on-site. Moreover, the probe LXY has also been successfully applied to Fe3+ image in Caenorhabditis elegans, adult mice, and plant tissues. Thus, LXY was considered to have some potential for application in bioimaging.

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“…Owing to their advantage over other analytical methods which include atomic absorption spectrometer (ABS) and inductively coupled plasma mass spectrometry (ICP-MS), fluorescent probes have received more and more attention in the past few decades (Ge et al, 2013 ; Chen et al, 2017 ; Han et al, 2017 ; Wang et al, 2017 ; Zhou et al, 2017 ; Liu et al, 2018 ; Tian et al, 2019 ; Pipattanawarothai and Trakulsujaritchok, 2020 ). Therefore, various kinds of probes have been reported, such as rhodamines (Zhang et al, 2020 ), phenanthroline (Nawaz et al, 2018 ), anthracene (Shree et al, 2019 ), coumarin (Qi et al, 2018 ; Qu et al, 2019 ; Zhu et al, 2020 ), and BODIPY (Cetinkaya et al, 2019 ; Fang et al, 2019 ; Xia et al, 2019 ). In contrast with other derivatives, coumarin derivatives represent good fluorescence properties, excellent photostability, and easy preparation (Zhang et al, 2014 ; Hossain et al, 2017 ; Kumari et al, 2017 ).…”

Section: Introductionmentioning

confidence: 99%

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

Zhang

Chen

et al. 2020

Front. Chem.

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The fluorescent probe L , based on naphthalimide-modified coumarin, was designed, synthesized, and characterized, which could recognize Cu 2+ from other cations selectively and sensitively in HEPES buffer (10 mM, Ph = 7. 4)/CH 3 CN (1:4, V/V). When the probe L interacted with Cu 2+ , the color and the fluorescent intensity changed obviously and it provided the naked-eye detection for Cu 2+ . The recognition mode between them was achieved by Job's plot, IR, MS, SEM, and 1 HNMR. In addition, test strips made from L could still interact with Cu 2+ in tap water effectively. The limit of detection (LOD) of L was 3.5 × 10 −6 M. Additionally, the density functional theory (DFT) calculation method was used to analyze the action mechanism of L toward Cu 2+ . Importantly, the fluorescent probe L could demonstrate favorable selectivity toward Cu 2+ in Caenorhabditis elegans . Thus, L was considered to have some potential for application in bioimaging.

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One-step synthesis of rhodamine-based Fe3+ fluorescent probes via Mannich reaction and its application in living cell imaging

Cited by 23 publications

References 35 publications

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

Novel Fluorescent Probe toward Fe³⁺ Based on Rhodamine 6G Derivatives and Its Bioimaging in Adult Mice, Caenorhabditis elegans, and Plant Tissues

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

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One-step synthesis of rhodamine-based Fe3+ fluorescent probes via Mannich reaction and its application in living cell imaging

Cited by 23 publications

References 35 publications

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

A Highly Sensitive and Selective Fluorescein-Based Cu2+ Probe and Its Bioimaging in Cell

Novel Fluorescent Probe toward Fe3+ Based on Rhodamine 6G Derivatives and Its Bioimaging in Adult Mice, Caenorhabditis elegans, and Plant Tissues

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

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Novel Fluorescent Probe toward Fe³⁺ Based on Rhodamine 6G Derivatives and Its Bioimaging in Adult Mice, Caenorhabditis elegans, and Plant Tissues