Novel Fluorescent Probe toward Fe<sup>3+</sup> Based on Rhodamine 6G Derivatives and Its Bioimaging in Adult Mice, <i>Caenorhabditis elegans</i>, and Plant Tissues

Zhang, Jie; Chen, Bai; Chen, Meng-Yu; Yue, Shao-Yun; Qin, Yuxin; Liu, Xinyu; Xu, Meng-Ya; Zheng, Qijun; Zhang, Lin; Li, Ruiqian; Qiao, Rui; Qu, Changqing

doi:10.1021/acsomega.1c00440

Cited by 11 publications

(4 citation statements)

References 42 publications

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“…Studies with L-02 cells and PC-12 rat pheochromocytoma cells confirmed its application in detecting exogenous Fe(III) in subcellular regions. Dyes 78 , 79 , 80a , and 81 – 83 similarly contain an amide linkage between the rhodamine and recognition unit, and respond to Fe(III) through a spirolactam ring-opening. − In addition, dyes 80b , 84 , and 85 are examples in which two rhodamine units were joined together in such a manner that the probe can coordinate two ferric ions simultaneously, resulting into a strong turn-on response (560-585 nm) owing to the ring opening of rhodamine. ,, These probes were then employed for cellular imaging of Fe(III) ions in PC-12, human gastric cell line (SGC-7901) and MCF-7 cells respectively. Dyes RBCS ( 86 ) and RBTM ( 87 ) are two thioamide-containing rhodamine B-based probes that selectively bind to Fe(III) in the ring-opened form to produce a strong fluorescence emission. , These probes were employed in HeLa and MKN-45 human gastric cancer cells, respectively, to visualize exogenously added ferric ions.…”

Section: Fluorescent Sensors For Ironmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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Although transition metals constitute less than 0.1% of the total mass within a human body, they have a substantial impact on fundamental biological processes across all kingdoms of life. Indeed, these nutrients play crucial roles in the physiological functions of enzymes, with the redox properties of many of these metals being essential to their activity. At the same time, imbalances in transition metal pools can be detrimental to health. Modern analytical techniques are helping to illuminate the workings of metal homeostasis at a molecular and atomic level, their spatial localization in real time, and the implications of metal dysregulation in disease pathogenesis. Fluorescence microscopy has proven to be one of the most promising non-invasive methods for studying metal pools in biological samples. The accuracy and sensitivity of bioimaging experiments are predominantly determined by the fluorescent metal-responsive sensor, highlighting the importance of rational probe design for such measurements. This review covers activity-and binding-based fluorescent metal sensors that have been applied to cellular studies. We focus on the essential redox-active metals: iron, copper, manganese, cobalt, chromium, and nickel. We aim to encourage further targeted efforts in developing innovative approaches to understanding the biological chemistry of redox-active metals. CONTENTS5908 8.2. Activity-Based Fluorescent Sensors for Ni(II) 5911 9. Outlook 5911 Author Information 5912 Corresponding Authors 5912

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Section: Fluorescent Sensors For Ironmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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“…Guo 2014; Ozdemir, Zhang, and Guo 2018;Aydin et al 2020). Another mechanism without the involvement of direct Fe 3þ -coordination, instead, a Fe 3þ -induced ring-opening of the rhodamine spiroclic lactone was proposed recently in a new rhodamine-based Fe 3þ probe RXY (Zhang et al 2021). However, RXY has a much lower Fe 3þ -binding constant (3.0 Â 10 4 M À1 ) (Zhang et al 2021) than for RhPK (1.54 Â 10 7 M À1 ).…”

Section: Reversibility In Fe 31 -Bindingmentioning

confidence: 99%

“…Interestingly, a number of "turn-on" or ratio metric probes for Fe 3þ have recently been reported (Aydin, Wei, and Guo 2012;Wei et al 2012;Zhu et al 2016;Zhou et al 2017;Qiao et al 2018;Wu et al 2019;Shellaiah et al 2020;Ghosh et al 2020;Li et al 2016;Liu et al 2020;Yang et al 2020;Kaur, Kaur, and Kumar 2018;Zhang et al 2014;Lohani and Lee 2010;Heng et al 2008;Ackerman, Lee, and Chang 2017;Lee et al 2016;Wang et al 2010;Mir et al 2019;Qiu et al 2014;Vishaka et al 2019;Kim et al 2019;Jothi et al 2021;Gao et al 2020;Zhang et al 2021;Wei et al 2010). Many iron probes, especially turn-on and ratiometric Fe 3þ probes, have been discussed in detail in recent review papers Crisponi 2019, Sun, Sun, andGuo 2021).…”

Section: Introductionmentioning

confidence: 99%

“…A recently developed rhodamine linked dansylamide Fe 3þ -selective ratiometric probe DRhFe also operates at pH > 5 (Gao et al 2020). A more recent rhodamine 6 G-based Fe 3þ -selective sensor LXY works at pH between 6.8-8.0 (Zhang et al 2021). All of these sensors are affected by the acidic pH in endosomes or lysosomes and thus do not have the capability to detect Fe 3þ in these cellular compartments.…”

Section: Introductionmentioning

confidence: 99%

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Highly Selective Fluorescent Probe With an Ideal pH Profile for the Rapid and Unambiguous Determination of Subcellular Labile Iron (III) Pools in Human Cells

et al. 2022

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A convenient tool for detecting iron ions in subcellular structures is desired for better understanding its roles in biological systems. In this work, a new Fe 3þ sensor, 2-(2-((1-(6-acetylpyridin-2-yl)ethylidene)amino)ethyl)-3',6'-bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one (RhPK), which operates across the entire cellular pH range and is capable of unambiguously detecting Fe 3þ ion in live human cells at subcellular resolution, is reported. The sensor exhibits high selectivity and sensitivity toward Fe 3þ with a rapid fluorescence response and a 12-fold increase in intensity upon the addition of 1 equivalent Fe 3þ at pH 7.3. RhPK forms a 1:1 complex with Fe 3þ with an apparent binding constant 1.54 Â 10 7 M À1 and a detection limit of 50 nM. The sensor is stable between pH 4.2 and 9.0 and operates across the whole cellular pH range. Cell imaging demonstrates the ability of the sensor to unambiguously detect basal level Fe 3þ as well as its dynamic changes in real-time in live cells at subcellular resolution, with one labile Fe 3þ pool identified in mitochondria in human primary fibroblast (ws1) cells for the first time and two Fe 3þ pools confirmed in mitochondria and endo/lysosomes in human SH-SY5Y neuroblastoma cells, suggesting different cell types have distinctive Fe 3þ storage in subcellular compartments. The RhPK probe is powerful for rapid and sensitive bioimaging of Fe 3þ at subcellular level, enabling the unambiguous detection of labile Fe 3þ pools at the entire cellular pH range, which is of great significance to understand the biological chemistry of Fe 3þ and its roles in physiological processes and diseases.

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A new intramolecular proton transfer (ESIPT)‐based fluorescent probe for selective visualization of cyanide ion

Chen

Zhang

Wen

et al. 2022

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Fluorescent probes for detection of CN − still have many limitations, such as small Stokes shift, irreversible, and background interference, which hamper their applications for on-site detection and bioimaging of CN − . In this work, we design a new CN − -activatable fluorescent probe (named AHMM) containing an ESIPT (excited-state intramolecular proton transfer) and hydrogen bond features, which show a large Stokes shift (225 nm) and molecular structural reversible detection. The probe AHMM exhibits an excellent selectivity for CN − without any interference from other anions in aqueous DMSO system. Furthermore, the mechanism of the interaction of AHMM with CN − is concluded by various experiments. The limit of detection of AHMM for CN − is calculated as low as 4.47 × 10 −8 M, lower than the concentration of CN − deemed acceptable by WHO (World Health Organization). AHMM can recognize CN − in tap water quantitatively and on-site by a smartphone APP. Moreover, food samples such as almond and cassava including CN − are visualized by fluorescence imaging. In addition, the probe shows practical applications of CN − imaging in cells and mice. This concept can be applied for designing multifunctional fluorescent probes with ESIPT and reversible characteristics for detection of CN − .

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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

Cited by 11 publications

References 42 publications

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Highly Selective Fluorescent Probe With an Ideal pH Profile for the Rapid and Unambiguous Determination of Subcellular Labile Iron (III) Pools in Human Cells

A new intramolecular proton transfer (ESIPT)‐based fluorescent probe for selective visualization of cyanide ion

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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

Cited by 11 publications

References 42 publications

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Highly Selective Fluorescent Probe With an Ideal pH Profile for the Rapid and Unambiguous Determination of Subcellular Labile Iron (III) Pools in Human Cells

A new intramolecular proton transfer (ESIPT)‐based fluorescent probe for selective visualization of cyanide ion

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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