Epub 2021 Mar 25. Yang et al. 1 N HCl, THF, rt, 12 = 55% over 2 steps; vii) TFA, CH2Cl2, rt, 13 = 55%, 14 = 84%; viii) N-phenyl-bis-(trifluoromethanesulfonimide), K2CO3, CH3CN, 0 C, to rt, 15 = 69%, 16 = 57%; ix) benzophenone imine, Pd(OAc)2, Cs2CO3, BINAP, toluene, 105 C; x) aq. Horsman M.R., Mortensen L.S., Petersen J.B., Busk M., Overgaard J. Meanwhile, their recognition mechanism and applications are particularly highlighted. Kikuchi, K. Design, synthesis and biological application of chemical probes for bio-imaging. focused in 2015 on the Hg2+-sensing behavior of rhodamine-derived probe 38 (Shen et al. PubMed, Jiqu, H.; Qixia, Y. Chem. 2015, Jung et al. Rhodamine and fluorescein, as the typical representatives of xanthene, have been paid much attention in biological imaging due to their high absorption coefficient, high fluorescence quantum yield, and water solubility (Kim et al. The fluorescence quantum yield of 5 with 15 equivalents of Cu2+ was 0.26 at an excitation wavelength of 530 nm, which was higher than what was previously reported. His research interests focus on developing fluorescent chemosensors. It is expected that the future development of metal ion probes will become more theory application driven. Org. Spectrochim. To explore the importance of the chelating ring size, nature, and orientation of coordinating atoms in the metal ion selective complex formation, they further synthesized three fluorescent probes 810 using a similar strategy (Chereddy et al. had a significant innovation in a new fluoroionphore-ionic liquid hybrid-based strategy to improve the performance of classic fluoroionphores via a synergistic extraction effect and realize simultaneous instrument-free detection and removal of heavy metal ions (HMIs; Jin et al. Chereddy, N. R.; Janakipriya, S.; Korrapati, P. S.; Thennarasu, S.; Mandal, A. Acidic pH; Fluorescence; Photoinduced electron transfer; Sensing; Xanthene. Inorg. 2013). Finally, probe 12 can be applied in the imaging of Cu2+ in living cells (Figure 10). Fujii T., Kamiya M., Urano Y. 2014a). PubMed, Wang, H.-H.; Xue, L.; Yu, C.-L.; Qian, Y.-Y. In addition, probe 56 exhibited high selectivity to calcium without interference from other metal ions. reported a novel rhodamine-based highly sensitive and selective colorimetric off-on fluorescent probe 29 for Hg2+ ions designed and prepared using the well-known thiospirolactam rhodamine chromophore and furfural hydrazone as signal-reporting groups (Wang et al. Lett.2014, 25, 7376.10.1016/j.cclet.2013.10.027Search in Google Scholar, Hayashi, G.; Okamoto, A. Based on the high selectivity of the BAPTA ligand, an optically controlled Ca2+ probe was developed to mimic natural calcium oscillations (Wu et al. A new rhodamine B-based fluorescent probe 39 containing pyrene moiety was designed and synthesized by Yao in 2016, which showed a colorimetric and fluorometric sensing ability for Hg2+ with high selectivity over other metal ions (Rui et al. He is now a professor at both Fourth Military Medical University and Northwest University. Actuators B Chem.2013b, 176, 482487.10.1016/j.snb.2012.07.035Search in Google Scholar, Yang, M.; Meng, W.; Ding, Q.; Su, N.; Liu, X.; Zhang, M.; Yang, B. Xanthene-based Fluorescence Turn-on Probe for Highly Acidic pH Range in Aqueous Solution . This work is funded by Science and Engineering Research Board (SERB), India (Project no. Grimm J.B., Lavis L.D. Inorg. 2011). https://doi.org/10.1039/c5sc01113b, Kim S, Fujitsuka M, Tohnai N et al (2015) The unprecedented J-aggregate formation of rhodamine moieties induced by 9-phenylanthracenyl substitution. A DPA unit is well known to be a classical receptor for zinc ions, which has been widely used for the design and development of various fluorescent probes for monitoring Zn2+ ion. Commun.2014, 50, 8487.10.1016/j.inoche.2014.10.026Search in Google Scholar, Carter, K. P.; Young, A. M.; Palmer, A. E. Fluorescent sensors for measuring metal ions in living systems. Nat Rev Mol Cell Biol 8:622632 The data from Jobs method exhibited a maximum absorbance when the molecular fraction of 1 was close to 50%, which also suggests a 1:1 stoichiometry for the 1-Cu2+ complex (Figure 4). His research interests include asymmetric catalysis, synthesis of chiral drugs, resolution of racemic compounds, analysis, and separation and determination of optical purity of chiral compounds. Therefore, a novel rhodamine-quinoline derivative-based probe 3 was designed and synthesized by Feng et al. Anal. Reprinted from Yang et al. devised a strategy for repurposing existing intensity-based probes for quantitative applications (Zhang et al. Most importantly, probe 34 could be employed to monitor Hg2+ in living cells using fluorescent imaging technique with satisfied results. Hanaoka et al. 1997). The fluorescence intensity was remarkably increased upon the addition of Cu2+ within 1 or 2 min, whereas the other 16 metal ions (Na+, Mg2+, Al3+, K+, Ca2+, Cr3+, Mn2+, Fe3+, Co2+, Ni2+, Hg2+, Zn2+, Ba2+, Pb2+, Ag+, and Cd2+) caused no significant effect. Tsien, R. Y. Biol.2004, 11, 16591666.10.1016/j.chembiol.2004.09.013Search in Google Scholar Chem. Fan, Based on our previous work, in 2015, we presented two rhodamine-based probes 47 and 48 for the specific monitoring of Fe3+ in cellular systems with sufficient high selectivity and sensitivity (Ma et al. Design strategies and progress on xanthene-based fluorescent probe for metal ions. Probes 3948 based on rhodamine with amine for detecting Fe3+. Recognition mechanism of probe 46 with Fe3+. Epub 2019 Sep 20. Copyright Clearance Center request page. As a library, NLM provides access to scientific literature. Coord Chem Rev 427:213550, Wu L, Huang C, Emery BP et al (2020) Frster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents. (2013). If you are an author contributing to an RSC publication, you do not need to request permission PubMed, Chu, K.-H.; Zhou, Y.; Fang, Y.; Wang, L.-H.; Li, J.-Y. Ma, Siyue, Wang, Yaqi, She, Mengyao, Wang, Shen, Yang, Zheng, Liu, Ping, Zhang, Shengyong and Li, Jianli. The synthetic strategy employed in the design of the ditopic probes offers distinct advantages toward facile structural modifications of both the fluorophore and the Zn2+-binding motifs. Fortunately, a DPA unit can be developed as fluorescent probes for Zn2+ with advantages of tunable emission wavelengths, high selectivity, excellent sensitivity, and good cell permeability. Design strategies and progress on xanthene-based fluorescent probe for metal ions. Chem. PubMed Reprinted from Yang et al. This is a preview of subscription content, access via https://doi.org/10.1016/j.bmcl.2013.12.025, Bender A, Woydziak ZR, Fu L et al (2013) Novel acid-activated fluorophores reveal a dynamic wave of protons in the intestine of caenorhabditis elegans. Reviews in Analytical Chemistry, Vol. https://doi.org/10.1002/asia.201901149, Hou JT, Ren WX, Li K et al (2017) Fluorescent bioimaging of pH: From design to applications. J Am Chem Soc 140:59255933. PubMed, Li, J.; Cheng, F.; Huang, H.; Li, L.; Zhu, J.-J. Development of fluorescent probes based on protection-deprotection of the key functional groups for biological imaging. If you want to reproduce the whole article Chem. Although BAPTA is a highly selective ligand for calcium, the sensitivity of probes possessing the moiety still needs to be improved. We use cookies to distinguish you from other users and to provide you with a better experience on our websites. Xanth-NPr exhibited quenched fluorescence as long as it is present in neutral or moderately acidic conditions. Analyst2012b, 137, 34663469.10.1039/c2an35559kSearch in Google Scholar Until now, various fluorescent probes have been developed based on a diverse range of fluorophores, such as cyanine, BODIPY, xanthene, coumarin, pyrene, and 1,8-naphthalimide, with different excitation and emission wavelengths (Chen et al. Soc. Moreover, fluorescence images of histamine-induced calcium oscillations in HeLa cells using these probes were employed to visualize changes in cytoplasmic calcium concentration. B. Solvent-assisted selective detection of sub-micromolar levels of Cu, Chu, K.-H.; Zhou, Y.; Fang, Y.; Wang, L.-H.; Li, J.-Y. (2015). The fluorescent moieties coumarin and xanthene (R6GCP) combined in a single molecule was designed and synthesized. The binding analysis using Jobs plot suggested 1:1 stoichiometry for the complexes formed for Hg2+. Introduction Fluorescent molecular probes are essential. Ding, Y.; Tang, Y.; Zhu, W.; Xie, Y. Fluorescent and colorimetric ion probes based on conjugated oligopyrroles. A rhodamine-based fluorescent probe for Cu(II) determination in aqueous solution. Conceptualization: Bhanu Priya, Roopa; Methodology: Bhanu Priya, Roopa, Naresh Kumar; Funding acquisition: Roopa; Investigation: Bhanu Priya, Vibha Mahajan, Roopa; Resources: Bhanu Priya, Vibha Mahajan; Supervision: Roopa, Naresh Kumar; Software: Naresh Kumar; Writing original draft: Priya Bhanu, Roopa; Writing review & editing: Roopa, Naresh Kumar. and transmitted securely. Chem. 14). However, there is a major limit on the application of these small-molecule ratiometric probes in quantifying mobile zinc due to the complex syntheses, small dynamic ranges, and narrow gaps between the wavelengths. Dyes Pigm.2012, 92, 13371343.10.1016/j.dyepig.2011.09.014Search in Google Scholar, She, M.; Yang, Z.; Hao, L.; Wang, Z.; Luo, T.; Obst, M.; Liu, P.; Shen, Y.; Zhang, S.; Li, J. You do not have JavaScript enabled. Recognition mechanism of probe 14 with Cu2+. Upon coordination with Fe3+, probes 4144 displayed good brightness and fluorescent enhancement. Chemical and schematic illustration of the preparation of SFIC MNPs probe 16 for Cu2+. Trends Mol Med 8:512519, Hunt JF, Fang K, Malik R et al (2000) Endogenous airway acidification: Implications for asthma pathophysiology. Recognition mechanism of probe 28 with Hg2+. Sarmiento AM, Grande JA, Lus AT et al (2018) Negative pH values in an open-air radical environment affected by acid mine drainage. This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. https://doi.org/10.1002/jcc.540141112, Kinashi K, Lee KP, Matsumoto S et al (2012) Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes. introduced rigid 8-aminoquinoline moiety and flexible 2-aminopyridine into rhodamine chromophore to synthesize fluorescent probes to evaluate the effect of complexation with cations (Huang et al. PubMed On the gradual addition of Hg2+ to a solution of probe 32, a new fluorescence emission band centered at 594 nm appeared, which was due to the ring opening of the rhodamine thiospirolactam. The model probe along with theoretical calculations was employed to explain the role of the PET process in regulating the fluorescence behavior of Xanth-NPr. J. ; Xue, Y.-L.; Zhang, Z.; Wu, X.-Y. Rev.2016, 45, 11821196.10.1039/C5CS00567ASearch in Google Scholar, Ge, F.; Ye, H.; Zhang, H.; Zhao, B.-X. His research interests focus on developing fluorescent chemosensors. Chem. Aydin, Z.; Wei, Y.; Guo, M. An off-on optical sensor for mercury ion detection in aqueous solution and living cells. To request permission to reproduce material from this article, please go to the A linear Stern-Volmer curve was observed with short response time. peer-reviewed at the time of posting. PubMed, Lee, M. H.; Kim, J. S.; Sessler, J. L. Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules. The structural rigidity introduced by multiple n-propylene bridges of rhodamine 101 moieties can shift the absorption and emission maxima to longer wavelengths, with higher molar extinction coefficients and higher quantum yields compared to rhodamine B. The 1:1 stoichiometric structure between probe 18 and Cu2+ could be formed because the copper ions are cooperated with the O atom of introduced moiety, O atom of carbonyl, and N atom of rhodamine B hydrazide. Rev.2015, 44, 45964618.10.1039/C4CS00298ASearch in Google Scholar, Liu, W. Y.; Li, H. Y.; Zhao, B. X.; Miao, J. Y. Synthesis, crystal structure and living cell imaging of a Cu2+-specific molecular probe. Actuators B Chem2013, 177, 2733.10.1016/j.snb.2012.10.077Search in Google Scholar, Woodroofe, C. C.; Masalha, R.; Barnes, K. R.; Frederickson, C. J.; Lippard, S. J. Membrane-permeable and -impermeable sensors of the Zinpyr family and their application to imaging of hippocampal zinc in vivo. 2011). Subsequently, the emission band changed with a blue shift in the maximum to 582 nm, which might be accounted for the intermolecular electron transfer between probe 32 and Hg2+. Zhao et al. (2017). The fluorescence intensity was significantly increased by about 40-fold with 10 equivalents of added Cu2+. Song F., Watanabe S., Floreancig P.E., Koide K. Oxidation-Resistant Fluorogenic Probe for Mercury Based on Alkyne Oxymercuration. Epub 2017 Jan 12. Zhang, J.; Yu, C.; Qian, S.; Lu, G.; Chen, J. This is a novelty design of the ratiometric probe of Fe3+ due to the CHEF process generated along with the PET process suppressed simultaneously. It is available as a dark orange/red powder slightly soluble in water and alcohol. ; Feng, Y.-C.; Huang, H.-Q. In Vivo Imaging of Intraperitoneally Disseminated Tumors in Model Mice by Using Activatable Fluorescent Small-Molecular Probes for Activity of Cathepsins. In addition, probe 47 was also found to be more sensitive with a detection limit of 0.9 m than the 5.0 m limitation of probe 48, indicating the superior properties of probe 47. 16), by the photoinduced electron transfer (PET) process: while the TMRM fluorescent moiety (xanthene, green . It exhibited a dual emission mode for the detection of Au3+ and a single emission mode for the detection of Hg2+ (Figure 22). Xanth-NPr is designed on the principle of photoinduced electron transfer (PET), which controls the fluorescence profile of the probe. PubMed, Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Luminescent chemodosimeters for bioimaging. Barigelletti F. Effect of Temperature on the Photophysics of Rhodamine 101 in a Polar Solvent. https://doi.org/10.1016/j.dyepig.2011.05.024, Kim S, Tachikawa T, Fujitsuka M, Majima T (2014) Far-red fluorescence probe for monitoring singlet oxygen during photodynamic therapy. Experimental results indicated that probe 14 can provide a rapid, selective, and sensitive response to Cu2+ with a linear dynamic range from 0.667 to 240 mol/l. Spectrochim. In 2012, a new probe 4 based on rhodamine B with 1,2,4-triazole as subunit was synthesized and characterized by Zhang (Zhang et al. In general, according to the different recognition mechanisms of these reported fluorescent probes, they can be divided into two categories: reversible and irreversible probes (Kartha et al. 2008, Chen et al. 2011a). Nat Rev Cancer 11:671677, Estrella V, Chen T, Lloyd M et al (2013) Acidity generated by the tumor microenvironment drives local invasion. The disorder of zinc metabolism has been correlated to epilepsy, diabetes, infantile diarrhea, and Alzheimer's disease because of its significance in . Thus, accurate detection of ONOO in physiological conditions is imperative for elucidating its functions. Adding mercury ions into the aqueous solution, its fluorescence intensity was enhanced significantly, whereas its color was changed from colorless to pink. Dujols, V.; Ford, F.; Czarnik, A. W. A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water. Detection of nitroaromatic explosives with fluorescent molecular assemblies and pi-gels. Especially, over the past decade, fluorescent probes based on xanthene have been focused on detecting those metal ions in living systems (Kikuchi 2010, Hayashi and Okamoto 2013, He et al. Synthesis and StructureActivity Relationships for 2,4-Dinitrobenzamide-5-mustards as Prodrugs for the Escherichia coli nfsB Nitroreductase in Gene Therapy. CHCl3 or Pd(PPh3)4), ligand (BINAP or Xantphos), Cs2CO3, toluene, 105 C, 7 = 20%, 8 = 41 %, 9 = further reaction without purification, 10 = 100%, 11 = 47%; vi) aq. which showed a highly Cu2+-selective fluorescence enhancement response in an aqueous pH 7 (Mao et al. ; Wang, S.; Sun, Y.-J. PubMed Central, Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Fluorescent and colorimetric probes for detection of thiols. B. Tuning copper(II) ion selectivity: the role of basicity, size of the chelating ring and orientation of coordinating atoms. 8600 Rockville Pike A xanthene-based probe, Xanth-NPr, is developed as a molecular system that exhibits sensitivity for the highly acidic environments with fluorescence turn-on behavior. As the most abundant trace element, iron plays an obligatory role in many biochemical processes at the cellular level. However, in the highly acidic pH range, it displayed a strong red-colored fluorescence at 592 nm as the protonation of dipropylaniline moiety inhibits the PET process. Int. Reprinted from Wang et al. Spectrosc.2015, 135, 172179.10.1016/j.saa.2014.07.007Search in Google Scholar Proc. * National Library of Medicine Xanthene fluorescent probes with DPA structure for detecting Zn2+. In 2011, our group introduced benzothiazole moiety for the first time to synthesize a turn-on probe 40 based on rhodamine B exhibiting high sensitivity and selectivity toward Fe3+ in methanol solution (Yin et al. Anal Chim Acta. Nat Rev Mol Cell Biol 8:622632, Article 36 (Issue 2), pp. Studies manifested that 11-Cu complex is selective and fully reversible in the presence of sulfide anions. ; Zhao, B.-X. Y. Wu, A. Shi, Y. Li, H. Zeng, X. Chen, J. Wu and X. Google Scholar, Mboge M, Mahon B, McKenna R, Frost S (2018) Carbonic anhydrases: role in pH control and cancer. The structure of Xanth-NPr contains the dipropylaniline group as a PET promoting unit. Keywords: Chem Soc Rev 49:51105139, Roopa, Kumar N, Kumar M, Bhalla V (2019) Design and applications of small molecular probes for calcium detection. Loas, A.; Radford, R. J.; Lippard, S. J. Nat Rev Microbiol 9:330343, Webb BA, Chimenti M, Jacobson MP, Barber DL (2011) Dysregulated pH: A perfect storm for cancer progression. Either its excess or deficiency has a great influence on human and animal health. This phenomenon likely resulted from the removal of Fe3+ from the binding complexes, resulting in the reconstitution of the spirolactam ring in the probes, thus indicating the reversible property of the probes. Read more about how to correctly acknowledge RSC content. Kamiya M., Asanuma D., Kuranaga E., Takeishi A., Sakabe M., Miura M., Nagano T., Urano Y. -Galactosidase Fluorescence Probe with Improved Cellular Accumulation Based on a Spirocyclized Rhodol Scaffold. The efficient energy transfer between the up-conversion host and the probes was analyzed and confirmed by spectral analysis and emission decay lifetime comparison. Fluorescence, Imaging probes, Peptides and proteins, Abstract Fluorophore bioconjugation to proteins, nucleic acids, and other important molecules can provide a powerful approach to sensing, imaging, and quantifying chemical and biological processes. Please enable it to take advantage of the complete set of features! Please enable JavaScript Humez S, Monet M, van Coppenolle F et al (2004) The role of intracellular pH in cell growth arrest induced by ATP. Xanth-NPr is designed on the principle of photoinduced electron transfer (PET), which controls the fluorescence profile of the probe. Bethesda, MD 20894, Web Policies J. Org. ; Miao, J.-Y. Authors Bhanu Priya 1 , Vibha Mahajan 1 , Naresh Kumar 2 , Roopa 3 Affiliations 1 Department of Chemical Sciences, IKG-Punjab Technical University, Kapurthala, 144603, Punjab, India. https://doi.org/10.1016/j.scitotenv.2018.06.381, https://doi.org/10.1152/ajpcell.00578.2003, EEQ/2019/000325/Science and Engineering Research Board, Luzio JP, Pryor PR, Bright NA (2007) Lysosomes: Fusion and function. These probes, in which a benzo-amide unit is linked to BAPTA, were employed to study protein-expressing animals and cultured cells. J. Org. A rhodamine-derived probe 37 was grafted onto the backbone of MCM-41 through a silane coupling reagent to control its loading content. Proc Natl Acad Sci U S A 93:654658. Accessibility please go to the Copyright Clearance Center request page. PubMed, Fernandez, A.; Vendrell, M. Smart fluorescent probes for imaging macrophage activity. Recognition mechanism of fluorescent probes based on xanthene for detecting metal ions. This may take some time to load. Spectrosc.2015, 149, 487493.10.1016/j.saa.2015.04.075Search in Google Scholar Rui, Q. Q.; Zhou, Y.; Fang, Y.; Yao, C. Spirolactone and spirothiolactone rhodamine-pyrene probes for detection of Hg. Recent progress in the fluorescent probe based on spiro ring opening of xanthenes and related derivatives. Chem.2006, 45, 555561.10.1021/ic051113sSearch in Google Scholar Yang, Z.; She, M.; Zhang, J.; Chen, X.; Huang, Y.; Zhu, H.; Liu, P.; Li, J.; Shi, Z. We hope that this review entices the scientific community into designing ever more highly sensitive and selective fluorescent probes for metal ions and might educate students new to the field as well as provide guidance in the selection of appropriate molecular modes for future applications in the environment and bioimaging. Chem.2012, 84, 42534257.10.1021/ac300676vSearch in Google Scholar 2014, Properzi and Marcantoni 2014, Chen et al. Chem Soc Rev 49:143179, Kumar N, Roopa, Bhalla V, Kumar M (2021) Beyond zinc coordination: Bioimaging applications of Zn(II)-complexes. 2012) and three probes 4244 (Yang et al. Reactivity of reduced fluorescein and typical fluorescein fluorophores on alkylation and amide coupling reactions. The Cu2+ recognition process is reversible and barely interfered by other coexisting metal ions, including Hg2+, Ag+, Pb2+, Sr2+, Ba2+, Cd2+, Ni2+, Co2+, Fe2+, Fe3+, Mn2+, Cu2+, Zn2+, Al3+, Cr3+, Mg2+, K+, and Na+. Upon mixing with Fe3+ in CH3CN/H2O (1:1, v/v), the spirolactam of 51 was opened, which resulted in the dramatic enhancement with 55 equivalents of added Fe3+, both fluorescence and absorbance intensity as well as the color change of the solution. Probe 55, a spiroamido-rhodamine derivative of BAPTA, underwent cycles of reversible transitions between a colorless closed state and a fluorescent open ring (Figure 36). Rec.2013, 13, 209217.10.1002/tcr.201200026Search in Google Scholar In 2016, a new rhodamine probe 18 with a high selectivity for Cu2+ was synthesized by Wang et al. The sensing mechanism was proposed to involve that the addition of Fe3+ induced the N atom of spirolactam to attack the C atom of carbonyl and the ring opening of the spirolactam of rhodamine because Fe3+ coordinates with N atom of benzothiazole of probe 40 by DFT calculations. Xanthene (9H-xanthene, 10H-9-oxaanthracene) is the organic compound with the formula CH2[C6H4]2O. A new probe for fluorescent recognition of Hg, Yin, W.; Cui, H.; Yang, Z.; Li, C.; She, M.; Yin, B.; Li, J.; Zhao, G.; Shi, Z. Facile synthesis and characterization of rhodamine-based colorimetric and off-on fluorescent chemosensor for Fe. Probe 12 formed a 1:1 complex with Cu2+ by cooperating the O and N of the 8-hydroxyquinoline unit and carbonyl O and N of rhodamine hydrazide unit. Schematic of the strategy for studying the structure-property relationships of nine modular Cu2+ fluorescent probes and single-cell scale maps showing the sorption of Cu2+ to cell-EPS-mineral aggregates. 2014). Probe 28 is cell permeable and can visualize the changes of intracellular mercury ions in living cells using fluorescence microscopy (Figure 18). Therefore, it exhibited favorable features, including reversibility, high sensitivity with a large fluorescence enhancement (80-fold) and a low detection limit of 0.19 m, high selectivity for Cu2+ over other heavy and transition metal (HTM) ions in Tris-HCl/ethanol (7:3, v/v, pH 7.4), working well at physiological pH, and good cell membrane permeability. your institution. Activity-Based Sensing and Theranostic Probes Based on Photoinduced Electron Transfer. to this content. Chem. He et al. Goldsmith, C. R.; Lippard, S. J. PubMed 2013a). PubMed, Loas, A.; Radford, R. J.; Lippard, S. J. Detection of LacZ-Positive Cells in Living Tissue with Single-Cell Resolution. His research interests focus on the synthesis and research methods for organic substance, functional biological fluorescent sensors, and organic chemical energy. (A) Recognition mechanism of probes 4144 with Fe3+ and (B) fluorescent images of HeLa cells incubated with 20 m probes 4244 for 30 min. The focus has been on the design strategies to improve the selectivity and sensitivity of fluorescent probes by introducing different recognition moieties. A rhodamine chromene-based turn-on fluorescence probe for selectively imaging Cu2+ in living cell. Ferrichrome-Fe3+ complex and Fe3+-hyroxamate complex. Efficacious Fluorescence Turn-On Probe for High-Contrast Imaging of Human Cells Overexpressing Quinone Reductase Activity. Reagents and conditions: i) CH3I, K2CO3, DMF, rt, 86% for 19, 87% for 24; ii) benzyl bromide, DBU, acetone, rt, 98% for 20, 71% for 25; iii) EDC, HOBt, iPrNEt2, DMF, rt, 50% for 21, 8% for 26. Soc. 2013a, Li et al. Li, X.; Gao, X.; Shi, W.; Ma, H. Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. 2008, Huang et al. Chem.2014, 53, 64916493.10.1021/ic500732zSearch in Google Scholar Sci Total Environ 644:12441253. 5(6)-Carboxyfluorescein has two characteristic properties: It has 2 wavelengths for maximum absorbance (465 and 490nm). It was anticipated that probe 14 can be a good candidate probe and has potential applications for Cu2+ determination. A novel rhodamine-based fluorescent and colorimetric off-on chemosensor and investigation of the recognizing behavior towards Fe3+. Shengyong Zhang is an academician of the National Academy of Engineering. https://doi.org/10.1007/s10895-020-02522-1, Marder S, Gwaltney SR, Scott CN et al (2020) New design strategy toward NIR i xanthene-based dyes. B. Solvent-assisted selective detection of sub-micromolar levels of Cu2+ ions in aqueous samples and live-cells. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. Soc. Rep.2016, 6, 28972.10.1038/srep28972Search in Google Scholar new tab], The content is available under CC BY NC ND 4.0 License, D O I: 10.26434/chemrxiv-2022-pn3x0 [opens in a new tab]. Actuators B Chem.2011, 156, 428432.10.1016/j.snb.2011.04.075Search in Google Scholar, Huang, J.; Xu, Y.; Qian, X. Rhodamine-based fluorescent off-on sensor for Fe3+ in aqueous solution and in living cells: 8-aminoquinoline receptor and 2:1 binding. 2016). Moreover, this probe is applied for in vivo imaging in rat Schwann cells to confirm that it can be used as a fluorescent probe for monitoring Hg2+ in living cells with satisfying results, which further demonstrates its value of practical applications in environmental and biological systems (Figure 19). Acc Chem Res. And its fluorescence emission, at 515nm(max. National Library of Medicine Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Fluorescent and colorimetric probes for detection of thiols. J Am Chem Soc 136:1170711715. https://doi.org/10.1039/c5cc03969j. Li, Y.; Zhao, Y.; Chan, W.; Wang, Y.; You, Q.; Liu, C.; Zheng, J.; Li, J.; Yang, S.; Yang, R. Selective tracking of lysosomal Cu. A model probe Xanth-M without any PET promoting unit was also synthesized. ; Yao, C. Rhodamine-pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: different sensing behavior between a spirolactone and a spirothiolactone. The limit of detection of Cu2+ (3108m) was lower than the values reported for several other rhodamine-based Cu2+ probes. J. Therefore, the aim of this review is to highlight the advances on xanthene-based fluorescent probes for metal ions, which cover mostly works published since 2011. https://doi.org/10.1021/cb300396j, Mohamed MBI, Aysha TS, Elmorsi TM et al (2020) Colorimetric Chemosensor and turn on fluorescence probe for pH monitoring based on xanthene dye derivatives and its bioimaging of living Escherichia coli bacteria. Probe 16 exhibited a clear color change from colorless to pink selectively and sensitively with the addition of Cu2+ in the experiments of UV-visible spectra, and the detection limit was measured up to 5.99106m in solutions of CH3CN/H2O (1:10). Rec.2016, 16, 124140.10.1002/tcr.201500226Search in Google Scholar Tang, Y.; Lee, D.; Wang, J.; Li, G.; Yu, J.; Lin, W.; Yoon, J. U. S. A.2004, 101, 11291134.10.1073/pnas.0308079100Search in Google Scholar The results revealed that probe 2 is a good colorimetric probe to Cu2+ in the red region (Figure 5). (A) Recognition mechanism of probe 4 with Cu2+ and (B) confocal fluorescence images in MCF-7 cells. Here, we report the synthesis, spectroscopic characterization, and applications of 3-phosphonofluoresceins. A sensitive fluorescent probe for Cu. https://doi.org/10.1164/ajrccm.161.3.9911005, Bishop JB, Morris RW, Seely JC et al (1997) Alterations in the reproductive patterns of female mice exposed to xenobiotics. Soc. Actuators B Chem.2013b, 181, 215220.10.1016/j.snb.2013.01.048Search in Google Scholar, Goldsmith, C. R.; Lippard, S. J. Chem.2013, 52, 743752.10.1021/ic301872qSearch in Google Scholar Chereddy, N. R.; Korrapati, P. S.; Thennarasu, S.; Mandal, A. In 2011, a novel fluorescent probe 28 has been reported by Jiang to detect Hg2+ in aqueous buffer solution, which demonstrated high selectivity for sensing Hg2+ with about 383-fold enhancement in fluorescence emission intensity and micromolar sensitivity (Kd=7.5106 mol/l; Wang et al. 2016a). China. DOI: 10.1039/C8AN01107A. 2014 Apr 11;820:146-51. doi: 10.1016/j.aca.2014.02.029. volume31,pages 853860 (2021)Cite this article. Importantly, the NOF2 probe displays good performances for the detection of endogenous ONOO not only in living cells but also in a mouse inflammation model. https://doi.org/10.1021/ja504279r, Despras G, Zamaleeva AI, Dardevet L et al (2015) H-Rubies, a new family of red emitting fluorescent pH sensors for living cells. A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Wu, L.; Dai, Y.; Marriott, G. Optical control of calcium affinity in a spiroamido-rhodamine based calcium chelator. Among the various fluorophores, rhodamine and fluorescein, as the typical representatives of xanthene, have been paid much attention in biological imaging due to their high absorption coefficient, high fluorescence quantum yield, and water solubility. 2017 Apr 15;177:6-13. doi: 10.1016/j.saa.2017.01.024. in a third-party publication (excluding your thesis/dissertation for which permission is not required) A core-shell structured inorganic-organic hybrid nanocomposite for Hg(II) sensing and removal was designed and fabricated in 2015 by Yang, where the core was composed of superparamagnetic Fe3O4 and the shell consisted of molecular silica sieve MCM-41 (Jiqu and Qixia 2015). PubMed, Kartha, K. K.; Sandeep, A.; Praveen, V. K.; Ajayaghosh, A. Therefore, they have potential applications in detecting metal ions as reversible fluorescence probes. Careers. This review highlights the recent advances on chelation-based xanthene fluorescent probes that have been used for detecting metal ions. Fundam Appl Toxicol 40:191204. This review covers the recent progress made in small molecular, spirocyclic xanthene-based probes containing different heteroatoms (e.g., oxygen, silicon, carbon) in position 10'. 2015). Recognition mechanism of probe 1 with Cu2+. Xanthene-based fluorescence probes with high signal-to-noise ratios are highly useful for bioimaging. (A) Structure of probe 51 and (B) laser confocal scanning microscopy experiments. 2015, Singha et al. )2014, 50, 11191121.10.1039/C3CC48436JSearch in Google Scholar Chem. ; Zhao, B.-X. to construct a BAPTA-based Si-rhodamine calcium probe 56 and its cell-permeable derivative 57 (Figure 37; Egawa et al. 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