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A Xanthene Dye‐based Sensor for Viscosity and Cell Imaging

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Abstract

A new xanthene dye, namely ImX, has been facilely prepared by reaction of 4-(1H-Imidazol-1-yl)benzaldehyde with N, N-diethyl-3-aminophenol in concentrated propionic acid, and then treated by p-chloranil. ImX presents the maximum absorption and emission band centered at 562 nm and 583 nm in water, respectively. Fluorescent spectra investigations demonstrate that ImX shows viscosity-selective fluorescent response and emission enhancement when the solvent viscosity increases from 1.1 cp. (water) to 1248 cp. (98 % glycerol). In addition, this viscosity-selective fluorescence response covers a wide pH range from 2.5 to 10.0. More significantly, ImX demonstrates low cytotoxicity and can be employed as tracer for the detection of Monensin-triggered viscosity enhancement by cell imaging.

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References

  1. Ueno T, Nagano T (2011) Fluorescent probes for sensing and imaging. Nat Methods 8:642–645

    Article  CAS  Google Scholar 

  2. Aron AT, Ramos-Torres KM, Cotruvo JA Jr, Chang CJ (2015) Recognition-and reactivity-based fluorescent probes for studying transition metal signaling in living systems. Acc Chem Res 48:2434–2442

    Article  CAS  Google Scholar 

  3. Yue YK, Huo FJ, Cheng FQ, Zhu XJ, Mafireyi TD, Strongin RM, Yin C (2019) Functional synthetic probes for selective targeting and multi-analyte detection and imaging. Chem Soc Rev 48:4155–4177

    Article  CAS  Google Scholar 

  4. Liu C, Liu K, Tian M, Lin WA (2019) ratiometric fluorescent probe for hydrazine detection with large fluorescence change ratio and its application for fluorescence imaging in living cells. Spectrochim Acta Part A 212:42–47

    Article  CAS  Google Scholar 

  5. Qiu Q, Yu B, Huang K, Qin DB (2020) A Fluoran-based Cu2+-selective fluorescent probe and its application in cell imaging. J Fluoresce 30:859–866

    Article  CAS  Google Scholar 

  6. Kuimova MK (2012) Mapping viscosity in cells using molecular rotors. Phys Chem Chem Phys 14:12671–12686

    Article  CAS  Google Scholar 

  7. Yang Z, Cao J, He Y, Yang JH, Kim T, Peng X, Kim JS (2014) Macro-/micro-environment-sensitive chemosensing and biological imaging. Chem Soc Rev 43:4563–4601

    Article  CAS  Google Scholar 

  8. Dragan A, Graham AE, Geddes CD (2014) Fluorescence-based broad dynamic range viscosity probes. J Fluoresc 24:397–402

    Article  CAS  Google Scholar 

  9. Stutts MJ, Canessa CM, Olsen JC, Hamrick M, Cohn JA, Rossier BC, Boucher RC (1995) CFTR as a cAMP-dependent regulator of sodium channels. Science 269:847–850

    Article  CAS  Google Scholar 

  10. Akers W, Haidekker MA (2004) A molecular rotor as viscosity sensor in aqueous colloid solutions. J Biomech Eng 126:340–345

    Article  CAS  Google Scholar 

  11. Zhang G, Ni Y, Zhang D, Li H, Wang N, Yu C, Li L, Huang W (2019) Rational design of NIR fluorescence probes for sensitive detection of viscosity in living cells. Spectrochim Acta Part A 214:339–347

    Article  CAS  Google Scholar 

  12. Lee SC, Heo J, Woo HC, Lee JA, Seo YH, Lee CL, Kim S, Kwon OP (2018) Fluorescent molecular rotors for viscosity sensors. Chem Eur J 24:13706–13718

    Article  CAS  Google Scholar 

  13. Zhang X, Sun Q, Huang Z, Huang L, Xiao Y (2019) Immobilizable fluorescent probes for monitoring the mitochondria microenvironment: a next step from the classic. J Mater Chem B 7:2749–2758

    Article  CAS  Google Scholar 

  14. Phatangare KR, Lanke SK, Sekar N (2014) Fluorescent coumarin derivatives with viscosity sensitive emission-synthesis, photophysical properties and computational studies. J Fluoresc 24:1263–1274

    Article  CAS  Google Scholar 

  15. Han D, Yi J, Liu C, Liang L, Huang K, Jing L, Qin D (2020) A fluoran-based viscosity probe with high-performance for lysosome-targeted fluorescence imaging. Spectrochim Acta Part A 238:118405

    Article  CAS  Google Scholar 

  16. Ren M, Wang L, Lv X, Liu J, Chen H, Wang J, Guo W (2019) Development of a benzothiazole-functionalized red-emission pyronin dye and its dihydro derivative for imaging lysosomal viscosity and tracking endogenous peroxynitrite. J Mater Chem B 7:6181–6186

    Article  CAS  Google Scholar 

  17. Guo R, Yin J, Ma Y, Wang Q, Lin W (2018) A novel mitochondria-targeted rhodamine analogue for the detection of viscosity changes in living cells, zebra fish and living mice. J Mater Chem B 6:2894–2900

    Article  CAS  Google Scholar 

  18. Wang L, Xiao Y, Tian W, Deng L (2013) Activatable rotor for quantifying lysosomal viscosity in living cells. J Am Chem Soc 135:2903–2906

    Article  CAS  Google Scholar 

  19. Kuimova MK, Yahioglu G, Levitt JA, Suhling K (2008) Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 130:6672–6673

    Article  CAS  Google Scholar 

  20. Zhang P, Chen H, Huang H, Qiu K, Zhang C, Chao H, Zhang Q (2019) A viscosity-sensitive iridium (iii) probe for lysosomal microviscosity quantification and blood viscosity detection in diabetic mice. Dalton Trans 48:3990–3997

    Article  CAS  Google Scholar 

  21. Li X, Zhao R, Wang Y, Huang C (2018) A new GFP fluorophore-based probe for lysosome labelling and tracing lysosomal viscosity in live cells. J Mater Chem B 6:6592–6598

    Article  CAS  Google Scholar 

  22. Shim SH, Xia C, Zhong G, Babcock HP, Vaughan JC, Huang B, Wang X, Xu C, Bi GQ, Zhuang X (2012) Super-resolution fluorescence imaging of organelles in live cells with photoswitchable membrane probes. Proc Natl Acad Sci USA 109:13978–13983

    Article  CAS  Google Scholar 

  23. Guo R, Ma Y, Tang Y, Xie P, Wang Q, Lin W (2019) A novel mitochondria-targeted near-infrared (NIR) probe for detection of viscosity changes in living cell, zebra fishes and living mice. Talanta 204:868–874

    Article  CAS  Google Scholar 

  24. Yang Z, He Y, Lee JH, Park N, Suh M, Chae WS, Cao J, Peng X, Jung H, Kang C, Kim JS (2013) A self-calibrating bipartite viscosity sensor for mitochondria. J Am Chem Soc 135:9181–9185

    Article  CAS  Google Scholar 

  25. Peng X, Yang Z, Wang J, Fan J, He Y, Song F, Wang B, Sun S, Qu J, Qi J, Yan M (2011) Fluorescence ratiometry and fluorescence lifetime imaging: using a single molecular sensor for dual mode imaging of cellular viscosity. J Am Chem Soc 133:6626–6635

    Article  CAS  Google Scholar 

  26. Scholz N, Jadhav A, Shreykar M, Behnke T, Nirmalananthan N, Resch-Genger U, Sekar N (2017) Coumarin-rhodamine hybrids-novel probes for the optical measurement of viscosity and polarity. J Fluoresce 27:1949–1956

    Article  CAS  Google Scholar 

  27. Marfin YS, Vodyanova OS, Merkushev DA, Usoltsev SD, Kurzin VO, Rumyantsev EV (2016) Effect of π-extended substituents on photophysical properties of BODIPY dyes in solutions. J Fluoresc 26:1975–1985

    Article  CAS  Google Scholar 

  28. Balter A, Szubiakowski J (1993) Fluorescence probes of viscosity: A comparative study of the fluorescence anisotropy decay of perylene and 3,9-dibromoperylene in glycerol. J Fluoresce 3:247–249

    Article  CAS  Google Scholar 

  29. Li J, Zhang Y, Zhang H, Xuan X, Xie M, Xia S, Qu G, Guo H (2016) Nucleoside -based ultrasensitive fluorescent probe for the dual-mode imaging of microviscosity in living cells. Anal Chem 88:5554–5560

    Article  CAS  Google Scholar 

  30. Wang X, Song F, Peng X (2016) A versatile fluorescent probe for imaging viscosity and hypochlorite in living cells. Dyes Pigments 125:89–94

    Article  CAS  Google Scholar 

  31. Haidekker MA, Theodorakis EA (2010) Environment-sensitive behavior of fluorescent molecular rotors. J Biol Eng 4:11

    Article  Google Scholar 

  32. Chen T, Chen Z, Liu R. Zheng S (2019) A NIR fluorescent probe for detection of viscosity and lysosome imaging in live cells. Org Biomol Chem 17:6398–6403

    Article  CAS  Google Scholar 

  33. Yuan L, Lin W, Cao Z, Wang J, Chen B (2012) Development of FRET-based dual-excitation ratiometric fluorescent pH probes and their photocaged derivatives. Chem Eur J 18:1247–1255

    Article  CAS  Google Scholar 

  34. Beija M, Afonso CA, Martinho JM (2009) Synthesis and applications of Rhodamine derivatives as fluorescent probes. Chem Soc Rev 38:2410–2433

    Article  CAS  Google Scholar 

  35. Chen X, Pradhan T, Wang F, Kim JS, Yoon J (2012) Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chem Rev 112:1910–1956

    Article  CAS  Google Scholar 

  36. Yuan L, Lin W, Yang Y, Chen H (2012) A unique class of near-infrared functional fluorescent dyes with carboxylic-acid-modulated fluorescence ON/OFF switching: rational design, synthesis, optical properties, theoretical calculations, and applications for fluorescence imaging in living animals. J Am Chem Soc 134:1200–1211

    Article  CAS  Google Scholar 

  37. Uchida N, Smilowitz H, Ledger PW, Tanzer ML (1980) Kinetic studies of the intracellular transport of procollagen and fibronectin in human fibroblasts. Effects of the monovalent ionophore, monensin. J Biol Chem 255:8638–8644

    Article  CAS  Google Scholar 

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Acknowledgements

We gratefully acknowledge the Natural Science Foundation of China (52009053), Key Program of the Educational Department of Sichuan Province, China (18ZA0263), the Program of Science & Technology Bureau of Mianyang City, China (2020YFZJ005) and General Program of Science & Technology Department of Sichuan Province, China (2018JY0223).

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Authors and Affiliations

  1. College of Resources and Environmental Engineering, Mianyang Normal University, Mianyang, 621000, Sichuan, China

    Bo Yu, Lihua Dou & Yunyun Li

  2. Ecological Security and Protection Key Laboratory of Sichuan Province, Mianyang Normal University, 621000, Mianyang, Sichuan, China

    Bo Yu & Lihua Dou

  3. Library of City College, Southwest University of Science and technology, 621000, Sichuan, China

    Ying Zhou

  4. Department of Environmental Engineering, School of Architecture and Civil Engineering, Chengdu University, Chengdu, 610106, Sichuan, China

    Zhengwen Huang

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  1. Bo Yu
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Correspondence to Zhengwen Huang.

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Yu, B., Zhou, Y., Dou, L. et al. A Xanthene Dye‐based Sensor for Viscosity and Cell Imaging. J Fluoresc 31, 719–725 (2021). https://doi.org/10.1007/s10895-021-02705-4

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  • DOI: https://doi.org/10.1007/s10895-021-02705-4

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