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A simple fluorescent pH probe and its application in cells

  • Jian-bin ChaoEmail author
  • Ming Li
  • Yong-bin Zhang
  • Cai-xia Yin
  • Fang-jun Huo
Original Paper
First Online:
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Abstract

It is very important to measure the pH in the cells because abnormal pH in the body can cause many neurological diseases. In this work, a simple emission fluorescent pH probe 2-(benzothiazol-2-yl)-1-((pyren-3-yl) methylene) hydrazine (BMH) was synthesized by connecting pyrene-1-carboxaldehyde and 2-hydrazinobenzothiazole. BMH displayed fluorescence emission characteristics in which the pKa was 3.49 and responded linearly to measure pH range from 4.70 to 3.16. Meanwhile, it possessed high fluorescence quantum yield (64.60%). Moreover, BMH exhibited good stability and highly selectivity which promotes its ability in analytical application and the detection limit of approach was 0.41 μΜ. Simultaneously, it was fully able to image pH fluctuations due to its cell membrane permeability, biocompatibility and no auto-fluorescence effects.

Keywords

pH probe Fluorescence characteristics Large stokes shift Image pH fluctuations 
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Notes

Acknowledgements

The work was supported by the National Nature Science Foundation of China (Nos. 21472118, 21672131), the Program for the Top Young and Middle-aged Innovative Talents of Higher Learning Institutions of Shanxi (No. 2013802), Talents Support Program of Shanxi Province (No. 2014401), Shanxi Province Outstanding Youth Fund (No. 2014021002), Natural Science Foundation of Shanxi Province of China (No. 201701D121018).

References

  1. Buanafinas MMDO, Cosgrove DJ, Fincher G, Höfte H (2009) Feruloylation in grasses: current and future perspectives. Mol Plant 2:861.  https://doi.org/10.1093/mp/ssp067 CrossRefGoogle Scholar
  2. Chao J, Wang H, Zhang Y, Yin C, Huo F, Song K, Li Z, Zhang T, Zhao Y (2017) A novel “donor-π-acceptor” type fluorescence probe for sensing pH: mechanism and application in vivo. Talanta 174:468.  https://doi.org/10.1016/j.talanta.2017.06.051 CrossRefGoogle Scholar
  3. Cooper ME, Gregory S, Adie E, Kalinka S (2002) pH-sensitive cyanine dyes for biological applications. J Fluoresc 12:425–429.  https://doi.org/10.1023/A:1021366010681 CrossRefGoogle Scholar
  4. Depedro HM, Urayama P (2009) Using LysoSensor yellow/blue DND-160 to sense acidic pH under high hydrostatic pressures. Anal Biochem 384:359.  https://doi.org/10.1016/j.ab.2008.10.007 CrossRefGoogle Scholar
  5. Donoso P, Beltrã NM, Hidalgo C (1996) Luminal pH regulated calcium release kinetics in sarcoplasmic reticulum vesicles. Biochemistry 35:13419–13425.  https://doi.org/10.1021/bi9616209 CrossRefGoogle Scholar
  6. Fan L, Liu Q, Lu D, Shi H, Yang Y, Li Y, Dong C, Shuang S (2013) A novel far-visible and near-infrared pH probe for monitoring near-neutral physiological pH changes: imaging in live cells. J Mater Chem B 1:4281–4288.  https://doi.org/10.1039/C3TB20547A CrossRefGoogle Scholar
  7. Galindo F, Burguete MI, Vigara L, Luis SV, Kabir N, Gavrilovic J, Russell D (2010) Synthetic macrocyclic peptidomimetics as tunable pH probes for the fluorescence imaging of acidic organelles in live cells. Angew Chem 117:6662–6666.  https://doi.org/10.1002/anie.200501920 CrossRefGoogle Scholar
  8. Han J, Burgess K (2010) Fluorescent indicators for intracellular pH. Chem Rev 110:2709–2728.  https://doi.org/10.1021/cr900249z CrossRefGoogle Scholar
  9. He S, Mason RP, Hunjan S, Mehta VD, Arora V, Katipally R, Kulkarni PV, Antich PP (1998) Development of novel 19F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B6 analogues. Bioorg Med Chem 6:1631–1639.  https://doi.org/10.1016/S0968-0896(98)00104-7 CrossRefGoogle Scholar
  10. Hesse SJA, Ruijter GJG, Dijkema C, Visser J (2000) Measurement of intracellular (compartmental) pH by 31 P NMR in Aspergillus niger. J Biotechnol 77:5–15.  https://doi.org/10.1016/S0168-1656(99)00203-5 CrossRefGoogle Scholar
  11. Holopainen JM, Saarikoski J, Kinnunen PK, Järvelä I (2001) Elevated lysosomal pH in neuronal ceroid lipofuscinoses (NCLs). FEBS J 268:5851–5856.  https://doi.org/10.1046/j.0014-2956.2001.02530.x Google Scholar
  12. Hu J, Wu F, Feng S, Xu J, Xu Z, Chen Y, Tang T, Weng X, Zhou X (2014) A convenient ratiomeric pH probe and its application for monitoring pH change in living cells. Sensor Actuat B Chem 196:194–202.  https://doi.org/10.1016/j.snb.2014.01.119 CrossRefGoogle Scholar
  13. Humez S, Monet M, Van CF, Delcourt P, Prevarskaya N (2004) The role of intracellular pH in cell growth arrest induced by ATP. Am J Physiol Cell 287:C1733.  https://doi.org/10.1152/ajpcell.00578.2003 CrossRefGoogle Scholar
  14. Hunte C, Screpanti E, Venturi M, Rimon A, Padan E, Michel H (2005) Structure of a Na +/H + antiporter and insights into mechanism of action and regulation by pH. Nature 435:1197.  https://doi.org/10.1038/nature03692 CrossRefGoogle Scholar
  15. Izumi H, Torigoe T, Ishiguchi H, Uramoto H, Yoshida Y, Tanabe M, Ise T, Murakami T, Yoshida T, Nomoto M, Kohno K (2003) Cellular pH regulators: potentially promising molecular targets for cancer chemotherapy. Cancer Treat Rev 29:541–549.  https://doi.org/10.1016/S0305-7372(03)00106-3 CrossRefGoogle Scholar
  16. Sun KM, McLaughlin CK, Dean R, Lantero A, Richard A, Manderville A (2007) Biomarkers for phenol carcinogen exposure act as pH-sensing fluorescent probes. J Am Chem Soc 129:1894–1895.  https://doi.org/10.1021/ja068416l CrossRefGoogle Scholar
  17. Kiani MJ, Razak MAA, Harun FKC, Ahmadi MT, Rahmani M (2015) SWCNT-Based biosensor modelling for pH detection. J. Nanomater 2015:102.  https://doi.org/10.1155/2015/721251 CrossRefGoogle Scholar
  18. Krulwich TA, Sachs G, Padan E (2011) Molecular aspects of bacterial pH sensing and homeostasis. Nat Rev Microbiol 9:330.  https://doi.org/10.1038/nrmicro2549 CrossRefGoogle Scholar
  19. Kwon HN, Jee AY, Lee MY (2009) DND-189 as an amyloid aggregation probe. Kor Chem Soc.  https://doi.org/10.5012/bkcs.2009.30.6.1237 Google Scholar
  20. Lakadamyali M, Rust MJ, Babcock HP, Zhuang X (2003) Visualizing infection of individual influenza viruses. Proc Natl Acad Sci USA 100:9280–9285.  https://doi.org/10.1073/pnas.0832269100 CrossRefGoogle Scholar
  21. Li GL, Zhang B, Song XB, Xiao Y, Song YT (2017) Ratiometric imaging of mitochondrial pH in living cells with a colorimetric fluorescent probe based on fluorescein derivative. Sensor Actuat B Chem 253:58–68.  https://doi.org/10.1016/j.snb.2017.06.065 CrossRefGoogle Scholar
  22. Lin HJ, Herman P, Lakowicz JR (2003) Fluorescence lifetime-resolved pH imaging of living cells. Cytom Part A 52:77–89.  https://doi.org/10.1002/cyto.a.10028 CrossRefGoogle Scholar
  23. Liu Z, Li GP, Wang YN, Li JL, Mi Y (2019) Quinoline-based ratiometric fluorescent probe for detection of physiological pH changes in aqueous solution and living cells. Talanta 192:6–13.  https://doi.org/10.1016/j.talanta.2018.09.026 CrossRefGoogle Scholar
  24. Liu YY, Wu M, Zhu LN, Feng XZ, Kong DM (2015) Colorimetric and fluorescent bimodal ratiometric probes for pH sensing of living cells. Chem Asian J 10:1304–1310.  https://doi.org/10.1002/asia.201500106 CrossRefGoogle Scholar
  25. Loving G, Imperiali B (2008) A versatile amino acid analogue of the solvatochromic fluorophore 4-N, N-dimethylamino-1,8-naphthalimide: a powerful tool for the study of dynamic protein interactions. J Am Chem Soc 130:13630–13638.  https://doi.org/10.1021/ja804754y CrossRefGoogle Scholar
  26. Niu W, Nan M, Fan L, Wong MS, Shuang S, Dong C (2016) A novel pH fluorescent probe based on indocyanine for imaging of living cells. Dyes Pigm 126:224–231.  https://doi.org/10.1016/j.dyepig.2015.11.027 CrossRefGoogle Scholar
  27. Otomo T, Higaki K, Nanba E, Ozono N (2011) Lysosomal storage causes cellular dysfunction in mucolipidosis II skin fibroblasts. J Biol Chem 286:35283–35290.  https://doi.org/10.1074/jbc.M111.267930 CrossRefGoogle Scholar
  28. Smith DG, Mcmahon BK, Pal R, Parker D (2012) Live cell imaging of lysosomal pH changes with pH responsive ratiometric lanthanide probes. Chem Commun 48:8520–8522.  https://doi.org/10.1039/C2CC34267G CrossRefGoogle Scholar
  29. Tang B, Yu F, Li P, Tong L, Duan X, Xie T, Wang XK (2009) A near-infrared neutral pH fluorescent probe for monitoring minor pH changes: imaging in living HepG2 and HL-7702 cells. J Am Chem Soc 131:3016.  https://doi.org/10.1021/ja809149g CrossRefGoogle Scholar
  30. Yin J, Hu Y, Yoon J (2014) Fluorescent probes and bioimaging: alkali metals, alkaline earth metals and pH. Chem Soc Rev 44:4619.  https://doi.org/10.1039/c4cs00275j CrossRefGoogle Scholar
  31. Yuan CX, Li JY, Xi H (2018) A sensitive pyridine-containing turn-off fluorescent probe for pH detection. Mater Lett 236:9–12.  https://doi.org/10.1016/j.matlet.2018.10.060 CrossRefGoogle Scholar
  32. Zhang RG, Kelsen SG, Lamanna JC (1990) Measurement of intracellular pH in hamster diaphragm by absorption spectrophotometry. J Appl Physiol 68:1101.  https://doi.org/10.1152/jappl.1990.68.3.1101 CrossRefGoogle Scholar
  33. Zhou J, Zhang L, Tian Y (2016) A micro electrochemical pH sensor applicable for real-time ratiometric monitoring of pH values in rat brains. Anal Chem 88:2113.  https://doi.org/10.1021/acs.analchem.5b03634 CrossRefGoogle Scholar
  34. Zhou LP, Jin ZC, Fan XX, Yao YH, Zhang WP, Qian JH (2018) Synthesis of 1,8-naphthalimide-based fluorescent nano-probes and their application in pH detection. Chin Chem Lett 29:1500–1502.  https://doi.org/10.1016/j.cclet.2018.07.018 CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  • Jian-bin Chao
    • 1
    Email author
  • Ming Li
    • 1
    • 2
  • Yong-bin Zhang
    • 4
  • Cai-xia Yin
    • 3
  • Fang-jun Huo
    • 4
  1. 1.Scientific Instrument CenterShanxi UniversityTaiyuanChina
  2. 2.School of Chemistry and Chemical EngineeringShanxi UniversityTaiyuanChina
  3. 3.Institute of Molecular ScienceShanxi UniversityTaiyuanChina
  4. 4.Research Institute of Applied ChemistryShanxi UniversityTaiyuanChina

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