Recent progress in fluorescent imaging probes

Sensors (Switzerland)

Volumn 15, Issue 9, 2015, Pages 24374-24396

  Pak, Yen Leng ^a   Swamy, K M K ^a   Yoon, Juyoung ^a  

^a Ewha Womans University   (South Korea)

Author keywords

Fluorescent chemosensors; Fluorescent chemosensors for biothiols; Fluorescent chemosensors for metal ions; Fluorescent chemosensors for ROS; Fluorescent probes; Imaging probes

Indexed keywords

ADENOSINETRIPHOSPHATE; COPPER; MERCURY (METAL); METAL IONS; METALS; PHYSIOLOGY; PROBES;

BIOTHIOLS; FLUORESCENT CHEMOSENSORS; FLUORESCENT IMAGING; FLUORESCENT PROBES; IMAGING PROBE; LOW DETECTION LIMIT; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES;

FLUORESCENCE;

FLUORESCENT DYE; HYDROGEN PEROXIDE; METAL; THIOL DERIVATIVE;

ANIMAL; CHEMISTRY; HUMAN; MOLECULAR IMAGING; PROCEDURES;

ANIMALS; FLUORESCENT DYES; HUMANS; HYDROGEN PEROXIDE; METALS; MOLECULAR IMAGING; SULFHYDRYL COMPOUNDS;

EID: 84942134014     PISSN: 14248220     EISSN: None     Source Type: Journal    
DOI: 10.3390/s150924374     Document Type: Review

References (59)

1. Zhou, X.; Lee, S.; Xu, Z.; Yoon, J. Recent Progress on the Development of Chemosensors for Gases. Chem. Rev. 2015, 115, 7944–8000.
2. Wu, J.; Kwon, B.; Liu, W.; Anslyn, E.V.; Wang, P.; Kim, J.S. Chromogenic/Fluorogenic Ensemble Chemosensing Systems. Chem. Rev. 2015, 115, 7893–7943.
3. Shamirian, A.; Ghai, A.; Snee, P.T. QD-Based FRET Probes at a Glance. Sensors 2015, 15, 13028–13051.
4. Yin, J.; Hu, Y.; Yoon, J. Fluorescence probes and bioimaging: Alkali metals, alkaline earth metals and protons. Chem. Soc. Rev. 2015, 44, 4619–4644.
5. Miller, E.W.; Chang, C.J. Fluorescent probes for nitric oxide and hydrogen peroxide in cell signaling. Curr. Opin. Chem. Biol. 2007, 11, 620–625.
6. Guo, Z.; Shin, I.; Yoon, J. Recognition and Sensing of Various Species Using Boronic Acid Derivatives. Chem. Commun. 2012, 48, 5956–5967.
7. Thomas, J.A. Optical imaging probes for biomolecules: An introductory perspective. Chem. Soc. Rev.2015, 44, 4494–4500.
8. Zhou, Y.; Zhang, J.F.; Yoon, J. Fluorescent and Colorimetric Chemosensors for Detection of Fluoride Ion. Chem. Rev. 2014, 114, 5511–5571.
9. Lee, S.; Yuen, K.K.Y.; Jolliffe, K.A.; Yoon, J. Fluorescent and Colorimetric Chemosensors for Pyrophosphate. Chem. Soc. Rev.2015, 44, 1749–1762.
10. Chen, X.; Pradhan, T.; Wang, F.; Kim, J.S.; Yoon, J. Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives. Chem. Rev. 2012, 112, 1910–1956.
11. Guo, Z.; Park, S.; Yoon, J.; Shin, I. Recent Progress on Near-Infrared Fluorescent Probes for Bioimaging Applications. Chem. Soc. Rev. 2014, 43, 16–29.
12. Amiot, C.L.; Xu, S.; Liang, S.; Pan, L.; Zhao, J.X. Near-Infrared Fluorescent Materials for Sensing of Biological Targets. Sensors 2008, 8, 3082–3105.
13. Kim, H.M.; Cho, B.R. Two-Photon Probes for Intracellular Free Metal Ions, Acidic Vesicles, and Lipid Rafts in Live Tissues. Acc. Chem. Res.2009, 42, 863–872.
14. Zhang, X.; Yin, J.; Yoon, J. Recent Advances in Development of Chiral Fluorescent and Colorimetric Sensors. Chem. Rev. 2014, 114, 4918–4959.
15. De Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.A.; Huxley, T.M.; McCoy, C.P.; Rademacher J.T.; Rice, T.E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515–1566.
16. Czarnik, A.W. Chemical Communication in Water Using Fluorescent Chemosensors. Acc. Chem. Res. 1994, 27, 302–308.
17. Yoon, J.; Czarnik, A.W. Fluorescent Chemosensors of Carbohydrates. A Means of Chemically Communicating the Binding of Polyols in Water Based on Chelation-Enhanced Quenching. J. Am. Chem. Soc. 1992, 114, 5874–5875.
18. Tang, Y.; Lee, D.; Wang, J.; Li, G.; Lin, W.; Yoon, J. Development of fluorescent probes based on protection-deprotection of aldehyde, hydroxyl, and amino functional groups for biological imaging. Chem. Soc. Rev.2015, 44, 5003–5015.
19. Jun, M.E.; Roy, B.; Ahn, K.H. Turn-on fluorescent sensing with reactive probes. Chem. Commun.2011, 47, 7583–7601.
20. Yeung, M.C.-L.; Yam, V.W.-W. Luminescent cation sensors: From host-guest chemistry, supramolecular chemistry to reaction-based mechanisms. Chem. Soc. Rev.2015, 44, 4192–4202.
21. Jung, H.S.; Chen, X.; Kim, J.S.; Yoon, J. Recent progress in luminescent and colorimetric chemosensors for detection of thiols. Chem. Soc. Rev. 2013, 42, 6019–6031.
22. Chen, X.; Ko, S.-K.; Kim, M.J.; Shin, I.; Yoon, J. A Thiol-Specific Fluorescent Probe and Its Application for Bioimaging. Chem. Commun. 2010, 46, 2751–2753.
23. Yang, X.; Guo, Y.; Strongin, R.M. Conjugate Addition/Cyclization Sequence Enables Selective and Simultaneous Fluorescence Detection of Cysteine and Homocysteine. Angew. Chem. Int. Ed. 2011, 50, 10690–10693.
24. Guo, Z.; Nam, S.W.; Park, S.; Yoon, J. A Highly Selective Ratiometric Near-Infrared Fluorescent Cyanine Sensor for Cysteine with Remarkable Shift and Its Application Bioimaging. Chem. Sci. 2012, 3, 2760–2765.
25. Lee, H.Y.; Choi, Y.P.; Kim, S.K.; Yoon, T.; Guo, Z.; Swamy, K.M.K.; Kim, G.; Lee, J.Y.; Shin, I.; Yoon, J. Selective Homocysteine Turn-on Fluorescent Probes and Their Bioimaging Applications. Chem. Commun. 2014, 50, 6967–6969.
26. Hu, Y.; Heo, C.H.; Kim, G.; Jun, E.J.; Yin, J.; Kim, H.M.; Yoon, J. One-Photon and Two-Photon Sensing of Biothiols Using A Bis-Pyrene-Cu(II) Ensemble and Its Application to Image GSH in the Cells and Tissues. Anal. Chem. 2015, 87, 3308–3313.
27. Yin, J.; Kwon, Y.; Kim, D.; Lee, D.; Kim, G.; Hu, Y.; Ryu, J.-H.; Yoon, J. A Cyanine Based Fluorescence Probe for Highly Selective Detection of Glutathione in Cell Cultures and Live Mice Tissues. J. Am. Chem. Soc.2014, 136, 5351–5358.
28. Lee, D.; Kim, G.; Yin, J.; Yoon, J. Aryl-thioether substituted nitrobenzothiadiazole probe for selective detection of cysteine and homocysteine. Chem. Commun.2015, 51, 6518–6520.
29. Chen, X.; Tian, X.; Shin, I.; Yoon, J. Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species. Chem. Soc. Rev. 2011, 40, 4783–4804.
30. Chen, X.; Lee, K.-A.; Ha, E.-M.; Lee, K.M.; Seo, Y.Y.; Choi, H.K.; Kim, H.N.; Kim, M.J.; Cho, C.-S.; Lee, S.Y., et al. A specific and sensitive method for detection of hypochlorous acid for the imaging of microbe-induced HOCl production. Chem. Commun. 2011, 47, 4373–4375.
31. Xu, Q.; Lee, K.-A.; Lee, S.; Lee, K.M.; Lee, W.-J.; Yoon, J. A Highly Specific Fluorescent Probe for Hypochlorous Acid and Its Application in Imaging Microbe-Induced HOCl Production. J. Am. Chem. Soc. 2013, 135, 9944–9949.
32. Xu, Q.; Heo, C.H.; Kim, G.; Lee, H.W.; Kim, H.M.; Yoon, J. Development of Imidazoline-2-Thiones Based Two-Photon Fluorescence Probes for Imaging Hypochlorite Generation in a Co-Culture System. Angew. Chem. Int. Ed. 2015, 54, 4890–4894.
33. Sun, X.; Xu, Q.; Kim, G.; Flower, S.E.; Lowe, J.P.; Yoon, J.; Fossey, J.S.; Qian, X.; Bull, S.D.; James, T.D. A water-soluble boronate-based fluorescent probe for the selective detection of peroxynitrite and imaging in living cells. Chem. Sci. 2014, 5, 3368–3373.
34. Zhou, X.; Kwon, Y.; Kim, G.; Ryu, J.-H.; Yoon, J. A ratiometric fluorescent probe based on a coumarin-hemicyanine scaffold for sensitive and selective detection of endogenous peroxynitrite. Biosens. Bioelectron. 2015, 64, 285–291.
35. Kim, D.; Kim, G.; Nam, S.-J.; Yin, J.; Yoon, J. Visualization of Endogenous and Exogenous Hydrogen Peroxide Using A Lysosome-Targetable Fluorescent Probe. Sci. Rep. 2015, 5, 8488.
36. Xu, Z.; Yoon, J.; Spring, D.R. Fluorescent Chemosensors for Zn2+. Chem. Soc. Rev.2010, 39, 1996–2006.
37. Xu, Z.; Kim, G.-H.; Han, S.J.; Jou, M.J.; Lee, C.; Shin, I.; Yoon, J. An NBD-based colorimetric and fluorescent chemosensor for Zn2+ and its use for detection of intracellular zinc ions. Tetrahedron 2009, 65, 2307–2312.
38. Xu, Z.; Baek, K.-H.; Kim, H.N.; Cui, J.; Qian, X.; Spring, D.R.; Shin, I.; Yoon, J. Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell–Permeable and Ratiometric Fluorescent Sensor. J. Am. Chem. Soc.2010, 132, 601–610.
39. Guo, Z.; Kim, G.-H.; Shin, I.; Yoon, J. A Cyanine-Based Fluorescent Sensor for Detecting Endogenous Zinc Ions in Live Cells and Organisms. Biomaterials 2012, 33, 7818–7827.
40. Guo, Z.; Kim, G.-H.; Yoon, J.; Shin, I. Synthesis of a highly Zn2+-selective cyanine-based probe and its use for tracing endogenous zinc ions in cells and organisms. Nat. Protocol. 2014, 9, 1245–1254.
41. Palmiter, R.D. The elusive function of metallothioneins. Proc. Natl. Acad. Sci. USA 1998, 95, 8428–8430.
42. Kim, H.N.; Ren, W.X.; Kim, J.S.; Yoon, J. Fluorescent and Colorimetric Sensors for Detection of Lead, Cadmium, and Mercury Ions. Chem. Soc. Rev. 2012, 41, 3210–3244.
43. Park, S.; Kim, W.; Swamy, K.M.K.; Jung, J.Y.; Kim, G.; Kim, Y.; Kim, S.-J.; Yoon, J. Rhodamine Hydrazone Derivatives Bearing Thiophene Group as Fluorescent and Colorimetric Chemosensors for Hg2+. Dyes Pigm. 2013, 99, 323–328.
44. Kwon, J.Y.; Jang, Y.J.; Lee, Y.J.; Kim, K.-M.; Seo, M.-S.; Nam, W.; Yoon, J. A Highly Selective Fluorescent Chemosensor for Pb2+. J. Am. Chem. Soc. 2005, 127, 10107–10111.
45. Kim, H.N.; Nam, S.-W.; Swamy, K.M.K.; Jin, Y.; Chen, X.; Kim, Y.; Kim, S.-J.; Park, S.; Yoon, J. Rhodamine Hydrazone Derivatives as Hg2+ Selective Fluorescent and Colorimetric Chemosensors and Their Applications to Bioimaging and Microfluidic System. Analyst 2011, 136, 1339–1343.
46. Kwon, S.K.; Kim, H.N.; Rho, J.H.; Swamy, K.M.K.; Shanthakumar, S.M.; Yoon, J. Rhodamine Derivative Bearing Histidine Binding Site as a Fluorescent Chemosensor for Hg2+. Bull. Korean Chem. Soc. 2009, 30, 719–721.
47. Chen, X.; Baek, K.-H.; Kim, Y.; Kim, S.-J.; Shin, I.; Yoon, J. A Selenolactone-Based Fluorescent Chemodosimeter to Monitor Mercury/ Methylmercury Species in vitro and in vivo. Tetrahedron 2010, 66, 4016–4021.
48. Ko, S.-K.; Chen, X.; Yoon, J.; Shin, I. Zebrafish as a good vertebrate model for molecular imaging using fluorescent probes. Chem. Soc. Rev. 2011, 40, 2120–2130.
49. Swamy, K.M.K.; Ko, S.-K.; Kwon, S.K.; Lee, H.N.; Mao, C.; Kim, J.-M.; Lee, K.-H.; Kim, J.; Shin, I.; Yoon, J. Boronic Acid-Linked Fluorescent and Colorimetric Probes for Copper Ions. Chem. Commun. 2008, 5915–5917.
50. Jou, M.J.; Chen, X.; Swamy, K.M.K.; Kim, H.N.; Kim, H.-J.; Lee, S.-G.; Yoon, J. Highly Selective Fluorescent Probe for Au3+ Based on Cyclization of Propargylamide. Chem. Commun.2009, 14, 7218–7220.
51. Choi, J.Y.; Kim, G.-H.; Guo, Z.; Swamy, K.M.K.; Lee, H.Y.; Pai, J.; Shin, S.; Shin, I.; Yoon, J. Highly Selective Ratiometric Fluorescent Probe for Au3+ and Its Application to Bioimaging. Biosens. Bioelectron. 2013, 49, 438–441.
52. Wang, F.; Wang, L.; Chen, X.; Yoon, J. Recent progress in the development of fluorometric and colorimetric chemosensors for detection of cyanide ion. Chem. Soc. Rev.2014, 43, 4312–4324.
53. Chen, X.; Nam, S.-W.; Kim, G.-H.; Song, N.; Jeong, Y.; Shin, I.; Kim, S.K.; Kim, J.; Park, S.; Yoon, J. A Near-Infrared Fluorescent Sensor for Detection of Cyanide in Aqueous Solution and Its Application for Bioimaging. Chem. Commun.2010, 46, 8953–8955.
54. Xu, Z.; Kim, S.K.; Yoon, J. Revisit to Imidazolium Receptors for the Recognition of Anions: Highlighted Research During 2006–2009. Chem. Soc. Rev. 2010, 39, 1457–1466.
55. Kim, S.K.; Singh, N.J.; Kwon, J.; Hwang, I.-C.; Park, S.J.; Kim, K.S.; Yoon, J. Fluorescent Imidazolium Receptors for the Recognition of Pyrophosphate. Tetrahedron 2006, 62, 6065–6072.
56. Kim, S.K.; Kang, B.-G.; Koh, H.S.; Yoon, Y.J.; Jung, S.J.; Jeong, B.; Lee, K.-D.; Yoon, J. A New ImidazoliumCavitand for the Recognition of Dicarboxylates. Org. Lett. 2004, 6, 4655–4658.
57. Xu, Z.; Singh, N.J.; Lim, J.; Pan, J.; Kim, H.N.; Park, S.; Kim, K.S.; Yoon, J. Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH. J. Am. Chem. Soc.2009, 131, 15528–15533.
58. Kolemen, S.; Işık, M.; Kim, G.M.; Kim, D.; Geng, H.; Buyuktemiz, M.; Karatas, T.; Zhang, X.-F.; Dede, Y.; Yoon, J., et al. Intracellular Modulation of Excited-State Dynamics in a Chromophore Dyad: Differential Enhancement of Photocytotoxicity Targeting Cancer Cells. Angew. Chem. Int. Ed. 2015, 54, 5340–5344.
59. Kim, E.-J.; Bhuniya, S.; Lee, H.; Kim, H.M.; Cheong, C.; Maiti, S.; Hong, K.S.; Kim, J.S. An Activatable Prodrug for the Treatment of Metastatic Tumor. J. Am. Chem. Soc.2014, 136, 13888–13894.