Citation: Luo Xiao, Li Jin, Zhao Jie, Gu Luyan, Qian Xuhong, Yang Youjun. A general approach to the design of high-performance near-infrared (NIR) D-π-A type fluorescent dyes[J]. Chinese Chemical Letters, ;2019, 30(4): 839-846. doi: 10.1016/j.cclet.2019.03.012 shu

A general approach to the design of high-performance near-infrared (NIR) D-π-A type fluorescent dyes

Luo Xiao ^a ,
Li Jin ^b ,
Zhao Jie ^b ,
Gu Luyan ^b ,
Qian Xuhong ^a,b,*, ,
Yang Youjun ^b,*,

a.
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
b.
State Key Laboratory of Bioreactor Engineering, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

Author Bio:

Professor Youjun Yang got his bachelor's degree from the University of Science and Technology of China (USTC) and PhD from Louisiana State University (LSU) under the guidance of Prof. Robert M. Strongin, with a focus on xanthene and benzoxanthene synthesis. He then did postdoctoral study with Prof. Eric V. Anslyn in the University of Texas at Austin. In 2010, he started his independent career in the School of Pharmacy of East China University of Science and Technology (ECUST) in Shanghai. He was appointed as a full professor in 2015. The theme of his research is the development of dyes and probes for bioimaging and theranostics. His group has developed high-performance dyes (EC dyes) with absorption and emission wavelengths in the deep NIR spectral region (800 nm and beyond), novel Hill-type pH fluorescent probes (with a sharp acid-base transition width of ~0.5-1.2 pH unit), xanthene based potent antibiotic compounds (effective toward many high-priority drug-resistance pathogens), and novel molecular tools to study the implications of various substrates (NO/NO⁺, Hg²⁺/MeHg⁺, OONO^-/ HOONO, Sarin, radicals, etc.) in human health and diseases. The awards he has received include the Excellent Young Scholar of the National Science Foundation of China (NSFC), the Czarnik Emerging Investigator award of the Molecular Sensors and Molecular Logic Gate symposium (MSMLG), the Rising-Star award of Shanghai Municipal of Science and Technology Commission (SMSCT), and the Presidential award of East China University of Science and Technology

xhqian@ecust.edu.cn

youjunyang@ecust.edu.cn

Received Date: 28 January 2019
Revised Date: 26 February 2019
Accepted Date: 28 February 2019
Available Online: 7 April 2019

Figures(10)

Near infrared (NIR) absorbing and emitting dyes are sought after for their potentials in bioimaging and theranostic applications. They are typically not as stable as dyes absorbing and emitting in the visible spectral range, as the result of a reduced HOMO-LUMO band-gap. Also, they are not as efficient fluorescence emitters due to accelerated internal conversion kinetics. In addition, their large conjugative backbone render them high tendency to form aggregate and low aqueous solubility. In this tutorial, we have described a four-step approach for rational design of organic dyes with an overall high-performance to meet the rigorous requirements of biological applications. Also, some background regarding "NIR" is provided along with some recent breakthroughs of the field.
- Near infrared,
- Polymethine cyanine,
- Fluorescence,
- Steric protection,
- Rigidity
1. [1]
  J.V. Frangioni, Curr. Opin. Chem. Biol. 7(2003) 626-634. doi: 10.1016/j.cbpa.2003.08.007
2. [2]
  Q.T. Nguyen, E.S. Olson, T.A. Aguilera, et al., Proc. Natl. Acad. Sci. U. S. A. 107(2010) 4317-4322. doi: 10.1073/pnas.0910261107
3. [3]
  A.W. Czarnik, Chem. Biol. 2(1995) 423-428. doi: 10.1016/1074-5521(95)90257-0
4. [4]
  E. Haustein, P. Schwille, HFSP J. 1(2007) 169-180. doi: 10.2976/1.2778852
5. [5]
  J. Mei, Y. Huang, H. Tian, ACS Appl. Mater. Interfaces 10(2018) 12217-12261. doi: 10.1021/acsami.7b14343
6. [6]
  R. Weissleder, Science 312(2006) 1168-1171. doi: 10.1126/science.1125949
7. [7]
  M. Rudin, R. Weissleder, Nat. Rev. Drug Disc. 2(2003) 123-131. doi: 10.1038/nrd1007
8. [8]
  K. Pap, S. Plehati, I. Rajkovi c, D. Žigman, International Design Conference-Design, (2010), pp. 1857-1862.
9. [9]
  BSI ISO 20473: 2007 Optics and Photonics. Spectral Bands, British Standards Institution (BSI) and International Organization for Standardisation (ISO), 2007 checked 2015.
10. [10]
  C.M. Lin, S.M. Usama, K. Burgess, Molecules 23(2018) 2900. doi: 10.3390/molecules23112900
11. [11]
  M. Manley, Chem. Soc. Rev. 43(2014) 8200-8214. doi: 10.1039/C4CS00062E
12. [12]
  M. Kamper, H. Ta, N.A. Jensen, S.W. Hell, S. Jakobs, Nat. Commun. 9(2018) 4762. doi: 10.1038/s41467-018-07246-2
13. [13]
  Z.H. Lei, X.R. Li, X. Luo, et al., Angew. Chem. Int. Ed. 56(2017) 2979-2983. doi: 10.1002/anie.201612301
14. [14]
  Z.Y. Wang, Near-Infrared Organic Materials and Emerging Applications, CRC Press, New York, 2013.
15. [15]
  J.R. Hou, D. Jin, B. Chen, L.L. Si, Y. Li, Chin. Chem. Lett. 28(2017) 1875-1877. doi: 10.1016/j.cclet.2017.06.017
16. [16]
  M.S. Lin, B.A. Rasco, A.G. Cavinato, M. Al-Holy, Infrared Spectroscopy for Food Quality Analysis and Control, Elsevier Publishing, Burlington, MA, USA, 2009.
17. [17]
  B.A. Kairdolf, A.M. Smith, T.H. Stokes, et al., Annu. Rev. Anal. Chem. 6(2013) 143-162. doi: 10.1146/annurev-anchem-060908-155136
18. [18]
  J. Qian, B.Z. Tang, Chemisty 3(2017) 56-91.
19. [19]
  Z.Q. Guo, S. Park, J. Yoon, I. Shin, Chem. Soc. Rev. 43(2014) 16-29. doi: 10.1039/C3CS60271K
20. [20]
  K.Y. Zhang, Q. Yu, H.J. Wei, et al., Chem. Rev. 118(2018) 1770-1839. doi: 10.1021/acs.chemrev.7b00425
21. [21]
  R. Weissleder, M.J. Pittet, Nature 452(2008) 580-589. doi: 10.1038/nature06917
22. [22]
  J. Zhang, R.E. Campbell, A.Y. Ting, et al., Nat. Rev. Mol. Cell Biol. 3(2002) 906-918. doi: 10.1038/nrm976
23. [23]
  W.R. Zipfel, R.M. Williams, W.W. Webb, Nat. Biotechnol. 21(2003) 1369-1377. doi: 10.1038/nbt899
24. [24]
  B. Huang, M. Bates, X.W. Zhuang, Annu. Rev. Biochem. 78(2009) 993-1016. doi: 10.1146/annurev.biochem.77.061906.092014
25. [25]
  V. Ntziachristos, Annu. Rev. Biomed. Eng. 8(2006) 1-33. doi: 10.1146/annurev.bioeng.8.061505.095831
26. [26]
  D.W. Domaille, E.L. Que, C.J. Chang, Nat. Chem. Biol. 4(2008) 168-175. doi: 10.1038/nchembio.69
27. [27]
  J.H. Rao, A. Dragulescu-Andrasi, H.Q. Yao, Curr. Opin. Biotechnol. 18(2007) 17-25. doi: 10.1016/j.copbio.2007.01.003
28. [28]
  S.L. Luo, E.L. Zhang, Y.P. Su, T.M. Cheng, C.M. Shi, Biomaterials 32(2011) 7127-7138. doi: 10.1016/j.biomaterials.2011.06.024
29. [29]
  E.A. Specht, E. Braselmann, A.E. Palmer, Ann. Rev. Physiol. 79(2017) 93-117. doi: 10.1146/annurev-physiol-022516-034055
30. [30]
  S.L. Jacques, Phys. Med. Biol. 58(2013) R37-R61. doi: 10.1088/0031-9155/58/11/R37
31. [31]
  L.Y. Shi, L.A. Sordillo, A. Rodríguez-Contreras, R. Alfano, J. Biophotonics 9(2016) 38-43. doi: 10.1002/jbio.201500192
32. [32]
  Z.P. Qin, J.C. Bischof, Chem. Soc. Rev. 41(2012) 1191-1217. doi: 10.1039/C1CS15184C
33. [33]
  K. Welsher, Z. Liu, S.P. Sherlock, et al., Nat. Nanotechnol. 4(2009) 773-780. doi: 10.1038/nnano.2009.294
34. [34]
  P.Y. Wang, Y. Fan, L.F. Lu, et al., Nat. Commun. 9(2018) 2898. doi: 10.1038/s41467-018-05113-8
35. [35]
  J.Y. Zhao, D. Zhong, S.B. Zhou, Mater. Chem. B 6(2018) 349-365.
36. [36]
  A.L. Antaris, H. Chen, K. Cheng, et al., Nat. Mater. 15(2016) 235-242. doi: 10.1038/nmat4476
37. [37]
  S. Zhu, Z. Hu, R. Tian, et al., Adv. Mater. 30(2018) 1802546. doi: 10.1002/adma.v30.34
38. [38]
  V.J. Pansare, S. Hejazi, W.J. Faenza, R.K. Prud'homme, Chem. Mater. 24(2012) 812-827. doi: 10.1021/cm2028367
39. [39]
  E. Hemmer, A. Benayas, F. Légaré, F. Vetrone, Nanoscale Horiz. 1(2016) 168-184. doi: 10.1039/C5NH00073D
40. [40]
  J. Gao, X. Chen, Z. Cheng, Curr. Top Med. Chem. 10(2010) 1147-1157. doi: 10.2174/156802610791384162
41. [41]
  G. Qian, Z.Y. Wang, Chem. Asian J. 5(2010) 1006-1029. doi: 10.1002/asia.200900596
42. [42]
  M. Baloban, D.M. Shcherbakova, S. Pletnev, et al., Chem. Sci. 8(2017) 4546-4557. doi: 10.1039/C7SC00855D
43. [43]
  J. Piccard, Ber. Dtsch. Chem. Ges. 46(1913) 1843-1860.
44. [44]
  A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, G.B. Behera, Chem. Rev. 100(2000) 1973-2012. doi: 10.1021/cr990402t
45. [45]
  S. Daehne, Ute. Resch-Genger, O.S. Wolfbeis, Near-Infrared Dyes for High Technology Applications, Springer Science & Business Media, Berlin/Heidelberg, Germany, 2012.
46. [46]
  J. Yao, M. Yang, Y.X. Duan, Chem. Rev. 114(2014) 6130-6178. doi: 10.1021/cr200359p
47. [47]
  M.V. Marshall, J.C. Rasmussen, I. Tan, et al., Open Surg. Oncol. J. 2(2010) 12-25. doi: 10.2174/1876504101002020012
48. [48]
  I.J. Fox, E.H. Wood, Proc. Staff Meet. Mayo Clin. 35(1960) 732-744.
49. [49]
  Z. Starosolski, R. Bhavane, K.B. Ghaghada, et al., PLoS One 12(2017) e0187563. doi: 10.1371/journal.pone.0187563
50. [50]
  J.T. Alander, I. Kaartinen, A. Laakso, et al., Int. J. Biomed. Imaging 2012(2012) 940585.
51. [51]
  M.L. Landsman, G. Kwant, G.A. Mook, W.G. Zijlstra, J. Appl. Physiol. 40(1976) 575-583. doi: 10.1152/jappl.1976.40.4.575
52. [52]
  W. Holzer, M. Mauerer, A. Penzkofer, et al., J. Photochem. Photobiol. B Biol. 47(1998) 155-164. doi: 10.1016/S1011-1344(98)00216-4
53. [53]
  S. Yoneya, T. Saito, Y. Komatsu, et al., Invest. Ophthalmol. Visual Sci. 39(1998) 1286-1290.
54. [54]
  E. Engel, T. Schraml, T. Maisch, et al., Invest. Ophthalmol. Visual Sci. 49(2008) 1777-1783. doi: 10.1167/iovs.07-0911
55. [55]
  D.H. Oushiki, H. Kojima, T. Terai, et al., J. Am. Chem. Soc. 132(2010) 2795-2801. doi: 10.1021/ja910090v
56. [56]
  W. Sun, S.G. Guo, C. Hu, J.L. Fan, X.J. Peng, Chem. Rev. 116(2016) 7768-7817. doi: 10.1021/acs.chemrev.6b00001
57. [57]
  M.T. Sun, H. Yu, H.J. Zhu, et al., Anal. Chem. 86(2014) 671-677. doi: 10.1021/ac403603r
58. [58]
  K. Kundu, S.F. Knight, N. Willett, et al., Angew. Chem. Int. Ed. 48(2009) 299-303. doi: 10.1002/anie.v48:2
59. [59]
  X.T. Jia, Q.Q. Chen, Y.F. Yang, et al., J. Am. Chem. Soc.138(2016) 10778-10781. doi: 10.1021/jacs.6b06398
60. [60]
  G.T. Dempsey, M. Bates, W.E. Kowtoniuk, et al., J. Am. Chem. Soc. 131(2009) 18192-18193. doi: 10.1021/ja904588g
61. [61]
  H. Niu, X. Jiang, J. He, et al., Tetrahedron Lett. 50(2009) 6668-6671. doi: 10.1016/j.tetlet.2009.09.079
62. [62]
  L. Yuan, W.Y. Lin, K.B. Zheng, L.W. He, W.M. Huang, Chem. Soc. Rev. 42(2013) 622-661. doi: 10.1039/C2CS35313J
63. [63]
  M.Y. Li, P.C. Cui, K. Li, et al., Chin. Chem. Lett. 29(2018) 992-994. doi: 10.1016/j.cclet.2017.11.011
64. [64]
  Y. Yang, H. Wang, Y.L. Wei, et al., Chin. Chem. Lett. 28(2017) 2023-2026. doi: 10.1016/j.cclet.2017.08.051
65. [65]
  S. Dähne, Science 199(1978) 1163-1167. doi: 10.1126/science.199.4334.1163
66. [66]
  J. Griffiths, Colour and Constitution of Organic Molecules, Academic Press, London, 1976.
67. [67]
  R.L.M. Allen, Colour Chemistry, 1st ed., Appleton-Century-Crofts, New York, 1971.
68. [68]
  J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd ed., Oxford University Press, 2001.
69. [69]
  R.L. Christensen, A. Faksh, J.A. Meyers, et al., J. Phys. Chem. A 108(2004) 8229-8236. doi: 10.1021/jp048421g
70. [70]
  J. Rissler, Chem. Phys. Lett. 395(2004) 92-96. doi: 10.1016/j.cplett.2004.07.058
71. [71]
  C.B. Gorman, E.J. Ginsburg, S.R. Marder, R.H. Grubbs, Angew. Chem. Int. Ed. 28(1989) 1571-1574.
72. [72]
  K. Mullen, G. Wegner, Electronic Materials: The Oligomer Approach, WileyVCH, Berlin, 1998.
73. [73]
  R. Duval, C. Duplaisb, Nat. Prod. Rep. 34(2017) 161-193. doi: 10.1039/C6NP00111D
74. [74]
  W.P. Chen, R.F. Chen, Q.P. Liu, Y. He, K. He, Chem. Sci. 8(2017) 4917-4925. doi: 10.1039/C7SC00475C
75. [75]
  J.M. Gao, S.X. Yang, J.C. Qin, Chem. Rev. 113(2013) 4755-4811. doi: 10.1021/cr300402y
76. [76]
  J. Bendig, U. Schedler, T. Harder, et al., J. Photochem. Photobiol. A 91(1995) 53-57. doi: 10.1016/1010-6030(95)04108-R
77. [77]
  S.A. Tikhonov, V.I. Vovna, N.A. Gelfand, et al., J. Phys. Chem. A 120(2016) 7361-7369. doi: 10.1021/acs.jpca.6b07242
78. [78]
  A. Chaudhuri, Y. Venkatesh, K.K. Behara, N.D.P. Singh, Org. Lett. 19(2017) 1598-1601. doi: 10.1021/acs.orglett.7b00416
79. [79]
  S. Imazeki, A. Mukoh, T. Yoneyama, M. Kaneko, Mol. Cryst. Liq. Cryst. 145(1987) 79-93. doi: 10.1080/00268948708080215
80. [80]
  Y.M. Shen, Z.H. Shang, Y.H. Yang, et al., J. Org. Chem. 80(2015) 5906-5911. doi: 10.1021/acs.joc.5b00242
81. [81]
  Y. Xiao, F.Y. Liu, Z. Chen, et al., Chem. Commun. 51(2015) 6480-6488. doi: 10.1039/C4CC09846C
82. [82]
  A. Treibs, K. Jacob, Justus Liebigs Ann. Chem. 699(1966) 153-167.
83. [83]
  A. Schmitt, B. Hinkeldey, M. Wild, G. Jung, J. Fluoresc. 19(2009) 755-758. doi: 10.1007/s10895-008-0446-7
84. [84]
  M.Y. Fu, Y. Xiao, X.H. Qian, D.F. Zhao, Y.F. Xu, Chem. Commun.15(2008) 1780-1782.
85. [85]
  G. Sathyamoorthi, M.L. Soong, T.W. Ross, J.H. Boyer, Heteroat. Chem. 4(1993) 603-608.
86. [86]
  A.K.-Y. Jen, Y.Q. Liu, L.X. Zheng, et al., Adv. Mater. 11(1999) 452-455.
87. [87]
  Y.Y. Cheng, G.C. Li, Y. Liu, et al., J. Am. Chem. Soc. 138(2016) 4730-4738. doi: 10.1021/jacs.5b09241
88. [88]
  W.M. Liu, B.J. Zhou, G. Niu, et al., ACS Appl. Mater. Interfaces 7(2015) 7421-7427. doi: 10.1021/acsami.5b01429
89. [89]
  L. Yuan, W.Y. Lin, Y.T. Yang, H. Chen, J. Am. Chem. Soc. 134(2012) 1200-1211. doi: 10.1021/ja209292b
90. [90]
  M. Sibrian-Vazquez, J.O. Escobedo, M. Lowry, R.M. Strongin, Pure Appl. Chem. 84(2012) 2443-2456. doi: 10.1351/PAC-CON-11-11-06
91. [91]
  E. Azuma, N. Nakamura, K. Kuramochi, et al., J. Org. Chem. 77(2012) 3492-3500. doi: 10.1021/jo300177b
92. [92]
  A.B. Descalzo, K. Rurack, Chem. Eur. J. 15(2009) 3173-3185. doi: 10.1002/chem.v15:13
93. [93]
  R.S. Lepkowicz, C.M. Cirloganu, O.V. Przhonska, et al., Chem. Phys. 306(2004) 171-183. doi: 10.1016/j.chemphys.2004.07.021
94. [94]
  A. Treibs, K. Jacob, Angew. Chem. Int. Ed. 4(1965) 694-694.
95. [95]
  X.Z. Song, J.W. Foley, Dyes Pigm. 78(2008) 60-64. doi: 10.1016/j.dyepig.2007.10.006
96. [96]
  B.H. Li, L.F. Lu, M.Y. Zhao, Z.H. Lei, F. Zhang, Angew. Chem. Int. Ed. 57(2018) 7483-7487. doi: 10.1002/anie.201801226
97. [97]
  B.L. Guennic, D. Jacquemin, Acc. Chem. Res. 48(2015) 530-537. doi: 10.1021/ar500447q
98. [98]
  K.Z. Gu, Y.S. Xu, H. Li, et al., J. Am. Chem. Soc. 138(2016) 5334-5340. doi: 10.1021/jacs.6b01705
99. [99]
  N. Karton-Lifshin, L. Albertazzi, M. Bendikov, et al., J. Am. Chem. Soc. 134(2012) 20412-20420. doi: 10.1021/ja308124q
100. [100]
  H.Y. Li, X.H. Li, W. Shi, Y.H. Xu, H.M. Ma, Angew. Chem. Int. Ed. 57(2018) 12830-12834. doi: 10.1002/anie.201808400
101. [101]
  L. Strekowski, Heterocyclic Polymethine Dyes: Synthesis, Properties and Applications, Springer-Verlag, Berlin, 2008.
102. [102]
  K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, K. Suzuki, J. Am. Chem. Soc. 130(2008) 1550-1551. doi: 10.1021/ja077756j
103. [103]
  M. Irie, Chem. Rev. 100(2000) 1685-1716. doi: 10.1021/cr980069d
104. [104]
  G.L. Niu, W.M. Liu, B.J. Zhou, et al., J. Org. Chem. 81(2016) 7393-7399. doi: 10.1021/acs.joc.6b00981
105. [105]
  D. Wu, Y.Z. Shen, J.H. Chen, et al., Chin. Chem. Lett. 28(2017) 1979-1982. doi: 10.1016/j.cclet.2017.07.004
106. [106]
  F.L. Song, R. Liang, J.D. Deng, Z.W. Liu, X.J. Peng, Chin. Chem. Lett. 28(2017) 1997-2000. doi: 10.1016/j.cclet.2017.08.023
107. [107]
  Z.H. Lei, Z.H. Zeng, X.H. Qian, Y.J. Yang, Chin. Chem. Lett. 28(2017) 2001-2004. doi: 10.1016/j.cclet.2017.09.023
108. [108]
  P. Ning, W.J. Wang, M. Chen, Y. Feng, X.M. Meng 28(2017) 1943-1951.
109. [109]
  X.T. Jia, Q.Q. Chen, Y.F. Yang, et al., J. Am. Chem. Soc.138(2016) 10778-10781. doi: 10.1021/jacs.6b06398
110. [110]
  A.P. Gorka, R.R. Nani, J.J. Zhu, S. Mackem, M.J. Schnermann, J. Am. Chem. Soc. 136(2014) 14153-14159. doi: 10.1021/ja5065203
111. [111]
  X. Jing, C. He, L. Zhao, C.Y. Duan, Acc. Chem. Res. 52(2019) 100-109. doi: 10.1021/acs.accounts.8b00463
112. [112]
  S.Y. Hsueh, C.C. Lai, Y.H. Liu, et al., Org. Lett. 9(2007) 4523-4526. doi: 10.1021/ol702050w
113. [113]
  A.G. Cheetham, T.D.W. Claridge, H.L. Anderson, Org. Biomol. Chem. 5(2007) 457-462. doi: 10.1039/b616621k
114. [114]
  E.J.F. Klotz, T.D.W. Claridge, H.L. Anderson, J. Am. Chem. Soc. 128(2006) 15374-15375. doi: 10.1021/ja0665139
115. [115]
  E. Arunkumar, C.C. Forbes, B.C. Noll, B.D. Smith, J. Am. Chem. Soc. 127(2005) 3288-3289. doi: 10.1021/ja042404n
116. [116]
  Z.M. Tao, G.S. Hong, C. Shinji, et al., Angew. Chem. Int. Ed. 125(2013) 13240-13244. doi: 10.1002/ange.201307346
117. [117]
  S. Hecht, J.M.J. Frechet, Angew. Chem. Int. Ed. 40(2001) 74-91. doi: 10.1002/1521-3773(20010105)40:1<>1.0.CO;2-6
118. [118]
  K. Yanagi, K. Iakoubovskii, H. Matsui, et al., J. Am. Chem. Soc. 129(2007) 4992-4997. doi: 10.1021/ja067351j
119. [119]
  X.M. Wu, S. Chang, X.R. Sun, Chem. Sci. 4(2013) 1221-1228. doi: 10.1039/c2sc22035k
120. [120]
  J.E.H. Buston, J.R. Young, H.L. Anderson, Chem. Commun.11(2000) 905-906.
121. [121]
  M. Cooper, A. Ebner, M. Briggs, et al., J. Fluoresc. 14(2004) 145-150. doi: 10.1023/B:JOFL.0000016286.62641.59
122. [122]
  C.Y. Fan, J.C. Hsiang, R.M. Dickson, ChemPhysChem 13(2012) 1023-1029. doi: 10.1002/cphc.201100671
123. [123]
  B. Li, Z. He, H. Zhou, H. Zhang, T. Cheng, Chin. Chem. Lett. 28(2017) 1929-1934. doi: 10.1016/j.cclet.2017.08.055
124. [124]
  J.L. Bricks, A.D. Kachkovskii, Y.L. Slominskii, A.O. Gerasov, S.V. Popov, Dyes Pigm. 121(2015) 238-255. doi: 10.1016/j.dyepig.2015.05.016
125. [125]
  M.S. Michie, R. Götz, C. Franke, et al., J. Am. Chem. Soc. 139(2017) 12406-12409. doi: 10.1021/jacs.7b07272
126. [126]
  M.L. Korb, Y.E. Hartman, J. Kovar, et al., J. Surg. Res. 188(2014) 119-128. doi: 10.1016/j.jss.2013.11.1089
127. [127]
  A. Baeyer, Ber. Dtsch. Chem. Ges. 4(1871) 555-558.
128. [128]
  Y.J. Yang, M. Lowry, X.Y. Xu, et al., Proc. Natl. Acad. Sci. U. S. A. 105(2008) 8829-8834. doi: 10.1073/pnas.0710341105
129. [129]
  J.B. Grimm, A.J. Sung, W.R. Legant, et al., ACS Chem. Biol. 8(2013) 1303-1310. doi: 10.1021/cb4000822
130. [130]
  T. Egawa, Y. Koide, K. Hanaoka, et al., Chem. Commun. 47(2011) 4162-4164. doi: 10.1039/c1cc00078k
131. [131]
  A. Fukazawa, S. Suda, M. Taki, et al., Chem. Commun. 52(2016) 1120-1123. doi: 10.1039/C5CC09345G
132. [132]
  J.B. Grimm, B.P. English, J.J. Chen, et al., Nat. Methods 12(2015) 244-250. doi: 10.1038/nmeth.3256
133. [133]
  L. Wu, K. Burgess, Org. Lett. 10(2008) 1779-1782. doi: 10.1021/ol800526s
134. [134]
  Y. Koide, Y. Urano, K. Hanaoka, T. Terai, T. Nagano, ACS Chem. Biol. 6(2011) 600-608. doi: 10.1021/cb1002416
135. [135]
  C. Aaron, C.C. Barker, J. Chem. Soc. (1963) 2655-2662.
136. [136]
  X.Q. Zhou, R. Lai, J.R. Beck, H. Li, C.I. Stains, Chem. Commun. 52(2016) 12290-12293. doi: 10.1039/C6CC05717A
137. [137]
  J. Liu, Y.Q. Sun, H.X. Zhang, et al., ACS Appl. Mater. Interfaces 8(2016) 22953-22962. doi: 10.1021/acsami.6b08338
138. [138]
  M. Sauer, K.T. Han, R. Muller, et al., J. Fluoresc. 5(1995) 247-261. doi: 10.1007/BF00723896
139. [139]
  M. Sauer, K.T. Han, R. Muller, et al., J. Fluoresc. 3(1993) 131-139. doi: 10.1007/BF00862730
140. [140]
  O.O. Abugo, R. Nair, J.R. Lakowicz, Anal. Biochem. 279(2000) 142-150. doi: 10.1006/abio.2000.4486
141. [141]
  A.V. Anzalone, T.Y. Wang, Z.X. Chen, V.W. Cornish, Angew. Chem. Int. Ed. 52(2013) 650-654. doi: 10.1002/anie.201205369
142. [142]
  J. Arden-Jacob, J. Frantzeskos, N.U. Kemnitzer, A. Zilles, K.H. Drexhage, Spectrochimica Acta Part A 57(2001) 2271-2283. doi: 10.1016/S1386-1425(01)00476-0
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