Journal of the American Chemical Society
Communication
directly injected into the tail of mice bearing subcutaneously
implanted tumors. Five minutes after injection, strong
fluorescence signals were observed at the mouse tumor site
and increased with increasing SP1 concentration (0.1 to 2
mM). Clearly, only the tumor site displayed strong fluorescence
images and no fluorescence signal was obtained from other
normal organs. These results indicate that SP1 can be
employed for real-time visualization of tyrosine kinases in
(10) Radford, R. J.; Chyan, W.; Lippard, S. J. Chem. Sci. 2013, 4,
3
080.
(
11) Li, S. J.; Li, C. Y.; Li, Y. F.; Fei, J. J.; Wu, P.; Yang, B.; Ou-Yang,
J.; Nie, S. X. Anal. Chem. 2017, 89, 6854−6860.
12) Peng, T.; Hang, C. H. J. Am. Chem. Soc. 2016, 138, 14423−
4433.
13) Chapin, B. M.; Metola, P.; Vankayala, S. L.; Woodcock, H. L.;
(
1
(
Mooibroek, T. J.; Lynch, V. M.; Larkin, J. D.; Anslyn, E. V. J. Am.
Chem. Soc. 2017, 139, 5568−5578.
3
5,36
tumors.
(14) Lin, W.; Buccella, D.; Lippard, S. J. J. Am. Chem. Soc. 2013, 135,
13512−13520.
In conclusion, we reported the molecular sensor ability of a
PET-quenched fluorogenic protein-tyrosine kinase receptor
inhibitor. The fluorescence signal is selectively and quickly
generated by interaction with protein-tyrosine kinase receptors
accumulating on the cell membranes of cancer cells. The “off−
on” fluorescence enhancement results from the restrained PET
following SP1 binding to protein-tyrosine kinase receptors on
the cell membrane. SP1 permits the rapid, highly selective and
sensitive identification of cancer cells via imaging of the tumor
cell membranes, the chick embryo CAM and tumors in a
mouse model by fluorescence microscopy. Therefore, SP1
would be useful in the realization of early cancer diagnosis.
(15) Lee, M. H.; Jeon, H. M.; Han, J. H.; Park, N.; Kang, C.; Sessler,
J. L.; Kim, J. S. J. Am. Chem. Soc. 2014, 136, 8430−8437.
(16) Manning, H. C.; Merchant, N. B.; Foutch, A. C.; Virostko, J. M.;
Wyatt, S. K.; Shah, C.; McKinley, E. T.; Xie, J. P.; Mutic, N. J.;
Washington, M. K.; LaFleur, B.; Tantawy, M. N.; Peterson, T. E.;
Ansari, M. S.; Baldwin, R. M.; Rothenberg, M. L.; Bornhop, D. J.;
Gore, J. C.; Coffey, R. Clin. Cancer Res. 2008, 14, 7413−7422.
(17) Levashova, Z.; Backer, M.; Backer, J. M.; Blankenberg, F. G. J.
Nucl. Med. 2009, 50, 2058−2062.
(18) Patra, M.; Awuah, S. G.; Lippard, S. J. J. Am. Chem. Soc. 2016,
138, 12541−12551.
(19) Li, Y. H.; Sun, Y.; Li, J. C.; Su, Q. Q.; Yuan, W.; Dai, D.; Han, C.
M.; Wang, Q. H.; Feng, W.; Li, F. Y. J. Am. Chem. Soc. 2015, 137,
6
(
407.
20) Cella, D.; Davis, M. P.; Negrier, S.; Figlin, R. A.; Michaelson, M.
ASSOCIATED CONTENT
■
*
S
Supporting Information
D.; Bushmakin, A. G.; Cappelleri, J. C.; Sandin, R.; Korytowsky, B.;
Charbonneau, C.; Matczak, E.; Motzer, R. J. Cancer 2014, 120, 1871.
(21) Schedlbauer, A.; Coudevylle, N.; Auer, R.; Kloiber, K.; Tollinger,
M.; Konrat, R. J. Am. Chem. Soc. 2009, 131, 6038−6039.
spectra and MS data (PDF)
(
22) Zhang, H.; Fan, J. L.; Wang, J. Y.; Zhang, S. Z.; Dou, B. R.;
Peng, X. J. J. Am. Chem. Soc. 2013, 135, 11663−11669.
23) Escriba, P. V.; Busquets, X.; Inokuchi, J.; Balogh, G.; To
Horvath, I.; Harwood, J. L.; Vígh, L. Prog. Lipid Res. 2015, 59, 38−53.
24) Bai, X. Y.; Huang, Y. Y.; Lu, M. Y.; Yang, D. Angew. Chem. 2017,
29, 13053−13057.
25) Lozano-Torres, B.; Galiana, I.; Rovira, M.; Garrido, E.; Chaib,
S.; Bernardos, A.; Munoz-Espín, D.; Serrano, M.; Martínez-Manez, R.;
Sancenon, F. J. Am. Chem. Soc. 2017, 139, 8808−8811.
26) Singer, S. J.; Nicolson, G. L. Science 1972, 175, 720−31.
27) Zhuang, Y. D.; Chiang, P. Y.; Wang, C. W.; Tan, K. T. Angew.
(
́
̈ ̈
rok, Z.;
́
AUTHOR INFORMATION
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1
(
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̃
ORCID
́
(
(
Notes
Chem., Int. Ed. 2013, 52, 8124−8128.
(
28) Liu, P.; Calderon, A.; Konstantinidis, G.; Hou, J.; Voss, S.; Chen,
The authors declare no competing financial interest.
X.; Li, F.; Banerjee, S.; Hoffmann, J. E.; Theiss, C.; Dehmelt, L.; Wu,
Y. W. Angew. Chem., Int. Ed. 2014, 53, 10049−10055.
ACKNOWLEDGMENTS
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29) Liu, G. G.; Chen, D. D.; Kong, L. W.; Shi, J. B.; Tong, B.; Zhi, J.
This work was supported by the NSFC (Nos. 21501020 and
1421005).
G.; Feng, X.; Dong, Y. P. Chem. Commun. 2015, 51, 8555−8558.
(30) Liu, L.; Liu, X. X.; Xu, Q.; Wu, P.; Zuo, X. L.; Zhang, J. J.; Deng,
H. L.; Wu, Z. M.; Ji, A. M. Int. J. Nanomed. 2014, 9, 3509−3526.
2
(31) Meng, F. F.; Liu, Y.; Niu, J.; Lin, W. Y. RSC Adv. 2017, 7, 16087.
(32) Shan, Y. P.; Wang, H. D. Chem. Soc. Rev. 2015, 44, 3617−3638.
(33) Li, Z.; Qu, T. J.; Ding, C.; Ma, C.; Sun, H. C.; Li, S. R.; Liu, X.
REFERENCES
■
(
1) Chang, S. K.; Rizvi, I.; Solban, N.; Hasan, T. Clin. Cancer Res.
008, 14, 4146−4153.
2) Faes, S.; Uldry, E.; Planche, A.; Santoro, T.; Pythoud, C.;
Demartines, N.; Dormond, O. Oncotarget 2016, 7, 1−13.
3) Yue, Y. K.; Huo, F. J.; Ning, P.; Zhang, Y. B.; Chao, J. B.; Meng,
X. M.; Yin, C. X. J. Am. Chem. Soc. 2017, 139, 3181−3185.
4) Li, L.; Zhang, C. W.; Ge, J. Y.; Qian, L. H.; Chai, B. H.; Zhu, Q.;
Lee, J. S.; Lim, K. L.; Yao, S. Q. Angew. Chem., Int. Ed. 2015, 54, 10821.
2
H. Acta Biomater. 2015, 13, 88−100.
34) Gu, K. Z.; Xu, Y. S.; Li, H.; Guo, Z. Q.; Zhu, S. J.; Zhu, S. Q.;
Shi, P.; James, T. D.; Tian, H.; Zhu, W. H. J. Am. Chem. Soc. 2016, 138,
334.
35) Yin, J.; Kwon, Y.; Kim, D.; Lee, D.; Kim, G.; Hu, Y.; Ryu, J. H.;
Yoon, J. J. Am. Chem. Soc. 2014, 136, 5351−5358.
36) Cheng, D.; Pan, Y.; Wang, Lu; Zeng, Z. B.; Yuan, L.; Zhang, X.
B.; Chang, Y. T. J. Am. Chem. Soc. 2017, 139, 285−292.
(
(
(
5
(
(
(
(
(
5) Michaelson, M. D. Cancer 2012, 118, 1744−1766.
6) Komatsu, T.; Johnsson, K.; Okuno, H.; Bito, H.; Inoue, T.;
Nagano, T.; Urano, Y. J. Am. Chem. Soc. 2011, 133, 6745−6751.
7) Kobayashi, T.; Komatsu, T.; Kamiya, M.; Campos, C.; Gonzalez-
Gaitan, M.; Terai, T.; Hanaoka, K.; Nagano, T.; Urano, Y. J. Am. Chem.
Soc. 2012, 134, 11153−11160.
8) Dai, Z. R.; Feng, L.; Jin, Q.; Cheng, H. L.; Li, Y.; Ning, J.; Yu, Y.;
Ge, G. B.; Cui, J. N.; Yang, L. Chem. Sci. 2017, 8, 2795−2803.
9) Boonstra, M. C.; de Geus, S. W. L.; Prevoo, H. A. J. M.;
(
́
́
(
(
Hawinkels, L. J. A. C.; van de Velde, C. J. H.; Kuppen, P. J. K.;
Vahrmeijer, A. L.; Sier, C. F. M. Biomarkers Cancer 2016, 8, 119−133.
D
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX