Communication
ChemComm
followed by injection of 0.5 mmol TPA–BTD–MT for 10 min, Conflicts of interest
strong fluorescence was clearly observed (Fig. 3F). The average
The authors declare no conflicts of interest.
fluorescence intensity from the abdominal area is calculated as
shown in Fig. 3G. The fluorescence from the mice injected with
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Notes and references
TPA–BTD–MT and CN is 11.5-fold larger than that from the
mice with TPA–BTD–MT. This indicates that TPA–BTD–MT can
be deservedly used as a sensitive fluorescence probe to monitor
the changes in the CN level in biological systems.
1 J. Mondal, A. K. Manna and G. K. Patra, Inorg. Chim. Acta, 2018, 474,
2–29.
Y. Shiraishi, S. Sumiya and T. Hirai, Chem. Commun., 2011, 47,
953–4955.
3 S.-Y. Chung, S.-W. Nam, J. Lim, S. Park and J. Yoon, Chem. Commun.,
009, 2866–2868.
2
2
ꢀ
4
The practical application of the TMP–BTD–MT probe in food
samples was evaluated in sprouting potatoes, cassava, bitter apricot
2
4
Z.-Z. Dong, C. Yang, K. Vellaisamy, G. Li, C.-H. Leung and D.-L. Ma,
ACS Sens., 2017, 2, 1517–1522.
9
seeds, and apple seeds. A calibration curve was first obtained by the
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successive addition of CN aqueous solution into the THF solution
5 Guidelines for Drinking-Water Quality, World Health Organization,
Geneva, Switzerland, 2008.
T. Li, L. Wang, S. Lin, X. Xu, M. Liu, S. Shen, Z. Yan and R. Mo,
of TMP–BTD–MT (Fig. S11–S13, ESI†). The fluorescence response
6
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increased linearly with the increase in the CN concentration from
Bioconjugate Chem., 2018, 29, 2838–2845.
0
.025 to 10.0 mM. The limit of detection (LOD) was calculated to be
7 W. Jiang, Q. Fu, H. Fan, J. Ho and W. Wang, Angew. Chem., Int. Ed.,
2007, 46, 8445–8448.
30
0.087 mM on the basis of 3s/S, which is far lower than the
8
L. Long, M. Huang, N. Wang, Y. Wu, K. Wang, A. Gong, Z. Zhang and
J. L. Sessler, J. Am. Chem. Soc., 2018, 140, 1870–1875.
permissible limit (1.9 mM) set by the WHO and comparable with
those in the previous reports (Table S2, ESI†). According to the
calibration curve, four food samples containing CN were detected
9 Q. Niu, L. Lan, T. Li, Z. Guo, T. Jiang, Z. Zhao, Z. Feng and J. Xi, Sens.
Actuators, B, 2018, 276, 13–22.
ꢀ
10 B. Shi, P. Zhang, T. Wei, H. Yao, Q. Lin and Y. Zhang, Chem.
by the standard addition method and acceptable recoveries between
Commun., 2013, 49, 7812–7814.
9
7% and 102% were obtained (Table S3, ESI†). The results indicate 11 X. Lou, L. Qiang, J. Qin and Z. Li, ACS Appl. Mater. Interfaces, 2009, 1,
2529–2535.
that the analysis based on the proposed TMP–BTD–MT probe is
reliable for CN sensing in food analysis.
1
1
2 A. Panja and K. Ghosh, ChemistrySelect, 2018, 3, 1809–1814.
3 L. Long, X. Yuan, S. Cao, Y. Han, W. Liu, Q. Chen, Z. Han and
K. Wang, ACS Omega, 2019, 4, 10784–10790.
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In conclusion, a novel fluorescent ‘‘turn-on’’ probe (TPA–BTD–MT)
was designed by inserting an electron-deficient BTD into a
fluorescence ‘‘turn-off’’ probe TPA–MT molecule to change its
structure and enlarge its conjugation system. TPA–BTD–MT
showed low cytotoxicity to BEAS-2B cells and it could be used
1
4 P. Liu, W. Li, S. Guo, D. Xu, M. Wang, J. Shi, Z. Cai, B. Tong and
Y. Dong, ACS Appl. Mater. Interfaces, 2018, 10, 23667–23673.
5 K. Mutoh, N. Miyashita, K. Arai and J. Abe, J. Am. Chem. Soc., 2019,
141, 5650–5654.
1
1
1
6 Z. Liu, X. Wang, Z. Yang and W. He, J. Org. Chem., 2011, 76, 10286–10290.
7 M. Zhang, H. N. Tsao, W. Pisula, C. Yang, A. K. Mishra and
K. M u¨ llen, J. Am. Chem. Soc., 2007, 129, 3472–3473.
ꢀ
to monitor CN in living cells and living animals with strong
‘
‘turn-on’’ fluorescence. The probe TPA–BTD–MT exhibited 18 J. Guo, H. He, Z. Ye, K. Zhu, Y. Wu and F. Zhang, Org. Lett., 2018, 20,
ꢀ
5692–5695.
highly sensitive and selective CN detection with a low LOD
and it was successfully employed to determine CN in four
1
9 Y. Cheng, G. Yang, H. Jiang, S. Zhao, Q. Liu and Y. Xie, ACS Appl.
Mater. Interfaces, 2018, 10, 38880–38891.
ꢀ
real food samples with appreciable accuracy. The study pro- 20 S. Amari, S. Ando, S. Miyanishi and T. Yamaguchi, Ind. Eng. Chem.
Res., 2018, 57, 16095–16102.
vides a new strategy for creation of chemosensors to monitor
cyanide.
This work was supported by the Natural Science Foundation
of Higher Education Institutions in Anhui Province (No.
KJ2019ZD37 and KJ2018ZD035), the Horizontal Cooperation
2
2
1 Y. Li, T. Ren and W.-J. Dong, J. Photochem. Photobiol., A, 2013, 251, 1–9.
2 S. Lohar, K. Dhara, P. Roy, S. P. S. Babu and P. Chattopadhyay, ACS
Omega, 2018, 3, 10145–10153.
3 G. Fu, H. Zhang, Y. Yan and C. Zhao, J. Org. Chem., 2012, 77, 1983–1990.
4 P. G. Rao, B. Saritha and T. S. Rao, J. Photochem. Photobiol., A, 2019,
2
2
372, 177–185.
Project of Fuyang Municipal Government and Fuyang Normal 25 D. Patra and C. Barakat, Spectrochim. Acta, Part A, 2011, 79, 1034–1041.
2
2
6 C. Reichardt, Chem. Rev., 1994, 94, 2319–2358.
7 Y. Shiraishi, M. Nakamura, K. Yamamoto and T. Hirai, Chem.
Commun., 2014, 50, 11583–11586.
University (No. XDHX201701 and XDHX201704), the National
Natural Science Foundation of China (No. 91643113 and
2
1637004), the Natural Science Foundation of Anhui Province 28 A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899–926.
2
9 W.-C. Lin, S.-K. Fang, J.-W. Hu, H.-Y. Tsai and K.-Y. Chen, Anal.
Chem., 2014, 86, 4648–4652.
(No. 1708085MB43), the National Training Programs of Innova-
tion and Entrepreneurship for Undergraduates (201910371009)
and the Anhui provincial teaching team program (2017jxtd025).
30 C. Long, J.-H. Hu, P. Ni, Z. Yin and Q. Fu, New J. Chem., 2018, 42,
17056–17061.
1
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