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Journal Name
staining. In order to check whether PEMC-2 exhibits higher 9. M. Hergert, M. Bender, K. Seehafer and U. H. F. Bunz, Chem.
Eur. J., 2018, 24, 3132-3135.
0. A. Barattucci, E. Deni, P. Bonaccorsi, M. G. Ceraolo, T. Papalia,
DOI: 10.1039/C9CC02162K
fluorescence intensity upon interacting with RNA, the
fluorescent intensity of the macrocycle was examined as the
amounts of RNA increased (Fig. 2b). The fluorescent intensity of
PEMC-2 was slightly increased upon mixing with the excess
amounts of NAs, but no intensity differences between RNA and
DNA were observed from the macrocycle. The increased
emission intensity, blue-shifted emission maximum, and
decreased spectral width of PEMC-2/NA imply the slightly
reduced - stacking between the two PE trimers in the cycle
1
A. Santoro, M. T. Sciortino and F. Puntoriero, J. Org. Chem.,
2
014, 79, 5113-5120.
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1
1
1. C. Nie, S. Li, B. Wang, L. Liu, R. Hu, H. Chen, F. Lv, Z. Dai and S.
Wang, Adv. Mater., 2016, 28, 3749-3754.
2. J. Wang, L. Zhou, H. Sun, F. Lv, L. Liu, Y. Ma and S. Wang, Chem.
Mater., 2018, 30, 5544-5549.
3. S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders and J.
F. Stoddart, Angew. Chem.Int. Ed., 2002, 41, 898-952.
upon interacting with NAs. The PE trimer control exhibits very 14. S. Grimme, S. Ehrlich and L. Goerigk, J.Comput. Chem., 2011,
small changes in emission upon NA complexation (Fig. 2b). From
the observations, we concluded that PEMC-2 has higher affinity
to RNA over DNA. The distinguishable nucleus staining after
RNase treatment indicates that relatively small amounts of
PEMC-2 were also bound to DNA and the fluorescent signals
became visible once the intense signals from RNA-bound PEMC-
32, 1456-1465.
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1
1
1
1
5. H. Li, Y. Li, H. Zhang, G. Xu, Y. Zhang, X. Liu, H. Zhou, X. Yang, X.
Zhang and Y. Tian, Chem. Commun., 2017, 53, 13245-13248.
6. R. Feng, L. Li, B. Li, J. Li, D. Peng, Y. Yu, Q. Mu, N. Zhao, X. Yu
and Z. Wang, RSC Adv., 2017, 7, 16730-16736.
7. G. Niu, W. Liu, B. Zhou, H. Xiao, H. Zhang, J. Wu, J. Ge and P.
Wang, J. Org. Chem., 2016, 81, 7393-7399.
8. L. Guo, M. S. Chan, D. Xu, D. Y. Tam, F. Bolze, P. K. Lo and M. S.
Wong, ACS Chem. Biol., 2015, 10, 1171-1175.
9. Y.-J. Lu, Q. Deng, D.-P. Hu, Z.-Y. Wang, B.-H. Huang, Z.-Y. Du, Y.-
X. Fang, W.-L. Wong, K. Zhang and C.-F. Chow, Chem.
Commun., 2015, 51, 15241-15244.
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were removed by digestion of RNA. The PE trimer control
sharing the same primary amine-containing side chains exhibits
a somewhat similar imaging pattern to that of PEMC-2 (Fig. 5g-
i). However, the overall fluorescent intensity and the contrast
between nucleus and nucleolus is much lower, implying that
cyclization of PE trimers to a macrocycle can enhance the 20. J. S. Andersen, Y. W. Lam, A. K. L. Leung, S. E. Ong, C. E. Lyon,
A. I. Lamond and M. Mann, Nature, 2005, 433, 77-83.
1. M. Derenzini, D. Trere, A. Pession, M. Govoni, V. Sirri and P.
Chieco, J. Pathol., 2000, 191, 181-186.
2. Q. Li, Y. Kim, J. Namm, A. Kulkarni, G. R. Rosania, Y.-H. Ahn and
Y.-T. Chang, Chem. Biol., 2006, 13, 615-623.
3. B. Shirinfar, N. Ahmed, Y. S. Park, G.-S. Cho, I. S. Youn, J.-K.
Han, H. G. Nam and K. S. Kim, J. Am. Chem. Soc., 2013, 135, 90-
brightness and RNA selectivity of COs.
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In conclusion, we have demonstrated a highly efficient
synthetic method of macrocycles by combining multiple
fluorophores into a cyclic molecule with a defined molecular
weight. We also discovered that the RNA selectivity in live cells
could be improved by a straightforward cyclization of two rigid
PE oligomers with the flexible amine side chains. Considering
the availability of various COs with different colours and
functional groups, our demonstration could lead to realization
of highly selective labelling and sensing of target intracellular
organelles in live cells, which will provide pivotal biological
information of cells.
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3.
Conflicts of interest
There are no conflicts to declare.
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