Chemistry - An Asian Journal
10.1002/asia.201600986
COMMUNICATION
A mixture of compound 8 (7.9 mg, 0.013 mmol) and Pd(OAc)
2
(0.2 mg, 5
S. C. Dodani, C. J. Chang, Nat. Chem. 2012, 4, 973-984; d) M. E. Jun,
B. Roy, K. H. Ahn, Chem. Commun. 2011, 47, 7583-7601.
W. R. Zipfel, R. M. Williams, R. Christie, A. Y. Nikitin, B. T. Hyman, W.
W. Webb, Proc. Natl. Acad. Sci. USA 2003, 100, 7075-7080.
a) D. Kim, H. G. Ryu, K. H. Ahn, Org. Biomol. Chem. 2014, 12, 4550-
4566; b) H. M. Kim, B. R. Cho, Chem. Rev. 2015, 115, 5014-5055; c) W.
R. Zipfel, R. M. Williams, W. W. Webb, Nat. Biotech. 2003, 21, 1369-
1377.
mol% Pd), DPPP (1,3-bis(diphenylphosphino)propane, 0.6 mg, 10 mol%)
in ethylene glycol (250 μL) under argon at 25 °C was degassed three
times, and then it was treated with 2-hydroxyethyl vinyl ether (6.0 μL,
[2]
[3]
0.067 mmol) and distilled triethylamine (5.0 μL, 0.036 mmol). The
resulting mixture was heated to 145 °C for 4 h. After being cooled to
2
5 °C, the mixture was treated with 2 N HCl (500 μL) and stirred at 25 °C
[
19]
overnight.
The mixture was diluted with dichloromethane (10 mL), and
solution (5
mL), and brine (5 mL). The organic layer was dried over anhydrous
MgSO , filtered and concentrated in vacuo. The crude product was
purified by silica gel flash column chromatography (eluent: EtOAc/hexane
1/19 to 1/9) to give anthradan 1 as an orange solid (2.6 mg, 35%).
washed sequentially with water (5 mL), 5% aqueous NaHCO
3
[4]
[5]
H. M. Kim, B. R. Cho, Chem-Asian J. 2011, 6, 58-69.
D. Kim, H. Moon, S. H. Baik, S. Singha, Y. W. Jun, T. Wang, K. H. Kim,
B. S. Park, J. Jung, I. Mook-Jung, K. H. Ahn, J. Am. Chem. Soc. 2015,
137, 6781-6789.
4
=
[6]
a) S. Singha, D. Kim, B. Roy, S. Sambasivan, H. Moon, A. S. Rao, J. Y.
Kim, T. Joo, J. W. Park, Y. M. Rhee, T. Wang, K. H. Kim, Y. H. Shin, J.
Jung, K. H. Ahn, Chem. Sci. 2015, 6, 4335-4342; b) S. Singha, D. Kim,
H. Moon, T. Wang, K. H. Kim, Y. H. Shin, J. Jung, E. Seo, S. J. Lee, K.
H. Ahn, Anal. Chem. 2015, 87, 1188-1195; c) H. Moon, Q. P. Xuan, D.
Kim, Y. Kim, J. W. Park, C. H. Lee, H.-J. Kim, A. Kawamata, S. Y. Park,
K. H. Ahn, Cryst. Growth Des. 2014, 14, 6613-6619; d) D. Kim, Q. P.
Xuan, H. Moon, Y. W. Jun, K. H. Ahn, Asian J. Org. Chem. 2014, 3,
OPM/TPM imaging of tissue samples
Preparation of mouse organ tissue samples and their TPM imaging: The
experimental procedures for mouse tissue samples were performed in
accordance with the protocols approved by the Pohang University of
Science and Technology Committee on Animal Research and also by
following the guidelines for the use of experimental animals established
by The Korean Academy of Medical Science. We made every effort to
minimize animal suffering and reduce the number of mice used to
prepare samples for imaging.
1089-1096; e) A. S. Rao, D. Kim, H. Nam, H. Jo, K. H. Kim, C. Ban, K.
H. Ahn, Chem. Commun. 2012, 48, 3206-3208; f) I. Kim, D. Kim, S.
Sambasivan, K. H. Ahn, Asian J. Org. Chem. 2012, 1, 60-64; g) D. Kim,
S. Singha, T. Wang, E. Seo, J. H. Lee, S. J. Lee, K. H. Kim, K. H. Ahn,
Chem. Commun. 2012, 48, 10243-10245; h) D. Kim, S. Sambasivan, H.
Nam, K. H. Kim, J. Y. Kim, T. Joo, K. H. Lee, K. T. Kim, K. H. Ahn,
Chem. Commun. 2012, 48, 6833-6835; i) M. Tasior, D. Kim, S. Singha,
M. Krzeszewski, K. H. Ahn, D. T. Gryko, J. Mater. Chem. C 2015, 3,
1421-1446.
A customized designed two-photon microscope (TCS SP5 II, Leica) with
a Ti-Sapphire laser (Chameleon Vision II, Coherent) at 140 fs pulse width
and 80 MHz pulse repetition rate was used. Coupling with various one-
photon excitation lasers based on continuous wavelength also enabled
this two-photon microscope to image the same region. 3D imaging was
performed by using high-aperture optimized confocal and two-photon 20×
objective lenses (HCX APO L 20× / 1.0 NA W, Leica) with the stepwise
increment of 2 μm in the depth direction from the surface of specimen
down to about 50 μm deep. The excitation laser was tuned to 488 nm
and 950 nm for OPM and TPM images of fluorescence signals of
anthradan 1, respectively. The emission light was spectrally resolved
within 525–625 nm and 495–620 nm using dichroic mirrors for OPM and
TPM, respectively. Power of the excitation laser was approximately 5
mW and 7 mW for OPM and TPM at the focal point, respectively. Both
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R. S. C. Lopes, A. J. R. da Silva, A. L. M. Albert, C. C. Lopes,
Tetrahedron Letters 2013, 54, 2587-2590.
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12-bit OPM and TPM images were acquired on 300 μm × 300 μm of
field-of-view (FOV) consisting of 1024 × 1024 pixels, and the imagine
speed was 0.195 frames/s (200 Hz/frame). Image processing was
performed by using LAS AF Lite (Leica, Germany).
[
[
[
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3
Acknowledgements
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This work was supported by Ministry of Health & Welfare
(
HI13C1378) and through National Research Foundation of
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Korea (NRF, 2014K1A1A2064569; 2014K2A1A2044402) funded
by Ministry of Science, ICT & Future Planning (MSIP). K. H. Kim
thanks to the NRF (Grant No. 2011-0030075) funded by the
MSIP and Grant (W15-653) from the Asan Institute for Life
Sciences, Asan Medical Center, Seoul, Korea. J. Jung thanks to
the NRF (Grant No. 2011-0030072) funded by the MSIP. We
thank Mr. Y. Jung in POSTECH for assessing cell viability.
2
7
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Keywords: Dipolar dye • Two-photon • Anthracene • Red-
emitting dye • Bio-imaging
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