Journal of the American Chemical Society
Communication
Bo
Angew. Chem., Int. Ed. 2012, 51, 1071−1074.
2) Chatani, S.; Sheridan, R. J.; Podgorski, M.; Nair, D. P.; Bowman,
C. N. Chem. Mater. 2013, 25, 3897−3901.
3) (a) Leong, T.; Gu, Z.; Koh, T.; Gracias, D. H. J. Am. Chem. Soc.
006, 128, 11336−11337. (b) Ye, H.; Randall, C. L.; Leong, T. G.;
Slanac, D. A.; Call, E. K.; Gracias, D. H. Angew. Chem., Int. Ed. 2007,
6, 4991−4994.
4) Adzima, B. J.; Tao, Y.; Kloxin, C. J.; DeForest, C. A.; Anseth, K.
S.; Bowman, C. N. Nat. Chem. 2011, 3, 256−259.
5) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed.
001, 40, 2004−2021.
6) DeForest, C. A.; Polizzotti, B. D.; Anseth, K. S. Nat. Mater. 2009,
, 659−664.
7) Fluorescein was encapsulated and locally released to achieve
internal tattooing of tissues for surgical guidance in rats; see:
a) Couture, O.; Pannacci, N.; Babataheri, A.; Servois, V.; Tabeling,
̈
rner, H. G.; Greiner, A. M.; Bastmeyer, M.; Berner-Kowollik, C.
(15) Ultrasound-triggered release of composite droplets in a cell-
culture plate. The composite droplets of A were diluted in a DMSO
solution of B (0.15% w/v, degassed prior to injection) and injected in
an OptiCell plate made of two plastic membranes, transparent to both
ultrasound and light, separated by 2 mm. The bottom membrane was
placed at the focus of a 5 MHz ultrasound probe which was immersed
in a water bath maintained at 12 °C. The ultrasonic probe was driven
by a clinical ultrasound scanner (Aixplorer, Supersonic Imagine,
France), emitting a single pulse of 2 cycles on each spot of the release,
where the distance between the several spots of the release is equal to
the pitch number of the transducer (0.3 mm). Release spots could be
selected anywhere on the plate using a software interface. The
chemical cloud was excited with a UV light, while the observation of
the Eiffel tower was performed through a UV filter.
(
(
2
4
(
(
2
(
8
(
(
P.; Tanter, M. Med. Phys. 2011, 38, 1116−1123. (b) Couture, O.;
Dransart, E.; Dehay, S.; Nemati, F.; Decaudin, D.; Johannes, L.;
Tanter, M. Mol. Imaging 2011, 10, 135−143. For other examples of
localized delivery, see: (c) Fabiilli, M. L.; Haworth, K. J.; Sebastian, I.
E.; Kripfgans, O. D.; Carson, P. L.; Fowlkes, J. B. Ultrasound in Med. &
Biol. 2010, 36, 1364−1375. (d) Fabiilli, M. L.; Lee, J. A.; Kripfgans, O.
D.; Carson, P. L.; Fowlkes, J. B. Pharm. Res. 2010, 27, 2753−2765.
(
8) (a) Srinivasan, R.; Li, J.; Ng, S. L.; Kalesh, K. A.; Yao, S. Q. Nat.
Protoc. 2007, 2, 2655−2664. (b) Evans, M. J.; Saghatelian, A.;
Sorensen, E. J.; Cravatt, B. F. Nat. Biotechnol. 2005, 23, 1303−1307.
(
9) (a) Franc, G.; Kakkar, A. Chem. Commun. 2008, 5267−5276.
(
b) Malkoch, M.; Vestberg, R.; Gupta, N.; Mespouille, L.; Dubois, P.;
Mason, A. F.; Hedrick, J. L.; Liao, Q.; Frank, C. W.; Kingsbury, K.;
Hawker, C. J. Chem. Commun. 2006, 2774−2776. (c) Polizzotti, B. D.;
Fairbanks, B. D.; Anseth, K. S. Biomacromolecules 2008, 9, 1084−1087.
(
10) (a) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36,
1
249−1262. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org.
Chem. 2002, 67, 3057−3064. (c) Franke, R.; Doll, C.; Eichler, J.
Tetrahedron Lett. 2005, 46, 4479−4482.
(
6
11) (a) Sletten, E. M.; Bertozzi, C. R. Acc. Chem. Res. 2011, 9, 666−
76. (b) Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. J. Am. Chem. Soc.
2
010, 132, 3688−3690. (c) Kuzmin, A.; Poloukhtine, A.; Wolfert, M.
A.; Popik, V. V. Bioconjugate Chem. 2010, 21, 2076−2085. (d) Sletten,
E. M.; Nakamura, H.; Jewett, J. C.; Bertozzi, C. R. J. Am. Chem. Soc.
2
010, 132, 11799−11805. (e) Dommerholt, J.; Schmidt, S.; Temming,
R.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; van Hest, J. C. M.; Lefeber, D.
J.; Friedl, P.; van Delft, F. L. Angew. Chem., Int. Ed. 2010, 49, 9422−
9425. (f) Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.;
Popik, V. V. J. Am. Chem. Soc. 2009, 131, 15769−15776. (g) Ning, X.;
Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem., Int. Ed. 2008, 47,
2253−2255. (h) Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, C.
R. J. Am. Chem. Soc. 2008, 130, 11486−11493. (i) Baskin, J. M.;
Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.;
Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2007,
1
04, 16793−16797. (j) Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. A. J.
Am. Chem. Soc. 2004, 126, 15046−15047.
12) Stockmann, H.; Neves, A. A.; Stairs, S.; Ireland-Zecchini, H.;
Brindle, K. M.; Leeper, F. J. Chem. Sci. 2011, 2, 932−936.
13) (a) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.;
(
(
Wang, Q. A. Org. Lett. 2004, 24, 4603−4606. (b) Zhou, Z.; Fahrni, C.
J. J. Am. Chem. Soc. 2004, 126, 8862−8863.
(
14) Ultrasound-triggered release of composite droplets in a
microfluidic channel. Composite droplets of A were suspended by
magnetic stirring in a DMSO solution of B (0.3% w/v) and injected in
the microfluidic channel using a pressure controller (Fluigent, MFCS-
1
00). The microfluidic channel was 100 μm in width and 40 μm in
depth. It was placed at the focus of a 2.25 MHz single-element
transducer, which was immersed in a water bath. A single pulse of 30
cycles was emitted, which triggered a camera (Andor iXon, 34 Hz)
mounted on a fluorescent microscope (Leica, 10× or 20×, DAPI) that
recorded the fluorescence induced during the reaction.
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