Journal of the American Chemical Society
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peripheral functionality manipulated to display highly de-
6.
Hawker, C. J.; Wooley, K. L., Science, 2005, 309,
1
2
3
4
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sired reactive groups. These unique dendrimers exhibited a
dual function as a consequence of their disassembly capabil-
ity in a reductive environment. To one end, the dendrimers
act as macromolecular scaffolds that fully collapses within 15
minutes upon exposure to the reducing reagent DTT into a
novel set of thiol-functional building blocks suited for mate-
rials science. Further to this, the physiological environment
with enzymatic redox systems, such as GSH-Grx and Trx
present in all living cells, enabled selective rupturing of the
dendrimers. Initial promising results detailed dendrimer
collapse in short time periods, at relevant concentrations,
and in the presence of human lung carcinoma A549 cells.
Due to the intracellular disassembly of the dendrimers a
cytotoxic amount of ROS was produced. To the authors’ best
knowledge, this is the first report of a dendrimer family with
rupturing dual-capacity suited for both materials sciences as
well as for nanomedicine.
1200-1205
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Holst, H.; Malkoch, M., J Mater Chem B, 2013, 1, 6015-6019
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Hed, Y.; Oberg, K.; Berg, S.; Nordberg, A.; von
ASSOCIATED CONTENT
Supporting Information
Gillies, E. R.; Jonsson, T. B.; Frechet, J. M. J., J Am
Experimental details, structure and synthetic procedure of
small molecules and dendritic polymers, fragmentation con-
Grayson, S. M.; Frechet, J. M. J., Org Lett, 2002, 4,
1
ditions. Analytical data including H, 13C-NMR, SEC traces,
Yesilyurt, V.; Ramireddy, R.; Thayumanavan, S.,
MALDI-TOF-MS analysis and optimization, analysis of frag-
ments. (PDF)
The Supporting Information is available free of charge on the
ACS Publications website.
Angew Chem Int Edit, 2011, 50, 3038-3042
17. Szalai, M. L.; McGrath, D. V., Tetrahedron, 2004,
60, 7261-7266
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Nazemi, A.; Schon, T. B.; Gillies, E. R., Org Lett,
2013, 15, 1830-1833
AUTHOR INFORMATION
Corresponding Author
19.
Castonguay, A.; Wilson, E.; Al-Hajaj, N.; Petitjean,
L.; Paoletti, J.; Maysinger, D.; Kakkar, A., Chem Commun,
2011, 47, 12146-12148
Prof. Michael Malkoch
20.
Ong, W.; McCarley, R. L., Macromolecules, 2006,
Royal Institute of Technology, School of Chemical Science
and Engineering, Fibre and Polymer Technology,
Teknikringen 56-58, SE-100 44 Stockholm, Sweden
E-mail: malkoch@kth.se.
39, 7295-7301
21.
4699-4701
22.
Ong, W.; McCarley, R. L., Chem Commun, 2005, 0,
Neus, F. T.; Walter, M. V.; Montanez, M. I.;
Kunzmann, A.; Hult, A.; Nystrom, A.; Malkoch, M.; Fadeel,
B., Toxicol Lett, 2012, 211, S203-S204
23.
267, 6102-6109
24.
Immunol, 1997, 15, 351-369
25.
2001, 31, 1287-1312
26.
E. S. J.; Gustafsson, J. A.; Damdimopoulos, A. E., Bba-Mol Cell
Res, 2009, 1793, 1588-1596
27.
Shah, P. K.; Stansbury, J. W.; Bowman, C. N., Dent Mater,
2015, 31, 1255-1262
28.
A.; Malkoch, M., J Polym Sci Pol Chem, 2015, 53, 2431-2439
29. Newkome, G. R.; Yao, Z. Q.; Baker, G. R.; Gupta, V.
K., J Org Chem, 1985, 50, 2003-2004
Notes
The authors declare no competing financial interests.
Arner, E. S. J.; Holmgren, A., Eur J Biochem, 2000,
ACKNOWLEDGMENT
Nakamura, H.; Nakamura, K.; Yodoi, J., Annu Rev
The authors acknowledge Knut och Alice Wallenberg Foun-
dation (KAW) (Grant number: 2012-0196), Seventh Frame-
work Programme (Grant number: 60418) for financial sup-
port, Vetenskapsrådet and Swedish Research Council (VR)
for financial support.
Nordberg, J.; Arner, E. S. J., Free Radical Bio Med,
Damdimopoulou, P. E.; Miranda-Vizuete, A.; Arner,
Podgorski, M.; Becka, E.; Claudino, M.; Flores, A.;
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