Organic Letters
Letter
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nuclear membrane with the cargo. Since it is covalently bound,
the triazole aminocoumarin group constitutes a substantial part
of compound 12, and its position on the amino acid residue does
not appear to compromise the cell-penetrating property. This
work represents a distinct use of a small uncharged cyclopeptide
acting as a transmembrane vector. Further work will be necessary
to identify the functional and structural determinants that will
retain, impair, or improve the cell-membrane permeability of this
tetra-cyclopeptide scaffold.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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M.; Jacobson, M. P.; Lokey, R. S. J. Am. Chem. Soc. 2015, 137, 715.
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S
Biological assay conditions, experimental procedures, and
full spectroscopic data for all new compounds (PDF)
(8) Nielsen, D. S.; Hoang, H. N.; Lohman, R.-J.; Hill, T. A.; Lucke, A. J.;
Craik, D. J.; Edmonds, D. J.; Griffith, A. A.; Rotter, C. J.; Ruggeri, R. B.;
Price, D. A.; Liras, S.; Fairlie, D. P. Angew. Chem., Int. Ed. 2014, 53,
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(10) Furukawa, A.; Townsend, C. E.; Schwochert, J.; Pye, C. R.;
Bednarek, M. A.; Lokey, R. S. J. Med. Chem. 2016, 59, 9503.
AUTHOR INFORMATION
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Corresponding Author
ORCID
Notes
(11) Traore,
́
M.; Mietton, F.; Maubon, D.; Peuchmaur, M.; Francisco
The authors declare no competing financial interest.
Hilario, F.; Pereira de Freitas, R.; Bougdour, A.; Curt, A.; Maynadier, M.;
́
Vial, H.; Pelloux, H.; Hakimi, M.-A.; Wong, Y.-S. J. Org. Chem. 2013, 78,
3655.
ACKNOWLEDGMENTS
Financial supports by “Agence Nationale de la Recherche” under
“programme Labex” (ARCANE Project No. ANR-11-LABX-
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(12) Mori, H.; Urano, Y.; Kinoshita, T.; Yoshimura, S.; Takase, S.;
Hino, M. J. Antibiot. 2003, 56, 181.
(13) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.;
003), “fondation pour le dev
substances naturelles et ses applications” Institut de France/
Academie des Sciences, and CNRS are gratefully acknowledged.
́
eloppement de la chimie des
Wang, Q. Org. Lett. 2004, 6, 4603.
(14) Ferreira, S. Z.; Carneiro, H. C.; Lara, H. A.; Alves, R. B.; Resende,
J. M.; Oliveira, H. M.; Silva, L. M.; Santos, D. A.; Pereira de Freitas, R.
ACS Med. Chem. Lett. 2015, 6, 271.
́
Financial support from the Swiss National Science Foundation
(P300P3 158507) and the Pierre Mercier Foundation is also
acknowledged. F.F.H. was supported by a fellowship (PDSE
(15) (a) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704.
(b) Nebel, K.; Mutter, M. Tetrahedron 1988, 44, 4793.
(16) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586.
9712-11-9) from the CAPES Foundation (Coordenaca̧ o de
̃
̈
(17) Girard, C.; Onen, E.; Aufort, M.; Beauviere, S.; Samson, E.;
́
Aperfeico̧ amento de Pessoal de Nivel Superior), Ministry of
Herscovici, J. Org. Lett. 2006, 8, 1689.
Education of Brazil. The Brazilian agencies FAPEMIG, CNPq,
and CAPES are acknowledged for fellowships to F.F.H and
R.P.d.F. The P. falciparum 3D7 strain was obtained through the
Malaria Research and Reference Reagent Resource Center
Montpellier RIO imaging facility of the MRI-DBS University of
Montpellier for her assistance. ICMG (Institut de Chimie
(18) (a) Zhou, Y.; Liu, K.; Li, J.-Y.; Fang, Y.; Zhao, T.-C.; Yao, C. Org.
Lett. 2011, 13, 1290. (b) Ast, S.; Schwarze, T.; Mueller, H.; Sukhanov,
A.; Michaelis, S.; Wegener, J.; Wolfbeis, O. S.; Koerzdoerfer, T.;
Duerkop, A.; Holdt, H.-J. Chem. - Eur. J. 2013, 19, 14911.
(19) Bantscheff, M.; Hopf, C.; Savitski, M. M.; Dittmann, A.; Grandi,
P.; Michon, A.-M.; Schlegl, J.; Abraham, Y.; Becher, I.; Bergamini, G.;
Boesche, M.; Delling, M.; Duempelfeld, B.; Eberhard, D.; Huthmacher,
C.; Mathieson, T.; Poeckel, D.; Reader, V.; Strunk, K.; Sweetman, G.;
Kruse, U.; Neubauer, G.; Ramsden, N. G.; Drewes, G. Nat. Biotechnol.
2011, 29, 255.
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Moleculaire de Grenoble) Chemistry Nanobio Platform is
acknowledged for analysis and characterization facilities.
(20) Quiclet-Sire, B.; Zard, S. Z. Chem. - Eur. J. 2006, 12, 6002.
(21) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron Lett.
1992, 33, 5709.
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