Development and Biological Assessment of Fully Water-Soluble Helical Aromatic Amide Foldamers†
Elizabeth R. Gillies Dr.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Current address: Departments of Chemistry and Chemical and Biochemical Engineering, The University of Western Ontario, London N6A 5B7, Canada
Search for more papers by this authorFrédérique Deiss
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorCathy Staedel Dr.
Université Bordeaux Victor Segalen 2, INSERM U869, 146 rue Léo Saignat, 33076 Bordeaux, France
Search for more papers by this authorJean-Marie Schmitter Prof.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorIvan Huc Dr.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorElizabeth R. Gillies Dr.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Current address: Departments of Chemistry and Chemical and Biochemical Engineering, The University of Western Ontario, London N6A 5B7, Canada
Search for more papers by this authorFrédérique Deiss
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorCathy Staedel Dr.
Université Bordeaux Victor Segalen 2, INSERM U869, 146 rue Léo Saignat, 33076 Bordeaux, France
Search for more papers by this authorJean-Marie Schmitter Prof.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorIvan Huc Dr.
Université Bordeaux 1 – CNRS UMR5248, Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac, France, Fax: (+33) 540-002-215
Search for more papers by this authorThis work was supported by the European Commission (Marie Curie Postdoctoral Fellowship to E.R.G.) and by the Conseil Régional d'Aquitaine. We thank Katell Bathany for mass spectroscopy data.
Graphical Abstract
Nicht biologisch, aber biologisch aktiv: Helicale Arylamid-Oligomere, die sich in ihren Strukturen deutlich von den α-Peptiden, β-Peptiden und Peptoiden unterscheiden, sind dennoch vergleichbar gut zellgängig, kaum toxisch und überdies absolut beständig gegen Zersetzung durch Proteasen. TFA−=Trifluoracetat.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2007/z700301_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aD. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893;
- 1bR. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219;
- 1cD. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodiversity 2004, 1, 1111;
- 1dI. Huc, Eur. J. Org. Chem. 2004, 17;
- 1e“Versatile Oligo(N-subtituted) Glycines: The Many Roles of Peptoids in Drug Discovery” by J. A. Patch, K. Kirshenbaum, S. L. Seurynck, R. N. Zuckermann, A. E. Barron in Pseudo-Peptides in Drug Discovery (Ed.: ), Wiley-VCH, Weinheim, 2004, p. 1.
10.1002/3527601902.ch1 Google Scholar
- 2J. A. Kritzer, J. Tirado-Rives, S. A. Hart, J. D. Lear, W. L. Jorgensen, A. Schepartz, J. Am. Chem. Soc. 2005, 127, 167; P. R. LePlae, J. D. Fisk, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 6820.
- 3Y. Hamuro, J. P. Schneider, W. F. DeGrado, J. Am. Chem. Soc. 1999, 121, 12200; E. A. Porter, X. Wang, H. S. Lee, B. Weisblum, S. H. Gellman, Nature 2000, 404, 565; P. I. Arvidsson, N. S. Ryder, H. M. Weiss, G. Gross, O. Kretz, R. Woessner, D. Seebach, ChemBioChem 2003, 4, 1345; D. Liu, W. F. DeGrado, J. Am. Chem. Soc. 2001, 123, 7553; E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 7324.
- 4T. Kimmerlin, K. Namoto, D. Seebach, Helv. Chim. Acta 2003, 86, 2104.
- 5J. A. Kritzer, O. M. Stephens, D. A. Guarracino, S. K. Reznik, A. Schepartz, Bioorg. Med. Chem. 2005, 13, 11; J. A. Kritzer, N. W. Luedtke, E. A. Harker, A. Schepartz, J. Am. Chem. Soc. 2005, 127, 14584; J. K. Murray, B. Farooqi, J. D. Sadowsky, M. Scalf, W. A. Freund, L. M. Smith, J. D. Chen, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 13271; O. M. Stephens, S. Kim, B. D. Welch, M. E. Hodsdon, M. S. Kay, A. Schepartz, J. Am. Chem. Soc. 2005, 127, 13126.
- 6P. Armand, K. Kirshenbaum, R. A. Goldsmith, S. Farr-Jones, A. E. Barron, K. T. V. Truong, K. A. Dill, D. F. Mierke, F. E. Cohen, R. N. Zuckermann, E. Bradley, Proc. Natl. Acad. Sci. USA 1998, 95, 4309; K. Kirshenbaum, A. E. Barron, R. E. Goldsmith, P. Armand, E. K. Bradley, K. T. V. Truong, K. A. Dill, F. E. Cohen, R. N. Zuckermann, Proc. Natl. Acad. Sci. USA 1998, 95, 4303; C. W. Wu, T. J. Sanborn, R. N. Zuckermann, A. E. Barron, J. Am. Chem. Soc. 2001, 123, 2958.
- 7J. A. Patch, A. E. Barron, J. Am. Chem. Soc. 2003, 125, 12092.
- 8J. E. Murphy, T. Uno, J. D. Hamer, F. E. Cohen, V. Dwarki, R. N. Zuckermann, Proc. Natl. Acad. Sci. USA 1998, 95, 1517.
- 9T. Hara, S. R. Durell, M. C. Myers, D. H. Appella, J. Am. Chem. Soc. 2006, 128, 1995.
- 10J. V. Schreiber, J. Frackenpohl, F. Moser, T. Fleischmann, H. P. E. Kohler, D. Seebach, ChemBioChem 2002, 3, 424;
10.1002/1439-7633(20020503)3:5<424::AID-CBIC424>3.0.CO;2-0 CAS PubMed Web of Science® Google ScholarJ. Frackenpohl, P. I. Arvidsson, J. V. Schreiber, D. Seebach, ChemBioChem 2001, 2, 445;10.1002/1439-7633(20010601)2:6<445::AID-CBIC445>3.0.CO;2-R CAS PubMed Web of Science® Google ScholarS. M. Miller, R. J. Simon, S. Ng, R. N. Zuckermann, J. M. Kerr, W. H. Moos, Bioorg. Med. Chem. Lett. 1994, 4, 2657.
- 11D. H. Liu, S. Choi, B. Chen, R. J. Doerksen, D. J. Clements, J. D. Winkler, M. L. Klein, W. F. DeGrado, Angew. Chem. 2004, 116, 1178; Angew. Chem. Int. Ed. 2004, 43, 1158; G. N. Tew, D. H. Liu, B. Chen, R. J. Doerksen, J. Kaplan, P. J. Carroll, M. L. Klein, W. F. DeGrado, Proc. Natl. Acad. Sci. USA 2002, 99, 5110; S. Choi, D. J. Clements, V. Pophristic, I. Ivanov, S. Vemperala, J. S. Bennett, M. L. Klein, J. D. Winkler, W. F. DeGrado, Angew. Chem. 2005, 117, 6843; Angew. Chem. Int. Ed. 2005, 44, 6685; L. Arnt, K. Nusslein, G. N. Tew, J. Polym. Sci. Part A-1 2004, 42, 3860.
- 12J. T. Ernst, J. Becerril, H. S. Park, H. Yin, A. D. Hamilton, Angew. Chem. 2003, 115, 553; Angew. Chem. Int. Ed. 2003, 42, 535.
- 13V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J.-M. Lehn, Nature 2000, 407, 720;
V. Berl, I. Huc, R. G. Khoury, J.-M. Lehn, Chem. Eur. J. 2001, 7, 2810;
10.1002/1521-3765(20010702)7:13<2810::AID-CHEM2810>3.0.CO;2-5 CAS PubMed Web of Science® Google ScholarV. Berl, I. Huc, R. G. Khoury, J.-M. Lehn, Chem. Eur. J. 2001, 7, 2798.10.1002/1521-3765(20010702)7:13<2798::AID-CHEM2798>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 14H. Jiang, J.-M. Léger, I. Huc, J. Am. Chem. Soc. 2003, 125, 3448; H. Jiang, J.-M. Léger, C. Dolain, P. Guionneau, I. Huc, Tetrahedron 2003, 59, 8365; C. Dolain, A. Grélard, M. Laguerre, H. Jiang, V. Maurizot, I. Huc, Chem. Eur. J. 2005, 11, 6135; C. Dolain, J.-M. Léger, N. Delsuc, H. Gornitzka, I. Huc, Proc. Natl. Acad. Sci. USA 2005, 102, 16146.
- 15E. R. Gillies, C. Dolain, J.-M. Léger, I. Huc, J. Org. Chem. 2006, 71, 7931.
- 16N. Delsuc, J.-M. Léger, S. Massip, I. Huc, Angew. Chem. 2007, 119, 218;
10.1002/ange.200603390 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 214.
- 17B. Gong, Chem. Eur. J. 2001, 7, 4336;
10.1002/1521-3765(20011015)7:20<4336::AID-CHEM4336>3.0.CO;2-1 CAS PubMed Web of Science® Google ScholarL. Yuan, H. Zeng, K. Yamato, A. R. Sanford, W. Feng, H. S. Atreya, D. K. Sukumaran, T. Szyperski, B. Gong, J. Am. Chem. Soc. 2004, 126, 16528; J. Zhu, R. D. Parra, H. Zeng, E. Skrzypczak-Jankun, X. C. Zeng, B. Gong, J. Am. Chem. Soc. 2000, 122, 4219; Y. Hamuro, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1997, 119, 10587; Y. Hamuro, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1996, 118, 7529.
- 18E. A. Goun, T. H. Pillow, L. R. Jones, J. B. Rothbard, P. A. Wender, ChemBioChem 2006, 7, 1497; N. Umezawa, M. A. Gelman, M. C. Haigis, R. T. Raines, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 368; Y. A. Fillon, J. P. Anderson, J. Chmielewski, J. Am. Chem. Soc. 2005, 127, 11798; T. B. Potocky, A. K. Menon, S. H. Gellman, J. Am. Chem. Soc. 2005, 127, 3686; E. L. Snyder, S. F. Dowdy, Pharm. Res. 2004, 21, 389; D. J. Mitchell, D. T. Kim, L. Steinman, C. G. Fathman, J. B. Rothbard, J. Pept. Res. 2000, 56, 318; J. L. Zaro, T. E. Rajapaksa, C. T. Okamoto, W.-C. Shen, Mol. Pharm. 2006, 3, 181.
- 19L. Ghosez, B. Haveaux, H. G. Viehe, Angew. Chem. 1969, 81, 468;
10.1002/ange.19690811209 Google ScholarAngew. Chem. Int. Ed. Engl. 1969, 8, 454.
- 20G. Malich, B. Markovic, C. Winder, Toxicology 1997, 124, 179.
- 21N. Malik, R. Wiwattanapatapee, R. Klopsch, K. Lorenz, H. Frey, J. W. Weener, E. W. Meijer, W. Paulus, R. Duncan, J. Controlled Release 2000, 65, 133; D. Sgouras, R. Duncan, J. Mater. Sci. Mater. Med. 1990, 1, 61; G. Carreño-Gómez, R. Duncan, Int. J. Pharm. 1997, 148, 231; Y.-B. Lim, S.-M. Kim, H. Suh, J.-S. Park, Bioconjugate Chem. 2002, 13, 952.
- 22While the reasons are not yet well understood, the aspect ratio of nanomaterials is believed to have an important influence on toxicity. See: A. Magrez, S. Kasas, V. Salicio, N. Pasquier, J. W. Seo, M. Celio, S. Catsicas, B. Schwaller, L. Forró, Nano Lett. 2006, 6, 1121.
- 23D. Y. Kwoh, C. C. Coffin, C. P. Lollo, J. Jovenal, M. G. Banaszczyk, P. Mullen, A. Phillips, A. Amini, J. Fabrycki, R. M. Bartholomew, S. W. Brostoff, D. J. Carlo, Biochim. Biophys. Acta 1999, 1444, 171.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.