Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2017; 28(08): 924-928
DOI: 10.1055/s-0036-1588689
DOI: 10.1055/s-0036-1588689
letter
Tuning the Properties of Penetrating Peptides by Oxime Conjugation
Further Information
Publication History
Received: 14 October 2016
Accepted after revision: 20 December 2016
Publication Date:
25 January 2017 (online)
Abstract
We here describe the application of oxime bond formation between a peptide scaffold and different aldehydes to modify the transporting capabilities of penetrating peptides. We show that bonds such as oximes offer a great synthetic advantage for the modification of the properties of model penetrating peptides. We believe that this approach will allow the development of improved intracellular delivery vehicles.
Key words
peptide chemistry - penetrating peptides - supramolecular chemistry - membrane transport - solid-phase peptide synthesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588689.
- Supporting Information
-
References
- 1 Fischer PM. Med. Res. Rev. 2007; 27: 755
- 2 Duchardt F, Fotin-Mleczek M, Schwarz H, Fischer R, Brock R. Traffic 2007; 8: 848
- 3 Stewart KM, Horton KL, Kelley SO. Org. Biomol. Chem. 2008; 6: 2242
- 4 Langel Ü. Cell-Penetrating Peptides: Methods and Protocols. Humana Press Inc.; Totowa, NJ: 2011
- 5 Koren E, Torchilin VP. Trends Mol. Med. 2012; 18: 386
- 6 Kauffman WB, Fuselier T, He J, Wimley WC. Trends Biochem. Sci. 2015; 40: 749
- 7 Stanzl EG, Trantow BM, Vargas JR, Wender PA. Acc. Chem. Res. 2013; 46: 2944
- 8 Blum AP, Kammeyer JK, Gianneschi NC. Chem. Sci. 2016; 7: 989
- 9 Bai Y, Nguyen L, Song Z, Peng S, Lee J, Zheng N, Kapoor I, Hagler LD, Cai K, Cheng J, Chan HY. E, Zimmerman SC. J. Am. Chem. Soc. 2016; 138: 9498
- 10 Madani F, Lindberg S, Langel Ü, Futaki S, Gräslund A. J. Biophys. 2011; 2011: 1
- 11 Richard JP, Melikov K, Vives E, Ramos C, Verbeure B, Gait MJ, Chernomordik LV, Lebleu B. J. Biol. Chem. 2003; 278: 585
- 12 Nakase I, Takeuchi T, Tanaka G, Futaki S. Adv. Drug. Deliv. Rev. 2008; 60: 598
- 13 Herce HD, Garcia AE, Cardoso MC. J. Am. Chem. Soc. 2014; 136: 17459
- 14 Gasparini G, Bang E.-K, Montenegro J, Matile S. Chem. Commun. 2015; 51: 10389
- 15 Hansen M, Kilk K, Langel Ü. Adv. Drug. Deliv. Rev. 2008; 60: 572
- 16 Magzoub M, Eriksson LE. G, Gräslund A. Biochim. Biophys. Acta 2002; 1563: 53
- 17 Eiríksdóttir E, Konate K, Langel Ü, Divita G, Deshayes S. Biochim. Biophys. Acta 2010; 1798: 1119
- 18 Appelbaum JS, La Rochelle JR, Smith BA, Balkin DM, Holub JM, Schepartz A. Chem. Biol. 2012; 19: 819
- 19 Montenegro J, Matile S. Chem. Asian J. 2010; 6: 681
- 20 Gehin C, Montenegro J, Bang E.-K, Cajaraville A, Takayama S, Hirose H, Futaki S, Matile S, Riezman H. J. Am. Chem. Soc. 2013; 135: 9295
- 21 Priegue JM, Montenegro J, Granja JR. Small 2014; 10: 3613
- 22 Gasparini G, Sargsyan G, Bang E.-K, Sakai N, Matile S. Angew. Chem. 2015; 127: 7436
- 23 Priegue JM, Crisan DN, Martínez-Costas J, Granja JR, Fernandez-Trillo F, Montenegro J. Angew. Chem. Int. Ed. 2016; 55: 7492
- 24 Montenegro J, Bang E.-K, Sakai N, Matile S. Chem. Eur. J. 2012; 18: 10436
- 25 Bode SA, Wallbrecher R, Brock R, van Hest JC. M, Löwik DW. P. M. Chem. Commun. 2013; 50: 415
- 26 Mahon CS, Fulton DA. Chem. Sci. 2013; 4: 3661
- 27 Bartolami E, Bessin Y, Gervais V, Dumy P, Ulrich S. Angew. Chem. Int. Ed. 2015; 54: 10183
- 28 Bartolami E, Bessin Y, Bettache N, Gary-Bobo M, Garcia M, Dumy P, Ulrich S. Org. Biomol. Chem. 2015; 13: 9427
- 29 Takeuchi T, Montenegro J, Hennig A, Matile S. Chem. Sci. 2011; 2: 303
- 30 Montenegro J, Fin A, Matile S. Org. Biomol. Chem. 2011; 9: 2641
- 31 Montenegro J, Braun J, Fischer-Onaca O, Meier W, Matile S. Org. Biomol. Chem. 2011; 9: 6623