Cyclization of a cell-penetrating peptide via click-chemistry increases proteolytic resistance and improves drug delivery

Journal of Peptide Science

Volumn , Issue , 2016, Pages 421-426

  Reichart, Florian ^a   Horn, Mareike ^a   Neundorf, Ines ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

cell penetrating peptides; click reaction; drug delivery; peptide synthesis

Indexed keywords

CELL PENETRATING PEPTIDE; COPPER; DAUNORUBICIN; DRUG CARRIER; TRIAZOLE;

AMINO ACID SEQUENCE; ARTICLE; BREAST CANCER CELL LINE; CELL VIABILITY; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLIZATION; DRUG CYTOTOXICITY; DRUG TRANSPORT; FEMALE; HUMAN; HUMAN CELL; METABOLIC STABILITY; MOLECULAR STABILITY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN SECONDARY STRUCTURE;

EID: 84975062697     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2885     Document Type: Article

References (24)

1. Reissmann S. Cell penetration: scope and limitations by the application of cell-penetrating peptides. J. Pept. Sci. 2014; 20: 760–84.
2. Neundorf I, Beck-Sickinger AG. Calcitonin-derived carrier peptides. Curr. Pharm. Des. 2005; 11: 3661–9.
3. Schmidt MC, Rothen-Rutishauser B, Rist B, Beck-Sickinger A, Wunderli-Allenspach H, Rubas W, Sadee W, Merkle HP. Translocation of human calcitonin in respiratory nasal epithelium is associated with self-assembly in lipid membrane. Biochemistry 1998; 37: 16582–90.
4. Rennert R, Neundorf I, Beck-Sickinger AG. Calcitonin-derived peptide carriers: mechanisms and application. Adv. Drug Deliv. Rev. 2008; 60: 485–98.
5. Machova Z, Muhle C, Krauss U, Trehin R, Koch A, Merkle HP, Beck-Sickinger AG. Cellular internalization of enhanced green fluorescent protein ligated to a human calcitonin-based carrier peptide. Chembiochem 2002; 3: 672–7.
6. Neundorf I, Hoyer J, Splith K, Rennert R, Peindy N'dongo HW, Schatzschneider U. Cymantrene conjugation modulates the intracellular distribution and induces high cytotoxicity of a cell-penetrating peptide. Chem. Commun. (Camb.) 2008; 43: 5604–6.
7. Krauss U, Kratz F, Beck-Sickinger AG. Novel daunorubicin-carrier peptide conjugates derived from human calcitonin segments. J. Mol. Recognit.: JMR 2003; 16: 280–7.
8. Walther C, Meyer K, Rennert R, Neundorf I. Quantum dot-carrier peptide conjugates suitable for imaging and delivery applications. Bioconjug. Chem. 2008; 19: 2346–56.
9. Neundorf I, Rennert R, Franke J, Kozle I, Bergmann R. Detailed analysis concerning the biodistribution and metabolism of human calcitonin-derived cell-penetrating peptides. Bioconjug. Chem. 2008; 19: 1596–603.
10. Richter S, Bouvet V, Wuest M, Bergmann R, Steinbach J, Pietzsch J, Neundorf I, Wuest F. (18)F-Labeled phosphopeptide-cell-penetrating peptide dimers with enhanced cell uptake properties in human cancer cells. Nucl. Med. Biol. 2012; 39: 1202–12.
11. Hoyer J, Neundorf I. Knockdown of a G protein-coupled receptor through efficient peptide-mediated siRNA delivery. J. Control Release 2012; 161: 826–34.
12. Rennert R, Neundorf I, Jahnke HG, Suchowerskyj P, Dournaud P, Robitzki A, Beck-Sickinger AG. Generation of carrier peptides for the delivery of nucleic acid drugs in primary cells. ChemMedChem 2008; 3: 241–53.
13. Lattig-Tunnemann G, Prinz M, Hoffmann D, Behlke J, Palm-Apergi C, Morano I, Herce HD, Cardoso MC. Backbone rigidity and static presentation of guanidinium groups increases cellular uptake of arginine-rich cell-penetrating peptides. Nat. Commun. 2011; 2: 453–458.
14. Qian Z, LaRochelle JR, Jiang B, Lian W, Hard RL, Selner NG, Luechapanichkul R, Barrios AM, Pei D. Early endosomal escape of a cyclic cell-penetrating peptide allows effective cytosolic cargo delivery. Biochemistry 2014; 53: 4034–46.
15. Cascales L, Henriques ST, Kerr MC, Huang YH, Sweet MJ, Daly NL, Craik DJ. Identification and characterization of a new family of cell-penetrating peptides cyclic cell-penetrating peptides. J. Biolog. Chem. 2011; 286: 36932–43.
16. Shirazi AN, El-Sayed NS, Mandal D, Tiwari RK, Tavakoli K, Etesham M, Parang K. Cysteine and arginine-rich peptides as molecular carriers. Bioorg. Med. Chem. Lett. 2016; 26: 656–61.
17. Rothbard JB, Kreider E, VanDeusen CL, Wright L, Wylie BL, Wender PA. Arginine-rich molecular transporters for drug delivery: role of backbone spacing in cellular uptake. J. Med. Chem. 2002; 45: 3612–8.
18. Traboulsi H, Larkin H, Bonin MA, Volkov L, Lavoie CL, Marsault E. Macrocyclic cell penetrating peptides: a study of structure-penetration properties. Bioconjug. Chem. 2015; 26: 405–11.
19. Chu Q, Moellering RE, Hilinski GJ, Kim YW, Grossmann TN, Yeh JTH, Verdine GL. Towards understanding cell penetration by stapled peptides. MedChemComm 2015; 6: 111–9.
20. Danial M, Perrier S, Jolliffe KA. Effect of the amino acid composition of cyclic peptides on their self-assembly in lipid bilayers. Org. Biomol. Chem. 2015; 13: 2464–73.
21. Moroz E, Matoori S, Leroux JC. Oral delivery of macromolecular drugs: where we are after almost 100 years of attempts. Adv. Drug Deliv. Rev. 2016 doi: 10.1016/j.addr.2016.01.010.
22. Horn M, Reichart F, Natividad-Tietz S, Diaz D, Neundorf I. Tuning the properties of a novel short cell-penetrating peptide by intramolecular cyclization with a triazole bridge. Chem. Commun. (Camb.) 2016; 52: 2261–4.
23. Huisgen R, Christl M. 1,3-Dipolar cycloadditions of fulminic acid. Angew. Che. Int. Ed. 1967; 6: 456–457.
24. Walther C, Ott I, Gust R, Neundorf I. Specific labeling with potent radiolabels alters the uptake of cell-penetrating peptides. Biopolymers 2009; 92: 445–51.