Penetratin-Mediated Transepithelial Insulin Permeation: Importance of Cationic Residues and pH for Complexation and Permeation

AAPS Journal

Volumn 17, Issue 5, 2015, Pages 1200-1209

  Kristensen, Mie ^a   Franzyk, Henrik ^a   Klausen, Mia Thorne ^a   Iversen, Anne ^a   Bahnsen, Jesper Søborg ^a   Skyggebjerg, Rikke Bjerring ^b   Foderà, Vito ^a   Nielsen, Hanne Mørck ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NOVO NORDISK A S   (Denmark)

Author keywords

Caco 2 cell culture model; carrier peptide; insulin; penetratin; transepithelial permeation

Indexed keywords

ARGININE; CARRIER PROTEIN; CATION; INSULIN; PENETRATIN; PENETRATIN DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGHT SCATTERING; MALE; NONHUMAN; PH; PHYSICAL CHEMISTRY; PROTEIN STRUCTURE; RAT; TRANSMISSION ELECTRON MICROSCOPY; CACO-2 CELL LINE; CHEMISTRY; COMPARATIVE STUDY; INTESTINE ABSORPTION; INTESTINE MUCOSA; METABOLISM; PHOTON CORRELATION SPECTROSCOPY;

CACO-2 CELLS; CARRIER PROTEINS; CATIONS; DYNAMIC LIGHT SCATTERING; HUMANS; HYDROGEN-ION CONCENTRATION; INSULIN; INTESTINAL ABSORPTION; INTESTINAL MUCOSA; MICROSCOPY, ELECTRON, TRANSMISSION;

EID: 84939569624     PISSN: None     EISSN: 15507416     Source Type: Journal    
DOI: 10.1208/s12248-015-9747-3     Document Type: Article

References (23)

1. Margus H, Padari K, Pooga M. Cell-penetrating peptides as versatile vehicles for oligonucleotide delivery. Mol Ther. 2012;20(3):525–33.
2. Mie M, Takahashi F, Funabashi H, Yanagida Y, Aizawa M, Kobatake E. Intracellular delivery of antibodies using TAT fusion protein A. Biochem Biophys Res Commun. 2003;310(3):730–4.
3. Khafagya E-S, Kamei N, Nielsena EJB, Nishiod R, Takeda-Morishitaa M. One-month subchronic toxicity study of cell-penetrating peptides for insulin nasal delivery in rats. Eur J Pharm Biopharm. 2013;85:736–43.
4. Lundberg P, Langel U. A brief introduction to cell-penetrating peptides. J Mol Recognit. 2003;16(5):227–33.
5. Mitchell DJ, Kim DT, Steinman L, Fathman CG, Rothbard JB. Polyarginine enters cells more efficiently than other polycationic homopolymers. J Pept Res. 2000;56(5):318–25.
6. Ziegler A, Seelig J. Contributions of glycosaminoglycan binding and clustering to the biological uptake of the nonamphipathic cell-penetrating peptide WR9. Biochemistry. 2011;50:4650–64.
7. Derossi D, Joliot AH, Chassaing G, Prochiantz A. The third helix of the Antennapedia homeodomain translocates through biological membranes. J Biol Chem. 1994;269(14):10444–50.
8. Khafagy E-S, Morishita M, Ida N, Nishio R, Isowa K, Takayama K. Structural requirements of penetratin absorption enhancement efficiency for insulin delivery. J Control Release. 2010;143(3):302–10.
9. Kamei N, Morishita M, Eda Y, Ida N, Nishio R, Takayama K. Usefulness of cell-penetrating peptides to improve intestinal insulin absorption. J Control Release. 2008;132(1):21–5.
10. Khafagy E-S, Morishita M. Oral biodrug delivery using cell-penetrating peptide. Adv Drug Deliv Rev. 2012;64(6):531–9.
11. Liang JF, Yang VC. Insulin-cell penetrating peptide hybrids with improved intestinal absorption efficiency. Biochem Biophys Res Commun. 2005;335(3):734–8.
12. Bahnsen JS, Franzyk H, Sandberg-Schaal A, Nielsen HM. Antimicrobial and cell-penetrating properties of penetratin analogs: effect of sequence and secondary structure. Biochim Biophys Acta. 2013;1828(2):223–32.
13. Fodera V, Pagliara S, Otto O, Keyser UF, Donald AM. Micro fluidics reveals a flow-induced large-scale polymorphism of protein aggregates. J Phys Chem Lett. 2012;3:2803–7.
14. Cory AH, Owen TC, Barltrop JA, Cory JG. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun. 1991;3(7):207–12.
15. Gregory N, Hackbarth H, Morton D, Warwick MC. Recommendations for euthanasia of experimental animals: part 2. Lab Anim. 1997;31:1–32.
16. Lucas M. Determination of acid surface pH in vivo in rat proximal jejunum. Gut. 1983;24(8):734–9.
17. Kaarsholm NC, Havelund S, Hougaard P. Ionization behavior of native and mutant insulins: pK perturbation of B13-Glu in aggregated species. Arch Biochem Biophys. 1990;283(2):496–502.
18. Kamei N, Morishita M, Takayama K. Importance of intermolecular interaction on the improvement of intestinal therapeutic peptide/protein absorption using cell-penetrating peptides. J Control Release. 2009;136(3):179–86.
19. Khafagy E-S, Morishita M, Takayama K. The role of intermolecular interactions with penetratin and its analogue on the enhancement of absorption of nasal therapeutic peptides. Int J Pharm. 2010;388(1–2):209–12.
20. Kamei N, Kikuchi S, Takeda-morishita M, Terasawa Y, Yasuda A, Yamamoto S, et al. Determination of the optimal cell-penetrating peptide sequence for intestinal insulin delivery based on molecular orbital analysis with self-organizing maps. J Pharm Sci. 2013;102(2):469–79.
21. Bechara C, Pallerla M, Zaltsman Y, Burlina F, Alves ID, Lequin O, et al. Tryptophan within basic peptide sequences triggers glycosaminoglycan-dependent endocytosis. Biochemistry. 2013;27:1–12.
22. Tünnemann G, Ter-Avetisyan G, Martin GM, Stoockl M, Hermann A, Cardoso C. Live-cell analysis of cell penetration ability and toxicity of oligo-arginines. J Pept Sci. 2008;14:469–76.
23. Bendifallah N, Rasmussen FW, Zachar V, Ebbesen P, Nielsen PE, Koppelhus U. Evaluation of cell-penetrating peptides (CPPs) as vehicles for intracellular delivery of antisense peptide nucleic acid (PNA). Bioconjug Chem. 2006;17(3):750–8.