Enzyme-activatable cell-penetrating peptides through a minimal side chain modification

Bioconjugate Chemistry

Volumn 26, Issue 5, 2015, Pages 850-856

  Bode, Saskia A ^a   Hansen, Morten B ^a   Oerlemans, Roy A J F ^a   Van Hest, Jan C M ^a   Löwik, Dennis W P M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CELL MEMBRANES; CHAINS; CHEMICAL ACTIVATION; CONTROLLED DRUG DELIVERY; PEPTIDES; TARGETED DRUG DELIVERY;

ACTIVATABLE CELL PENETRATING PEPTIDES; ACTIVATION PROCESS; CELL SURFACES; ENZYMATIC REACTION; EXTERNAL STIMULUS; LYSINE SIDE CHAINS; SIDE CHAIN MODIFICATIONS; TAT PEPTIDE;

ENZYMES;

AMINOPEPTIDASE; CELL PENETRATING PEPTIDE; CELL SURFACE PROTEIN; DIPEPTIDYL PEPTIDASE IV; GLYCYLARGINYLLYSYLLYSYLARGINYLARGINYLGLUTAMYLARGINYLARGINYLARGINYL EPSILON AMINOHEXANOIC ACID CYSTEINAMINE; LYSINE; UNCLASSIFIED DRUG; DIPEPTIDYL PEPTIDASE; TRANSACTIVATOR PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; CELL VIABILITY; CONFOCAL LASER MICROSCOPY; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG SELECTIVITY; DRUG UPTAKE; FLOW CYTOMETRY; HEK293 CELL LINE; HUMAN; HUMAN CELL; PROTEIN DOMAIN; PROTEIN MODIFICATION; CHEMISTRY; METABOLISM;

AMINO ACID SEQUENCE; AMINOPEPTIDASES; CELL-PENETRATING PEPTIDES; DIPEPTIDYL-PEPTIDASES AND TRIPEPTIDYL-PEPTIDASES; GENE PRODUCTS, TAT; HEK293 CELLS; HUMANS; LYSINE;

EID: 84930202661     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.5b00066     Document Type: Article

References (29)

1. Järver, P., Mäger, I., and Langel, Ü. (2010) In vivo biodistribution and efficacy of peptide mediated delivery Trends Pharmacol. Sci. 31, 528-35
2. Stewart, K. M., Horton, K. L., and Kelley, S. O. (2008) Cell-penetrating peptides as delivery vehicles for biology and medicine Org. Biomol. Chem. 6, 2242-55
3. Verdurmen, W. P., Thanos, M., Ruttekolk, I. R., Gulbins, E., and Brock, R. (2010) Cationic cell-penetrating peptides induce ceramide formation via acid sphingomyelinase: Implications for uptake J. Controlled Release 147, 171-179
4. Bode, S. A., Wallbrecher, R., Brock, R., van Hest, J. C. M., and Löwik, D. W. P. M. (2014) Activation of cell-penetrating peptides by disulfide bridge formation of truncated precursors Chem. Commun. 50, 415-7
5. Zhang, W., Song, J., Zhang, B., Liu, L., Wang, K., and Wang, R. (2011) Design of acid-activated cell penetrating peptide for delivery of active molecules into cancer cells Bioconjugate Chem. 22, 1410-5
6. Jin, E., Zhang, B., Sun, X., Zhou, Z., Ma, X., Sun, Q., Tang, J., Shen, Y., Van Kirk, E., and Murdoch, W. J. 2013, Acid-active cell-penetrating peptides for in vivo tumor-targeted drug delivery J. Am. Chem. Soc. 135, 933-40
7. Hansen, M. B., van Gaal, E., Minten, I., Storm, G., van Hest, J. C. M., and Löwik, D. W. P. M. (2012) Constrained and uv-activatable cell-penetrating peptides for intracellular delivery of liposomes J. Controlled Release 164, 87-94
8. Zhu, L., Kate, P., and Torchilin, V. P. (2012) Matrix metalloprotease 2-responsive multifunctional liposomal nanocarrier for enhanced tumor targeting ACS Nano 6, 3491-8
9. van Duijnhoven, S. M., Robillard, M. S., Nicolay, K., and Grüll, H. (2011) Tumor targeting of MMP-2/9 activatable cell-penetrating imaging probes is caused by tumor-independent activation J. Nucl. Med. 52, 279-86
10. Yuan, X., Lin, X., Manorek, G., and Howell, S. B. (2011) Challenges associated with the targeted delivery of gelonin to claudin-expressing cancer cells with the use of activatable cell penetrating peptides to enhance potency BMC Cancer 11, 61
11. Jiang, T., Olson, E. S., Nguyen, Q. T., Roy, M., Jennings, P. A., and Tsien, R. Y. (2004) Tumor imaging by means of proteolytic activation of cell-penetrating peptides Proc. Natl. Acad. Sci. U.S.A. 101, 17867-72
12. Myrberg, H., Zhang, L., Mäe, M., and Langel, Ü. (2007) Design of a tumor-homing cell-penetrating peptide Bioconjugate Chem. 19, 70-75
13. Takara, K., Hatakeyama, H., Kibria, G., Ohga, N., Hida, K., and Harashima, H. (2012) Size-controlled, dual-ligand modified liposomes that target the tumor vasculature show promise for use in drug-resistant cancer therapy J. Controlled Release 162, 225-32
14. Tan, M., Lan, K. H., Yao, J., Lu, C. H., Sun, M., Neal, C. L., Lu, J., and Yu, D. (2006) Selective inhibition of erbb2-overexpressing breast cancer in vivo by a novel tat-based erbb2-targeting signal transducers and activators of transcription 3-blocking peptide Cancer Res. 66, 3764-72
15. Ganta, S., Devalapally, H., Shahiwala, A., and Amiji, M. (2008) A review of stimuli-responsive nanocarriers for drug and gene delivery J. Controlled Release 126, 187-204
16. Wender, P. A., Mitchell, D. J., Pattabiraman, K., Pelkey, E. T., Steinman, L., and Rothbard, J. B. (2000) The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters Proc. Natl. Acad. Sci. U.S.A. 97, 13003-13008
17. Sjöström, H., Norén, O., and Olsen, J. (2002) Structure and function of aminopeptidase N Cellular Peptidases in Immune Functions and Diseases 2, 25-34
18. De Meester, I., Korom, S., Van Damme, J., and Scharpé, S. (1999) CD26, let it cut or cut it down Immunol. Today 20, 367-375
19. Saiki, I., Fujii, H., Yoneda, J., Abe, F., Nakajima, M., Tsuruo, T., and Azuma, I. (1993) Role of aminopeptidase N (CD13) in tumor-cell invasion and extracellular matrix degradation Int. J. Cancer 54, 137-43
20. Pasqualini, R., Koivunen, E., Kain, R., Lahdenranta, J., Sakamoto, M., Stryhn, A., Ashmun, R. A., Shapiro, L. H., Arap, W., and Ruoslahti, E. (2000) Aminopeptidase N is a receptor for tumor-homing peptides and a target for inhibiting angiogenesis Cancer Res. 60, 722-7
21. Fontijn, D., Duyndam, M. C. A., van Berkel, M. P. A., Yuana, Y., Shapiro, L. H., Pinedo, H. M., Broxterman, H. J., and Boven, E. (2006) CD13/aminopeptidase N overexpression by basic fibroblast growth factor mediates enhanced invasiveness of 1F6 human melanoma cells Br. J. Cancer 94, 1627-36
22. Yeager, C. L., Ashmun, R. A., Williams, R. K., Cardellichio, C. B., Shapiro, L. H., Look, A. T., and Holmes, K. V. (1992) Human aminopeptidase N is a receptor for human coronavirus 229E Nature 357, 420-422
23. Söderberg, C., Giugni, T. D., Zaia, J. A., Larsson, S., Wahlberg, J. M., and Möller, E. (1993) CD13 (human aminopeptidase N) mediates human cytomegalovirus infection J. Virol. 67, 6576-85
24. Bonin, A., Hühn, J., and Fleischer, B. (1998) Dipeptidyl-peptidase IV/CD26 on T cells: Analysis of an alternative t-cell activation pathway Immun. Rev. 161, 43-53
25. Heins, J., Welker, P., Schönlein, C., Born, I., Hartrodt, B., Neubert, K., Tsuru, D., and Barth, A. (1988) Mechanism of proline-specific proteinases: (I) substrate specificity of dipeptidyl peptidase IV from pig kidney and proline-specific endopeptidase from flavobacterium meningosepticum Biochim. Biophys. Acta 954, 161-9
26. Dong, X., An, B., Salvucci Kierstead, L., Storkus, W. J., Amoscato, A. A., and Salter, R. D. (2000) Modification of the amino terminus of a class II epitope confers resistance to degradation by CD13 on dendritic cells and enhances presentation to T cells J. Immunol. 164, 129-135
27. Dos Santos, S., Chandravarkar, A., Mandal, B., Mimna, R., Murat, K., Saucède, L., Tella, P., Tuchscherer, G., and Mutter, M. (2005) Switch-peptides: Controlling self-assembly of amyloid beta-derived peptides in vitro by consecutive triggering of acyl migrations J. Am. Chem. Soc. 127, 11888-9
28. Richard, J. P., Melikov, K., Vives, E., Ramos, C., Verbeure, B., Gait, M. J., Chernomordik, L. V., and Lebleu, B. (2003) Cell-penetrating peptides. A reevaluation of the mechanism of cellular uptake J. Biol. Chem. 278, 585-590
29. Kaiser, E., Colescott, R. L., Bossinger, C. D., and Cook, P. I. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides Anal. Biochem. 34, 595-598