Activable Cell-Penetrating Peptide Conjugated Prodrug for Tumor Targeted Drug Delivery

ACS Applied Materials and Interfaces

Volumn 7, Issue 29, 2015, Pages 16061-16069

  Cheng, Hong ^a   Zhu, Jing Yi ^a   Xu, Xiao Ding ^a   Qiu, Wen Xiu ^a   Lei, Qi ^a   Han, Kai ^a   Cheng, Yin Jia ^a   Zhang, Xian Zheng ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

cell penetrating peptide; cellular uptake; prodrug; targeted drug delivery; tumor therapy

Indexed keywords

CELLS; CHEMICAL ACTIVATION; DRUG PRODUCTS; ENZYME ACTIVITY; PEPTIDES; PH; SHIELDING; TUMORS;

CELL-PENETRATING PEPTIDE; CELLULAR UPTAKE; PRODRUGS; TARGETED DRUG DELIVERY; TUMOR THERAPY;

CYTOLOGY;

ANTINEOPLASTIC ANTIMETABOLITE; CELL PENETRATING PEPTIDE; DELAYED RELEASE FORMULATION; DOXORUBICIN; NANOCAPSULE; NANOCONJUGATE; PRODRUG;

ADMINISTRATION AND DOSAGE; ANIMAL; APOPTOSIS; CELL SURVIVAL; CHEMISTRY; CHLOROCEBUS AETHIOPS; COS 1 CELL LINE; DELAYED RELEASE FORMULATION; DIFFUSION; DRUG EFFECTS; HELA CELL LINE; HUMAN; METABOLISM; MOLECULARLY TARGETED THERAPY; NEOPLASMS; PATHOLOGY; PROCEDURES; SYNTHESIS; TREATMENT OUTCOME; ULTRASTRUCTURE;

ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; APOPTOSIS; CELL SURVIVAL; CELL-PENETRATING PEPTIDES; CERCOPITHECUS AETHIOPS; COS CELLS; DELAYED-ACTION PREPARATIONS; DIFFUSION; DOXORUBICIN; HELA CELLS; HUMANS; MOLECULAR TARGETED THERAPY; NANOCAPSULES; NANOCONJUGATES; NEOPLASMS; PRODRUGS; TREATMENT OUTCOME;

EID: 84938408305     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b04517     Document Type: Article

References (37)

1. Jones, B. Tumor Genetics: Evaluating Oncogene Cooperativities Nat. Rev. Genet. 2012, 13, 598 10.1038/nrg3325
2. Maksimenko, A.; Dosio, F.; Mougin, J.; Ferrero, A.; Wack, S.; Reddy, L. H.; Weyn, A.; Lepeltier, E.; Bourgaux, C.; Stella, B.; Cattel, L.; Couvreur, P. A Unique Squalenoylated and Nonpegylated Doxorubicin Nanomedicine with Systemic Long-Circulating Properties and Anticancer Activity Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 217-226 10.1073/pnas.1313459110
3. Cai, T. T.; Lei, Q.; Yang, B.; Jia, H. Z.; Cheng, H.; Liu, L. H.; Zeng, X.; Feng, J.; Zhuo, R. X.; Zhang, X. Z. Utilization of H-Bond Interaction of Nucleobase Uralic with Antitumor Methotrexate to Design Drug Carrier with Ultrahigh Loading Efficiency and pH-Responsive Drug Release Regen. Biomater. 2014, 1, 27-35 10.1093/rb/rbu010
4. Wu, H.; Zhu, L.; Torchilin, V. P. pH-Sensitive Poly(histidine)-PEG/DSPE-PEG Co-Polymer Micelles for Cytosolic Drug Delivery Biomaterials 2013, 34, 1213-1222 10.1016/j.biomaterials.2012.08.072
5. Mahato, R.; Tai, W.; Cheng, K. Prodrug for Improving Tumor Target Ability and Efficiency Adv. Drug Delivery Rev. 2011, 63, 659-670 10.1016/j.addr.2011.02.002
6. Giang, I.; Boland, E. L.; Poon, G. M. K. Prodrug Application for Targeted Cancer Therapy AAPS J. 2014, 16, 899-913 10.1208/s12248-014-9638-z
7. Jiang, T.; Li, Y. M.; Lv, Y.; Cheng, Y. J.; He, F.; Zhuo, R. X. Amphipilic Polycarbonate Conjugates of Doxorubicin with pH-Sensitive Hydrazone Linker for Controlled Release Colloids Surf., B 2013, 111, 542-548 10.1016/j.colsurfb.2013.06.054
8. Li, Y.; Liu, R. Y.; Yang, J.; Ma, G. H.; Zhang, Z. Z.; Zhang, X. Dual Sensitive and Temporally Controlled Camptothecin Prodrug Liposomes Codelivery of siRNA for High Efficiency Tumor Therapy Biomaterials 2014, 35, 9731-9745 10.1016/j.biomaterials.2014.08.022
9. Hochdorffer, K.; Ajaj, K. A.; Obodozie, C. S.; Kratz, F. Development of Novel Bisphosphonate Prodrugs of Doxorubicin for Targeting Bone Metastases That Are Cleaved pH Dependently or by Cathepsin B: Synthesis, Cleavage Properties, and Binding Properties to Hydroxyapatite as Well as Bone Matrix J. Med. Chem. 2012, 55, 7502-7515 10.1021/jm300493m
10. Toriyabe, N.; Hayashi, Y.; Harashima, H. The Transfection Activity of R8-Modified Nanoparticles and siRNA Condensation Using pH Sensitive Stearylated- Octahistidine Biomaterials 2013, 34, 1337-1343 10.1016/j.biomaterials.2012.10.043
11. Yang, Y. F.; Yang, Y.; Xie, X. Y.; Cai, X. S.; Zhang, H.; Gong, W.; Wang, Z. Y.; Mei, X. G. PEGylated Liposomes with NGR Ligand and Heat-Activable Cell-Penetrating Peptide-Doxorubicin Conjugate for Tumor-Specific Therapy Biomaterials 2014, 35, 4368-4381 10.1016/j.biomaterials.2014.01.076
12. Ookubo, N.; Michiue, H.; Kitamatsu, M.; Kamamura, M.; Nishiki, T.; Matsui, H. The Transdermal Inhibition of Melanogenesis by A Cell-Membrane-Permeable Peptide Delivery System Based on Poly-Arginine Biomaterials 2014, 35, 4508-4516 10.1016/j.biomaterials.2014.01.052
13. Ye, J. X.; Shin, M. C.; Liang, Q. L.; He, H. N.; Yang, V. C. 15 Years of ATTEMPTS: A Macromolecular Drug Delivery System Based on the CPP-Mediated Intracellular Drug Delivery and Antibody Targeting J. Controlled Release 2015, 205, 58-69 10.1016/j.jconrel.2014.12.002
14. Jiang, T.; Olson, E. S.; Nguyen, Q. T.; Roy, M.; Jennings, P. A.; Tsien, R. Y. Tumor Imaging by Means of Proteolytic Activation of Cell-Penetrating Peptides Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 17867-17872 10.1073/pnas.0408191101
15. Olson, E. S.; Jiang, T.; Aguilera, T. A.; Nguyen, Q. T.; Ellies, L. G.; Scadeng, M.; Tsien, R. Y. Activatable Cell Penetrating Peptides Linked to Nanoparticles as Dual Probes for In Vivo Fluorescence and MR Imaging of Proteases Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 4311-4316 10.1073/pnas.0910283107
16. Nguyen, Q. T.; Olson, E. S.; Aguilera, T. A.; Jiang, T.; Scadeng, M.; Ellies, L. G.; Tsien, R. Y. Surgery with Molecular Fluorescence Imaging Using Activatable Cell-Penetrating Peptides Decreases Residual Cancer and Improves Survival Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 4317-4322 10.1073/pnas.0910261107
17. Jin, E. L.; Zhang, B.; Sun, X. R.; Zhou, Z. X.; Ma, X. P.; Sun, Q. H.; Tang, J. B.; Shen, Y. Q.; Van Kirk, E.; Murdoch, W. J.; Radosz, M. Acid-Active Cell-Penetrating Peptides for In Vivo Tumor-Targeted Drug Delivery J. Am. Chem. Soc. 2013, 135, 933-940 10.1021/ja311180x
18. van Duijnhoven, S. M. J.; Robillard, M. S.; Nicolay, K.; Grull, H. Tumor Targeting of MMP-2/9 Activatable Cell-Penetrating Imaging Probes Is Caused by Tumor-Independent Activation J. Nucl. Med. 2011, 52, 279-286 10.2967/jnumed.110.082503
19. Kluger, R.; Lam, C. H. External General Base Catalysis and General Acid Catalysis in Reactions of Norbornenylanilic Acids J. Am. Chem. Soc. 1978, 100, 2191-2197 10.1021/ja00475a033
20. Lee, Y.; Fukushima, S.; Bae, Y.; Hiki, S.; Ishii, T.; Kataoka, K. A Protein Nanocarrier from Charge-Conversion Polymer in Response to Endosomal pH J. Am. Chem. Soc. 2007, 129, 5362-5363 10.1021/ja071090b
21. Lee, Y.; Miyata, K.; Oba, M.; Ishii, T.; Fukushima, S.; Han, M.; Koyama, H.; Nishiyama, N.; Kataoka, K. Charge-Conversion Ternary Polyplex with Endosome Disruption Moiety: A Technique for Efficient and Safe Gene Delivery Angew. Chem., Int. Ed. 2008, 47, 5163-5166 10.1002/anie.200800963
22. Zhou, Z. X.; Shen, Y. Q.; Tang, J. B.; Fan, M. H.; Kirk, E. A V.; Murdoch, W. J.; Radosz, M. Charge-Reversal Drug Conjugate for Targeted Cancer Cell Nuclear Drug Delivery Adv. Funct. Mater. 2009, 19, 3580-3589 10.1002/adfm.200900825
23. Du, J. Z.; Du, X. J.; Mao, C. Q.; Wang, J. Tailor-Made Dual pH-Sensitive Polymer-Doxorubicin Nanoparticles for Efficient Anticancer Drug Delivery J. Am. Chem. Soc. 2011, 133, 17560-17563 10.1021/ja207150n
24. Li, L.; Yang, Q. Q.; Zhou, Z.; Zhong, J. J.; Huang, Y. Doxorubicin-Loaded, Charge Reversible, Folate Modified HPMA Copolymer Conjugates for Active Cancer Cell Targeting Biomaterials 2014, 35, 5171-5187 10.1016/j.biomaterials.2014.03.027
25. Ding, D.; Kwok, R. T. K.; Yuan, Y. Y.; Feng, G. X.; Tang, B. Z.; Liu, B. A Fluorescent Light-up Nanoparticle Probe with Aggregation-Induced Emission Characteristics and Tumor-Acidity Responsiveness for Targeted Imaging and Selective suppression of Cancer Cells Mater. Horiz. 2015, 2, 100-105 10.1039/C4MH00164H
26. Jiang, L.; Li, L.; He, X. D.; Yi, Q. Y.; He, B.; Cao, J.; Pan, W. S.; Gu, Z. W. Overcoming Drug-Resistant Lung Cancer by Paclitaxel Loaded Dual-Functional Liposomes with Mitochondria Targeting and pH-Response Biomaterials 2015, 52, 126-139 10.1016/j.biomaterials.2015.02.004
27. Dong, C. H.; Liu, Z. Y.; Zhang, L.; Guo, W. S.; Li, X.; Liu, J. Q.; Wang, H. J.; Chang, J. pHe-Induced Charge-Reversible NIR Fluorescence Nanoprobe for Tumor-Specific Imaging ACS Appl. Mater. Interfaces 2015, 7, 7566-7575 10.1021/am509011y
28. Podgorski, I.; Sloane, B. F. Cathepsin B and Its Role(s) in Cancer Progression Biochem. Soc. Symp. 2003, 70, 263-276 10.1042/bss0700263
29. Zhong, Y. J.; Shao, L. H.; Li, Y. Cathepsin B-Cleavable Doxorubicin Prodrugs for Targeted Cancer Therapy (Review) Int. J. Oncol. 2013, 42, 373-383 10.3892/ijo.2012.1754
30. Schmid, B.; Chung, D. E.; Warnecke, A.; Fichtner, I.; Kratz, F. Albumin-Binding Prodrugs of Camptothecin and Doxorubicin with An Ala-Leu-Ala-Leu-Linker That Are Cleaved by Cathepsin B: Synthesis and Antitumor Efficacy Bioconjugate Chem. 2007, 18, 702-716 10.1021/bc0602735
31. Abu Ajaj, K.; Graeser, R.; Fichtner, I.; Kratz, F. In Vitro and In Vivo Study of An Albumin-Binding Prodrug of Doxorubicin That Is Cleaved by Cathepsin B Cancer Chemother. Pharmacol. 2009, 64, 413-418 10.1007/s00280-009-0942-8
32. Han, K.; Chen, S.; Chen, W. H.; Lei, Q.; Liu, Y.; Zhuo, R. X.; Zhang, X. Z. Synergistic Gene and Drug Tumor Therapy Using A Chimeric Peptide Biomaterials 2013, 34, 4680-4689 10.1016/j.biomaterials.2013.03.010
33. Oh, N. M.; Kwag, D. S.; Oh, K. T.; Youn, Y. S.; Lee, E. S. Electrostatic Charge Coversion Processes in Engineered Tumor-Identifying Polypeptides for Targeted Chemotherapy Biomaterials 2012, 33, 1884-1893 10.1016/j.biomaterials.2011.11.026
34. Li, L.; Yang, Q. Q.; Zhou, Z.; Zhong, J. J.; Huang, Y. Doxorubicin-Loaded, Charge Reversible, Folate Modified HPMA Copolymer Conjugates for Active Cancer Cell Targeting Biomaterials 2014, 35, 5171-5187 10.1016/j.biomaterials.2014.03.027
35. Chen, J. X.; Xu, X. D.; Chen, W. H.; Zhang, X. Z. Multi-Functional Envelope-Type Nanoparticles Assembled from Amphiphilic Peptidic Prodrug with Improved Anti-Tumor Activity ACS Appl. Mater. Interfaces 2014, 6, 593-598 10.1021/am404680n
36. Santra, S.; Kaittanis, C.; Santiesteban, O. J.; Perez, J. M. Cell-Specific, Activatable, and Theranostic Prodrug for Dual-Targeted Cancer Imaging and Therapy J. Am. Chem. Soc. 2011, 133, 16680-16688 10.1021/ja207463b
37. Yuan, Y. Y.; Liu, J.; Liu, B. Conjugated-Polyelectrolyte-Based Polyprodrug: Targeted and Image-Guided Photodynamic and Chemotherapy with On-Demand Drug Release upon Irradiation with a Single Light Source Angew. Chem., Int. Ed. 2014, 53, 7163-7168 10.1002/anie.201402189