Cell-penetrating hyperbranched polyprodrug amphiphiles for synergistic reductive milieu-triggered drug release and enhanced magnetic resonance signals

Journal of the American Chemical Society

Volumn 137, Issue 1, 2015, Pages 362-368

  Hu, Xianglong ^a,b   Liu, Guhuan ^a   Li, Yang ^a   Wang, Xiaorui ^a   Liu, Shiyong ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b SOUTH CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILES; CARDIOVASCULAR SYSTEM; CHEMOTHERAPY; DIAGNOSIS; MAGNETIC RESONANCE IMAGING; TUMORS;

BLOOD CIRCULATION; CAMPTOTHECIN (CPT); CANCER CHEMOTHERAPY; CELLULAR INTERNALIZATION; DIAGNOSTIC IMAGING; HYDROPHILIC CORONA; THERAPEUTIC EFFICACY; TRIGGERED DRUG RELEASE;

MAGNETIC RESONANCE;

AMPHOPHILE; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CELL PENETRATING PEPTIDE; CONTRAST MEDIUM; DRUG CARRIER; GUANIDINE; NANOCARRIER; PRODRUG; NANOPARTICLE; POLYMER; SURFACTANT;

ARTICLE; CHEMOTHERAPY; CIRCULATION; CONJUGATION; CYTOSOL; DRUG EFFICACY; DRUG RELEASE; HALF LIFE TIME; HUMAN; HUMAN CELL; HYDROPHILICITY; IMAGING; INTERNALIZATION; NEOPLASM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE IMAGING; TUMOR CELL; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; HEPG2 CELL LINE; METABOLISM; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG LIBERATION; GUANIDINE; HEP G2 CELLS; HUMANS; MAGNETIC RESONANCE IMAGING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NANOPARTICLES; OXIDATION-REDUCTION; POLYMERS; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE-ACTIVE AGENTS;

EID: 84921038463     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5105848     Document Type: Article

References (63)

1. Kataoka, K.; Harada, A.; Nagasaki, Y. Adv. Drug Delivery Rev. 2012, 64, 37-48
2. Ge, Z. S.; Liu, S. Y. Chem. Soc. Rev. 2013, 42, 7289-7325
3. Bannister, I.; Billingham, N. C.; Armes, S. P.; Rannard, S. P.; Findlay, P. Macromolecules 2006, 39, 7483-7492
4. Du, W.; Li, Y.; Nyström, A. M.; Cheng, C.; Wooley, K. L. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3487-3496
5. Lutz, J.-F.; Sumerlin, B.; Matyjaszewski, K. Macromol. Rapid Commun. 2014, 35, 377-377
6. Calderon, M.; Quadir, M. A.; Sharma, S. K.; Haag, R. Adv. Mater. 2010, 22, 190-218
7. Fox, M. E.; Szoka, F. C.; Frechet, J. M. J. Acc. Chem. Res. 2009, 42, 1141-1151
8. Li, X. J.; Qian, Y. F.; Liu, T.; Hu, X. L.; Zhang, G. Y.; You, Y. Z.; Liu, S. Y. Biomaterials 2011, 32, 6595-6605
9. Wang, D.; Zhao, T.; Zhu, X.; Yan, D.; Wang, W. Chem. Soc. Rev. 2014, 10.1039/C4CS00229F
10. Wilms, D.; Stiriba, S.-E.; Frey, H. Acc. Chem. Res. 2009, 43, 129-141
11. Jin, H.; Huang, W.; Zhu, X.; Zhou, Y.; Yan, D. Chem. Soc. Rev. 2012, 41, 5986-5997
12. Fox, M. E.; Guillaudeu, S.; Frechet, J. M. J.; Jerger, K.; Macaraeg, N.; Szoka, F. C. Mol. Pharmaceutics 2009, 6, 1562-1572
13. Krasia-Christoforou, T.; Georgiou, T. K. J. Mater. Chem. B 2013, 1, 3002-3025
14. Wang, Z.; Niu, G.; Chen, X. Pharm. Res. 2013, 1-19
15. Xie, J.; Lee, S.; Chen, X. Y. Adv. Drug Delivery Rev. 2010, 62, 1064-1079
16. Ai, H.; Flask, C.; Weinberg, B.; Shuai, X.; Pagel, M. D.; Farrell, D.; Duerk, J.; Gao, J. M. Adv. Mater. 2005, 17, 1949-1952
17. Nasongkla, N.; Bey, E.; Ren, J. M.; Ai, H.; Khemtong, C.; Guthi, J. S.; Chin, S. F.; Sherry, A. D.; Boothman, D. A.; Gao, J. M. Nano Lett. 2006, 6, 2427-2430
18. Mantle, M. D. Curr. Opin. Colloid Interface Sci. 2013, 18, 214-227
19. Pourtau, L.; Oliveira, H.; Thevenot, J.; Wan, Y.; Brisson, A. R.; Sandre, O.; Miraux, S.; Thiaudiere, E.; Lecommandoux, S. Adv. Healthcare Mater. 2013, 2, 1420-1424
20. Berret, J.-F.; Schonbeck, N.; Gazeau, F.; El Kharrat, D.; Sandre, O.; Vacher, A.; Airiau, M. J. Am. Chem. Soc. 2006, 128, 1755-1761
21. Liu, T.; Qian, Y. F.; Hu, X. L.; Ge, Z. S.; Liu, S. Y. J. Mater. Chem. 2012, 22, 5020-5030
22. Hu, J. M.; Qian, Y. F.; Wang, X. F.; Liu, T.; Liu, S. Y. Langmuir 2012, 28, 2073-2082
23. Hu, J. M.; Liu, T.; Zhang, G. Y.; Jin, F.; Liu, S. Y. Macromol. Rapid Commun. 2013, 34, 749-758
24. Ye, M. Z.; Qian, Y.; Tang, J. B.; Hu, H. J.; Sui, M. H.; Shen, Y. Q. J. Controlled Release 2013, 169, 239-245
25. Ye, M. Z.; Tang, J. B.; Wang, X. P.; Xu, J. X.; Sui, M. H.; Shen, Y. Q. J. Controlled Release 2011, 152, 256-257
26. Thurecht, K. J.; Blakey, I.; Peng, H.; Squires, O.; Hsu, S.; Alexander, C.; Whittaker, A. K. J. Am. Chem. Soc. 2010, 132, 5336-5337
27. Liu, T.; Li, X. J.; Qian, Y. F.; Hu, X. L.; Liu, S. Y. Biomaterials 2012, 33, 2521-2531
28. Li, Y.; Qian, Y. F.; Liu, T.; Zhang, G. Y.; Hu, J. M.; Liu, S. Y. Polym. Chem. 2014, 5, 1743-1750
29. Tang, J. B.; Sheng, Y. Q.; Hu, H. J.; Shen, Y. Q. Prog. Polym. Sci. 2013, 38, 462-502
30. Villaraza, A. J. L.; Bumb, A.; Brechbiel, M. W. Chem. Rev. 2010, 110, 2921-2959
31. Theato, P.; Sumerlin, B. S.; OReilly, R. K.; Epps, I. I. I. T. H. Chem. Soc. Rev. 2013, 42, 7055-7056
32. Major, J. L.; Meade, T. J. Acc. Chem. Res. 2009, 42, 893-903
33. Liu, Y. J.; Zhang, N. Biomaterials 2012, 33, 5363-5375
34. Hu, X. L.; Hu, J. M.; Tian, J.; Ge, Z. S.; Zhang, G. Y.; Luo, K. F.; Liu, S. Y. J. Am. Chem. Soc. 2013, 135, 17617-17629
35. Zhou, Z.; Ma, X.; Murphy, C. J.; Jin, E.; Sun, Q.; Shen, Y.; Van Kirk, E. A.; Murdoch, W. J. Angew. Chem., Int. Ed. 2014, 53, 10949-10955
36. Khan, A. R.; Magnusson, J. P.; Watson, S.; Grabowska, A. M.; Wilkinson, R. W.; Alexander, C.; Pritchard, D. Polym. Chem. 2014, 5, 5320-5329
37. Rao, N. V.; Mane, S. R.; Kishore, A.; Das Sarma, J.; Shunmugam, R. Biomacromolecules 2012, 13, 221-230
38. Yuan, Y. Y.; Liu, J.; Liu, B. Angew. Chem., Int. Ed. 2014, 53, 7163-7168
39. Crielaard, B. J.; Rijcken, C. J. F.; Quan, L. D.; van der Wal, S.; Altintas, I.; van der Pot, M.; Kruijtzer, J. A. W.; Liskamp, R. M. J.; Schiffelers, R. M.; van Nostrum, C. F.; Hennink, W. E.; Wang, D.; Lammers, T.; Storm, G. Angew. Chem., Int. Ed. 2012, 51, 7254-7258
40. Johnson, J. A.; Lu, Y. Y.; Burts, A. O.; Xia, Y.; Durrell, A. C.; Tirrell, D. A.; Grubbs, R. H. Macromolecules 2010, 43, 10326-10335
41. Parrott, M. C.; Finniss, M.; Luft, J. C.; Pandya, A.; Gullapalli, A.; Napier, M. E.; Desimone, J. M. J. Am. Chem. Soc. 2012, 134, 7978-7982
42. Wu, X. M.; Sun, X. R.; Guo, Z. Q.; Tang, J. B.; Shen, Y. Q.; James, T. D.; Tian, H.; Zhu, W. H. J. Am. Chem. Soc. 2014, 136, 3579-3588
43. Bhuniya, S.; Maiti, S.; Kim, E. J.; Lee, H.; Sessler, J. L.; Hong, K. S.; Kim, J. S. Angew. Chem., Int. Ed. 2014, 53, 4469-4474
44. Lee, M. H.; Kim, J. Y.; Han, J. H.; Bhuniya, S.; Sessler, J. L.; Kang, C.; Kim, J. S. J. Am. Chem. Soc. 2012, 134, 12668-12674
45. Tao, L.; Liu, J. Q.; Tan, B. H.; Davis, T. P. Macromolecules 2009, 42, 4960-4962
46. Lutz, J.-F.; Sumerlin, B.; Matyjaszewski, K. Macromol. Rapid Commun. 2014, 35, 122-122
47. Gregory, A.; Stenzel, M. H. Prog. Polym. Sci. 2012, 37, 38-105
48. Boyer, C.; Stenzel, M. H.; Davis, T. P. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 551-595
49. Boyer, C.; Bulmus, V.; Davis, T. P.; Ladmiral, V.; Liu, J.; Perrier, S. Chem. Rev. 2009, 109, 5402-5436
50. Zhang, Y.; Teo, B. M.; Postma, A.; Ercole, F.; Ogaki, R.; Zhu, M. F.; Stadler, B. J. Phys. Chem. B 2013, 117, 10504-10512
51. Zhang, M. J.; Liu, H. H.; Shao, W.; Ye, C. N.; Zhao, Y. L. Macromolecules 2012, 45, 9312-9325
52. Vogt, A. P.; Sumerlin, B. S. Macromolecules 2008, 41, 7368-7373
53. Bütün, V.; Bannister, I.; Billingham, N. C.; Sherrington, D. C.; Armes, S. P. Macromolecules 2005, 38, 4977-4982
54. Xu, J.; Luo, S. Z.; Shi, W. F.; Liu, S. Y. Langmuir 2006, 22, 989-997
55. Ruiz-Sanchis, P.; Wohl, B. M.; Smith, A. A. A.; Zuwala, K.; Melchjorsen, J.; Tolstrup, M.; Zelikin, A. N. Adv. Healthcare Mater. 2014, 10.1002/adhm.201400307
56. Kularatne, S. A.; Venkatesh, C.; Santhapuram, H. K. R.; Wang, K.; Vaitilingam, B.; Henne, W. A.; Low, P. S. J. Med. Chem. 2010, 53, 7767-7777
57. Canton, I.; Battaglia, G. Chem. Soc. Rev. 2012, 41, 2718-2739
58. Wender, P. A.; Galliher, W. C.; Goun, E. A.; Jones, L. R.; Pillow, T. H. Adv. Drug Delivery Rev. 2008, 60, 452-472
59. Lu, H.; Wang, D.; Kazane, S.; Javahishvili, T.; Tian, F.; Song, F.; Sellers, A.; Barnett, B.; Schultz, P. G. J. Am. Chem. Soc. 2013, 135, 13885-13891
60. Hu, X. L.; Tian, J.; Liu, T.; Zhang, G. Y.; Liu, S. Y. Macromolecules 2013, 46, 6243-6256
61. Gratton, S. E. A.; Ropp, P. A.; Pohlhaus, P. D.; Luft, J. C.; Madden, V. J.; Napier, M. E.; DeSimone, J. M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 11613-11618
62. Funhoff, A. M.; van Nostrum, C. F.; Lok, M. C.; Fretz, M. M.; Crommelin, D. J. A.; Hennink, W. E. Bioconjugate Chem. 2004, 15, 1212-1220
63. Treat, N. J.; Smith, D.; Teng, C.; Flores, J. D.; Abel, B. A.; York, A. W.; Huang, F.; McCormick, C. L. ACS Macro Lett. 2011, 1, 100-104