Pt(IV) prodrugs designed to bind non-covalently to human serum albumin for drug delivery

Journal of the American Chemical Society

Volumn 136, Issue 24, 2014, Pages 8790-8798

  Zheng, Yao Rong ^a   Suntharalingam, Kogularamanan ^a   Johnstone, Timothy C ^a   Yoo, Hyunsuk ^a   Lin, Wei ^a   Brooks, Jamar G ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; DRUG DELIVERY; LIQUID CHROMATOGRAPHY; PLATINUM; PLATINUM COMPOUNDS; PROTEINS;

FAST PROTEIN LIQUID CHROMATOGRAPHY; HEXADECYL CHAINS; HUMAN SERUM ALBUMINS; RATE OF REDUCTION; SUCCINATE LIGANDS; SYSTEMATIC VARIATION; THERAPEUTIC POTENTIALS; TUMOR ACCUMULATION;

LIGANDS;

ALKYL GROUP; ASCORBIC ACID; CISPLATIN; HUMAN SERUM ALBUMIN; LIGAND; OCTANOL; PLATINUM DERIVATIVE; PRODRUG; SUCCINIC ACID; ANTINEOPLASTIC AGENT; PLATINUM COMPLEX; SERUM ALBUMIN;

AQUEOUS SOLUTION; ARTICLE; BIOCOMPATIBILITY; CELL CYCLE; CELL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG POTENCY; DRUG PROTEIN BINDING; FAST PROTEIN LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; OXIDATION REDUCTION REACTION; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; DRUG SCREENING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOPLATINUM COMPOUNDS; PRODRUGS; SERUM ALBUMIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84902665558     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5038269     Document Type: Article

References (57)

1. Wang, D.; Lippard, S. J. Nat. Rev. Drug Discovery 2005, 4, 307
2. Kelland, L. Nat. Rev. Cancer 2007, 7, 573
3. Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R. Dalton Trans. 2010, 39, 8113
4. Jamieson, E. R.; Lippard, S. J. Chem. Rev. 1999, 99, 2467
5. Todd, R. C.; Lippard, S. J. Metallomics 2009, 1, 280
6. Miller, R. P.; Tadagavadi, R. K.; Ramesh, G.; Reeves, W. B. Toxins 2010, 2, 2490
7. Hall, M. D.; Hambley, T. W. Coord. Chem. Rev. 2002, 232, 49
8. Hall, M. D.; Dolman, R. C.; Hambley, T. W. In Metal Complexes in Tumor Diagnosis and as Anticancer Agents; Sigel, A.; Sigel, H., Eds.; Metal Ions in Biological Systems, Vol. 42; Marcel Dekker: New York, 2004; p 297.
9. Hall, M. D.; Mellor, H. R.; Callaghan, R.; Hambley, T. W. J. Med. Chem. 2007, 50, 3403
10. Johnstone, T. C.; Wilson, J. J.; Lippard, S. J. Inorg. Chem. 2013, 52, 12234
11. Shamsuddin, S.; Santillan, C. C.; Stark, J. L.; Whitmire, K. H.; Siddik, Z. H.; Khokhar, A. R. J. Inorg. Biochem. 1998, 71, 29
12. Hambley, T. W.; Battle, A. R.; Deacon, G. B.; Lawrenz, E. T.; Fallon, G. D.; Gatehouse, B. M.; Webster, L. K.; Rainone, S. J. Inorg. Biochem. 1999, 77, 3
13. Khan, S. R. A.; Huang, S.; Shamsuddin, S.; Inutsuka, S.; Whitmire, K. H.; Siddik, Z. H.; Khokhar, A. R. Bioorg. Med. Chem. 2000, 8, 515
14. Gramatica, P.; Papa, E.; Luini, M.; Monti, E.; Gariboldi, M. B.; Ravera, M.; Gabano, E.; Gaviglio, L.; Osella, D. J. Biol. Inorg. Chem. 2010, 15, 1157
15. Mukhopadhyay, S.; Barnés, C. M.; Haskel, A.; Short, S. M.; Barnes, K. R.; Lippard, S. J. Bioconjugate Chem. 2008, 19, 39
16. Graf, N.; Mokhtari, T. E.; Papayannopoulos, I. A.; Lippard, S. J. J. Inorg. Biochem. 2012, 110, 58
17. Barnes, K. R.; Kutikov, A.; Lippard, S. J. Chem. Biol. 2004, 11, 557
18. Ang, W. H.; Khalaila, I.; Allardyce, C. S.; Juillerat-Jeanneret, L.; Dyson, P. J. J. Am. Chem. Soc. 2005, 127, 1382
19. Dhar, S.; Lippard, S. J. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 22199
20. Yang, J.; Sun, X.; Mao, W.; Sui, M.; Tang, J.; Shen, Y. Mol. Pharmaceutics 2012, 9, 2793
21. Suntharalingam, K.; Song, Y.; Lippard, S. J. Chem. Commun. 2014, 50, 2465
22. Dhar, S.; Gu, F. X.; Langer, R.; Farokhzad, O. C.; Lippard, S. J. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 17356
23. Dhar, S.; Kolishetti, N.; Lippard, S. J.; Farokhzad, O. C. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 1850
24. Johnstone, T. C.; Lippard, S. J. Inorg. Chem. 2013, 52, 9915
25. Xu, X.; Xie, K.; Zhang, X.-Q.; Pridgen, E. M.; Park, G. Y.; Cui, D. S.; Shi, J. J.; Wu, J.; Kantoff, P. W.; Lippard, S. J.; Langer, R.; Walker, G. C.; Farokhzad, O. C. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 18638
26. Li, J.; Yap, S. Q.; Chin, C. F.; Tian, Q.; Yoong, S. L.; Pastorin, G.; Ang, W. H. Chem. Sci. 2012, 3, 2083
27. Chaney, S. G.; Wyrick, S.; Till, G. K. Cancer Res. 1990, 50, 4539
28. Carr, J. L.; Tingle, M. D.; McKeage, M. J. Cancer Chemother. Pharmacol. 2002, 50, 9
29. A.D.A.M. Medical Encyclopedia; A.D.A.M., Inc.: Atlanta, GA, 2005; Vol. 2014.
30. Voet, D.; Voet, J. G. Biochemistry, 4 th ed.; John Wiley & Sons: Hoboken, NJ, 2011.
31. Hawkins, M. J.; Soon-Shiong, P.; Desai, N. Adv. Drug Delivery Rev. 2008, 60, 876
32. Vishnu, P.; Roy, V. Breast Cancer: Basic Clin. Res. 2011, 53
33. Liu, H.; Moynihan, K. D.; Zheng, Y.; Szeto, G. L.; Li, A. V.; Huang, B.; Van Egeren, D. S.; Park, C.; Irvine, D. J. Nature 2014, 507, 519-522
34. Kratz, F. J. Controlled Release 2008, 132, 171
35. Park, K. J. Controlled Release 2012, 157, 3
36. Ivanov, A. I.; Christodoulou, J.; Parkinson, J. A.; Barnham, K. J.; Tucker, A.; Woodrow, J.; Sadler, P. J. J. Biol. Chem. 1998, 273, 14721
37. Espósito, B. P.; Najjar, R. Coord. Chem. Rev. 2002, 232, 137
38. Timerbaev, A. R.; Aleksenko, S. S.; Polec-Pawlak, K.; Ruzik, R.; Semenova, O.; Hartinger, C. G.; Oszwaldowski, S.; Galanski, M.; Jarosz, M.; Keppler, B. K. Electrophoresis 2004, 25, 1988
39. Pichler, V.; Mayr, J.; Heffeter, P.; Dömötör, O.; Enyedy, é. A.; Hermann, G.; Groza, D.; Köllensperger, G.; Galanksi, M.; Berger, W.; Keppler, B. K.; Kowol, C. R. Chem. Commun. 2013, 49, 2249
40. Dhar, S.; Daniel, W. L.; Giljohann, D. A.; Mirkin, C. A.; Lippard, S. J. J. Am. Chem. Soc. 2009, 131, 14652
41. Wilson, J. J.; Lippard, S. J. Chem. Rev. 2014, 114, 4470
42. Giandomenico, C. M.; Abrams, M. J.; Murrer, B. A.; Vollano, J. F.; Rheinheimer, M. I.; Wyer, S. B.; Bossard, G. E.; Higgins, J. D., III Inorg. Chem. 1995, 34, 1015
43. Wilson, J. J.; Lippard, S. J. Inorg. Chem. 2011, 50, 3103
44. Tetko, I. V.; Tanchuk, V. Y. J. Chem. Inf. Comput. Sci. 2002, 42, 1136
45. Olive, P. L.; Banáth, J. P. Cytometry, Part B 2009, 76B, 79
46. Revet, I.; Feeney, L.; Bruguera, S.; Wilson, W.; Dong, T. K.; Oh, D. H.; Dankort, D.; Cleaver, J. E. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 8663
47. Sudlow, G.; Birkett, D. J.; Wade, D. N. Mol. Pharmacol. 1975, 11, 824
48. Sudlow, G.; Birkett, D. J.; Wade, D. N. Mol. Pharmacol. 1976, 12, 1052
49. Concepts and Applications of Molecular Similarity; Johnson, M. A.; Maggiora, G. M., Eds.; Wiley: New York, 1990.
50. Braddock, P. D.; Connors, T. A.; Jones, M.; Khokhar, A. R.; Melzack, D. H.; Tobe, M. L. Chem.-Biol. Interact. 1975, 11, 145
51. Reithofer, M. R.; Bytzek, A. K.; Valiahdi, S. M.; Kowol, C. R.; Groessl, M.; Hartinger, C. G.; Jakupec, M. A.; Galanski, M.; Keppler, B. K. J. Inorg. Biochem. 2011, 105, 46
52. New, E. J.; Duan, R.; Zhang, J. Z.; Hambley, T. W. Dalton Trans. 2009, 3092
53. Wilson, J. J.; Lippard, S. J. Inorg. Chim. Acta 2012, 389, 77
54. Song, Y.; Suntharalingam, K.; Yeung, J. S.; Royzen, M.; Lippard, S. J. Bioconjugate Chem. 2013, 24, 1733
55. Montagner, D.; Yap, S. Q.; Ang, W. H. Angew. Chem., Int. Ed. 2013, 52, 11785
56. Curry, S.; Mandelkow, H.; Brick, P.; Franks, N. Nat. Struct. Biol. 1998, 5, 827
57. Erdlenbruch, B.; Nier, M.; Kern, W.; Hiddemann, W.; Pekrun, A.; Lakomek, M. Eur. J. Clin. Pharmacol. 2001, 57, 393