Adamantane-platinum conjugate hosted in β-cyclodextrin: Enhancing transport and cytotoxicity by noncovalent modification

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 24, 2011, Pages 7421-7425

  Prashar, Deepali ^a   Shi, Yi ^a   Bandyopadhyay, Debjyoti ^a   Dabrowiak, James C ^a   Luk, Yan Yeung ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

Anticancer agents; Cyclodextrins; DNA; Host guest chemistry; Noncovalent modification; Solvation

Indexed keywords

ADAMANTANE CARBOPLATIN; ADAMANTANE DERIVATIVE; BETA CYCLODEXTRIN; CARBOPLATIN; DNA; FLUORESCEIN ISOTHIOCYANATE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DNA BINDING; DRUG BINDING; DRUG CONJUGATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROPHOBICITY; MASS SPECTROMETRY; NEUROBLASTOMA CELL;

ADAMANTANE; ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CARBOPLATIN; CELL LINE, TUMOR; CELL SURVIVAL; DRUG CARRIERS; FLUORESCEIN-5-ISOTHIOCYANATE; HUMANS; MASS SPECTROMETRY; MICROSCOPY, CONFOCAL; PLASMIDS; PLATINUM;

EID: 81255154461     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.10.006     Document Type: Article

References (41)

1. F.J. Otero-Espinar, J.J. Torres-Labandeira, C. Alvarez-Lorenzo, and J. Blanco-Mendez J. Drug Delivery Sci. Technol. 20 2010 289
2. M.E. Davis, and M.E. Brewster Nat. Rev. Drug Discovery 3 2004 1023
3. T. Loftsson, and M.E. Brewster J. Pharm. Sci. 85 1996 1017
4. K. Uekama, F. Hirayama, and T. Irie Chem. Rev. 98 1998 2045
5. J. Szejtli Chem. Rev. 98 1998 1743
6. J.C. Dabrowiak Metals in Medicine 1st ed. 2009 Wiley & Sons Chichester
7. B. Rosenberg, L. VanCamp, J.E. Trosko, and V.H. Mansour Nature 222 1969 385
8. L. Kelland Nat. Rev. Cancer 7 2007 573
9. M.D. Hall, M. Okabe, D.-W. Shen, X.-J. Liang, and M.M. Gottesman Annu. Rev. Pharmacol. Toxicol. 48 2008 495
10. A.M. Krause-Heuer, R. Gruenert, S. Kuehne, M. Buczkowska, N.J. Wheate, D.D. Le Pevelen, L.R. Boag, D.M. Fisher, J. Kasparkova, J. Malina, P.J. Bednarski, V. Brabec, and J.R. Aldrich-Wright J. Med. Chem. 52 2009 5474
11. S. Abu-Surrah Adnan Mini-Rev. Med. Chem. 7 2007 203
12. J. Reedijk Pure Appl. Chem. 59 1987 181
13. C.R. Centerwall, J. Goodisman, D.J. Kerwood, and J.C. Dabrowiak J. Am. Chem. Soc. 127 2005 12768
14. A.J. Di Pasqua, J. Goodisman, D.J. Kerwood, B.B. Toms, R.L. Dubowy, and J.C. Dabrowiak Chem. Res. Toxicol. 20 2007 896
15. D. Wang, and S.J. Lippard Nat. Rev. Drug Discovery 4 2005 307
16. A. Halamikova, P. Heringova, J. Kasparkova, F.P. Intini, G. Natile, A. Nemirovski, D. Gibson, and V. Brabec J. Inorg. Biochem. 102 2008 1077
17. J. Zhang, X. Wang, C. Tu, J. Lin, J. Ding, L. Lin, Z. Wang, C. He, C. Yan, X. You, and Z. Guo J. Med. Chem. 46 2003 3502
18. S. Komeda, T. Moulaei, K.K. Woods, M. Chikuma, N.P. Farrell, and L.D. Williams J. Am. Chem. Soc. 128 2006 16092
19. A.M. Krause-Heuer, N.J. Wheate, M.J. Tilby, D.G. Pearson, C.J. Ottley, and J.R. Aldrich-Wright Inorg. Chem. 47 2008 6880
20. N.J. Wheate J. Inorg. Biochem. 102 2008 2060
21. A.I. Rosenbaum, G. Zhang, D.J. Warren, and F.R. Maxfield Proc. Natl. Acad. Sci. U.S.A. 107 2010 5477
22. T. Wennekes, R.J.B.H.N. Van den Berg, W. Donker, G.A. van der Marel, A. Strijland, J.M.F.G. Aerts, and H.S. Overkleeft J. Org. Chem. 72 2007 1088
23. C.J. Boreham, J.A. Broomhead, and D.P. Fairlie Aust. J. Chem. 34 1981 659
24. A.J. Di Pasqua, J. Goodisman, D.J. Kerwood, B.B. Toms, R.L. Dubowy, and J.C. Dabrowiak Chem. Res. Toxicol. 19 2006 139
25. Y. Shi, B.B. Toms, N. Dixit, N. Kumari, L. Mishra, J. Goodisman, and J.C. Dabrowiak Chem. Res. Toxicol. 23 2010 1417
26. M. Ishiyama, H. Tominaga, M. Shiga, K. Sasamoto, Y. Ohkura, and K. Ueno Biol. Pharm. Bull. 19 1996 1518
27. S.A. O'Toole, B.L. Sheppard, E.P.J. McGuinness, N.C. Gleeson, M. Yoneda, and J. Bonnar Cancer Detect. Prev. 27 2003 47
28. A.J. Di Pasqua, D.J. Kerwood, Y. Shi, J. Goodisman, and J.C. Dabrowiak Dalton Trans. 40 2011 4821
29. S.K. Rodal, G. Skretting, O. Garred, F. Vilhardt, B. Van Deurs, and K. Sandvig Mol. Biol. Cell 10 1999 961
30. S. Mukherjee, R.N. Ghosh, and F.R. Maxfield Physiol. Rev. 77 1997 759
31. K. Teranishi, and T. Nishiguchi Anal. Biochem. 325 2004 185
32. A. Ghezzi, M. Aceto, C. Cassino, E. Gabano, and D. Osella J. Inorg. Biochem. 98 2004 73
33. G.L. Cohen, W.R. Bauer, J.K. Barton, and S.J. Lippard Science 203 1979 1014
34. W.M. Scovell, and F. Collart Nucleic Acids Res. 13 1985 2881
35. M.V. Keck, and S.J. Lippard J. Am. Chem. Soc. 114 1992 3386
36. R.S. Sorokanich, A.J. Di Pasqua, M. Geier, and J.C. Dabrowiak Chem. Biodiversity 5 2008 1540
37. C.-M. Che, and F.-M. Siu Curr. Opin. Chem. Biol. 14 2010 255
38. B.T. Benedetti, E.J. Peterson, P. Kabolizadeh, A. Martinez, R. Kipping, and N.P. Farrell Mol. Pharm. 8 2011 940
39. K. Becker, C. Herold-Mende, J.J. Park, G. Lowe, and R.H. Schirmer J. Med. Chem. 44 2001 2784
40. Y.-C. Lo, T.-P. Ko, W.-C. Su, T.-L. Su, and A.H.J. Wang J. Inorg. Biochem. 103 2009 1082
41. F. Arnesano, A. Boccarelli, D. Cornacchia, F. Nushi, R. Sasanelli, M. Coluccia, and G. Natile J. Med. Chem. 52 2009 7847