Theoretical insights into the formation, structure, and electronic properties of anticancer oxaliplatin drug and cucurbit[n]urils n = 5 to 8

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 66, Issue 3, 2010, Pages 213-218

  Suvitha, Ambigapathy ^a   Venkataramanan, Natarajan Sathiyamoorthy ^a   Mizuseki, Hiroshi ^a   Kawazoe, Yoshiyuki ^a   Ohuchi, Nobiaki ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Cancer drugs; Cucurbit n urils; DFT; Inclusion complex; Oxaliplatin

Indexed keywords

EID: 77952288047     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9601-2     Document Type: Review

References (30)

1. Sherman, S. E., Lippard, S. J.: Structural aspects of platinum anticancer drug interactions with DNA. Chem. Rev. 87, 1153-1181 (1987).
2. Lippert, B. (ed.): Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug. John Wiley and Sons Ltd, New York (1999).
3. Safra, T., Molho, R. B., Grisaru, D., Spigel, S., Geva, R., Matcejevsk, D., Inbar, M., Menzcer, J., Levy, T.: A phase-II study evaluating safety and efficacy with weekly paclitaxel and carboplatin as a primary treatment for patients with advanced epithelial ovarian cancer (EOC). J. Clin. Oncol. 24, 5077 (2006).
4. Chabner, B. A., Longo, D. L. (eds.): Cancer Chemotherapy and Biotherapy, Principles and Practice. Lippincott Williams and Wilkins (2006).
5. Ozols, R. F.: Ovarian cancer: is dose intensity dead. J. Clin. Oncol. 25, 4157-4158 (2007).
6. Li, X., Jasai, B. R. (eds.): Design of controlled release drug delivery systems. The Mc Graw-Hill companies (2006).
7. Krause-Heuer, A. M., Grant, M. P., Orkey, N., Aldrich-Wright, J. R.: Drug delivery devices and targeting agents for platinum (II) anticancer complexes. Aust. J. Chem. 61, 675-681 (2008).
8. Kemp, S., Wheate, N. J., Wang, S., Collins, J. G., Ralph, S. F., Day, A. I., Higgins, V. J., Aldrich-Wright, J. R.: Encapsulation of platinum(II)-based DNA intercalators within cucurbit[6, 7, 8]urils. J. Biol. Inorg. Chem. 12, 969-979 (2007).
9. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., Isaacs, L.: The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844-4870 (2005).
10. Tian, Z. C., Ni, X. L., Xiao, X., Wu, F., Zhang, Y. Q., Zhu, Q. J., Xue, S. F., Tao, Z.: Interaction models of three alkyl substituted cucurbit[6]uril with a hydrochloride salt of 4, 4′-dipyridyl guest. J. Mol. Struct. 888, 48-54 (2008).
11. Wang, R., Yuan, L., Ihmels, H., Macartney, D. H.: Cucurbit[8]uril/cucurbit[7]uril controlled off/on fluorescence of the acridizinium and 9-aminoacridizinium cations in aqueous solution. Chem.-A Eur. J. 13, 6468-6473 (2007).
12. Li, L. S., Ge, Y. H., Huang, Z. H., Li, Y. P.: Study on the molecular recognition of perhydroxycucurbit[6]uril with methyl orange by spectroscopic methods. Specrosc. Spectr. Anal. 27, 1393-1397 (2007).
13. Wyman, I. W., Macartney, D. H.: Cucurbit[7]uril host-guest complexes with small polar organic guests in aqueous solution. Org. Biomol. Chem. 6, 1796-1801 (2008).
14. Wheate, N. J., Kumar, P. G. A., Torres, A. M., Aldrich-Wright, J. R., Price, W. S.: Examination of cucurbit[7]uril and its host-guest complexes by diffusion nuclear magnetic resonance. J. Phys. Chem. B. 112, 2311-2314 (2008).
15. Liu, S. M., Shukla, A. D., Gadde, S., Wagner, B. D., Kaifer, A. E., Isaacs, L.: Ternary complexes comprising cucurbit[10]uril, porphyrins and guests. Angew. Chem. Int. Ed. 47, 2657-2660 (2008).
16. Liu, J. X., Long, L. S., Huang, R. B., Zheng, L. S.: Interesting anion-inclusion behavior of cucurbit[5]uril and its lanthanide-capped molecular capsule. Inorg. Chem. 46, 10168-10173 (2007).
17. Freeman, W. A., Mock, W. L., Shih, N. Y.: Cucurbituril. J. Am. Chem. Soc. 103, 7367-7368 (1981).
18. Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K., Kim, K.: New cucurbituril homologues: synthesis, isolation, characterization, and X-ray crystal structure of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 122, 540-541 (2000).
19. Wheate, N. J.: Improving platinum(II)-based anticancer drug delivery using cucurbit[n]urils. J. Inorg. Biochem. 102, 2060-2066 (2008).
20. Jeon, Y. J., Kim, S.-Y., Ko, Y. H., Sakamoto, S., Yamaguchi, K., Kim, K.: Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug. Org. Biomol. Chem. 3, 2122-2125 (2005).
21. Marquez, C., Hudgins, R. R., Nau, W. M.: Mechanism of host-guest complexation by cucurbituril. J. Am. Chem. Soc. 126, 5806-5816 (2004).
22. Pichierri, F.: DFT study of cucurbit[n]uril, n = 5-10. J. Mol. Struct. (Theochem.) 765, 151-152 (2006).
23. Buschmann, H.-J., Wego, A., Zielesny, A., Schollmeyer, E.: Structure, electronic properties and NMR-shielding of cucurbit[n]urils. J. Incl. Phenom. Macrocycl. Chem. 54, 85-88 (2006).
24. Oh, K. S., Yoon, J., Kim, K. S.: Structural stabilities and self-assembly of cucurbit[n]uril (n = 4-7) and decamethylcucurbit[n]uril (n = 4-6): a theoretical study. J. Phys. Chem. B. 105, 9726-9731 (2001).
25. Bakovets, V. V., Masliy, A. N., Kuznetsov, A. M.: Formation thermodynamics of cucurbit[6]uril macrocycle molecules: a theory study. J. Phys. Chem. B. 112, 12010-12013 (2008).
26. Pinjari, R. V., Gejj, S. P.: Electronic, structure, molecular electrostatic potential and NMR chemical shifts in cucurbit[n]urils (n = 5-8), ferrocene and their complexes. J. Phys. Chem. A. 112, 12679-12686 (2008).
27. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A. Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A.: Gaussian 03, revision D. 01. Gaussian, Inc., Wallingford, CT (2004).
28. Reed, A. L., Curtiss, L. A., Weinhold, F.: Intermolecular interactions from a natural bond orbital, donor-acceptor view point. Chem. Rev. 88, 899-926 (1988).
29. Bushchmann, H.-J., Wego, A., Zielesny, A., Schollmeyer, E.: Structure, stability, electronic properties and NMR-shielding of the cucurbit[6]uril-spermine-complex. J. Incl. Phenom. Macrocycl. Chem. 54, 241-246 (2006).
30. Tyagi, P., Gahlot, P., Kakkar, R.: Structural aspects of the anti-cancer drug oxaliplatin: a combined theoretical and experimental study. Polyhedron 27, 3567-3574 (2008).