Host-guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 68, Issue 3-4, 2010, Pages 359-367

  Wheate, Nial J ^a   Vora, Virendra ^a   Anthony, Nahoum G ^a   McInnes, Fiona J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Cucurbituril; Isoniazid; Pyrazinamide; Tuberculosis

Indexed keywords

EID: 78649446693     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9795-3     Document Type: Article

References (72)

1. Cole, S. T., Eisenach, K. D., McMurray, D. N., Jacobs, W. R. Jr. (eds.): Tuberculosis and the tubercle bacillus. ASM Press, Washington (2005).
2. American thoracic society/Centers for disease control and prevention/Infectious diseases society of America: treatment of tuberculosis. Am. J. Respir. Crit. Care Med. 167, 603-662 (2003).
3. Mugnaini, C., Pasquini, S., Corelli, F.: The 4-quinolone-3-carboxylic acid motif as a multivalent scaffold in medicinal chemistry. Curr. Med. Chem. 16, 1746-1767 (2009).
4. Manetti, F., Magnani, M., Castagnolo, D., Passalacqua, L., Botta, M., Corelli, F., Saddi, M., Deidda, D., De Logu, A.: Ligand-based virtual screening, parallel solution-phase and microwave-assisted synthesis as tools to identify and synthesize new inhibitors of Mycobacterium tuberculosis. ChemMedChem 1, 973-989 (2006).
5. Chhabria, M., Jani, M. H.: Design, synthesis and antimycobacterial activity of some novel imidazo[1, 2-c]pyrimidines. Eur. J. Med. Chem. 44, 3837-3844 (2009).
6. Chhabria, M., Jani, M., Patel, S.: New frontiers in the therapy of tuberculosis: fighting with the global menace. Mini. Rev. Med. Chem. 9, 401-430 (2009).
7. Rogoza, L. N., Salakhutdinov, N. F., Tolstikov, G. A.: Natural and synthetic compounds with an antimycobacterial activity. Mini. Rev. Org. Chem. 6, 135-151 (2009).
8. Mendez, M. P., Landon, M. E., McCloud, M. K., Davidson, P., Christensen, P. J.: Co-infection with pansensitive and multidrug-resistant strains of Mycobacterium tuberculosis. Emerg. Infect. Dis. 15, 578-580 (2009).
9. Mathema, B., Kurepina, N. E., Bifani, P. J., Kreiswirth, B. N.: Molecular epidemiology of tuberculosis: current insights. Clin. Microbiol. Rev. 19, 658-685 (2006).
10. Isaacs, L.: Cucurbit[n]urils: from mechanism to structure and function. Chem. Commun. 619-629 (2009).
11. Kim, K., Selvapalam, N., Ko, Y. H., Park, K. M., Kim, D., Kim, J.: Functionalized cucurbiturils and their applications. Chem. Soc. Rev. 36, 267-279 (2007).
12. Uzunova, V. D., Cullinane, C., Brix, K., Nau, W. M., Day, A. I.: Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org. Biomol. Chem. 8, 2037-2042 (2010).
13. Walker, S., Kaur, R., McInnes, F. J., Wheate, N. J.: Oral drug formulations. Great Britian Patent Application No. 0906003. 9, April 2009, 24 pp.
14. McInnes, F. J., Anthony, N. G., Kennedy, A. R., Wheate, N. J.: Solid state stabilisation of the orally delivered drugs atenolol, glibenclamide, memantine and paracetamol through their complexation with cucurbit[7]uril. Org. Biomol. Chem. 8, 765-773 (2010).
15. Kennedy, A. R., Florence, A. F., McInnes, F. J., Wheate, N. J.: A chemical preformulation study of a host-guest complex of cucurbit[7]uril and a multinuclear platinum agent for enhanced anticancer drug delivery. Dalton Trans. 7695-7700 (2009).
16. Wheate, N. J.: Improving platinum(II)-based anticancer drug delivery using cucurbit[n]urils. J. Inorg. Biochem. 102, 2060-2066 (2008).
17. Wheate, N. J., Taleb, R. I., Krause-Heuer, A. M., Cook, R. L., Wang, S., Higgins, V. J., Aldrich-Wright, J. R.: Novel platinum(II)-based anticancer complexes and molecular hosts as their drug delivery vehicles. Dalton Trans. 5055-5064 (2007).
18. 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).
19. Kemp, S., Wheate, N. J., Stootman, F. H., Aldrich-Wright, J. R.: The host-guest chemistry of proflavine with cucurbit[6, 7, 8]urils. Supramol. Chem. 19, 475-484 (2007).
20. Wheate, N. J., Buck, D. P., Day, A. I., Collins, J. G.: Cucurbit[n]uril binding of platinum anticancer complexes. Dalton Trans. 451-458 (2006).
21. Wheate, N. J., Day, A. I., Blanch, R. J., Arnold, A. P., Cullinane, C., Collins, J. G.: Multi-nuclear platinum complexes encapsulated in cucurbit[n]uril as an approach to reduce toxicity in cancer treatment. Chem. Commun. 1424-1425 (2004).
22. Zhao, Y., Bali, M. S., Cullinane, C., Day, A. I., Collins, J. G.: Synthesis, cytotoxicity and cucurbituril binding of triamine linked dinuclear platinum complexes. Dalton Trans. 5190-5198 (2009).
23. 2 (M = Mo, Ti) with cucurbit[n]urils. Dalton Trans. 2328-2334 (2008).
24. 2+ and the effect on the reaction with cysteine. Dalton Trans. 5337-5344 (2006).
25. Wang, R., Bardelang, D., Waite, M., Udachin, K. A., Leek, D. M., Yu, K., Ratcliffe, C. I., Ripmesster, J. A.: Inclusion complexes of coumarin in cucurbiturils. Org. Biomol. Chem. 7, 2435-2439 (2009).
26. 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).
27. Choi, J., Kim, J., Kim, K., Yang, S.-T., Kim, J.-I., Jon, S.: A rationally designed macrocyclic cavitand that kills bacteria with high efficacy and good selectivity. Chem. Commun. 1151-1153 (2007).
28. Saleh, N. I., Koner, A. L., Nau, W. M.: Activation and stabilization of drugs by supramolecular pKa shifts: drug-delivery applications tailored for cucurbiturils. Angew. Chem. Int. Ed. 47, 5398-5401 (2008).
29. Lim, Y.-B., Kim, T., Lee, J. W., Kim, S.-M., Kim, H.-J., Kim, K., Park, J.-S.: Self-assembled ternary complex of cationic dendrimer, cucurbituril, and DNA: noncovalent strategy in developing a gene delivery carrier. Bioconjug. Chem. 13, 1181-1185 (2002).
30. Wang, R., Wyman, I. W., Wang, S., Macartney, D. H.: Encapsulation of a b-carboline in cucurbit[7]uril. J. Incl. Phenom. Macrocycl. Chem. 64, 233-237 (2009).
31. Park, K. M., Suh, K., Jung, H., Lee, D.-W., Ahn, Y., Kim, J., Baek, K., Kim, K.: Cucurbituril-based nanoparticles: a new efficient vehicle for targeted intracellular delivery of hydrophobic drugs. Chem. Commun. 71-73 (2009).
32. Angelos, S., Yang, Y.-W., Patel, K., Stoddart, J. F., Zink, J. I.: pH-responsive supramolecular nanovalves based on cucurbit[6]uril pseudorotaxanes. Angew. Chem. Int. Ed. 47, 2222-2226 (2008).
33. 2-receptor antagonist ranitine. Org. Biomol. Chem. 6, 1955-1960 (2008).
34. Lee, H. K., Park, K. M., Jeon, Y. J., Kim, D., Oh, D. H., Kim, H. S., Park, C. K., Kim, K.: Vesicle formed by amphiphilc cucurbit[6]uril: versatile, noncovalent modification of the vesicle surface, and multivalent binding of sugar-decorated vesicles to lectin. J. Am. Chem. Soc. 127, 5006-5007 (2005).
35. Kim, J., Ahn, Y., Park, K. M., Kim, Y., Ko, Y. H., Oh, D. H., Kim, K.: Carbohydrate wheels: cucurbituril-based carbohydrate clusters. Angew. Chem. Int. Ed. 46, 7393-7395 (2007).
36. Zhao, Y., Buck, D. P., Morris, D. L., Pourgholami, M. H., Day, A. I., Collins, J. G.: Solubilisation and cytotoxicity of albendazole encapsulated in cucurbit[n]uril. Org. Biomol. Chem. 6, 4509-4515 (2008).
37. Huang, X., Tan, Y., Zhou, Q., Wang, Y.: Fabrication of cucurbit[6]uril mediated alginate physical hydrogel beads and their application as drug carriers. e-polymers 95, 1-11 (2008).
38. Angelos, S., Khashab, N. M., Yang, Y.-W., Trabolsi, A., Khatib, H. A., Stoddart, J. F., Zink, J. I.: pH clock-operated mechanized nanoparticles. J. Am. Chem. Soc. 131, 12912-12914 (2009).
39. 129Xe NMR-based biosensors. Chem. Commun. 2756-2758 (2008).
40. Rekharsky, M. V., Yamamura, H., Ko, Y. H., Selvapalam, N., Kim, K., Inoue, Y.: Sequence recognition and self-sorting of a dipeptide by cucurbit[6]uril and cucurbit[7]uril. Chem. Commun. 2236-2238 (2008).
41. Rankin, M. A., Wagner, B. D.: Fluorescence enhancement of curcumin upon inclusion into cucurbituril. Supramol. Chem. 16, 513-519 (2004).
42. Li, C., Li, J., Jia, X.: Selective binding and highly sensitive fluorescent sensor of palmatine and dehydrocorydaline alkaloids by cucurbit[7]uril. Org. Biomol. Chem. 7, 2699-2703 (2009).
43. Wang, R., Yuan, L., Macartney, D. H.: A green to blue fluorescence switch of protonated 2-aminoanthracene upon inclusion in cucurbit[7]uril. Chem. Commun. 5867-5869 (2005).
44. Bailey, D. M., Hennig, A., Uzunova, V. D., Nau, W. M.: Supramolecular tandem enzyme assays for multiparameter sensor arrays and enantiomeric excess determination of amino acids. Chem.-Eur J. 14, 6069-6077 (2008).
45. Hennig, A., Bakirci, H., Nau, W. M.: Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes. Nat. Methods 4, 629-632 (2007).
46. Nau, W. M., Ghale, G., Hennig, A., Bakirci, H., Bailey, D. M.: Substrate-selective supramolecular tandem assays: monitoring enzyme inhibition of arginase and diamine oxidase by fluorescent dye displacement from calixarene and cucurbituril macrocycles. J. Am. Chem. Soc. 131, 11558-11570 (2009).
47. Huo, F.-J., Yin, C.-X., Yang, P.: The crystal structure, self-assembly, DNA-binding and cleavage studies of the [2]pseudorotaxane composed of cucurbit[6]uril. Bioorg. Med. Chem. Lett. 17, 932-936 (2007).
48. Isobe, H., Sato, S., Lee, J. W., Kim, H.-J., Kim, K., Nakamura, E.: Supramolecular modulation of action of polyamine on enzyme/DNA interactions. Chem. Commun. 1549-1551 (2005).
49. Ke, C.-F., Zhhang, H.-Y., Liu, Y., Feng, X.-Z.: Controllable DNA condensation through cucurbit[6]uril in 2D pseudopolyrotaxanes. Chem. Commun. 3374-3376 (2007).
50. Wang, R., MacGillivray, B. C., Macartney, D. H.: Stabilization of the base-off forms of vitamin B12 and coenzyme B12 by encapsulation of the a-axial 5, 6-dimethylbenzimidazole ligand with cucurbit[7]uril. Dalton Trans. 3584-3589 (2009).
51. Hennig, A., Ghale, G., Nau, W. M.: Effects of cucurbit[7]uril on enzymatic activity. Chem. Commun. 1614-1616 (2007).
52. Montes-Navajas, P., Gonzalez-Bejar, M., Scaiano, J. C., Garcia, H.: Cucurbituril complexes cross the cell membrane. Photochem. Photobiol. Sci. 8, 1743-1747 (2009).
53. Kim, S. K., Park, K. M., Singha, K., Kim, J., Ahn, Y., Kim, K., Kim, W. J.: Galatosylated cucurbituril-inclusion polyplex for hepatocyte-targeted gene delivery. Chem. Commun. 46, 692-694 (2010).
54. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., Isaacs, L.: The Cucurbit[n]uril Family. Angew. Chem. Int. Ed. 44, 4844-4870 (2005).
55. Bartulewicz, D., Bielawski, K., Bielawska, A.: Arch. Pharm. Pharm. Med. Chem. 9, 422-426 (2002).
56. Lee, M., Rhodes, A. L., Wyatt, M. D., D'Incalci, M., Forrow, S., Hartley, J. A.: In vitro cytotoxicity ofGC sequence directed alkylating agents related to distamycin. J. Med. Chem. 36, 863-870 (1993).
57. Becker, C., Dressman, J. B., Amidon, G. L., Junginger, H. E., Kopp, S., Midha, K. K., Shah, V. P., Stavchansky, S., Barends, D. M.: Biowaiver monographs for immediate release solid oral dosage forms: isoniazid. J. Pharm. Sci. 96, 522-531 (2007).
58. Becker, C., Dressman, J. B., Amidon, G. L., Junginger, H. E., Kopp, S., Midha, K. K., Shah, V. P., Stavchansky, S., Barends, D. M.: Biowaiver monographs for immediate release solid oral dosage forms: pyrazinamide. J. Pharm. Sci. 97, 3709-3720 (2008).
59. Zhou, Y., Yu, H., Zhang, L., Xu, H., Wu, L., Sun, J., Wang, L.: A new spectrofluorometric method for the determination of nicotine base on the inclusion interaction of methylene blue and cucurbit[7]uril. Microchim. Acta 164, 63-68 (2009).
60. Takaki, Y., Sasada, Y., Watanabe, T.: The crystal structure of α-pyrazinamide. Acta Cryst. 13, 693-702 (1960).
61. Rø, G., Sørum, H.: The crystal and molecular structure of δ-pyrazincarboxamide. Acta Cryst. B28, 1677-1684 (1972).
62. Tamura, C., Kuwano, H.: Crystallographic data of carboxylic acids and carboxyamides of picoline and pyrazine derivatives. Acta Cryst. 14, 693 (1961).
63. Jensen, L. H.: The crystal structure of isonicotinic acid hydrazide. J. Am. Chem. Soc. 76, 4663-4667 (1954).
64. Bhat, T. N., Singh, T. P., Vijayan, M.: Isonicotinic acid hydrazide-a reinvestigation. Acta Cryst. B30, 2921-2922 (1974).
65. Rastogi, R., Sultana, Y., Aqil, M., Kumar, S., Chuttani, K., Mishra, A. K.: Alginate microspheres of isoniazid for oral sustained drug delivery. Int. J. Pharm. 334, 71-77 (2007).
66. Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K., Kim, K.: New cucurbituril homologues: Syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 122, 540-541 (2000).
67. Bhutani, H., Singh, S., Jindal, K. C.: Drug-drug interaction studies on first-line anti-tuberculosis drugs. Pharm. Dev. Technol. 10, 517-524 (2005).
68. Brittain, H. G.: Polymorphism in Pharmaceutical Solids. Marcel Dekker Inc., New York (1999).
69. Day, A., Arnold, A. P., Blanch, R. J., Snushall, B.: Controlling factors in the synthesis of cucurbituril and its homologues. J. Org. Chem. 66, 8094-8100 (2001).
70. Maple, J. R., Hwang, M. J., Stockfisch, T. P., Dinur, U., Waldman, M., Ewig, C. S., Hagler, A. T.: Derivation of class II force fields. I. Methodology and quantum force field for the alkyl functional group and alkane molecules. J. Comput. Chem. 15, 162-182 (1994).
71. Chen, J., Brooks, C. L., Khandogin, J.: Recent advances in implicit solvent-based methods for biomolecular simulations. Curr. Opin. Struct. Biol. 18, 140-148 (2008).
72. de Oliveira, A. M., Custodio, F. B., Donnici, C. L., Montanari, C. A.: Eur. J. Med. Chem. 38, 141-155 (2003).