Host-guest complexes of cucurbit[7]uril with albendazole in solid state: Thermal and structural properties

Journal of Thermal Analysis and Calorimetry

Volumn 111, Issue 1, 2013, Pages 385-392

  Saleh, Na'Il ^a   Khaleel, Abbas ^a   Al Dmour, Hmoud ^b   Al Hindawi, Bassam ^a   Yakushenko, Elena ^c  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b MUTAH UNIVERSITY   (Jordan)

^c INSTITUTE OF CLINICAL IMMUNOLOGY   (Russian Federation)

Author keywords

Albendazole; Amorphous; Cucurbit 7 uril; Pharmaceutical solids; Thermal stability

Indexed keywords

ADSORPTION DESORPTION ISOTHERMS; ALBENDAZOLE; CUCURBIT[7]URIL; FOURIER; HOST GUEST COMPLEXES; INCLUSION COMPLEX; NMR PEAKS; SURFACE AREA; XRD;

AMORPHOUS MATERIALS; DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMOANALYSIS; THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS; X RAY POWDER DIFFRACTION;

LOW TEMPERATURE DRYING;

EID: 84872496389     PISSN: 13886150     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10973-012-2376-5     Document Type: Article

References (46)

1. Chieng N, Rades T, Aaltonen J. An overview of recent studies on the analysis of pharmaceutical polymorphs. J Pharm Biom Anal. 2011;55(4):618-44.
2. Brittain HG. Polymorphism in pharmaceutical solids. 2nd ed. New York: Informa Healthcare; 2009.
3. Yoshioka S, Stella VJ. Stability of drugs and dosage forms. Hingham: Kluwer Academic Publisher; 2000.
4. Freeman WA, Mock WL, Shih NY. Cucurbituril. J Am Chem Soc. 1981;103(24):7367-8.
5. Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. The cucurbit[n]uril family. Angew Chem Int Ed. 2005;44(31):4844-70.
6. Masson E, Ling X, Joseph R, Kyeremeh-Mensah L, Lu X. Cucurbituril chemistry: a tale of supramolecular success. RSC Adv 2012. doi: 10.1039/C1RA00768H.
7. Walker S, Oun R, McInnes FJ, Wheate NJ. The potential of cucurbit[n]urils in drug delivery. Isr J Chem. 2011;51(5-6):616-24.
8. a shifts to enhance the bioavailability of drugs. Adv Drug Deliv Rev. 2012. doi: 10.1016/j.addr.2012.01.015.
9. Shchepotina E, Pashkina E, Yakushenko E, Kozlov V. Cucurbiturils as containers for medicinal compounds. Nanotechnol Russ. 2011;6(11):773-9.
10. Moghaddam S, Yang C, Rekharsky M, Ko YH, Kim K, Inoue Y, et al. New ultrahigh affinity host-guest complexes of cucurbit[7]uril with bicyclo[2.2.2]octane and adamantane guests: thermodynamic analysis and evaluation of M2 affinity calculations. J Am Chem Soc. 2011;133(10):3570-81.
11. a shifts: drug-delivery applications tailored for cucurbiturils. Angew Chem Int Ed. 2008;47(29):5398-401.
12. Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K. Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. Acc Chem Res. 2003;36(8):621-30.
13. Kim J, Jung IS, Kim SY, Lee E, Kang JK, Sakamoto S, et al. New cucurbituril homologues: syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J Am Chem Soc. 2000;122(3):540-1.
14. Saleh N, Meetani M, Al-Kaabi L, Ghosh I, Nau WM. Effects of cucurbiturils on tropicamide and potential applications in ocular drug delivery. Supramol Chem. 2011;23(9):654-61.
15. Koner AL, Ghosh I, Saleh N, Nau WM. Supramolecular encapsulation of benzimidazole-derived drugs by cucurbit[7]uril. Can J Chem. 2011;89(2):139-47.
16. Uzunova VD, Cullinane C, Brix K, Nau WM, Day AI. Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org Biomol Chem. 2010;8(9):2037-42.
17. Jeon YJ, Kim SY, Ko YH, 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. 2005;3(11):2122-5.
18. Hettiarachchi G, Nguyen D, Wu J, Lucas D, Ma D, Isaacs L, et al. Toxicology and drug delivery by cucurbit[n]uril type molecular containers. PLoS ONE. 2010;5(5):e10514.
19. Bardelang D, Udachin KA, Leek DM, Margeson JC, Chan G, Ratcliffe CI, et al. Cucurbit[n]urils (n = 5-8): a comprehensive solid state study. Cryst Growth Des. 2011;11(12):5598-614.
20. Isaacs L. The mechanism of cucurbituril formation. Isr J Chem. 2011;51(5-6):578-91.
21. Kim E, Kim D, Jung H, Lee J, Paul S, Selvapalam N, et al. Facile, template-free synthesis of stimuli-responsive polymer nanocapsules for targeted drug delivery. Angew Chem Int Ed. 2010;49(26):4405-8.
22. Horton J. Albendazole: a review of anthelmintic efficacy and safety in humans. Parasitology. 2000;121:S113-32.
23. Hao D, Rizzo JD, Stringer S, Moore RV, Marty J, Dexter DL, et al. Preclinical antitumor activity and pharmacokinetics of methyl-2- benzimidazolecarbamate (FB642). Invest New Drugs. 2002;20(3):261-70.
24. Pourgholami MH, Szwajcer M, Chin M, Liauw W, Seef J, Galettis P, et al. Phase I clinical trial to determine maximum tolerated dose of oral albendazole in patients with advanced cancer. Cancer Chemother Pharmacol. 2010;65(3):597-605.
25. Zhao YJ, Buck DP, Morris DL, Pourgholami MH, Day AI, Collins JG. Solubilisation and cytotoxicity of albendazole encapsulated in cucurbit[n]uril. Org Biomol Chem. 2008;6(24):4509-15.
26. Zhao YJ, Pourgholami MH, Morris DL, Collins JG, Day AI. Enhanced cytotoxicity of benzimidazole carbamate derivatives and solubilisation by encapsulation in cucurbit[n]uril. Org Biomol Chem. 2010;8(14):3328-37.
27. Pranzo MB, Cruickshank D, Coruzzi M, Caira MR, Bettini R. Enantiotropically related albendazole polymorphs. J Pharm Sci. 2010;99(9):3731-42.
28. Castillo JA, Palomo-Canales J, Garcia JJ, Lastres JL, Bolas F, Torrado JJ. Preparation and characterization of albendazole β-cyclodextrin complexes. Drug Dev Ind Pharm. 1999;25(12):1241-8.
29. Moriwaki C, Costa GL, Ferracini CN, de Moraes FF, Zanin GM, Pineda EAG, et al. Enhancement of solubility of albendazole by complexation with β-cyclodextrin. Braz J Chem Eng. 2008;25(2):255-67.
30. Wheate NJ, Vora V, Anthony NG, McInnes FJ. Host-guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril. J Incl Phenom Macro Chem. 2010;68(3-4):359-67.
31. McInnes FJ, Anthony NG, Kennedy AR, Wheate NJ. Solid state stabilisation of the orally delivered drugs atenolol, glibenclamide, memantine and paracetamol through their complexation with cucurbit[7]uril. Org Biomol Chem. 2010;8(4):765-73.
32. Kennedy AR, Florence AJ, McInnes FJ, Wheate NJ. 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. 2009;37:7695-700.
33. Renu C, Poonam A, Sushma G, Singh JD. Complexation of nevirapine with β-cyclodextrins in the presence and absence of Tween 80: characterization, thermodynamic parameters, and permeability flux. J Therm Anal Calorim. 2011;105(3):1049-59.
34. Soares-Sobrinho JL, Soares MFD, Rolim-Neto PJ, Torres-Labandeira JJ. Physicochemical study of solid-state benznidazole-cyclodextrin complexes. J Therm Anal Calorim. 2011;106(2):319-25.
35. Giron D. Applications of thermal analysis and coupled techniques in pharmaceutical industry. J Therm Anal Calorim. 2002;68(2):335-57.
36. Gad SC. Pharmaceutical manufacturing handbook: production and processes. Wiley; 2008
37. Brunauer S, Emmett PH, Teller E. Adsorption of gases in multimolecular layers. J Am Chem Soc. 1938;60:309-19.
38. Lim S, Kim H, Selvapalam N, Kim KJ, Cho SJ, Seo G, et al. Cucurbit[6]uril: Organic molecular porous material with permanent porosity, exceptional stability, and acetylene sorption properties. Angew Chem Int Ed. 2008;47(18):3352-5.
39. Germain P, Letoffe JM, Merlin MP, Buschmann HJ. Thermal behaviour of hydrated and anhydrous cucurbituril - A DSC, TG and calorimetric study in temperature range from 100 to 800 K. Thermochim Acta. 1998;315(2):87-92.
40. Bardelang D, Udachin KA, Leek DM, Ripmeester JA. Highly symmetric columnar channels in metal-free cucurbit[n]uril hydrate crystals (n = 6, 8). CrystEngComm. 2007;9(11):973-5.
41. Bardelang D, Udachin KA, Anedda R, Moudrakovski I, Leek DM, Ripmeester JA, et al. Single-crystal to single-crystal phase transition of cucurbit[5]uril hydrochloride hydrates: large water-filled channels transforming to layers of unusual stability. Chem Commun. 2008;40:4927-9.
42. Nau WM, Florea M, Assaf KI. Deep inside cucurbiturils: physical properties and volume of their inner cavity determine the hydrophobic driving forces for host-guest complexation. Isr J Chem. 2011;51:559.
43. Alanazi FK, El-Badry M, Mahtous OA, Al-Sarra IA. Improvement of albendazole dissolution by preparing microparticles using spray-drying technique. Allemand. 2007;75(2):63-79.
44. Hwang I, Jeon WS, Kim HJ, Kim D, Kim H, Selvapalam N, et al. Cucurbit[7]uril: a simple macrocyclic, pH-triggered hydrogelator exhibiting guest-induced stimuli-responsive behavior. Angew Chem Int Ed. 2007;46(1-2):210-3.
45. Huang XL, Tan YB, Zhou QF, Wang YX. Fabrication of cucurbit[6]uril mediated alginate physical hydrogel beads and their application as a drug carriers. E Polym. 2008;095.
46. Barbato F, La Rotonda MI, Miro A, Morrica P, Quaglia F. Inclusion complexation of carbaryl and β-cyclodextrin in solution and in the solid state. J Incl Phenom Macro Chem. 2000;38(1-4):423-33.