Cucurbit[n]urils as excipients in pharmaceutical dosage forms

Supramolecular Chemistry

Volumn 28, Issue 9-10, 2016, Pages 849-856

  Wheate, Nial J ^a   Limantoro, Christina ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Cucurbituril; dosage form; drug delivery; formulation; pharmaceutics

Indexed keywords

EID: 84965082424     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610278.2016.1178746     Document Type: Article

References (41)

1. K.I.Assaf, ; W.M.Nau, Cucurbiturils:From Synthesis to High-affinity Binding Catalysis. Chem. Soc. Rev. 2014, 44, 394–418.
2. D.H.Macartney, Encapsulation of Drug Molecules by Cucurbiturils:Effects on their Chemical Properties in Aqueous Solution. Isr. J. Chem. 2011, 51, 600–615.10.1002/ijch.201100040
3. M.A.Gamal-Eldin, ; D.H.Macartney, Selective Molecular Recognition of Methlyated Lysines and Arginines By Cucurbit[6]urils And Cucurbit[7]uril In Aqueous Solution. Org. Biomol. Chem. 2013, 11, 488–495.10.1039/C2OB27007B
4. T.Minami, ; N.A.Esipenko, ; A.Akdeniz, ; B.Zhang, ; L.Isaacs, ; P.Anzenbacher, Jr. Multianalyte Sensing of Addictive Over-the-counter (OTC) Drugs. J. Am. Chem. Soc. 2013, 135, 15238–15243.10.1021/ja407722a
5. W.-J.Ma, ; J.-M.Chen, ; L.Jiang, ; J.Yao, ; T.-B.Lu, The Delivery of Triamterene by Cucurbit[7]uril:Synthesis, Structures and Pharmacokinetics Study. Mol. Pharm. 2013, 10, 4698–4705.10.1021/mp400529m
6. F.J.McInnes, ; N.G.Anthony, ; A.R.Kennedy, ; N.J.Wheate, 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, 765–773.10.1039/b918372h
7. Y.Zhao, ; D.P.Buck, ; D.L.Morris, ; M.H.Pourgholami, ; A.I.Day, ; J.G.Collins, Solubilisation and Cytotoxicity of Albendazole Encapsulated in Cucurbit[n]uril. Org. Biomol. Chem. 2008, 6, 4509–4515.10.1039/b813759e
8. Y.J.Jeon, ; S.-Y.Kim, ; Y.H.Ho Ko, ; S.Sakamoto, ; K.Yamaguchi, ; K.Kim, Org. Biomol. Chem. Novel Molecular Drug Carrier:Encapsulation of Oxaliplatin in Cucurbit[7]uril and its Effects on Stability and Reactivity of the Drug. 2005, 3 (11), 2122–2125.10.1039/b504487a
9. H.Chen, ; J.Y.W.Chan, ; S.Li, Shengke; J.Liu, ; I.W.Wyman, ; S.M.Y.Lee, ; D.H.Macartney, ; R.Wang, In Vivo Reversal of General Anesthesia by Cucurbit[7]uril with Zebra Fish Models. RSC Adv. 2015, 5, 63745–63752.10.1039/C5RA09406B
10. J.A.Plumb, ; B.Venugopal, ; R.Oun, ; N.Gomez-Roman, ; Y.Kawazoe, ; N.S.Venkataramanan, ; N.J.Wheate, Cucurbit[7]uril Encapsulated Cisplatin Overcomes Cisplatin Resistance Via a Pharmacokinetic Effect. Metallomics 2012, 4, 561–567.10.1039/c2mt20054f
11. N.Saleh, N.i.; M.A.Meetani, ; L.Al-Kaabi, ; I.Ghosh, ; W.M.Nau, Effect of Cucurbit[n]urils on Tropicamide and Potential Application in Ocular Drug Delivery. Supramol. Chem. 2011, 23 (9), 654–661.
12. Y.Huang, ; Q.-H.Hu, ; G.-X.Song, ; Z.Tao, ; S.-F.Xue, ; Q.-J.Zhu, ; Q.-D.Zhou, ; G.Wei, Cucurbit[7,8]urils Binding to Gefitinib and the Effect of Complex Formation on the Solubility and Dissolution Rate of the Drug. RSC Adv. 2014, 4, 3348–3354.10.1039/C3RA45017A
13. E.A.Appel, ; M.J.Rowland, ; X.J.Loh, ; R.M.Heywood, Enhanced Stability and Activity of Temozolomide in Primary Glioblastoma Multiforme cells with Cucurbit[n]uril. Chem. Commun. 2012, 48, 9843–9845.10.1039/c2cc35131e
14. C.P.Carvalho, ; V.D.Uzunova, ; J.P.Da Silva, ; W.M.Nau, ; U.Pischel, A Photoinduced pH JUMP Applied to Drug Release from Cucurbit[7]uril. Chem. Commun. 2011, 47, 8793–8795.10.1039/c1cc12954f
15. 129Xe NMR Contrast Agent. Chem. Commun. 2015, 51, 8982–8985.10.1039/C5CC01826A
16. G.Hettiarachchi, ; D.Hguyen, ; J.Wu, ; D.Lucas, ; D.Ma, ; L.Isaacs, ; V.Briken, Toxicology and Drug Delivery by Cucurbit[n]uril Type Molecular Containers. PLOS One 2010, 5 (5), e105014.
17. V.D.Uzunova, ; C.Cullinane, ; K.Brix, ; W.M.Nau, ; A.I.Day, Toxicity of Cucurbit[7]uril and Cucurbit[8]uril:An Exploratory in vitro and in vivo Study. Org. Biomol. Chem. 2010, 8, 2037–2042.10.1039/b925555a
18. R.Oun, ; R.S.Floriano, ; L.Isaacs, ; E.G.Rowan, ; N.J.Wheate, The ex Vivo Neurotoxic, Myotoxic and Cardiotoxic Activity of Cucurbituril-based Macrocyclic Drug Delivery Vehicles. Toxicol. Res. 2014, 3, 447–455.10.1039/C4TX00082J
19. H.Chen, ; J.Y.W.Chan, ; X.Yang, ; I.W.Wyman, ; D.Bardelang, ; D.H.Macartney, ; S.M.Y.Lee, ; R.Wang, Developmental and Organ-specific Toxicity of Cucurbit[7]uril:In vivo Study on Zebrafish Models. RSC Adv. 2015, 5, 30067–30074.10.1039/C5RA04335B
20. X.Miao, ; Y.Li, ; I.W.Wyman, ; S.M.Y.Lee, ; D.H.Macartney, ; Y.Zheng, ; R.Wang, Enhanced in vitro and in vivo Uptake of a Hydrophobic Model Drug Coumarin-6 in the Presence of Cucurbit[7]uril. Med. Chem. Commun. 2015, 6, 1370–1374.10.1039/C5MD00189G
21. L.I.Zon, ; R.T.Peterson, In vivo Drug Discovery in the Zebrafish. Nat. Rev. Drug Dis. 2005, 4, 35–44.10.1038/nrd1606
22. J.Lagona, ; P.Mukhopadhyay, ; S.Chakrabarti, ; L.Isaacs, The Cucurbit[n]uril Family Angew. Chem. Int. Ed. 2005, 44, 4844–4870.10.1002/(ISSN)1521-3773
23. S.Walker, ; R.Oun, ; F.J.McInnes, ; N.J.Wheate, The Potential of Cucurbiturils in Drug Delivery. Isr. J. Chem. 2011, 51 (5–6), 616–624.10.1002/ijch.201100033
24. J.J.Chu, ; M.G.Apps, ; N.J.Wheate, Chemical Factors Affecting Cucurbit[n]uril Formulation into Ocular Dosage Forms:Excipient Binding, Solubility, Corneal Permeability and Antibiotic Encapsulation. Supramol. Chem. 2014, 26 (9), 648–656.10.1080/10610278.2014.926361
25. A.L.Koner, ; I.Ghosh, ; N.Saleh, N.i.; W.M.Nau,. Supramolecular Encapsulation of Benzimidazole-Derived Drugs by Cucurbit[7]uril. Can. J. Chem. 2011, 89 (2), 139–147.10.1139/V10-079
26. S.Ahuja, ; K.Alsante, Eds.; Handbook of isolation and characterization of impurities in pharmaceuticals; 1st ed.; Academic Press, 2003.
27. A.Day, ; A.P.Arnold, ; R.J.Blanch, ; B.Snushall, Controlling Factors in the Synthesis of Cucurbituril and its Homologues. J. Org. Chem. 2001, 66 (24), 8094–8100.10.1021/jo015897c
28. D.Bardelang, ; K.A.Udachin, ; R.Anedda, ; I.Moudrakovski, ; D.M.Leek, ; J.A.Ripmeester, ; C.I.Ratcliffe, 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, 4927–4929.
29. N.Chieng, ; T.Rades, ; J.Aaltonen, An Overview of Recent Studies on the Analysis of Pharmaceutical Polymorphs. J. Pharm. Biomed. Anal. 2011, 55, 618–644.10.1016/j.jpba.2010.12.020
30. T.V.Sachin, ; M.N.Deodhar, ; V.Prakya, Advances in Analytical Techniques used in Predicting Drug-excipient Interactions. Int. J. Pharm. Tech. 2014, 6 (1), 6388–6417.
31. M.Seif, ; M.L.Impelido, ; M.G.Apps, ; N.J.Wheate, Topical Cream-Based Dosage Forms of the Macrocyclic Drug Delivery Vehicle Cucurbit[6]uril. PLoS ONE 2014, 9 (1), e85361.10.1371/journal.pone.0085361
32. S.Walker, ; R.Kaur, ; F.J.McInnes, ; N.J.Wheate, Synthesis, Processing and Solid State Excipient Interactions of Cucurbit[6]uril and its Formulation into Tablets for Oral Drug Delivery. Mol. Pharm. 2010, 7 (6), 2166–2172.10.1021/mp100191b
33. R.C.Rowe, ; P.J.Sheskey, ; W.G.Cook, ; M.E.Fenton, Handbook of pharmaceutical excipients7th ed.; Pharmaceutical Press:London, 2012.
34. L.N.Sansam, Eds.; Australian Pharmaceutical Formulary and Handbook:The Everyday Guide to Pharmacy Practice; 22nd ed.; Pharmaceutical Society of Australia:Canberra, 2012.
35. E.M.Ahmed, Hydrogel:Preparation, Characterization, and Applications:A Review. J. Adv. Res. 2015, 6 (2), 105–121.10.1016/j.jare.2013.07.006
36. D.Ding, ; Z.Zhu, ; R.Li, ; X.Li, ; W.Wu, ; X.Jiang, ; B.Liu, Nanospheres-incorporated Implantable Hydrogel as a Trans-tissue Drug Delivery System. ACS Nano. 2011, 5 (4), 2520–2534.10.1021/nn102138u
37. L.Yu, ; J.Ding, Injectable Hydrogels as Unique Biomedical Materials. Chem. Soc. Rev. 2008, 37 (8), 1473–1481.10.1039/b713009k
38. R.Oun, ; J.A.Plumb, ; N.J.Wheate, A Cisplatin Slow-release Hydrogel Drug Delivery System Based on a Formulation of the Macrocycle Cucurbit[7]uril, Gelatin and Polyvinyl Alcohol. J. Inorg. Biochem. 2014, 134, 100–105.10.1016/j.jinorgbio.2014.02.004
39. F.J.McInnes, ; P.Thapa, ; A.J.Baillie, ; P.G.Welling, ; D.G.Watson, ; I.Gibson, ; A.Nolan, ; H.N.E.Stevens, In vivo Evaluation of Nicotine Lyophilised Nasal Insert in Sheep. Int. J. Pharm. 2005, 304 (1–2), 72–82.10.1016/j.ijpharm.2005.07.025
40. F.J.McInnes, ; B.O’Mahony, ; B.Lindsay, ; J.Band, ; C.G.Wilson, ; L.A.Hodges, ; H.N.E.Stevens, Nasal Residence of Insulin Containing Lyophilised Nasal Insert Formulations, Using Gamma Scintigraphy Eur. J. Pharm. Sci. 2007, 31 (1), 25–31.10.1016/j.ejps.2007.02.002
41. S.Walker, Novel methods to deliver platinum(II) chemotherapeutics to the nose. Ph.D. Thesis, University of Strathclyde:Glasgow, Scotland, 2013.