Comparative macrocycle binding of the anticancer drug phenanthriplatin by cucurbit[n]urils, β-cyclodextrin and para-sulfonatocalix[4]arene: a 1H NMR and molecular modelling study View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2017-01-27

AUTHORS

Natalie Kahwajy, Alireza Nematollahi, Ryung Rae Kim, W. Bret Church, Nial J. Wheate

ABSTRACT

The potential anticancer drug phenanthriplatin, [cis-(NH3)2(phenanthridine)Cl]+, forms supramolecular complexes with cucurbit[n]urils (CB[n], n = 7 or 8), β-cyclodextrin and para-sulfonatocalix[4]arene (sCX[4]) as determined by 1H NMR spectroscopy and molecular modeling. The results show that cucurbit[7]uril binds over the long arm of the drug, where hydrophobic effects and two hydrogen bonds stabilise binding. For cucurbit[8]uril, two phenanthriplatin molecules can bind simultaneously within the macrocycle’s cavity. Unfortunately, Na+ was able to displace the drug from both CB[7] and CB[8] making the macrocycles unsuitable as delivery vehicles for phenanthriplatin. Drug binding to β-cyclodextrin occurs at the portal of the macrocycle with no part of the phenanthriplatin located within the cavity. Phenanthriplatin binding to sCX[4] occurs in a 2-to-1, macrocycle-to-drug, ratio with the formation of a capsule-like complex where each sCX[4] binds over opposing ends of the drug. The results indicate that para-sulfonatocalix[4]arene is the only suitable macrocycle of the four studied for further research into phenanthriplatin drug delivery. More... »

PAGES

251-258

References to SciGraph publications

  • 2012-03-27. Host–guest complexes of cucurbit[7]uril with albendazole in solid state in JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY
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    http://dx.doi.org/10.1007/s10847-017-0694-8

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