betadex and cucurbit(8)uril

We report the control of imazalil (IMZ) antifungal activity utilizing its non-covalent assembly with β-cyclodextrins (β-CD) and cucurbit[8]uril (CB8) macrocycles, as well as its stimuli-responsive disassembly with cadaverine. The NMR results are consistent with inclusion of a single IMZ molecule inside the cavities of either CB8 from its aromatic site or β-CD from its aliphatic end. Efficient complex formation with both host molecules and controlled released upon the addition of cadaverine is supported by NMR measurements. The stimuli-responsiveness of the same host-guest assemblies with cadaverine was validated against seven economically important plant pathogenic fungi which cause agriculturally important plant diseases across the globe. While loading the drug into macrocycles cavities suppressed its activity, subsequent adding of cadaverine efficiently restored it up. The results in the present paper enable researchers working in the area of mycology and plant pathology to inhibit or reduce the fungal growth on demand in order to control these economically important plant pathogenic fungi.

Topics: beta-Cyclodextrins; Bridged-Ring Compounds; Cadaverine; Fungi; Imidazoles; Macromolecular Substances; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Diseases

A heterowheel [3]pseudorotaxane was prepared by integrating two binary inclusion complexes of β-cyclodextrin-hydroxynaphthalene (β-CD·3) with a cucurbit[8]uril-viologen derivative (CB[8]·2), in which simultaneous molecular recognition of the adamantine moiety in 2 by β-CD and the charge-transfer interaction of 3 with the viologen nucleus of 2 in the cavity of CB[8] are two crucial factors for the formation of the quaternary complex.

Topics: beta-Cyclodextrins; Bridged-Ring Compounds; Imidazoles; Models, Molecular; Molecular Structure; Rotaxanes; Viologens