Aspergillus flavus is an opportunistic mold that represents a serious threat for human and animal health due to its ability to synthesize and release, on food and feed commodities, different toxic secondary metabolites. Among them, aflatoxin B1 is one of the most dangerous since it is provided with a strong cancerogenic and mutagenic activity. Controlling fungal contamination on the different crops that may host A. flavus is considered a priority by sanitary authorities of an increasing number of countries due also to the fact that, owing to global temperature increase, the geographic areas that are expected to be prone to experience sudden A. flavus outbreaks are widening. Among the different pre- and post-harvest strategies that may be put forward in order to prevent fungal and/or mycotoxin contamination, fungicides are still considered a prominent weapon. We have here analyzed different structural modifications of a natural-derived compound (cuminaldehyde thiosemicarbazone) for their fungistatic and anti-aflatoxigenic activity. In particular, we have focused our attention on one of the compound that presented a prominent anti-aflatoxin specificity, and performed a set of physiological and molecular analyses, taking also advantage of yeast (Saccharomyces cerevisiae) cell as an experimental model.
Naphthalenediimide
derivates are a class of π-conjugated
molecules largely investigated in the literature and used as building
blocks for metal–organic frameworks or coformers for hydrogen-bond-based
cocrystals. However, their tendency to establish halogen-bond interactions
remains unexplored. By using a crystalline engineering approach, we
report here four new cocrystals with
N
,
N
′-di(4-pyrydyl)-naphthalene-1,4,5,8-tetracarboxidiimide and
diiodo-substituted coformers, easily obtained via a mechanochemical
protocol. Cocrystals were characterized via NMR, electron ionization
mass spectrometry, thermogravimetric analysis, powder X-ray diffraction,
and single-crystal X-ray diffraction. Crystallographic structures
were then finely examined and correlated with energy framework calculations
to understand the relative contribution of halogen-bond and π–π
interactions toward framework stabilization.
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