Synthesis of hybrid benzimidazoles-metal sulfide nanoformulations as antifungal agents
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Date
2020
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Punjab Agricultural University, Ludhiana
Abstract
Three samples of MS-NSs viz. CuS-NSs, FeS-NSs and MnS-NSs were prepared using
sonochemical mediated reaction. Co-precipitation method produced three samples of MSNRs
viz. CuS-NRs, FeS-NRs and MnS-NRs in solid form. Statistical analysis of antifungal
potential of MS-NPs against phytopathogenic fungi of rice viz. D. oryzae, F. verticillioides, C.
lunata and S. oryzae indicated that CuS-NSs exhibited the best antifungal potential. A series
of 32 compounds containing benzimidazole and 1,2,4-triazole, in a single molecule, were
designed using variety of spacers between the two bioactive moieties. Only four compounds
viz. 1, 4, 5 and 8 were chosen for synthesis following the combined criteria of stronger
binding to tubulin and lanosterol 14 -demethylase (with docking score -5.9 and -
8.9Kcal/mol, respectively), Lipinski filtrations, FMO approach and Toxtree analysis.
Compound 8 (4-(1H-benzo[d]imidazol-2-yl)-2-methoxyphenyl 2-(1H-1, 2, 4-triazol-1-
ylamino) acetate) was found to be the best antifungal compound against all the test fungi
(ED50 16 μg/ml). U-CuS-NSs underwent in situ surface modification, via organic coating
with most active benzimidazolyl-1,2,4-triazole i.e compound 8 to produce their nanohybrid
(NH-CuS-8). Comparison of ED50 values led to the conclusion that hybridization of CuS-NSs
with compound 8 worked well in enhancing antifungal potential of CuS-NSs against all test
fungi. Priming the seeds with solutions of FeS-NSs and MnS-NSs resulted in improved seed
health but CuS-NSs had negative impact. Seed treatment evaluation studies revealed great
potential of NH-CuS-8 to reduce fungal infection.