Studies on saccharide benzimidazoles: 2-(β-D-gulofuranosyl)benzimidazole and 2-(β-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency

Sallam, Mohammed A.E.; Salem, Dalia M.S.A.; Labib, Gorgina M.H.; Youssef, Trevena N.M.A.; Matsuo, Koichi

doi:10.1016/j.carres.2020.108073

Cited by 5 publications

(3 citation statements)

References 21 publications

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“…Compounds were incorporated at a concentration of 2%. After the immersion of steel panels coated with the previously prepared coatings for two and four weeks, it was found that coatings containing benzimidazole derivatives 90-95 (Figure 4) showed a significant decrease in the biofilm coverage in comparison with the negative control and positive control panels, which suggests that these compounds were useful for the inhibition of the marine bacterial growth [73]. Moreover, the results of the chemical parameters (pH value, alkalinity, dissolved oxygen, oxidizable organic matter, important nutrient salts which are the dissolved inorganic forms of nitrogen (NO2 − , NO3 − , and NH4 + ), dissolved inorganic phosphate (PO4 3-), and silicate (SiO3 -) of the surrounding seawater) indicated that all coated panels with marine paint formulations containing compounds 90-95 did not present any bad effects on the seawater surrounding the coated panels.…”

Section: Other Coatingsmentioning

confidence: 99%

“…Sallam et al reported the synthesis of a series of benzimidazole derivatives, their incorporation into a marine coating, and the evaluation of the decrease in the biofilm bacterial number [73]. The marine paint was based on 25 g of oil binder material, 10 g of iron oxide, 24 g of zinc oxide, 13 g of complementary piment, and 38 g of xylene.…”

Section: Other Coatingsmentioning

confidence: 99%

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Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Pereira,

Almeida,

Cidade

et al. 2024

Marine Drugs

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Marine biofouling, caused by the deposition and accumulation of marine organisms on submerged surfaces, represents a huge concern for the maritime industries and also contributes to environmental pollution and health concerns. The most effective way to prevent this phenomenon is the use of biocide-based coatings which have proven to cause serious damage to marine ecosystems. Several research groups have focused on the search for new environmentally friendly antifoulants, including marine and terrestrial natural products and synthetic analogues. Some of these compounds have been incorporated into marine coatings and display interesting antifouling activities caused by the interference with the biofilm-forming species as well as by the inhibition of the settlement of macroorganisms. This review highlights the proof-of-concept studies of emerging natural or synthetic antifouling compounds in coatings, from lab-made to commercial ones, performed between 2019 and 2023 and their results in the field or in in vivo laboratorial tests.

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Section: Other Coatingsmentioning

confidence: 99%

Section: Other Coatingsmentioning

confidence: 99%

Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Pereira,

Almeida,

Cidade

et al. 2024

Marine Drugs

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“…With a great affinity displayed towards a numerous enzymes and receptors, the benzimidazoles could be potentially explored for the development of new pharmaceuticals. Numerous studies revealed that compounds derived from a benzimidazole nucleus exhibit analgesic and anti-inflammatory activity [ 41 ], as well as antiulcerative [ 42 ], anticancer [ 43 ], antiparasitic [ 44 ], antimicrobial [ 45 , 46 , 47 ], antioxidant [ 46 ], anticonvulsant [ 48 ], anticancer/antiestrogenic [ 49 , 50 ], antihypertensive [ 51 ], antifouling [ 52 ], and many others [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ] activities. Therefore, the strategies of developing compounds bearing the benzimidazole scaffold should be further explored to generate pharmacologically active molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of New Azole, Diazole and Triazole Derivatives Based on p-Aminobenzoic Acid

Sapijanskaitė-Banevič

Palskys

Vaickelionienė

et al. 2021

Molecules

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The p-aminobenzoic acid was applied for the synthesis of substituted 1-phenyl-5-oxopyrrolidine derivatives containing benzimidazole, azole, oxadiazole, triazole, dihydrazone, and dithiosemicarbazide moieties in the structure. All the obtained compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Salmonella enteritidis, Escherichia coli, and Pseudomonas aeruginosa by using MIC and MBC assays. This study showed a good bactericidal activity of γ-amino acid and benzimidazoles derivatives. The antimicrobial activity of the most promising compounds was higher than ampicillin. Furthermore, two benzimidazoles demonstrated good antimicrobial activity against L. monocytogenes (MIC 15.62 µg/mL) that was four times more potent than ampicillin (MIC 65 µg/mL). Further studies are needed to better understand the mechanism of the antimicrobial activity as well as to generate antimicrobial compounds based on the 1-phenyl-5-oxopyrrolidine scaffold.

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Discovery of novel benzimidazole acyclic C‐nucleoside DNA intercalators halting breast cancer growth

Abd Al Moaty,

El Kilany,

Awad

et al. 2023

Archiv der Pharmazie

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Breast cancer continues to be the most frequent cancer worldwide. In practice, successful clinical outcomes were achieved via targeting DNA. Along with the advances in introducing new DNA‐targeting agents, the “sugar approach” design was employed herein to develop new intercalators bearing pharmacophoric motifs tethered to carbohydrate appendages. Accordingly, new benzimidazole acyclic C‐nucleosides were rationally designed, synthesized and assayed via MTT (3‐[4,5‐dimethylthiazol‐2‐yl]‐2,5 diphenyl tetrazolium bromide) assay to evaluate their cytotoxicity against MCF‐7 and MDA‐MB‐231 breast cancer cells compared to normal fibroblasts (Wi‐38), compared to doxorubicin. (1S,2R,3S,4R)‐2‐(1,2,3,4,5‐Pentahydroxy)pentyl‐1H‐5,6‐dichlorobenzimidazole 7 and (1S,2R,3S,4R)‐2‐(1,2,3,4,5‐pentahydroxy)pentyl‐1H‐naphthimidazole 13 were the most potent and selective derivatives against MCF‐7 (half‐maximal inhibitory concentration [IC50] = 0.060 and 0.080 µM, selectivity index [SI] = 9.68 and 8.27, respectively) and MDA‐MB‐231 cells (IC50 = 0.299 and 0.166 µM, SI = 1.94 and 3.98, respectively). Thus, they were identified as the study hits for mechanistic studies. Both derivatives induced DNA damage at 0.24 and 0.29 μM, respectively. The DNA damage kinetics were studied compared to doxorubicin, where they both induced faster damage than doxorubicin. This indicated that 7 and 13 showed a more potent DNA‐damaging effect than doxorubicin. Docking simulations within the DNA double strands highlighted the role of both the heterocyclic core and the sugar side chain in exhibiting key H‐bond interactions with DNA bases.

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Studies on saccharide benzimidazoles: 2-(β-D-gulofuranosyl)benzimidazole and 2-(β-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency

Cited by 5 publications

References 21 publications

Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Proof of Concept of Natural and Synthetic Antifouling Agents in Coatings

Synthesis and Antibacterial Activity of New Azole, Diazole and Triazole Derivatives Based on p-Aminobenzoic Acid

Discovery of novel benzimidazole acyclic C‐nucleoside DNA intercalators halting breast cancer growth

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