Design, synthesis and screening of benzimidazole containing compounds with methoxylated aryl radicals as cytotoxic molecules on (HCT-116) colon cancer cells

Noha, Ryad M.; Abdelhameid, Mohammed K.; Ismail, M. Mohsen; Mohammed, Manal R.; Elmeligie, Salwa

doi:10.1016/j.ejmech.2020.112870

Cited by 17 publications

(11 citation statements)

References 32 publications

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“…Benzimidazothiazoles, as core rings, are polycyclic isosteres whose derivatives have been reported to exert anticancer [25] and anti-inflammatory [26,27] activities. However, no study has yet described its anti-tyrosinase and hyperpigmenting effects in vitro model.…”

Section: Introductionmentioning

confidence: 99%

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

et al. 2021

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Thirteen (Z)-2-(substituted benzylidene)benzimidazothiazolone analogs were synthesized and evaluated for their inhibitory activity against mushroom tyrosinase. Among the compounds synthesized, compounds 1–3 showed greater inhibitory activity than kojic acid (IC50 = 18.27 ± 0.89 μM); IC50 = 3.70 ± 0.51 μM for 1; IC50 = 3.05 ± 0.95 μM for 2; and IC50 = 5.00 ± 0.38 μM for 3, and found to be competitive tyrosinase inhibitors. In silico molecular docking simulations demonstrated that compounds 1–3 could bind to the catalytic sites of tyrosinase. Compounds 1–3 inhibited melanin production and cellular tyrosinase activity in a concentration-dependent manner. Notably, compound 2 dose-dependently scavenged ROS in B16F10 cells. Furthermore, compound 2 downregulated the protein kinase A (PKA)/cAMP response element-binding protein (CREB) and mitogen-activated protein kinase (MAPK) signaling pathways, which led to a reduction in microphthalmia-associated transcription factor (MITF) expression, and decreased tyrosinase, tyrosinase related protein 1 (TRP1), and TRP2 expression, resulting in anti-melanogenesis activity. Hence, compound 2 may serve as an anti-melanogenic agent against hyperpigmentation diseases.

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Section: Introductionmentioning

confidence: 99%

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

et al. 2021

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“…In 2020, benzimidazole derivative 46 (Figure C) with a 3,4,5-trimethoxybenzylidene moiety was designed and synthesized through fusing polycyclic core and aryl groups . It showed remarkable inhibitory effects on topo Iβ in a nanomolar concentration (IC 50 = 21 nM).…”

Section: Dual Inhibitors Of Tubulin and Other Tumor-related Targetsmentioning

confidence: 99%

Recent Progress on Tubulin Inhibitors with Dual Targeting Capabilities for Cancer Therapy

et al. 2021

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Microtubules play a crucial role in multiple cellular functions including mitosis, cell signaling, and organelle trafficking, which makes the microtubule an important target for cancer therapy. Despite the great successes of microtubule-targeting agents in the clinic, the development of drug resistance and dose-limiting toxicity restrict their clinical efficacy. In recent years, multitarget therapy has been considered an effective strategy to achieve higher therapeutic efficacy, in particular dual-target drugs. In terms of the synergetic effect of tubulin and other antitumor agents such as receptor tyrosine kinases inhibitors, histone deacetylases inhibitors, DNA-damaging agents, and topoisomerase inhibitors in combination therapy, designing dual-target tubulin inhibitors is regarded as a promising approach to overcome these limitations and improve therapeutic efficacy. In this Perspective, we discussed rational target combinations, design strategies, structure−activity relationships, and future directions of dual-target tubulin inhibitors.

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“…Cytotoxicity of benzimidazole derivatives is well known and, recently Noha et al reported compounds of benzimidazole which are N-(benzimidazothiazolone) acetamides (7) [35]. In vitro analyses provided the cytotoxic activity of (7) over HCT-116 colon cancer cells.…”

Section: Anticancer Activitymentioning

confidence: 99%

“…The upregulation of Wnt/β-catenin signaling in triple-negative breast cancer (TNBC), when compared to normal and other breast cancer subtypes, is inevitable. Benzimidazole compounds like SRI33576 (35) and SRI35889 (36) have a high cytotoxicity rate in TNBC cell lines. They are found to be active inhibitors of Wnt/β-catenin signaling and have therapeutic properties for treating TNBC (Figure 10).…”

Section: Anticancer Activitymentioning

confidence: 99%

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

Kavya¹,

Sivan²

2022

Benzimidazole

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Benzimidazole, one of the finest classes of heterocyclic aromatic compounds have the characteristic structure of benzene fused with a five-membered imidazole ring. Despite being made their first appearance in the late 1870s, they are considered as a ‘privileged molecule’. The applications of this wonder molecule range from medicinal chemistry to material science. Benzimidazole being a potent inhibitor for various enzymes has got therapeutic effects like anticancer, antimicrobial, anthelmintic, antioxidant, anticonvulsant, antifungal, anti-inflammatory, antiviral, antihistaminic, antipsychotic, etc. It has also made its existence in various branches of medical science viz ophthalmology, neurology, cardiology and more. The applications of benzimidazole are not only limited to the biological field but also expanded to the field of material chemistry as well. This chapter summarizes the pharmacological properties of benzimidazole, illustrated on numerous derivatives since 2016.

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Design, synthesis and screening of benzimidazole containing compounds with methoxylated aryl radicals as cytotoxic molecules on (HCT-116) colon cancer cells

Cited by 17 publications

References 32 publications

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

New Benzimidazothiazolone Derivatives as Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

Recent Progress on Tubulin Inhibitors with Dual Targeting Capabilities for Cancer Therapy

Exploring the Versatility of Benzimidazole Scaffolds as Medicinal Agents: A Brief Update

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