Synthesis of novel 1,2,3-triazole-substituted tomentosins

Zaki, Mohd; Oukhrib, Abdelouahd; Hakmaoui, Ahmed El; Hiebel, Marie‐Aude; Berteina‐Raboin, Sabine; Akssira, Mohamed

doi:10.1515/znb-2018-0225

Cited by 6 publications

(4 citation statements)

References 57 publications

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“…Presently, around 60% of used drugs for cancer treatment are procured from natural products. Furthermore, the modification of natural products is one of the most common and productive methodologies to obtain novel therapeutic agents using medicinal chemistry (Zaki et al, 2019). Thus, targeting fungal biofilms by either natural derivatives or synthetic analogs could be a novel approach.…”

Section: Natural Productsmentioning

confidence: 99%

Mechanistic Understanding of Candida albicans Biofilm Formation and Approaches for Its Inhibition

et al. 2021

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In recent years, the demand for novel antifungal therapies has increased several- folds due to its potential to treat severe biofilm-associated infections. Biofilms are made by the sessile microorganisms attached to the abiotic or biotic surfaces, enclosed in a matrix of exopolymeric substances. This results in new phenotypic characteristics and intrinsic resistance from both host immune response and antimicrobial drugs. Candida albicans biofilm is a complex association of hyphal cells that are associated with both abiotic and animal tissues. It is an invasive fungal infection and acts as an important virulent factor. The challenges linked with biofilm-associated diseases have urged scientists to uncover the factors responsible for the formation and maturation of biofilm. Several strategies have been developed that could be adopted to eradicate biofilm-associated infections. This article presents an overview of the role of C. albicans biofilm in its pathogenicity, challenges it poses and threats associated with its formation. Further, it discusses strategies that are currently available or under development targeting prostaglandins, quorum-sensing, changing surface properties of biomedical devices, natural scaffolds, and small molecule-based chemical approaches to combat the threat of C. albicans biofilm. This review also highlights the recent developments in finding ways to increase the penetration of drugs into the extracellular matrix of biofilm using different nanomaterials against C. albicans.

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Section: Natural Productsmentioning

confidence: 99%

Mechanistic Understanding of Candida albicans Biofilm Formation and Approaches for Its Inhibition

et al. 2021

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“…Currently, approximately 60% of drugs applied for treating cancers are obtained from natural sources. In addition, one of the most usual and productive methods of obtaining new therapeutic agents applying medicinal chemistry is to modify natural products (Zaki et al, 2019). Natural commodity screening has proven to be a hopeful strategy.…”

Section: Natural Productsmentioning

confidence: 99%

Intestinal Infection of Candida albicans: Preventing the Formation of Biofilm by C. albicans and Protecting the Intestinal Epithelial Barrier

Zhang

Tang

2022

Front. Microbiol.

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The large mortality and morbidity rate of C. albicans infections is a crucial problem in medical mycology. Because the generation of biofilms and drug resistance are growing concerns, the growth of novel antifungal agents and the looking for newer objectives are necessary. In this review, inhibitors of C. albicans biofilm generation and molecular mechanisms of intestinal epithelial barrier protection are elucidated. Recent studies on various transcription elements; quorum-sensing molecules; host responses to adherence; and changes in efflux pumps, enzymes, bud to hyphal transition, and lipid profiles have increased the knowledge of the intricate mechanisms underlying biofilm resistance. In addition, the growth of novel biomaterials with anti-adhesive nature, natural products, drugs, bioactive compounds, proteins, lipids, and carbohydrates are being researched. Recently, more and more attention has been given to various metal nanoparticles that have also appeared as antibiofilm agents in C. albicans. The intestinal epithelial obstacle exerts an crucial effect on keeping intestinal homeostasis and is increasingly associated with various disorders associated with the intestine such as inflammatory bowel disease (IBD), irritable bowel syndrome, metabolic syndrome, allergies, hepatic inflammation, septic shock, etc. However, whether their involvement in the prevention of other intestinal disorders like IBD are useful in C. albicans remains unknown. Further studies must be carried out in order to validate their inhibition functions in intestinal C. albicans. This provides innovates ideas for intestinal C. albicans treatment.

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“…These compounds were then reacted under Huisgen 1,3-dipolar cycloaddition reaction conditions by using different terminal alkynes. The compounds 5a-e and 6a-e obtained are depicted in Scheme 2 [28].…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Tomentosin Derivatives in NMDA-Induced Excitotoxicity

et al. 2022

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N-methyl-D-aspartate (NMDA) receptor stimulation may lead to excitotoxicity, which triggers neuronal death in brain disorders. In addition to current clinical therapeutic approaches, treatment strategies by phytochemicals or their derivatives are under investigation for neurodegenerative diseases. In the present study, novel amino and 1,2,3-triazole derivatives of tomentosin were prepared and tested for their protective and anti-apoptotic effects in NMDA-induced excitotoxicity. Amino-tomentosin derivatives were generated through a diastereoselective conjugate addition of several secondary amines to the α-methylene-γ-butyrolactone function, while the 1,2,3-triazolo-tomentosin was prepared by a regioselective Michael-type addition carried out in the presence of trimethylsilyl azide (TMSN3) and the α-methylene-γ-lactone function. The intermediate key thus obtained underwent 1,3-dipolar Huisgen cycloaddition using a wide range of terminal alkynes. The possible effects of the derivatives on cell viability and free-radical production following NMDA treatment were measured by Water-Soluble Tetrazolium Salts (WST-1) and Dichlorofluorescein Diacetate (DCF-DA) assays, respectively. The alterations in apoptosis-related proteins were examined by Western blot technique. Our study provides evidence that synthesized triazolo- and amino-tomentosin derivatives show neuroprotective effects by increasing cellular viability, decreasing ROS production, and increasing the Bcl-2/Bax ratio in NMDA-induced excitotoxicity. The findings highlight particularly 2e, 2g, and 6d as potential regulators and neuroprotective agents in NMDA overactivation.

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Synthesis of novel 1,2,3-triazole-substituted tomentosins

Cited by 6 publications

References 57 publications

Mechanistic Understanding of Candida albicans Biofilm Formation and Approaches for Its Inhibition

Mechanistic Understanding of Candida albicans Biofilm Formation and Approaches for Its Inhibition

Intestinal Infection of Candida albicans: Preventing the Formation of Biofilm by C. albicans and Protecting the Intestinal Epithelial Barrier

Design, Synthesis, and Biological Evaluation of Novel Tomentosin Derivatives in NMDA-Induced Excitotoxicity

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