Design, Synthesis and in Vivo Evaluation of Novel Glycosylated Sulfonylureas as Antihyperglycemic Agents

Suaifan, Ghadeer A. R. Y.; Shehadeh, Mayadah B.; Darwish, Rula M.; Al-Ijel, Hebah; Abbate, Vincenzo

doi:10.3390/molecules201119676

Cited by 12 publications

(9 citation statements)

References 55 publications

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“…Secondary metabolites of botanical origin are produced to support and enhance the permanence of the plant. Photosynthesis, glycolysis and the Krebs cycle are overflowing with several intermediates that manufacture these metabolites [ 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

2021

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Recently, significant advances in modern medicine and therapeutic agents have been achieved. However, the search for effective antidiabetic drugs is continuous and challenging. Over the past decades, there has been an increasing body of literature related to the effects of secondary metabolites from botanical sources on diabetes. Plants-derived metabolites including alkaloids, phenols, anthocyanins, flavonoids, stilbenoids, saponins, tannins, polysaccharides, coumarins, and terpenes can target cellular and molecular mechanisms involved in carbohydrate metabolism. In addition, they can grant protection to pancreatic beta cells from damage, repairing abnormal insulin signaling, minimizing oxidative stress and inflammation, activating AMP-activated protein kinase (AMPK), and inhibiting carbohydrate digestion and absorption. Studies have highlighted many bioactive naturally occurring plants’ secondary metabolites as candidates against diabetes. This review summarizes the current knowledge compiled from the latest studies published during the past decade on the mechanism-based action of plants-derived secondary metabolites that can target various metabolic pathways in humans against diabetes. It is worth mentioning that the compiled data in this review will provide a guide for researchers in the field, to develop candidates into environment-friendly effective, yet safe antidiabetics.

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Section: Introductionmentioning

confidence: 99%

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

2021

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“…Compound 4 was prepared by reacting D ‐(+)‐glucosamine hydrochloride with 4‐methoxybenzaldehyde to yield the glucosamine imine intermediate 1 . Following acetylation, amine deprotection, and neutralization, compound 4 was obtained (Dang et al, ; Myszka et al, ; Suaifan, Shehadeh, Darwish, Al‐Ijel, & Abbate, ).…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and biological evaluation of 1,8‐naphthyridine glucosamine conjugates as antimicrobial agents

Mohammed

Suaifan

Shehadeh

et al. 2018

Drug Development Research

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In the quest for discovering potent antimicrobial agents with lower toxicity, we envisioned the design and synthesis of nalidixic acid‐D‐(+)‐glucosamine conjugates. The novel compounds were synthesized and evaluated for their in vitro antimicrobial activity against Gram positive bacteria, Gram negative bacteria and fungi. Cytotoxicity using MTT assay over L6 skeletal myoblast cell line, ATCC CRL‐1458 was carried out. In vitro antimicrobial assay revealed that 1‐ethyl‐7‐methyl‐4‐oxo‐N‐(1,3,4,6‐tetra‐O‐acetyl‐2‐deoxy‐D‐glucopyranose‐2‐yl)‐[1,8]‐naphthyridine‐3‐carboxamide (5) and 1‐ethyl‐7‐methyl‐4‐oxo‐N‐(2‐deoxy‐D‐glucopyranose‐2‐yl)‐[1,8]‐naphthyridine‐3‐carboxamide(6) possess growth inhibitory activity against resistant Escherichia coli NCTC, 11954 (MIC 0.1589 mM) and Methicillin resistant Staphylococcus aureus ATCC, 33591 (MIC 0.1589 mM). Compound (5) was more active against Listeria monocytogenes ATCC 19115 (MIC 0.1113 mM) in comparison with the reference nalidixic acid (MIC 1.0765 mM). Interestingly, compound (6) had potential antifungal activity against Candida albicans ATCC 10231 (MIC <0.0099 mM). Remarkably, the tested compounds had low cytotoxic effect. This study indicated that glucosamine moiety inclusion into the chemical structure of the marketed nalidixic acid enhances antimicrobial activity and safety.

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“…Sulfonylurea compounds have a wide range of biological applications, including use as antidiabetics (e.g., glibenclamide), diuretics (e.g., torasemide), herbicides (e.g., chlorsulfuron), oncolytic (e.g., sulofenur), antimalarials, antifungals, and anticancer agents [ 7 ]. Agricultural workers may be exposed to various herbicides during activities such as transportation, mixing, application, or cleaning and maintenance of application equipment [ 8 ].…”

Section: Discussionmentioning

confidence: 99%

Can Sulfonylureas for Agricultural Use Cause Diabetes? A Report of Three Cases

Kampouraki¹,

Mavridou²,

Bakola³

et al. 2023

Cureus

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Sulfonylureas (SUs) are commonly used as herbicides. Many farmers and other professionals use SUs for cereal, strawberry, and grape crops. This study examines the possible association between exposure to SUs herbicides and the risk of developing type 2 diabetes (T2D). The study presents three cases of unrelated agronomists who had used SUs for more than three decades and developed T2D. The objective was to investigate the association between occupational dermal and inhalation exposure to herbicides and T2D. Further studies with a larger sample size are needed to determine the association and to help develop prevention strategies.

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Design, Synthesis and in Vivo Evaluation of Novel Glycosylated Sulfonylureas as Antihyperglycemic Agents

Cited by 12 publications

References 55 publications

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

Plants Secondary Metabolites as Blood Glucose-Lowering Molecules

Design, synthesis, and biological evaluation of 1,8‐naphthyridine glucosamine conjugates as antimicrobial agents

Can Sulfonylureas for Agricultural Use Cause Diabetes? A Report of Three Cases

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