Bioactive imidamide-based compounds targeted against nitric oxide synthase

Arias, Fabio; Franco-Montalbán, Francisco; Romero, Miguel; Ding, Juan; Carriòn, María Dora; Camacho, M. Encarnación

doi:10.1016/j.bioorg.2022.105637

Cited by 5 publications

(6 citation statements)

References 37 publications

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“…In addition, this substrate builds hydrogen bonds with the amide carbonyl of Trp372 (19). Another previous study on synthesized N-(3-hydroxy-3-(pyridine-3-yl)propyl)imidamide, indicated a tight hydrogen bonding of the imidamide moiety of this compound to Glu377 residue in the catalytic site of iNOS (20), which confirms the critical role of Glu377.…”

Section: Resultssupporting

confidence: 53%

Inhibitory effects of Indonesian temu kunci (Boesenbergia rotunda) rhizome extract on nitric oxide synthase production and on the kidneys of Wistar rats

et al. 2022

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Nitric oxide synthases (NOSs) are enzymes that function by generating nitric oxide (NO) from its substrate, L-arginine, in human tissues. There are three known isoforms of NOS, eNOS (endothelial NOS), nNOS (neuronal NOS), and iNOS (inducible NOS). iNOS is released in response to inflammation. The human iNOS inhibitor, S-ethylisothiourea (SEITU), has been found to attach to a Glu377 residue within the active-site cavity of the enzyme. The discovery of iNOS inhibitors is always challenging. Boesenbergia rotunda (B. rotunda) has been reported to reduce inflammation in an animal model. The present study examined the inhibitory effects of B. rotunda rhizome ethanolic extract (BRE) on iNOS using the fluorometric method and investigated the histopathological effects of higher concentrations of BRE (1,000, 2,000 and 4,000 mg/kg body weight) on the kidneys of male Wistar rats. Molecular docking simulation of quercetin and kaempferol towards iNOS was also performed. The phytochemical screening of BRE indicated the presence of polyphenolics, flavonoids, triterpenoids, and saponins. The in vitro experiment confirmed that BRE reduced NO production with a half-maximal inhibitory concentration value of 79.06 µg/ml. Both quercetin and kaempferol interacted with Glu377 by building hydrogen bonds. Furthermore, the animal experiment resulted in no mortality and no marked morphological changes in the rat kidneys at all concentrations, indicating the safety of BRE as regards this organ. Taken together, BRE may be further developed as a safe anti-inflammatory drug candidate.

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Section: Resultssupporting

confidence: 53%

Inhibitory effects of Indonesian temu kunci (Boesenbergia rotunda) rhizome extract on nitric oxide synthase production and on the kidneys of Wistar rats

et al. 2022

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“…These findings point to significant biological activity that contributes to the regulation of oxidative stress and, as a result, the inhibition of the inflammatory response. Several investigations have shown that both NO and O 2 •− are involved in numerous pathophysiological processes and are thus the important therapeutic targets [ 70 , 71 ].…”

Section: Resultsmentioning

confidence: 99%

Grapefruit Extract-Mediated Fabrication of Photosensitive Aluminum Oxide Nanoparticle and Their Antioxidant and Anti-Inflammatory Potential

et al. 2022

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Aluminum oxide nanoparticles (Al2O3 NPs) were synthesized using a simple, eco-friendly green synthesis approach in an alkaline medium from the extract of grapefruit peel waste. The pre-synthesized, nano-crystalline Al2O3 NPs were characterized by using spectroscopic (UV–vis, FTIR, XRD, and EDX) and microscopic (SEM and TEM) techniques. The formed Al2O3 NPs exhibited a pronounced absorption peak at 278 nm in the UV–vis spectrum. The average particle size of the as-prepared Al2O3 NPs was evaluated to be 57.34 nm, and the atomic percentages of O and Al were found to be 54.58 and 45.54, respectively. The fabricated Al2O3 NPs were evaluated for antioxidant, anti-inflammatory, and immunomodulatory properties. The Al2O3 NPs showed strong antioxidant potential towards all the four tested assays. The anti-inflammatory and immunomodulatory potential of Al2O3 NPs was investigated by measuring the production of nitric oxide and superoxide anion (O2•−), as well as proinflammatory cytokines tumour necrosis factor (TNF-α, IL-6) and inhibition of nuclear factor kappa B (NF- κB). The results revealed that Al2O3 NPs inhibited the production of O2•− (99.4%) at 100 μg mL−1 concentrations and intracellular NO•− (55%), proinflammatory cytokines IL-6 (83.3%), and TNF-α (87.9%) at 50 μg mL−1 concentrations, respectively. Additionally, the Al2O3 NPs inhibited 41.8% of nuclear factor kappa B at 20 μg mL−1 concentrations. Overall, the outcomes of current research studies indicated that Al2O3 NPs possess anti-inflammatory and immunomodulatory properties and could be used to treat chronic and acute anti-inflammatory conditions.

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“…Aminophenyl imidamides 10 – 18 were prepared following the previously reported methodology described in Scheme 1, [14] and pyridine imidamides 19 – 22 were synthesized as shown in Scheme 2. [15] In addition, the structural data of all the nitrophenyl intermediates 1 – 9 and final compounds are collected in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…In order to complete the spectroscopic information of these compounds, an intensive study of derivative 18 was carried out, using DMSO-d 6 to fix the labile protons bound to O and N. Two-dimensional 1 H/ 15 N correlation experiments were carried out to unequivocally assign all 1 H and 15 N signals. The 1 H/ 15 N HSQC (Figure 3) allowed us to locate nitrogens N-1 at δ = 123.25 ppm and N-3 at δ = 111.50 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…In the research on new NOS inhibitor agents, we have recently designed and synthesized a novel set of aryl-and heteroaryl-imidamide derivatives 10-22, aiming to find potent and selective molecules that could be useful as nNOS or iNOS inhibitors. [14,15] The structural elucidation of these compounds has been performed on the basis of different standard techniques by analyzing their spectroscopic ( 1 H and 13 C 1D NMR) and spectrometric (MS) data; nevertheless, a detailed NMR study, including 2D NMR [heteronuclear single quantum correlation (HSQC) and heteronuclear multiple bond correlation (HMBC)] techniques, has been carried out in some derivatives, to confirm their structures unambiguously.…”

Section: Introductionmentioning

confidence: 99%

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NMR spectroscopy study of new imidamide derivatives as nitric oxide synthase inhibitors

Arias

Camacho

Carriòn

2022

Magnetic Reson in Chemistry

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Bioactive imidamide-based compounds targeted against nitric oxide synthase

Cited by 5 publications

References 37 publications

Inhibitory effects of Indonesian temu kunci (Boesenbergia rotunda) rhizome extract on nitric oxide synthase production and on the kidneys of Wistar rats

Inhibitory effects of Indonesian temu kunci (Boesenbergia rotunda) rhizome extract on nitric oxide synthase production and on the kidneys of Wistar rats

Grapefruit Extract-Mediated Fabrication of Photosensitive Aluminum Oxide Nanoparticle and Their Antioxidant and Anti-Inflammatory Potential

NMR spectroscopy study of new imidamide derivatives as nitric oxide synthase inhibitors

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