Synthesis and potential vasorelaxant effect of a novel ruthenium-based nitro complex

Neto, Joselito de Oliveira; Marinho, Márcia Machado; Silveira, João Alison de Moraes; Rocha, Danilo Galvão; Lima, Natália Cavalcante Barbosa; Júnior, Florêncio Sousa Gouveia; Lopes, Luiz Gonzaga de França; Sousa, Eduardo Henrique Silva; Martins, Alice Maria Costa; Jorge, Roberta Jeane Bezerra; Monteiro, Helena Serra Azul

doi:10.1016/j.jinorgbio.2021.111666

Cited by 4 publications

(3 citation statements)

References 67 publications

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“…The physicochemical properties and BBB permeability of 1–4 were predicted by SwissADME public server and admet SAR server (Daina et al., 2017). The results showed that all compounds exhibited drug‐like characteristics according to Muegge's perspectives (molecular weight (MW) ≤600, octanol–water partition coefficients (CLogP) ≤5, the number of H‐bond donors (HBD) ≤5, the number of H‐bond acceptors (HBA) ≤10 and the number of rotatable bonds (RBC) ≤15) and polar surface area (PSA) ≤150 Å 2 (Neto et al., 2022). And all compounds might be able to cross the BBB as shown in Table S1.…”

Section: Resultsmentioning

confidence: 99%

Diosmetin derivatives as multifunctional anti‐AD ligands: Design, synthesis, and biological evaluation

Yang,

Yi,

Zhang

et al. 2024

Chem Biol Drug Des

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With the increasing aging population, rational design of drugs for Alzheimer's disease (AD) treatment has become an important research area. Based on the multifunctional design strategy, four diosmetin derivatives (1–4) were designed, synthesized, and characterized by 1H NMR, 13C NMR, and MS. Docking study was firstly applied to substantiate the design strategies and then the biological activities including cholinesterase inhibition, metal chelation, antioxidation and β‐amyloid (Aβ) aggregation inhibition in vitro were evaluated. The results showed that 1–4 had good acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition, metal chelation (selective chelation of Cu2+ ions), antioxidation, self‐induced, Cu2+‐induced, and AChE‐induced Aβ aggregation inhibition activities, and suitable blood–brain barrier (BBB) permeability. Especially, compound 3 had the strongest inhibitory effect on AChE (10−8 M magnitude) and BuChE (10−7 M magnitude) and showed the best inhibition on AChE‐induced Aβ aggregation with 66.14% inhibition ratio. Furthermore, compound 3 could also reduce intracellular reactive oxygen species (ROS) levels in Caenorhabditis elegans and had lower cytotoxicity. In summary, 3 might be considered as a potential multifunctional anti‐AD ligand.

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Section: Resultsmentioning

confidence: 99%

Diosmetin derivatives as multifunctional anti‐AD ligands: Design, synthesis, and biological evaluation

Yang,

Yi,

Zhang

et al. 2024

Chem Biol Drug Des

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“…While this latter compound may be dangerous due to the cyano groups, it is also restricted to use within a hospital because of its potent and fast vasodilatory effect caused by a substitution reaction of the nitrosyl (•NO) by a water molecule (Figure 13) [51]. To overcome this problem, some ruthenium complexes were analyzed for a more controlled realization of •NO [52] There is a wide variety of options when it comes to •NO donors since most are organic nitrocompounds (sometimes mentioned as organic nitrates), but some others are organometallic coordination complexes such as sodium nitroprusside. While this latter compound may be dangerous due to the cyano groups, it is also restricted to use within a hospital because of its potent and fast vasodilatory effect caused by a substitution reaction of the nitrosyl (•NO) by a water molecule (Figure 13) [51].…”

Section: Vasodilatory Activitymentioning

confidence: 99%

“…While this latter compound may be dangerous due to the cyano groups, it is also restricted to use within a hospital because of its potent and fast vasodilatory effect caused by a substitution reaction of the nitrosyl (•NO) by a water molecule (Figure 13) [51]. To overcome this problem, some ruthenium complexes were analyzed for a more controlled realization of •NO [52], in some cases, under visible light (445 nm), showing that [RuNOPy 2 (NO 2 ) 2 OH]•H 2 O (a known •NO donor) has promising results under this conditions. Unlike nitroprusside 27a, [RuNOPy 2 (NO 2 ) 2 OH]•H 2 O 28a releases •NO slowly when exposed to visible light.…”

Section: Vasodilatory Activitymentioning

confidence: 99%

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

et al. 2022

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The search for new and efficient pharmaceuticals is a constant struggle for medicinal chemists. New substances are needed in order to treat different pathologies affecting the health of humans and animals, and these new compounds should be safe, effective and have the fewest side effects possible. Some functional groups are known for having biological activity; in this matter, the nitro group (NO2) is an efficient scaffold when synthesizing new bioactive molecules. Nitro compounds display a wide spectrum of activities that include antineoplastic, antibiotic, antihypertensive, antiparasitic, tranquilizers and even herbicides, among many others. Most nitro molecules exhibit antimicrobial activity, and several of the compounds mentioned in this review may be further studied as lead compounds for the treatment of H. pylori, P. aeruginosa, M. tuberculosis and S. mutans infections, among others. The NO2 moiety triggers redox reactions within cells causing toxicity and the posterior death of microorganisms, not only bacteria but also multicellular organisms such as parasites. The same effect may be present in humans as well, so the nitro groups can be considered both a pharmacophore and a toxicophore at the same time. The role of the nitro group itself also has a deep effect on the polarity and electronic properties of the resulting molecules, and hence favors interactions with some amino acids in proteins. For these reasons, it is fundamental to analyze the recently synthesized nitro molecules that show any potential activity in order to develop new pharmacological treatments that enhance human health.

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Novel Ruthenium‐based Nitrosyl Complexes: NO Donation and Vasorelaxant Potentials for Cardiovascular Therapeutics

Gouveia Júnior,

de Sousa,

da Silva

et al. 2024

Eur J Inorg Chem

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Nitrosyl ruthenium complexes have emerged as promising platforms for the controlled delivery of nitric oxide (NO) and nitroxyl (HNO), both of which possess significant therapeutic implications. Considering this scenario, we synthesized and characterized the metal complex cis‐[RuNO(phen)2(2MIM)]3+ and its precursors, where phen and 2MIM correspond to 1,10‐phenantroline and 2‐methylimidazole, respectively. Comprehensive structural elucidation was undertaken using a combination of spectroscopic and electrochemical methodologies, including XANES/EXAFS experiments. This structural data was further validated through DFT computational analyses. We demonstrated that such compound can release NO and HNO in the presence of thiol‐based substrates. Not only this, but the same metal complex can also delivery nitric oxide under irradiation with visible light (λ=460 nm). The nitrosyl complex and its derivatives displayed marked vasodilatory capabilities as evidenced in assays involving isolated rat aorta rings. They also exhibited commendable antioxidant activity in free radical scavenging assays. Collectively, based on these data, this nitrosyl ruthenium compound is a potential therapeutic candidate, especially in the field of cardiovascular pathology like atherosclerosis, thereby deserving further in‐depth investigations.

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Synthesis and potential vasorelaxant effect of a novel ruthenium-based nitro complex

Cited by 4 publications

References 67 publications

Diosmetin derivatives as multifunctional anti‐AD ligands: Design, synthesis, and biological evaluation

Diosmetin derivatives as multifunctional anti‐AD ligands: Design, synthesis, and biological evaluation

The Diverse Biological Activity of Recently Synthesized Nitro Compounds

Novel Ruthenium‐based Nitrosyl Complexes: NO Donation and Vasorelaxant Potentials for Cardiovascular Therapeutics

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