Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin

Nieto, Carla I.; Cabildo, Pilar; Sanz, Dionísia; Claramunt, Rosa M.; Torralba, M. Carmen; Torres, M. Rosario; Elguero, José; García, José; López, Ana; Acuña-Castroviejo, Darı́o

doi:10.3390/molecules200915643

Cited by 21 publications

(10 citation statements)

References 79 publications

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“…[38] Curcumin phenylpyrazole in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) rodent model of PD exerts reduced tyrosine hydroxylase (TH), exacerbated oxidative stress and dopamine transporter and vesicular monoamine transporter 2 (VMAT2) expressions. [39] Curcumin phenylpyrazole 7, which has neurotrophic activity, enhances memory and blocks cell death in multiple toxicity assays related to ischemic stroke. [54] Curcumin phenylpyrazole 7 and cyclohexyl bisphenol have superior biological properties compared with parent compound curcumin.…”

Section: Curcumin Pyrazole and Isoxazole Analogs As Anti-neurodegenermentioning

confidence: 99%

“…Qualitative structure-activity analysis shows that the presence/absence of diverse substitu- ents confirms that fluorine group enhances the biological activity ( Table 3). [39] Curcumin phenylpyrazole 7, which has neurotrophic activity, enhances memory and blocks cell death in multiple toxicity assays related to ischemic stroke.…”

Section: Curcumin Pyrazole and Isoxazole Analogs As Anti-neurodegenermentioning

confidence: 99%

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Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

Patel

Halpani

2019

Chemistry & Biodiversity

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Curcumin is an admired, plant-derived compound that has been extensively investigated for diverse range of biological activities, but the use of this polyphenol is limited due to its instability. Chemical modifications in curcumin are reported to seize this limitation; such efforts are intensively performed to discover molecules with similar but improved stability and better properties. Focal points of these reviews are synthesis of stable pyrazole and isoxazole analogs of curcumin and application in various biological systems. This review aims to emphasize the latest evidence of curcumin pyrazole analogs as a privileged scaffold in medicinal chemistry. Manifold features of curcumin pyrazole analogs will be summarized herein, including the synthesis of novel curcumin pyrazole analogs and the evaluation of their biological properties. This review is expected to be a complete, trustworthy and critical review of the curcumin pyrazole analogs template to the medicinal chemistry community.

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Section: Curcumin Pyrazole and Isoxazole Analogs As Anti-neurodegenermentioning

confidence: 99%

Section: Curcumin Pyrazole and Isoxazole Analogs As Anti-neurodegenermentioning

confidence: 99%

Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

Patel

Halpani

2019

Chemistry & Biodiversity

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“…When hypertension occurs with decreasing NOS, vascular-dependent hypertension, the endothelial relaxant response becomes weaker. In the normal physiological state of the body, iNOS is generally not expressed, but cNOS (eNOS and nNOS) in endothelial cells continuously synthesizes a small amount of NO to regulate vascular tension and blood pressure [38]. Exposure to an endotoxin in pathological conditions involving various cytokines can induce the production of macrophages and iNOS gene expression in white blood cells; as a result, NO is produced to inhibit endotoxin and cytokines, and its hypotensive effect is strong and is involved in the pathological process [39].…”

Section: Discussionmentioning

confidence: 99%

Prophylactic Effects of Polymethoxyflavone-Rich Orange Peel Oil on Nω-Nitro-L-Arginine-Induced Hypertensive Rats

Wang

Cheng

et al. 2018

Applied Sciences

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Abstract:The prophylactic effects of the polymethoxyflavones (PMFs) in long-leaf orange peel oil (OPO) were determined using an N ω -nitro-L-arginine-induced hypertensive rat model. The OPO contained eight PMF components, namely sinensetin, hexamethoxyflavone, tetramethyl-Oisoscutellarein, nobiletin, tetramethyl-O-scutellarein, heptamethoxyflavone, 5-demethylnobiletin and tangeretin. After treatment with OPO, the SP (systolic pressure) and DP (diastolic pressure) in hypertensive rats were reduced. The NO (nitric oxide) contents in serum, heart, liver and kidney of OPO-treated N ω -nitro-L-arginine (L-NNA)-induced hypertensive rats were higher than those in untreated hypertensive rats, but the MDA (malondialdehyde) contents in OPO-treated rats were lower than those of the control rats (untreated hypertensive rats). ET-1 (endothelin-1), VEGF (vascular endothelial growth factor) and E-selectin serum levels in hypertensive rats could be reduced, but the CGRP (calcium gene-related peptide) level could be increased by OPO treatment. The results of the qPCR assay showed that OPO upregulated HO-1 (heme oxygenase-1), nNOS (neuronal nitric oxide synthase) and eNOS (endothelial nitric oxide synthase) mRNA expression and downregulated ADM (adrenomedullin), RAMP2 (receptor activity modifying protein 2) and iNOS (inducible nitric oxide synthase) expression in hypertensive rats. The Western blot results also proved that OPO upregulated nNOS and eNOS protein expression and downregulated iNOS expression in hypertensive rats. Based on this study, we could conclude that OPO showed good antihypertensive effects, and the effect was concentration dependent.

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“…The concentration of the extracted RNA was adjusted to 1 µg/µl. Total RNA (2 µl) was reverse transcribed into cDNA using 1 µl each of oligo (dT) 18 , RNase, deoxyribonucleotide triphosphate and M-MLV reverse transcriptase (Roche Diagnostics, Basel, Switzerland) in 5X buffer (10 µl). RT was performed with incubation at 37˚C for 120 min, 99˚C for 4 min and 4˚C for 3 min.…”

Section: Reverse Transcription-polymerase Chain Reaction (Rt-qpcr)mentioning

confidence: 99%

Gardenia jasminoides has therapeutic effects on L-NNA-induced hypertension in vivo

Chen

Sun

et al. 2017

Molecular Medicine Reports

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Gardenia jasminoides is a plant that has been used in traditional Chinese medicine. It has four key active components (genipin gentiobioside, geniposide, crocin 1 and crocin 2). The aim of the present study was to determine the anti‑hypertension effects of Gardenia jasminoidesin vivo. The chemical composition of Gardenia jasminoides was determined using liquid chromatography. The anti‑hypertensive effects of Gardenia jasminoides were determined by a L‑NG‑nitroarginine (L‑NNA)‑induced hypertension animal model. Both Gardenia jasminoides plants of the Jiangjin County variety (CJGJ) and the Lichuan City variety (HLGJ) were used. HLGJ contained more geniposide than CJGJ. L‑NNA was used to induce hypertension in mice, and the mice were subsequently treated with CJGJ and HLGJ. The Gardenia jasminoides‑treated mice exhibited lower systolic (SBP), diastolic (DBP) and mean blood pressure (MBP) than the experimental control mice. Additionally, HLGL has a more potent effect on SBP, MBP and DBP than CJGJ. Following Gardenia jasminoides treatment, the nitric oxide contents in serum, heart, liver, kidney and stomach of mice were higher than the L‑NNA‑induced control mice, and the malondialdehyde contents were lower; the levels in HLGJ‑treated mice were closer to those normal mice than the levels in CJGJ‑treated mice were. Serum levels of endothelin‑1 and vascular endothelial growth factor were reduced by HLGJ treatment in hypertensive mice, whereas the calcitonin gene‑related peptide level was raised. Reverse transcription‑polymerase chain reaction analysis of mouse heart and vessel tissue demonstrated that HLGJ‑treated mice exhibited higher heme oxygenase‑1, neuronal nitric oxide synthase (nNOS), endothelial NOS, Bax, caspase‑3, caspase‑8, caspase‑9 mRNA expression levels and lower adrenomedullin, receptor activity modifying protein, interleukin‑1β, tumor necrosis factor‑α, inducible NOS, Bcl‑2, monocyte chemoattractant protein‑1, nuclear factor‑κB and matrix metalloproteinase‑2 and ‑9 mRNA expression compared with control hypertensive mice and CJGJ‑treated mice. In conclusion, Gardenia jasminoides has anti‑hypertensive effects, and these effects may be associated with the active component, geniposide.

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Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin

Abstract: (13), is the best inhibitor of iNOS, being also more selective towards the other two isoforms.

Cited by 21 publications

References 79 publications

Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application

Prophylactic Effects of Polymethoxyflavone-Rich Orange Peel Oil on Nω-Nitro-L-Arginine-Induced Hypertensive Rats

Gardenia jasminoides has therapeutic effects on L-NNA-induced hypertension in vivo

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