Multicomponent Petasis‐borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies

Neto, Iris; Andrade, Joana M.; Fernandes, Ana Sofia; Reis, Catarina Pinto; Salunke, Jagadish K.; Priimägi, Arri; Candeias, Nuno R.; Rijo, Patrícia

doi:10.1002/cmdc.201600244

Cited by 34 publications

(34 citation statements)

References 54 publications

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“…The strong antimicrobial activity (MIC = 32–256 μ g/mL) also showed R. carthamoides root and rhizomes essential oil from commercial available material [17] but with lower activity against E. faecalis (ATCC 29212) (MIC = 265 μ g/mL) and P. aeruginosa (ATCC 27853) (MIC > 512 μ g/mL) than the root essential oils in the present study (MIC = 125 μ g/mL). A pure compound is usually used as a bactericide if the MBC is no more than four times the MIC value [29] which was observed for R. carthamoides HR and SGR essential oils. Therefore, these essential oils may be effective as bactericidal agents.…”

Section: Discussionmentioning

confidence: 99%

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Skała

Rijo

García

et al. 2016

Oxidative Medicine and Cellular Longevity

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The essential oils were isolated by hydrodistillation from the hairy roots (HR) and roots of soil-grown plants (SGR) of Rhaponticum carthamoides and were analyzed by GC-MS method. In the both essential oils 62 compounds were identified. The root essential oils showed the differences in the qualitative and quantitative composition. The sesquiterpene hydrocarbons (55–62%) dominated in both essential oils. The major compounds of HR essential oil were cyperene, 13-norcypera-1(5),11(12)-diene, and cadalene while aplotaxene, nardosina-1(10),11-diene, and dauca-4(11),8-diene dominated in SGR essential oil. Both essential oils showed antibacterial activity especially against Enterococcus faecalis (ATCC 29212) and Pseudomonas aeruginosa (ATCC 27853) (MIC value = 125 µg/mL). HR and SGR essential oils also decreased the expression of IL-1β, IL-6, and TNF-α and the ROS level in LPS-treatment astrocytes. This is the first report to describe the chemical composition of R. carthamoides essential oil from hairy roots, its protective effect against LPS-induced inflammation and ROS production in astrocytes, and its antimicrobial potential. The results show that R. carthamoides hairy roots may be a valuable source of the essential oil and may be an alternative to the roots of soil-grown plants.

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Section: Discussionmentioning

confidence: 99%

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Skała

Rijo

García

et al. 2016

Oxidative Medicine and Cellular Longevity

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“…Synthesis and spectral characterization of compounds HNPMI [25], THMPP [26] and THTMP [29] ( Figure 1A) were previously reported. These compounds and temozolomide (Sigma-Aldrich, St. Louis, MO, USA) were dissolved in dimethyl sulphoxide (DMSO, Sigma-Aldrich) to obtain a stock solution of 100 mM.…”

Section: Chemical Preparationmentioning

confidence: 81%

Glioblastoma Multiforme Stem Cell Cycle Arrest by Alkylaminophenol through the Modulation of EGFR and CSC Signaling Pathways

Doan

Musa

Murugesan

et al. 2020

Cells

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Cancer stem cells (CSCs), a small subpopulation of cells existing in the tumor microenvironment promoting cell proliferation and growth. Targeting the stemness of the CSC population would offer a vital therapeutic opportunity. 3,4-Dihydroquinolin-1(2H)-yl)(p-tolyl)methyl)phenol (THTMP), a small synthetic phenol compound, is proposed to play a significant role in controlling the CSC proliferation and survival. We assessed the potential therapeutic effects of THTMP on glioblastoma multiforme (GBM) and its underlying mechanism in various signaling pathways. To fully comprehend the effect of THTMP on the CSCs, CD133 + GBM stem cell (GSC) and CD133 -GBM Non-stem cancer cells (NSCC) population from LN229 and SNB19 cell lines was used. Cell cycle arrest, apoptosis assay and transcriptome analysis were performed for individual cell population. THTMP strongly inhibited NSCC and in a subtle way for GSC in a time-dependent manner and inhibit the resistance variants better than that of temozolomide (TMZ). THTMP arrest the CSC cell population at both G1/S and G2/M phase and induce ROS-mediated apoptosis. Gene expression profiling characterize THTMP as an inhibitor of the p53 signaling pathway causing DNA damage and cell cycle arrest in CSC population. We show that the THTMP majorly affects the EGFR and CSC signaling pathways. Specifically, modulation of key genes involved in Wnt, Notch and Hedgehog, revealed the significant role of THTMP in disrupting the CSCs' stemness and functions. Moreover, THTMP inhibited cell growth, proliferation and metastasis of multiple mesenchymal patient-tissue derived GBM-cell lines. THTMP arrests GBM stem cell cycle through the modulation of EGFR and CSC signaling pathways.

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“…Well diffusion method was chosen to evaluate the antimicrobial activity and minimum inhibitory concentration (MIC) of the synthesized compounds (Neto et al, ). The microorganisms used in the in vitro antimicrobial study include Gram‐positive bacterial strains S. aureus ATTCC 6538 and Bacillus subtilis ATCC 663 and Gram‐negative bacterial strains E. coli ATTCC 8739 and P. aeruginosa ATCC 9027 while C. albicans 10231 was used as fungal strain reference.…”

Section: Methodsmentioning

confidence: 99%

Investigation of a new horizon antifungal activity with enhancing the antimicrobial efficacy of ciprofloxacin and its binary mixture via their encapsulation in nanoassemblies: in vitro and in vivo evaluation

Taleb

Darwish

Abood

et al. 2019

Drug Development Research

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The main goal of this study was to prepare and evaluate nanosponges containing ciprofloxacin (CIP) or its binary mixture with N-acetyl carnosine (NAC). Nanosponges were prepared by ultrasound-assisted synthesis technique using hydroxypropyl βetacyclodextrin (HPβ-CD), as the polymer and diphenyl carbonate (DPC) as the crosslinker. Entrapment efficiency (EE%) of CIP or its binary mixture with NAC in nanosponges was deduced spectrophotometrically. Nanosponges were characterized using several methods. EE% of CIP or its binary mixture with NAC inside nanosponges ranged from 98.63 ± 3.1 to 100 ± 0.07%. Particle size of nanosponges ranged from 66.7 to 90.1 nm. Release of drugs from nanosponges was biphasic and the release pattern followed Korsmeyer-Peppas model. Ex vivo and in vivo studies results showed that the antibacterial effect was enhanced with encapsulation of drugs in the nanosponge system. Furthermore, a potent antifungal activity was obtained from all examined formulae against Candida albicans (10231). The study revealed that successful encapsulation of CIP or its binary mixture with NAC in nanosponge formulations has innovated a new promising therapeutic activity for both drugs. K E Y W O R D S antibacterial efficacy, antifungal activity, ciprofloxacin, N-acetyl carnosine, nanosponge, ocular

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Multicomponent Petasis‐borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies

Cited by 34 publications

References 54 publications

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

The Essential Oils of Rhaponticum carthamoides Hairy Roots and Roots of Soil‐Grown Plants: Chemical Composition and Antimicrobial, Anti‐Inflammatory, and Antioxidant Activities

Glioblastoma Multiforme Stem Cell Cycle Arrest by Alkylaminophenol through the Modulation of EGFR and CSC Signaling Pathways

Investigation of a new horizon antifungal activity with enhancing the antimicrobial efficacy of ciprofloxacin and its binary mixture via their encapsulation in nanoassemblies: in vitro and in vivo evaluation

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