Synthesis and antiproliferative activity of novel polynuclear heterocyclic compounds derived from 2,3-diaminophenazine

Mahran, Asma M.; Ragab, Sherif Shaban; Hashem, Ahmed I.; Ali, Mamdouh M.; Nada, A. A.

doi:10.1016/j.ejmech.2013.12.007

Cited by 18 publications

(12 citation statements)

References 24 publications

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“…These compounds also showed inhibitory activity of human tyrosine kinases. The experimental results of inhibiting human tyrosine kinase were consistent with cell cytotoxicity activity [20]. showed that the carboxyl substituents on position 7 did not interact with each other through hydrogen bonds.…”

Section: Benzo[a]pyran[23-c]phenazine Derivativessupporting

confidence: 70%

“…Phenazine derivatives display antibacterial activity mainly against methicillin-resistant due to redox properties [17]. According to reports in recent years, phenazine derivatives possessed antiproliferative activities against various cancer cell lines [18][19][20][21]. Additionally, phenazine derivatives were candidates to be developed as inhibitors of disease-related targets and reported to show activity of inhibition to multiple enzymes [22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

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Advances in Phenazines over the Past Decade: Review of Their Pharmacological Activities, Mechanisms of Action, Biosynthetic Pathways and Synthetic Strategies

et al. 2021

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Phenazines are a large group of nitrogen-containing heterocycles, providing diverse chemical structures and various biological activities. Natural phenazines are mainly isolated from marine and terrestrial microorganisms. So far, more than 100 different natural compounds and over 6000 synthetic derivatives have been found and investigated. Many phenazines show great pharmacological activity in various fields, such as antimicrobial, antiparasitic, neuroprotective, insecticidal, anti-inflammatory and anticancer activity. Researchers continued to investigate these compounds and hope to develop them as medicines. Cimmino et al. published a significant review about anticancer activity of phenazines, containing articles from 2000 to 2011. Here, we mainly summarize articles from 2012 to 2021. According to sources of compounds, phenazines were categorized into natural phenazines and synthetic phenazine derivatives in this review. Their pharmacological activities, mechanisms of action, biosynthetic pathways and synthetic strategies were summarized. These may provide guidance for the investigation on phenazines in the future.

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Section: Benzo[a]pyran[23-c]phenazine Derivativessupporting

confidence: 70%

Section: Introductionmentioning

confidence: 99%

Advances in Phenazines over the Past Decade: Review of Their Pharmacological Activities, Mechanisms of Action, Biosynthetic Pathways and Synthetic Strategies

et al. 2021

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“…reported the synthesis of novel phenazine derivatives with apoptotic activity in a variety of cancer cell lines; the exact mechanism of action was not determined [11] . In addition, derivatives of 2,3‐diaminophenazine were determined to slow lung carcinoma and colorectal cancer cell line proliferation through inhibition of human tyrosine kinase [12] . Some literature suggest that phenazines are capable of intercalating DNA and may have general toxicity [13] …”

Section: Resultsmentioning

confidence: 99%

Identification of Phenazine‐Based MEMO1 Small‐Molecule Inhibitors: Virtual Screening, Fluorescence Polarization Validation, and Inhibition of Breast Cancer Migration

et al. 2021

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Phosphorylation‐dependent protein–protein interactions play a significant role in biological signaling pathways; therefore, small molecules that are capable of influencing these interactions can be valuable research tools and have potential as pharmaceutical agents. MEMO1 (mediator of ErbB2‐cell driven motility) is a phosphotyrosine‐binding protein that interacts with a variety of protein partners and has been found to be upregulated in breast cancer patients. Herein, we report the first small‐molecule inhibitors of MEMO1 interactions identified through a virtual screening platform and validated in a competitive fluorescence polarization assay. Initial structure–activity relationships have been investigated for these phenazine‐core inhibitors and the binding sites have been postulated using molecular dynamics simulations. The most potent biochemical inhibitor is capable of disrupting the large protein interface with a KI of 2.7 μm. In addition, the most promising phenazine core compounds slow the migration of breast cancer cell lines in a scratch assay.

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“…In nature, phenazines with broad bioactivity are products of the idiophase of different bacteria, especially from Pseudomonas and Streptomyces strains [4,5]. Both natural and synthetic phenoxazines and phenazines known from the literature exhibit biological activities such as antibacterial [6][7][8], antitumoral [9], antiproliferative [10], and antioxidant [11] properties. The chemical route of phenazine synthesis requires the use of coupling agents and additives such as benzene, BBr 3 , DMF, and various other harsh, toxic, and mutagenic compounds [12].…”

Section: Introductionmentioning

confidence: 99%

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Polak

Wlizło

Pogni

et al. 2020

IJMS

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Novel sustainable processes involving oxidative enzymatic catalysts are considered as an alternative for classical organic chemistry. The unique physicochemical and bioactive properties of novel bio-products can be obtained using fungal laccase as catalyst. Among them are textile biodyes synthesised during oxidation of substrates belonging to the amine and methoxy organic derivatives. The process of synthesis occurs in mild conditions of pH, temperature, and pressure, and without using harmful oxidants. The effect of fungal laccase activity on the substrates mixture transformation efficiency was analysed in terms of antimicrobial dye synthesis on a large scale. Three new phenazine dyes, obtained in the presence of laccase from Cerrena unicolor, were studied for their structure and properties. The phenazine core structure of the products was a result of tri-molecular transformation of aminomethoxybenzoic acid and aminonaphthalene sulfonic acid isomers. One of the compounds from the synthesised dye, namely 10-((2-carboxy-6-methoxyphenyl)amino)-11-methoxybenzo[a]phenazine-8-carboxylic acid, was able to inhibit the growth of Staphylococcus aureus. The high concentration of substrates (5 g/L) was efficiently transformed during 72 h in the mild conditions of pH 4 with the use of laccase with an activity of 200 U per g of the substrates mixture. The new bioactive dye exhibited excellent dyeing properties with concomitant antibacterial and antioxidative activity. The proposed enzyme-mediated synthesis represents an alternative eco-friendly route for the synthesis of novel antimicrobial compounds with high importance for the medical textile industry.

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Synthesis and antiproliferative activity of novel polynuclear heterocyclic compounds derived from 2,3-diaminophenazine

Cited by 18 publications

References 24 publications

Advances in Phenazines over the Past Decade: Review of Their Pharmacological Activities, Mechanisms of Action, Biosynthetic Pathways and Synthetic Strategies

Advances in Phenazines over the Past Decade: Review of Their Pharmacological Activities, Mechanisms of Action, Biosynthetic Pathways and Synthetic Strategies

Identification of Phenazine‐Based MEMO1 Small‐Molecule Inhibitors: Virtual Screening, Fluorescence Polarization Validation, and Inhibition of Breast Cancer Migration

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

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