Diazenyl Derivatives and their Complexes as Anticancer Agents

Kaur, Harmeet; Yadav, Snehlata; Narasimhan, Balasubramanian

doi:10.2174/1871520616666160607012042

“…The products of coupling reaction are colorful azo compounds (R 1 -N=N-R 2 ), which are widely used as azo dyes and pigments in the textile, food, and cosmetics industries, and as therapeutic agents [69][70][71]. Currently, researchers are screening the aromatic azo compounds for their potential biomedical use, including cancer diagnosis and therapy [72]. The high reactivity of these reagents makes them good candidates for protein labeling, especially in the case of peptides containing a tyrosine residue.…”

Section: Capturing Tyrosine-containing Peptides By Diazonium Saltsmentioning

confidence: 99%

Veni, Vidi, Vici: Immobilized Peptide-Based Conjugates as Tools for Capture, Analysis, and Transformation

Kowalska

¹

,

Popiel

²

,

Walter

³

et al. 2022

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Analysis of peptide biomarkers of pathological states of the organism is often a serious challenge, due to a very complex composition of the cell and insufficient sensitivity of the current analytical methods (including mass spectrometry). One of the possible ways to overcome this problem is sample enrichment by capturing the selected components using a specific solid support. Another option is increasing the detectability of the desired compound by its selective tagging. Appropriately modified and immobilized peptides can be used for these purposes. In addition, they find application in studying the specificity and activity of proteolytic enzymes. Immobilized heterocyclic peptide conjugates may serve as metal ligands, to form complexes used as catalysts or analytical markers. In this review, we describe various applications of immobilized peptides, including selective capturing of cysteine-containing peptides, tagging of the carbonyl compounds to increase the sensitivity of their detection, enrichment of biological samples in deoxyfructosylated peptides, and fishing out of tyrosine–containing peptides by the formation of azo bond. Moreover, the use of the one-bead-one-compound peptide library for the analysis of substrate specificity and activity of caspases is described. Furthermore, the evolution of immobilization from the solid support used in peptide synthesis to nanocarriers is presented. Taken together, the examples presented here demonstrate immobilized peptides as a multifunctional tool, which can be successfully used to solve multiple analytical problems.

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“…Azo dyes are the most widely used class of colouring materials owing to various applications in various fields such as dying textile fibres, the colouring of different materials, biomedical studies and in advanced organic synthesis [21, 22]. Azo compounds and their derivatives are also known for their use as antibacterial, antifungal, antidiabetics, antineoplastics, anti-inflammatory, antiseptic and other useful chemotherapeutic agents [23, 24]. Several azo compounds particularly synthesized from β-naphthol, m -resorcinol, tyrosine, aspirin, paracetamol etc.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial, antioxidant and cytotoxic evaluation of diazenyl chalcones along with insights to mechanism of interaction by molecular docking studies

Kaur

¹

,

Singh

²

,

Narasimhan

³

2019

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Background In continuation of our work, new diazenyl chalcones scaffolds ( C-18 to C-27 ) were efficiently synthesized from substituted acetophenone azo dyes ( A – E ) by base catalyzed Claisen–Schmidt condensation with different substituted aromatic/heteroaromatic aldehydes. Methodology The synthesized chalcones were assessed for their in vitro antimicrobial potential towards several pathogenic microbial strains by tube dilution method and further evaluated for antioxidant potential by DPPH assay. These derivatives were also assessed for the cytotoxicity towards the human lung cancer cell line (A549) and normal cell line (HEK) by MTT assay. The most active antimicrobial compounds were docked using Schrodinger v 18.1 software with the various potential bacterial receptors to explore the mechanism of interaction. Results The derivative C-22 exhibited high antibacterial activity with very low MIC (1.95–3.90 µg ml −1 ) and MBC (3.90–7.81 µg ml −1 ) values. The derivatives C-23 , C-24 and C-27 have demonstrated good antioxidant potential (IC 50 = 7–18 µg ml −1 ) correlated to the ascorbic acid (IC 50 = 4.45 µg ml −1 ). The derivative C-25 had shown comparable cytotoxicity to camptothecin against A549 cell line. The docking studies predicted the bacterial dihydrofolate reductase (PDB ID: 3SRW) and bacterial DNA gyrase (PDB ID: 4ZVI) as the possible targets for most of the active antimicrobial compounds. These derivatives affirmed their safety by presenting less cytotoxicity towards HEK cells. Further the ADME prediction by qikprop module of the Schrodinger proved that these compounds exhibited drug-like attributes. Conclusion Hence, these compounds have shown their potential as lead for future expansion of novel antimicrobial and cytotoxic drugs. Electronic supplementary material The online version of this article (10.1186/s13065-019-0596-5) contains supplementary material, which is available to authorized users.

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“…diazeniumdiolate prodrugs, diazenecarboxamides, diazenyl complexes etc.) have been already reported for their cytotoxic potential against different cancer cell lines in recent years [28–30]. These derivatives also reported having antimicrobial activity [31, 32].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of novel naphthol diazenyl scaffold based Schiff bases as potential antimicrobial and cytotoxic agents against human colorectal carcinoma cell line (HT-29)

Kaur

¹

,

Singh

²

,

Narasimhan

³

2019

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Background In search of new antimicrobial and cytotoxic agents, a series of new naphthol diazenyl scaffold based Schiff bases ( NS1 – NS23 ) was efficiently synthesized by condensation of 2-hydroxy naphthaldehyde azo dyes with various substituted aromatic/heteroaromatic/aliphatic amines. Methodology The synthesized derivatives were characterized by various physicochemical and spectral techniques and assessed for in vitro antimicrobial and cytotoxic potential against human colorectal carcinoma cell line (HT-29). The active derivatives were further evaluated for their apoptotic potential by Annexin-V/propidium iodide double staining assay using flow cytometer and analyzed for cell-cycle arrest studies. Results and conclusion The derivative NS-2 was found maximum active against E . coli , S. enterica and B. subtilis . The derivatives NS-12 , NS-15 , NS-21 , and NS-23 showed maximum antifungal activity against A. fumigatus . The maximum cytotoxicity was observed from the derivatives NS-2 , NS-8 , NS-21 , and NS-23 towards HT-29 cell line with IC 50 between 4 and 19 μg/ml. More than 90% and 62% of the cells were found in the apoptotic phase on treatment with NS-2 and NS-21 respectively in comparison to the 68% for doxorubicin. Further, these derivatives arrested the cell growth in S and G2/M phase of the cell cycle. Electronic supplementary material The online version of this article (10.1186/s13065-019-0558-y) contains supplementary material, which is available to authorized users.

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Diazenyl Derivatives and their Complexes as Anticancer Agents

Cited by 7 publications

References 0 publications

Veni, Vidi, Vici: Immobilized Peptide-Based Conjugates as Tools for Capture, Analysis, and Transformation

Veni, Vidi, Vici: Immobilized Peptide-Based Conjugates as Tools for Capture, Analysis, and Transformation

Antimicrobial, antioxidant and cytotoxic evaluation of diazenyl chalcones along with insights to mechanism of interaction by molecular docking studies

Synthesis and evaluation of novel naphthol diazenyl scaffold based Schiff bases as potential antimicrobial and cytotoxic agents against human colorectal carcinoma cell line (HT-29)

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