Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies

Senwar, Kishna Ram; Sharma, Pankaj; Reddy, T. Srinivasa; Jeengar, Manish Kumar; Nayak, V. Lakshma; Naidu, V.G.M.; Kamal, Ähmed; Shankaraiah, Nagula

doi:10.1016/j.ejmech.2015.08.017

Cited by 119 publications

(53 citation statements)

References 23 publications

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“…DAPI nuclear staining revealed different responses in terms of apoptosis after the treatment with the tested samples, dependent of the cell line genotype (ER−/ER+). Typical signs of apoptosis (chromatin condensation and nuclear membrane blebbing) [62] were marked with yellow arrows, while alterations of cell nuclei morphology were highlighted by a yellow circle, considered also as a specific feature of apoptosis [63].…”

Section: Apoptosis Assessment Of Breast Adenocarcinoma Mcf-7 and Mda-mentioning

confidence: 99%

Lemon Balm Extracts Prevent Breast Cancer Progression In Vitro and In Ovo on Chorioallantoic Membrane Assay

Ghiulai

Avram

Stoian

et al. 2020

Evidence-Based Complementary and Alternative Medicine

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Breast cancer is the most frequently diagnosed malignant pathology, representing the primary cause of cancer death in women. Natural products are an appealing strategy to limit the progression of the disease. Targeting angiogenesis in breast cancer may positively impact on poor prognosis of breast cancer. As source of natural compounds, we investigated the leaves of Melissa officinalis L. (MO), known as lemon balm, an aromatic plant that spontaneously grows in the South and Western areas of Romania, being traditionally recommended as anxiolytic, antispasmodic, or as digestive remedy. Our aim was to investigate the phytochemical profiling and the antiangiogenic and chemopreventive bioactivity of MO from Banat region, on breast cancer. Two ethanolic extracts of MO (MOE96 and MOE70) and one methanolic extract (MOM80) were subjected to polyphenol and triterpene profiling by HPLC-MS, and the antioxidant capacity was evaluated. The antiangiogenic potential was investigated using the chorioallantoic membrane assay (CAM). The MTT(3-(4,5-dimethylthiazol-2-yl)-2-5-diphenyltetrazolium bromide) assay was used to investigate the cytotoxic effects on MCF-7 and MDA-MB-231breast cancer cells, as well as on MCF-10A normal breast epithelial cells, while apoptosis was performed by DAPI staining. Rosmarinic acid (RA) and ursolic acid (UA) were revealed as dominant phytocompounds. The highest concentration in phytochemicals were found in MOM80; MOE96 was more concentrated in UA, while MOE70 extracted more RA. MOE96 inhibited cancer progression and angiogenesis in the in ovo CAM model using MDA-MB-231 cells, inhibiting breast cancer progression and angiogenesis for the MDA-MB-231 breast cancer cell line; no secondary tumoral areas were registered, indicative for a preventive effect against breast tumor cell invasiveness. The highest cell inhibitory activity was also exhibited by MOE96, in particular against the estrogen receptor positive MCF7 breast cancer cell line, with no cytotoxic effect on healthy cells. The estrogen receptor positive MCF7 cell line proved to be more sensitive to the extract antiproliferative activity than the triple negative MDA-MB-231 breast cancer cell line. Nevertheless, the chemopreventive potential of MOE96 extract is phenotype-dependent and is rather related to the apoptosis and antiangiogenic effects suggesting a multitargeted mechanism of action due to its multiple compound composition next to a concentration ratio of RA : UA in favor of UA.

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Section: Apoptosis Assessment Of Breast Adenocarcinoma Mcf-7 and Mda-mentioning

confidence: 99%

Lemon Balm Extracts Prevent Breast Cancer Progression In Vitro and In Ovo on Chorioallantoic Membrane Assay

Ghiulai

Avram

Stoian

et al. 2020

Evidence-Based Complementary and Alternative Medicine

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“…The available chemotherapeutic drugs face several limitations such as drug resistance, high systemic toxicity, complex synthesis, and isolation procedures . Therefore, there is a demand for the development of efficient and secure anticancer agents with high efficiency and less toxicity as a major and immediate need of research across the world …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis of (Z)‐3‐benzyl‐5‐((1‐phenyl‐3‐(3‐((1‐ substituted phenyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐1H‐pyrazol‐4‐yl)methylene)thiazolidine‐2,4‐dione analogues as potential cytotoxic agents

Kolluri

Gurrapu

Edigi

et al. 2019

Journal of Heterocyclic Chem

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In an attempt to achieve promising cytotoxic agents, a series of new (Z)‐3‐benzyl‐5‐((1‐phenyl‐3‐(3‐((1‐substituted phenyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐1H‐pyrazol‐4‐yl)methylene)thiazolidine‐2,4‐diones 10 a‐n were designed, synthesized, and characterized by 1H NMR, 13C NMR, IR, and ESI‐MS techniques. These compounds synthesized from appropriate reaction procedures with better yields. All the novel synthesized compounds 10a‐n were evaluated for their cytotoxic activity against the MCF‐7 cell line (Human breast cancer cell line) at different concentrations of 0.625, 1.25, 2.5, 5, and 10 μM, respectively. The cytotoxic evaluation assay is presented in terms of IC50 values and percentage cell viability reduction compared against standard drug cisplatin. Among all novel synthesized compounds 10a‐n, some of the representative analogues particularly 10g and 10e exhibit remarkable cytotoxic activity with IC50 values 0.454 and 0.586 μM, comparable to that of the standard drug cisplatin, and some analogues 10d, 10f, 10k, and 10m also have shown significant activity.

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“…Among heterocyclic pharmacophores, the benzimidazole ring system is quite common, which was first synthesized by Hoebrecker and subsequent exploration by Ladnberg and Wundt during late 1870s . Such a heterocyclic scaffolds “benzimidazole” has been known as a “major scaffold” considering for their broad spectrum of biological profiles and empathies towards different targets .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Some New Benzimidazole Containing Pyrazoles and Pyrazolyl Thiazoles as Potential Antimicrobial Agents

Reddy

Zyryanov

Reddy

et al. 2018

Journal of Heterocyclic Chem

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A new class of bis heterocycles‐benzimidazolyl pyrazoles were prepared from the Michael acceptor (E)‐3‐(1H‐benzimidazol‐2‐yl)‐1‐aryl‐prop‐2‐en‐1‐one. The thiamide group was exploited to develop thiazole ring on treatment with p‐fluorophenacyl bromide to get tris heterocycles. All the lead compounds were tested for antimicrobial activity. The compound 7d having nitro substituent on the aromatic ring showed greater antimicrobial activity particularly against Pseudomonas aeruginosa and Penicillium chrysogenum.

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Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies

Cited by 119 publications

References 23 publications

Lemon Balm Extracts Prevent Breast Cancer Progression In Vitro and In Ovo on Chorioallantoic Membrane Assay

Lemon Balm Extracts Prevent Breast Cancer Progression In Vitro and In Ovo on Chorioallantoic Membrane Assay

Design, synthesis of (Z)‐3‐benzyl‐5‐((1‐phenyl‐3‐(3‐((1‐ substituted phenyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐1H‐pyrazol‐4‐yl)methylene)thiazolidine‐2,4‐dione analogues as potential cytotoxic agents

Design and Synthesis of Some New Benzimidazole Containing Pyrazoles and Pyrazolyl Thiazoles as Potential Antimicrobial Agents

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