Anticancer activity of a novel quinazolinone-chalcone derivative through cell cycle arrest in pancreatic cancer cell line

Wani, Zahoor A.; Pathania, Anup Singh; Mahajan, Girish; Behl, Akanksha; Mintoo, Mubashir J.; Guru, Santosh Kumar; Arutla, Viswanath; Malik, Fayaz; Kamal, Ähmed; Mondhe, Dilip M.

doi:10.5430/jst.v5n2p73

Cited by 12 publications

(8 citation statements)

References 25 publications

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“…Group A: Chalcones arrest the cell cycle at the G1/S phase, i.e., dimethyl cardamonin(27) [30], tetramethoxychalcone (34)[28], 2′-hydroxy-2,3,4′,6′-tetramethoxychalcone (35)[34], and tetrahydro-[1,2,4]triazolo[3,4-a]isoquinoline chalcones(36) [35]. Group B: Chalcones that arrest the cell cycle at the G2/M phase chalcone (1)[29], isoliquiritigenin(22) [36], (2E)-3-(acridin-9-yl)-1-(2,6-dimethoxyphenyl)prop-2-en-1-one (37)[37], and quinazolinone-chalcone(38) [38].…”

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Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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Chalcones belong to the flavonoid class of phenolic compounds. They form one of the largest groups of bioactive natural products. The potential anticancer, anti-inflammatory, antimicrobial, antioxidant, and antiparasitic properties of naturally occurring chalcones, and their unique chemical structural features inspired the synthesis of numerous chalcone derivatives. In fact, structural features of chalcones are easy to construct from simple aromatic compounds, and it is convenient to perform structural modifications to generate functionalized chalcone derivatives. Many of these synthetic analogs were shown to possess similar bioactivities as their natural counterparts, but often with an enhanced potency and reduced toxicity. This review article aims to demonstrate how bioinspired synthesis of chalcone derivatives can potentially introduce a new chemical space for exploitation for new drug discovery, justifying the title of this article. However, the focus remains on critical appraisal of synthesized chalcones and their derivatives for their bioactivities, linking to their interactions at the biomolecular level where appropriate, and revealing their possible mechanisms of action.

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Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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“…A number of studies have investigated the anticancer activity of quinazoline and quinazolinone derivatives [ 20 , 21 , 22 , 23 , 24 , 25 ]. Different types of cancers and cell targets were examined to achieve a novel quinazolinone derivative possessing significant anticancer activity.…”

Section: Biological Activities Of 4(3 H )-Quinazol...mentioning

confidence: 99%

“…Different types of cancers and cell targets were examined to achieve a novel quinazolinone derivative possessing significant anticancer activity. Wani and coworkers investigated the anticancer activity of a quinazolinone-chalcone derivative by cell cycle arrest in pancreatic cancer cell lines [ 20 ]. Chalcone, and its derivatives, is a well-studied chemical moiety with various biological activities such as anti-inflammatory, antimalarial, and anticancer activities.…”

Section: Biological Activities Of 4(3 H )-Quinazol...mentioning

confidence: 99%

“…Moreover, this study found that one compound significantly inhibited the growth of different cell lines including Ehrlich Ascites Carcinoma and Sarcoma-180. This research concluded that the anticancer activity of this derivative is exerted through the cell cycle arrest at the G2/M phase [ 20 ].…”

Section: Biological Activities Of 4(3 H )-Quinazol...mentioning

confidence: 99%

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Quinazolinones, the Winning Horse in Drug Discovery

2023

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Quinazolines are nitrogen-containing heterocycles that consist of a benzene ring fused with a pyrimidine ring. Quinazolinones, oxidized quinazolines, are promising compounds with a wide range of biological activities. In the pharmaceutical field, quinazolinones are the building blocks of more than 150 naturally occurring alkaloids isolated from different plants, microorganisms, and animals. Scientists give a continuous interest in this moiety due to their stability and relatively easy methods for preparation. Their lipophilicity is another reason for this interest as it helps quinazolinones in penetration through the blood–brain barrier which makes them suitable for targeting different central nervous system diseases. Various modifications to the substitutions around the quinazolinone system changed their biological activity significantly due to changes in their physicochemical properties. Structure–activity relationship (SAR) studies of quinazolinone revealed that positions 2, 6, and 8 of the ring systems are significant for different pharmacological activities. In addition, it has been suggested that the addition of different heterocyclic moieties at position 3 could increase activity. In this review, we will highlight the chemical properties of quinazolinones, including their chemical reactions and different methods for their preparation. Moreover, we will try to modify some of the old SAR studies according to their updated biological activities in the last twelve years.

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“…Clearly, as an anticancer agent it is necessary to find drugs with minimum adverse effects those provide more hope for patients. Hence, the use of chalcone derivatives was considered for minimizing unwanted side effects [22,23,24,25]. In addition, several studies revealed the ability of chalcone derivatives to become an important antimicrobial, antifungal, anti-mycobacterial, antimalarial, antiviral, anti-inflammatory, antioxidant, antileishmanial anti-tumor, and anticancer agents [26,27,28].…”

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confidence: 99%

Structure-Based Drug Design Studies Toward the Discovery of Novel Chalcone Derivatives as Potential Epidermal Growth Factor Receptor (EGFR) Inhibitors

2018

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Human Epidermal Growth Factor Receptor-1 (EGFR), a transmembrane tyrosine kinase receptor (RTK), has been associated with several types of cancer, including breast, lung, ovarian, and anal cancers. Thus, the receptor was targeted by a variety of therapeutic approaches for cancer treatments. A series of chalcone derivatives are among the most highly potent and selective inhibitors of EGFR described to date. A series of chalcone derivatives were proposed in this study to investigate the intermolecular interactions in the active site utilizing molecular docking and molecular dynamics simulations. After a careful analysis of docking results, compounds 1a and 1d were chosen for molecular dynamics simulation study. Extensive hydrogen bond analysis throughout 7 ns molecular dynamics simulation revealed the ability of compounds 1a and 1d to retain the essential interactions needed for the inhibition, especially MET 93. Finally, MM-GBSA calculations highlight on the capability of the ligands to bind strongly within the active site with binding energies of −44.04 and −56.6 kcal/mol for compounds 1a and 1d, respectively. Compound 1d showed to have a close binding energy with TAK-285 (−66.17 kcal/mol), which indicates a high chance for compound 1d to exhibit inhibitory activity, thus recommending to synthesis it to test its biological activity. It is anticipated that the findings reported here may provide very useful information for designing effective drugs for the treatment of EGFR-related cancer disease.

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Anticancer activity of a novel quinazolinone-chalcone derivative through cell cycle arrest in pancreatic cancer cell line

Cited by 12 publications

References 25 publications

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Quinazolinones, the Winning Horse in Drug Discovery

Structure-Based Drug Design Studies Toward the Discovery of Novel Chalcone Derivatives as Potential Epidermal Growth Factor Receptor (EGFR) Inhibitors

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