DNA binding ability and cytotoxicity, cell cycle arrest and apoptosis inducing properties of a benzochromene derivative against K562 human leukemia cells

Ahagh, Mina Hanifeh; Dehghan, Gholamreza; Mahdavi, Majid; Feizi, Mohammad Ali Hosseinpour; Teimuri‐Mofrad, Reza; Payami, Elmira; Mehdipour, Maryam; Rashtbari, Samaneh

doi:10.1080/15257770.2021.1937644

Cited by 3 publications

(4 citation statements)

References 37 publications

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“…The current investigation incorporates different substituents on the chromene moieties in order to optimize the biological performance of the target drug candidates. In the literature, there is a comparative analysis between molecules integrating nitrile functional moieties versus alkoxy carbonyl motifs in cancer therapeutics research [35,36,70]. Both possess promising antitumor activities; however, the anticancer performance varies in accordance with the molecular structure and the type of cancer cell line.…”

Section: Chemistrymentioning

confidence: 99%

“…In addition, they are potential succinate dehydrogenase inhibitors [31] and tyrosinase inhibitors [32], and they have utility as raw materials in dye and pigment production [33]. The 2-amino-4H-chromene skeleton is one of the preferred structural motifs in a wide range of natural products, as well as pharmaceuticals with a plethora of pharmacological effects, including anticancer, antibacterial, antioxidant, and antihypertensive properties; Chart 1 [34][35][36][37]. For instance, the high-affinity insulin-controlled aminopeptidase inhibitor 2-amino-4-aryl-4H-chromene (HFI-437) has the potential to be implemented in the treatment of neurodegenerative illness [34].…”

Section: Introductionmentioning

confidence: 99%

“…For instance, the high-affinity insulin-controlled aminopeptidase inhibitor 2-amino-4-aryl-4H-chromene (HFI-437) has the potential to be implemented in the treatment of neurodegenerative illness [34]. A tubulin inhibitor known as compound MX 58151 was employed; it binds at or near the colchicine site of tubulin [35]. EPC2407 (crinobulin) is also a potential apoptosis inducer and vascular-targeting anticancer drug in the therapy of progressed solid tumors [36].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

Alblewi,

Alsehli,

Hritani

et al. 2023

IJMS

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In this study, novel selective antitumor compounds were synthesized based on their fundamental pharmacophoric prerequisites associated with EGFR inhibitors. A molecular hybridization approach was employed to design and prepare a range of 4H-chromene-3-carboxylates 7a–g, 8, and 11a–e derivatives, each incorporating a sulfonamide moiety. The structures of these hybrid molecules were verified using comprehensive analytical and spectroscopic techniques. During the assessment of the newly synthesized compounds for their anticancer properties against three tumor cell lines (HepG-2, MCF-7, and HCT-116), compounds 7f and 7g displayed remarkable antitumor activity against all tested cell lines, outperforming the reference drug Cisplatin in terms of efficacy. Consequently, these promising candidates were selected for further investigation of their anti-EGFR, hCAII, and MMP-2 potential, which exhibited remarkable effectiveness against EGFR and MMP2 when compared to Sorafenib. Additionally, docking investigations regarding the EGFR binding site were implemented for the targeted derivatives in order to attain better comprehension with respect to the pattern in which binding mechanics occur between the investigated molecules and the active site, which illustrated a higher binding efficacy in comparison with Sorafenib.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

Alblewi,

Alsehli,

Hritani

et al. 2023

IJMS

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“…15 Their medicinal potency as anticancer and antitumor drugs is dependent on their DNA binding affinity. While the presence of polar functional groups on these drugs can form various classical hydrogen bonds with DNA, 16 the chirality of the drugs can also influence their DNA binding affinity. 17 Since these drugs are mostly used as racemic compounds, the correlation between the in silico and experimental DNA binding affinities can prove to be challenging.…”

Section: Introductionmentioning

confidence: 99%

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Zamisa

Ngubane

Adeleke

et al. 2022

Crystal Growth & Design

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Four 2-amino-4-(aryl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (Series I) and three 2-amino-1phenyl-7,7-dimethyl-5-oxo-4-(aryl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (Series II) derivatives were formed via multicomponent microwave reactions as racemic mixtures. The solid-state IR spectra revealed bands in the region between 3190 and 3414 cm −1 attributed to the amino functional group's asymmetric, symmetric, and bending overtone vibration modes. Furthermore, the IR spectra of some of the compounds in each series were similar and this served as an indication of similar structural features in the solid state. This was confirmed via single-crystal X-ray diffraction. A detailed survey of the related 2-amino-3-carbonitrile derivatives in the Cambridge Structural Database revealed 12 classical intermolecular hydrogen-bonding motifs involving the amino functional group. The vast variation in the hydrogen bonding motifs was found to be caused by the type of group bonded to the 4H-pyran (in Series I) or dihydropyridine (in Series II) moiety. In this work, an unprecedented hydrogen bonding motif comprising a non-classical hydrogen bond acceptor was found in one instance. For both Series I and II, the N−H•••N and N−H•••O hydrogen bonds were investigated using noncovalent interaction (NCI) plots and molecular pairwise energy calculations. The contributions of reciprocal N•••H and O•••H contacts (attributed to N−H•••N and N−H•••O, respectively) toward the Hirshfeld surface range between 9.9 and 15.3% in Series I and between 10.8 and 15.0% in Series II. In addition, the compounds showed moderate to good binding affinity to calf thymus DNA (CT-DNA) with intrinsic binding constants (K b ) between 8.00 × 10 4 and 5.00 × 10 5 M −1 for Series I compounds and between 6.60 × 10 4 and 1.45 × 10 5 M −1 for Series II. A relationship was established between the reciprocal N•••H to O•••H contributions ratio from the Hirshfeld surface analysis and K b . Molecular docking studies of each compound's respective enantiomers into DNA were done using canonical−DNA dodecamer (B-DNA) as a model for CT-DNA. The compounds were found to interact with DNA via a minor groove-binding mode. The S-enantiomer for most of the compounds bound favorably compared to their respective R-enantiomers. The ratio of calculated ΔG for the DNA binding of the Renantiomer to that of the S-enantiomer (ΔG R /ΔG S ) follows the same positive trend as the experimental K b value for each compound in Series I while a negative trend was observed for Series II. Finally, a relationship between the Hirshfeld surface analysis and calculated ΔG values was also established in this work.

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Enhancement of the stability and cytotoxicity of berberine by liposomal nanocarriers for gastric cancer treatment and its application in gummy candy

Abolhasanzadeh,

Dehghan,

Abbaspour-Ravasjani

2024

Front. Gastroenterol.

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IntroductionBerberine (BER), an isoquinoline alkaloid derived from the plant Berberis Vulgaris, is traditionally used to treat different types of disorders, such as cancer. However, its therapeutic application is limited due to poor solubility and low bioavailability. So, the main objective of the present work was to synthesize BER-loaded liposomes to enhance the solubility of BER. BER-loaded liposomes were synthesized using the thin-film hydration method.MethodsThe prepared liposomes were characterized for size, surface charge, in vitro release, and cytotoxicity. Then, the synthesized nano-liposomes were used to enrich gummy candies, and physicochemical properties such as water activity (aw), instrumental texture, and sensory perception of the products were tested.Results and DiscussionThe cell viability assay was performed on MKN-45P gastric cancer cell lines, and the results revealed that BER-loaded liposome had better cytotoxicity on MKN-45P cells than free BER. The IC50 values were calculated to be 66.72 µg/mL and 52.58 µg/mL for free BER and BER-loaded liposomes, respectively. Flow cytometric analysis demonstrated a significant anticancer effect of BER-loaded liposomes compared to free BER. These findings indicate that encapsulating BER preserves its antioxidant activity and enhances its bioavailability.

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DNA binding ability and cytotoxicity, cell cycle arrest and apoptosis inducing properties of a benzochromene derivative against K562 human leukemia cells

Cited by 3 publications

References 37 publications

Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

Classical Intermolecular Hydrogen Bonding Motifs of Heterocyclic rac-2-Amino-3-carbonitrile Derivatives: Linking Hirshfeld Surface Analysis, CT-DNA Binding Affinity, and Molecular Docking

Enhancement of the stability and cytotoxicity of berberine by liposomal nanocarriers for gastric cancer treatment and its application in gummy candy

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