scholarly journals Synthesis and Anticancer Activities of 4-[(Halophenyl)diazenyl]phenol and 4-[(Halophenyl)diazenyl]phenyl Aspirinate Derivatives against Nasopharyngeal Cancer Cell Lines

2017 ◽  
Vol 2017 ◽  
pp. 1-7 ◽  
Author(s):  
Boon Kui Ho ◽  
Zainab Ngaini ◽  
Paul Matthew Neilsen ◽  
Siaw San Hwang ◽  
Reagan Entigu Linton ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Cultured Cells ◽  
Colorimetric Assay ◽  
Biological Activities ◽  
Nasopharyngeal Cancer ◽  
Coupling Reaction ◽  
Basic Solution ◽  
Anticancer Activities ◽  
Low Cytotoxicity

Aspirin and azo derivatives have been widely studied and have drawn considerable attention due to diverse biological activities. In this study, a series of 4-[(halophenyl)diazenyl]phenyl aspirinate derivatives were synthesized from the reaction of aspirin with 4-[(halophenyl)diazenyl]phenol via esterification, in the presence of DCC/DMAP in DCM with overall yield of 45–54%. 4-[(Halophenyl)diazenyl]phenol was prepared prior to esterification from coupling reaction of aniline derivatives and phenol in basic solution. All compounds were characterized using elemental analysis, FTIR, and 1H and 13C NMR spectroscopies. All compounds were screened for their anticancer activities against nasopharyngeal cancer (NPC) HK-1 cell lines and the viability of cultured cells was determined by MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxylmethoxylphenyl)-2-(4-sulfophenyl)-2H-tetrazolium]-based colorimetric assay. 4-[(E)-(Fluorophenyl)diazenyl]phenol showed the highest anticancer activity against NPC HK-1 cell lines compared to other synthesized compounds. 4-[(Halophenyl)diazenyl]phenyl aspirinate showed low cytotoxicity against NPC HK-1 cell lines compared to 4-[(halophenyl)diazenyl]phenol but better anticancer activity than aspirin alone.

Synthesis and Characterization of Some Benzidine-Based Azomethine Derivatives with Molecular Docking Studies and Anticancer Activities

2021 ◽  
Author(s):  
Musa Erdoğan ◽  
ali yeşildağ ◽  
Barış Yıldız ◽  
Burak Tüzün ◽  
Özkan Özden
Keyword(s):  
Molecular Docking ◽  
Cell Lines ◽  
Colorimetric Assay ◽  
Biological Activities ◽  
Breast Adenocarcinoma ◽  
Tetrazolium Salt ◽  
Spectroscopic Techniques ◽  
Human Breast ◽  
Anticancer Activities ◽  
Anticancer Properties

Abstract In this paper, a new benzidine-based azomethine derivate 2 with a proposed new mechanism and its two derivatives 4a-b have been designed, synthesized and characterized by 1H, 13C NMR, FT-IR, and HRMS spectroscopic techniques, and their anticancer properties were investigated. The target compounds 2, 4a-b were obtained with excellent yields (91% and above) by condensation of benzidine (1) with three different aldehyde derivatives (formaldehyde, benzaldehyde 3a or p-nitrobenzaldehyde 3b) in refluxing EtOH. Surprisingly, treatment of benzidine (1) with formaldehyde afforded N4,N4,N4',N4'-tetrakis(ethoxymethyl)-[1,1'-biphenyl]-4,4'-diamine (2). The anticancer properties of these benzidine derivatives 2, 4a-b against two cell lines (MDA-MB-231 human breast adenocarcinoma and DLD1 human colorectal adenocarcinoma cell lines) were investigated with a colorimetric assay using the tetrazolium salt WST-8 (2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazolium, monosodium salts). The obtained results showed that the benzidine-based azomethine derivatives 2, 4a-b had a significant effect against human breast cancer cell line (MDA-MB-231). Then, molecular docking calculations were made to compare the biological activities of benzidine-based azomethine derivatives 2, 4a-b against cancer proteins. ADME/T analysis was performed to examine the drug properties of benzidine-based azomethine derivatives 2, 4a-b. The compounds 2, 4a-b are promising as potential anticancer drug candidates.

Anticancer Activity and Topoisomerase II Inhibition of Naphthalimides with ω-Hydroxylalkylamine Side-Chains of Different Lengths

2019 ◽  
Vol 15 (5) ◽  
pp. 550-560
Author(s):  
Mateusz D. Tomczyk ◽  
Anna Byczek-Wyrostek ◽  
Klaudia Strama ◽  
Martyna Wawszków ◽  
Przemysław Kasprzycki ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cancer Cells ◽  
Cell Lines ◽  
Inhibitory Activity ◽  
Topoisomerase Ii ◽  
Significant Activity ◽  
Anticancer Activities ◽  
Human Colon Cancer ◽  
Substitution Pattern ◽  
Topo Ii

Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Methods: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 µM to 7 µM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 µM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.

Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines

2020 ◽  
Vol 16 ◽  
Author(s):  
Délis Galvão Guimarães ◽  
Arlan de Assis Gonsalves ◽  
Larissa Araújo Rolim ◽  
Edigênia Cavalcante Araújo ◽  
Victória Laysna dos Anjos Santos ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Cancer Cell Lines ◽  
Molecular Structures ◽  
Cytotoxic Activities ◽  
Electrochemical Studies ◽  
Ic50 Values

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Method: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Result: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, being compounds 3 and 4 the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

scholarly journals Pyrrolizine-5-carboxamides: Exploring the impact of various substituents on anti-inflammatory and anticancer activities

2018 ◽  
Vol 68 (3) ◽  
pp. 251-273 ◽  
Author(s):  
Ahmed M. Gouda ◽  
Ahmed H. Abdelazeem ◽  
Ashraf N. Abdalla ◽  
Muhammad Ahmed
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Inflammatory Activity ◽  
Electronic Effects ◽  
Anticancer Activities ◽  
Phenyl Rings ◽  
Anti Inflammatory ◽  
New Compounds ◽  
The Impact ◽  
Mcf 7

Abstract Towards optimization of the pyrrolizine-5-carboxamide scaffold, a novel series of six derivatives (4a-c and 5a-c) was prepared and evaluated for their anti-inflammatory, analgesic and anticancer activities. The (EZ)-7-cyano-6-((4-hydroxybenzylidene)amino)-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4b) and (EZ)-6-((4-chlorobenzylidene)-amino)-7-cyano-N-(p-tolyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5b) bearing the electron donating methyl group showed the highest anti-inflammatory activity while (EZ)-6-((4-chlorobenzylidene)amino)-7-cyano-N-phenyl-2,3-dihydro-1H-pyrrolizine-5-carboxamide (5a) was the most active analgesic agent. Cytotoxicity of the new compounds was evaluated against the MCF-7, A2780 and HT29 cancer cell lines using the MTT assay. Compounds 4b and 5b displayed high anticancer activity with IC50 in the range of 0.30–0.92 μmol L−1 against the three cell lines, while compound (EZ)-N-(4-chlorophenyl)-7-cyano-6-((4-hydroxybenzylidene)-amino)-2,3-dihydro-1H-pyrrolizine-5-carboxamide (4c) was the most active against MCF-7 cells (IC50 = 0.08 μmol L−1). Both the anti-inflammatory and anticancer activities of the new compounds were dependent on the type of substituent on the phenyl rings. Substituents with opposite electronic effects on the two phenyl rings are preferable for high cytotoxicity against the MCF-7 and A2780 cells. COX inhibition was suggested as the molecular mechanism of the anti-inflammatory activity of the new compounds while no clear relationship could be observed between COX inhibition and anticancer activity. Compound 5b, the most active against the three cell lines, induced dose-dependent early apoptosis with 0.1–0.2 % necrosis in MCF-7 cells. New compounds showed promising drug-likeness scores while the docking study revealed high binding affinity to COX-2. Taken together, this study highlighted the significant impact of the substituents on the anti-inflammatory and anticancer activity of pyrrolizine-5-carboxamides, which could help in further optimization to discover good leads for the treatment of cancer and inflammation.

scholarly journals Design, Synthesis, and Structural Characterization of Novel Diazaphenothiazines with 1,2,3-Triazole Substituents as Promising Antiproliferative Agents

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4388 ◽  
Author(s):  
Morak-Młodawska ◽  
Pluta ◽  
Latocha ◽  
Jeleń ◽  
Kuśmierz
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Human Fibroblasts ◽  
Human Tumor ◽  
Design Synthesis ◽  
Human Tumor Cell Lines ◽  
Ic50 Values ◽  
Normal Human ◽  
Low Cytotoxicity

A series of novel 1,2,3-triazole-diazphenothiazine hybrids was designed, synthesized, and evaluated for anticancer activity against four selected human tumor cell lines (SNB-19, Caco-2, A549, and MDA-MB231). The majority of the synthesized compounds exhibited significant potent activity against the investigated cell lines. Among them, compounds 1d and 4c showed excellent broad spectrum anticancer activity, with IC50 values ranging from 0.25 to 4.66 μM and 0.25 to 6.25 μM, respectively. The most promising compound 1d, possessing low cytotoxicity against normal human fibroblasts NHFF, was used for gene expression analysis using reverse transcription–quantitative real-time PCR (RT–qPCR). The expression of H3, TP53, CDKN1A, BCL-2, and BAX genes revealed that these compounds inhibited the proliferation in all cells (H3) and activated mitochondrial events of apoptosis (BAX/BCL-2).

Do herbal drinks augment the cytotoxic effect against different cancer cells? Are they potent stimulators of innate and acquired immunity?

2020 ◽  
Vol 38 (15_suppl) ◽  
pp. e21657-e21657 ◽  
Author(s):  
Israa Adnan ◽  
Wamidh Talib
Keyword(s):  
Middle East ◽  
Cell Lines ◽  
Biological Activities ◽  
Neutral Red ◽  
Acquired Immunity ◽  
Anticancer Activities ◽  
Anti Cancer ◽  
Wild Thyme ◽  
Phagocytosis Activity ◽  
Mcf 7

e21657 Background: The herbal drinks are highly prevalent in the Middle East and are consumed in large quantities as daily drinks. Few studies have evaluated the biological activities of the herbal drinks produced from some plants.The current study aims to evaluate the anticancer and immunomodulatory activities of five herbal drinks consumed in the Middle East. These drinks are Palestinian Zhourat, Lebanese Zhourat, Lemon and Ginger combination, Wild Thyme, and Marjoram. Methods: The selected herbal drinks as concentrated water extracts were tested separately for: A. Anti-cancer effect on the cell lines (MCF-7, MDA-MB231, HCT-116, A549, and Vero-normal cells) by assessing: - Antiproliferation activities using MTT assay. Apoptosis (using the caspase-3 assay) and vascular endothelial growth factor (VEGF) expression (using ELISA kit) for the most potent antiproliferative extract. B. Immunomodulatory effect by evaluating: - Splenocytes proliferation using the mitogen proliferation assay. Phagocytosis activity using the nitro blue tetrazolium assay. - Pinocytosis function using the neutral red method. Results: The Lemon and Ginger combination was the most potent against MDA-MB231, MCF-7 and A549l cell lines with IC50 3.5,4, 6.5mg/ml, respectively. Lemon and Ginger combination and Wild thyme separately showed high apoptosis induction and angiogenesis suppression on the MDA-MB231cell line at concentrations 3.5 and 4.4 mg/ml for both extracts, respectively. Wild thyme was the most potent stimulant lymphocyte proliferation (with index 4.7), and Marjoram has the highest percentage (314.4%) in phagocytosis activity, while moderate stimulation by Zhourat was noted. Lemon and Ginger combination, Wild thyme, Marjoram, and the Lebanese herbal drink "Zhourat" were the most active extracts in stimulating pinocytosis with absorbance value 0.5745,0.4645,0.461,0.4575 nm, respectively. Meanwhile, the Palestinian herbal drink "Zhourat" had a moderate effect. Conclusions: The consumption ofthe mentioned herbal drinks has various Anti-cancer and immunomodulatory effects. Lemon and ginger combination exhibits the most potent anticancer activities. Wild thyme and marjoram are potent stimulators of innate and acquired immunity. The result achieved in this study is very optimistic and encouraging to be considered for further clinical trials.

Structural requirements of salicylaldehyde benzoylhydrazones and their Cu(II) complexes for anticancer activity

2012 ◽  
Vol 90 (9) ◽  
pp. 762-775 ◽  
Author(s):  
Shiow Jin Tan ◽  
Mahasin Alam Sk ◽  
Peter Peng Foo Lee ◽  
Yaw Kai Yan ◽  
Kok Hwa Lim
Keyword(s):  
Anticancer Activity ◽  
Density Functional ◽  
Chemical Potential ◽  
Biological Activities ◽  
Principal Component Regression ◽  
Principal Component ◽  
Atomic Charges ◽  
Anticancer Activities ◽  
Structural Requirements ◽  
Qsar Analysis

Salicylaldehyde benzoylhydrazone (H2sb) has a variety of biological activities including anticancer activity. The Cu(II) complexes of H2sbs possess enhanced anticancer activity as compared with their free ligands. A quantitative structure–activity relationship (QSAR) analysis was performed on a series of H2sb ligands and their corresponding Cu(II) complexes to capture the structural requirements that are responsible for the bioactivity. The predictive QSAR models were developed using statistical techniques such as multiple linear regression (MLR) and principal component regression analysis (PCRA). We used different combinations of various descriptors such as a physicochemical descriptor, electrotopological state atom (ETSA) indices, and descriptors derived from density functional theory (DFT) calculations. The DFT-derived descriptors used for QSAR analysis are HOMO and LUMO energies, atomic charges, chemical potential, and hardness. Our developed models showed the importance of the lipophilicity index (ClogP), ETSA indices, and atomic charges for anticancer activities of the H2sb analogs and their Cu(II) complexes. In addition, our MLR models revealed that, while the global lipophilicity index and hardness are important for anticancer activity of H2sb ligands, chemical potential and HOMO energy are important for the anticancer activity of Cu(II) complexes.

scholarly journals Antimutagenic Activities of Anisosciadium lanatum Extracts Could Predict the Anticancer Potential in Different Cell Lines

2017 ◽  
Vol 9 (2) ◽  
Author(s):  
Wael M. El-Sayed ◽  
Warda A. Hussin ◽  
Ahmad A. Mahmoud ◽  
Mohamed A. AlFredan
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Anticancer Drugs ◽  
Phytochemical Analysis ◽  
Antimutagenic Activity ◽  
Anticancer Activities ◽  
Screening Process ◽  
Tremendous Progress ◽  
Chlorophyll A And B ◽  
Botanical Extracts

In spite of the tremendous progress in the development of anticancer drugs yet the cancer is still one of the leading causes of death worldwide in addition to the economic and social burdens it causes. The high cost of chemotherapy, the resistance development and the severe adverse effects mandate the continuous screening for novel, cheap, and safe anticancer drugs. In our efforts to expedite the screening process in botanical extracts, we analyzed the flavonoid, lycopene, β-carotene, and chlorophyll a and b in four different extracts from Anisosciadium lanatum with different polarities in addition to the essential oil. In addition, we have also measured the antioxidant, peroxide and superoxide scavenging activities of the extracts and oil. We have also estimated the antimutagenic activities of these extracts in Salmonella typhimurium using Ames test against two mutagens; sodium azide (NaN3) and benzo(a)pyrene (B(a)P). All these features and measurements of the extracts were correlated with their anticancer activities in 5 cell lines; liver, lung, colon, breast, and prostate. The phytochemical and antioxidants studies did not precisely predict the potential anticancer activity of extracts or at least what is performed in the current study. Collectively, the antimutagenic activities of the extracts along with the reductions in mutant frequency reported correlates well with the anticancer activities. Therefore, we believe that the antimutagenic activity along with phytochemical analysis could serve as a plausible surrogate in the prediction of potential anticancer activity in the process of screening botanical extracts.

scholarly journals Partial Characterization, the Immune Modulation and Anticancer Activities of Sulfated Polysaccharides from Filamentous Microalgae Tribonema sp.

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 322 ◽  
Author(s):  
Xiaolin Chen ◽  
Lin Song ◽  
Hui Wang ◽  
Song Liu ◽  
Huahua Yu ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Hepg2 Cells ◽  
Immune Modulation ◽  
Biological Activities ◽  
Interleukin 10 ◽  
Biofuel Production ◽  
Sulfated Polysaccharides ◽  
Anticancer Activities ◽  
Macrophage Cells

Recently, Tribonema sp., a kind of filamentous microalgae, has been studied for biofuel production due to its accumulation of triacylglycerols. However, the polysaccharides of Tribonema sp. and their biological activities have rarely been reported. In this paper, we extracted sulfated polysaccharides from Tribonema sp. (TSP), characterized their chemical composition and structure, and determined their immunostimulation and anticancer activities on RAW264.7 macrophage cells and HepG2 cells. The results showed that TSP is a sulfated polysaccharide with a Mw of 197 kDa. TSP is a heteropolysaccharide that is composed mainly of galactose. It showed significant immune-modulatory activity by stimulating macrophage cells, such as upregulating interleukin 6 (IL-6), interleukin 10 (IL-10), and tumor necrosis factor α (TNF-α). In addition, TSP also showed significant dose-dependent anticancer activity (with an inhibition rate of up to 66.8% at 250 µg/mL) on HepG2 cells as determined by the 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The cycle analysis indicated that the anticancer activity of TSP is mainly the result of induced cell apoptosis rather than affecting the cell cycle and mitosis of HepG2 cells. These findings suggest that TSP might have potential as an anticancer resource, but further research is needed, especially in vivo experiments, to explore the anticancer mechanism of TSP.

Effective Pharmacophore for CDC25 Phosphatases Enzyme Inhibitors: Newly Synthesized Bromothiazolopyrimidine Derivatives

2020 ◽  
Vol 20 ◽  
Author(s):  
Mahmoud El-Shahat ◽  
Mowafia A.M. Salama ◽  
Ahmed F. El-Farargy ◽  
Mamdouh M. Ali ◽  
Dalia M. Ahmed
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Enzyme Inhibitors ◽  
Wide Spectrum ◽  
Hct116 Cell ◽  
Cytotoxic Activities ◽  
The Novel ◽  
Anticancer Activities ◽  
Starting Compound

Background: Thiazolopyrimidine analogues are versatile synthetic scaffold possessing wide spectrum of biological interests involving potential anticancer activity. Objective: To report the synthesis of novel bromothiazolopyrimidine derivatives and the study of both molecular modeling and in-vitro anticancer activity. Method: Novel bromothiazolopyrimidine derivatives 5–18 have been prepared from 2-bromo-3-(4-chlorophenyl)-1-(3,4- dimethylphenyl)-propenone 3 as a key starting compound. The anti-cancer activities of the new compounds were evaluated against HepG2, MCF-7, A549 and HCT116 cell lines. Results: The compounds 16, 17 and 18 showed cytotoxic and growth inhibitory activities on both colon and lung cells. The cytotoxic activities of the novel synthetic compounds 8, 9, 11, 16, 17 and 18 were due to CDC25 phosphatases inhibition as shown by the enzymatic binding assay. Although compounds 8, 9 and 11 have only demonstrated CDC25B phosphatases inhibition. Conclusion: The novel bromothiazolopyrimidine derivatives showed promising in vitro anticancer activities against colon cancer HCT116 and lung cancer A549 cell lines comparable to the anticancer drug doxorubicin.

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