Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins

Wu, Chun; Yaeghoobi, Marzieh; Rahman, Noorsaadah Abd.; Kang, Yew Beng; Pichika, Mallikarjuna Rao

doi:10.1016/j.ejmech.2014.03.002

Cited by 126 publications

(98 citation statements)

References 73 publications

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“…Apoptosis is considered to be promoted in cells with high Bax protein expression and inhibited in cells with high Bcl-2 protein expression. Several previous studies have also confirmed the role of both proteins in lung cancer cells (43)(44)(45). The current results suggest that in A549/DDP cells, I 131 and GA alone are able to regulate the protein expression levels of Bcl-2 and Bax.…”

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confidence: 71%

Role of gambogic acid and NaI131 in A549/DDP cells

et al. 2016

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Abstract. Resistance to platinum in tumor tissue is a considerable barrier against effective lung cancer treatment. Radionuclide therapy is the primary adjuvant treatment, however, the toxic side effects limit its dosage in the clinical setting. Therefore, the present study aimed to determine whether an NaI 131 radiosensitizer could help reduce the toxic side effects of radionuclide therapy. In vitro experiments were conducted to determine whether NaI 131 can inhibit platinum resistance in A549/DDP cells, which are cisplatin-resistant non-small cell lung cancer cells, and whether gambogic acid (GA) is an effective NaI 131 radiosensitizer. Cell proliferation following drug intervention was analyzed using MTT and isobolographic analysis. Apoptosis was assessed by flow cytometry. In addition, the mechanisms of drug intervention were analyzed by measuring the expression of P-glycoprotein (P-gP), B cell lymphoma 2 (Bcl-2), Bcl2-associated X protein (Bax) and P53 using western blot analysis and immunocytochemistry. According to isobolographic analysis, a low concentration of NaI 131 combined with GA had a synergistic effect on the inhibition of A549/DDP cell proliferation, which was consistent with an increased rate of apoptosis. Furthermore, the overexpression of Bax, and the downregulation of P-gP, P53 and Bcl-2 observed demonstrated the potential mechanism(s) of NaI 131 and GA intervention. NaI 131 may induce apoptosis in A549/DDP cells by regulating apoptosis-related proteins. A low concentration combination of NaI 131 and GA was able to significantly inhibit A549/DDP cell proliferation and induce cell apoptosis. Thus, the two drugs appear to have a synergistic effect on apoptosis of A549/DDP cells.

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confidence: 71%

Role of gambogic acid and NaI131 in A549/DDP cells

et al. 2016

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“…1,2 The recognition of their ability to interact with biological targets culminating in certain desired pharmacological response goes beyond promising in vivo and in vitro experiments carried out on laboratories. Many sulfonamide derivatives are used worldwide in the clinic for a long time as active pharmaceutical ingredients for treatment of bacterial and viral infections, hyperglycemia and hypertension, among others.…”

Section: Introductionmentioning

confidence: 99%

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

Castro¹,

Aragão²,

Silva³

et al. 2015

Journal of the Brazilian Chemical Society

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Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z' > 1 are found in three compounds as a consequence of conformerism. The chalcone molecular backbones are featured by different levels of planarity in their conformers. Another conformational variability is in its benzenesulfonamide moiety. In the compound came from N-(4-acetylphenyl) benzenesulfonamide and benzaldehyde, there is a rotation of ca. 180° on the bond axis bridging the sulfonamide and chalcone motifs of one conformer if the two others are taken as references. The cytotoxic activity of all compounds synthesized here and of two other related sulfonamide chalcones was also assessed against three cancer cell lines (SF-295, HCT-8 and MDA-MB-435). The para-nitro compounds were the most active ones among all those tested, regardless of substitution pattern in benzenesulfonamide core.

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“…The most predominant biological activity is observed for the class of 'antimicrobial agents'. Chalcones containing several functional groups have been exhibited a wide spectrum of biological activities including antitumor 6,7 , antibacterial 8,9 , antiinflammatory 13,14 and antitrypanosomal 15,16 activity 17 . Keeping this observation we have synthesized new chalcone derivatives which were characterized by IR and NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

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2017

IJPSR

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Despite significant progress made in the treatment of infectious diseases, caused by bacteria and fungi, it remains a major worldwide health problem due to rapid development of resistance against the existing antimicrobial drugs. In the present investigation, a novel series of chalcones 2a-2h were synthesized by the clasein-schmidt condensation of various aldehydes with methyl ketone in the presence of KOH in ethanol which lead to the formation of new chalcones. The structures of these compounds were elucidated by, IR, 1H-NMR spectral data. The in vitro antibacterial activity of these compounds was evaluated against two Gram positive and two Gram-negative bacteria Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Pseudomonas aeruginosa by microdilution method and then the minimum inhibitory concentration (MIC) of these compounds was determined. The results showed that compounds 2d, 2e and 2h showed most promising antibacterial activity as compared to the antibiotics ciprofloxacin in (Tables 1). Compound 2e which carries the nitro substituent appears to exhibit the highest antibacterial activity against all gram positive and gram negative bacteria.

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Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure–activity relationship analysis and regulation of apoptotic proteins

Cited by 126 publications

References 73 publications

Role of gambogic acid and NaI131 in A549/DDP cells

Role of gambogic acid and NaI131 in A549/DDP cells

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

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