Abstract
In this study, four compounds of 2-(phenylthio)-ethyl benzoate derivatives were synthesized and evaluated for their antitumor, antibacterial, and antifungal activities. These compounds were characterized and evaluated for their cytotoxic activity in MCF-7-human carcinoma cells that showed a significant decrease for compounds 2a–2d in the average of G2-M phase as 8.13 ± 1.4, 10.66 ± 1.5, 14 ± 2.2, and 3.66 ± 0.8%, respectively, compared with untreated cells (21 ± 2%; p < 0.05). The data suggest that 2d compound could have an anticancer potential in the G2-M phase arrest of MCF-7 cells ultimately leading to necrosis. The compounds were tested for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia, Proteus vulgaris, Enterococcus faecium, Pseudomonas aeruginosa, MRSA, and Candida albicans and showed antimicrobial potential with MIC value average (3.125–6.25 mg/ml), compared with ampicillin (0.001–3.125 mg/ml). When the MIC of the four compounds was compared with known references, we found that the 2a compound has the same MIC as fluconazole (1.56 mg/ml), inhibitor of Candida growth. Moreover, 2a, 2b,, and 2d have the same MIC as ampicillin (3.125 mg/ml) for the inhibition of S. aureus.
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References
Abu-Dahab, R.; Afifi, F.: Antiproliferative activity of selected medicinal plants of Jordan against a breast adenocarcinoma cell line (MCF7). Sci. Pharm. 75(3), 121–146 (2007)
Hawash, M.: Highlights on specific biological targets; cyclin-dependent kinases, epidermal growth factor receptors, ras protein, and cancer stem cells in anticancer drug development. Drug Res. 69(9), 471–478 (2019)
Mans, D.R.; Da Rocha, A.B.; Schwartsmann, G.: Anti-cancer drug discovery and development in Brazil: targeted plant collection as a rational strategy to acquire candidate anti-cancer compounds. Oncologist 5(3), 185–198 (2000)
Schwartsmann, G.: Marine organisms and other novel natural sources of new cancer drugs. Ann. Oncol. 11(3), 235–243 (2000)
Hawash, M.M.; Baytas, S.N.: Antiproliferative activities of some biologically important Scaffold. FABAD J. Pharm. Sci 43(1), 59–77 (2017)
Daniels, A.L.; Van Slambrouck, S.; Lee, R.K.; Arguello, T.S.; Browning, J.; Pullin, M.J.; Kornienko, A.; Steelant, W.F.: Effects of extracts from two Native American plants on proliferation of human breast and colon cancer cell lines in vitro. Oncol. Rep. 15(5), 1327–1331 (2006)
Hawash, M.M.; Kahraman, D.C.; Eren, F.; Cetin Atalay, R.; Baytas, S.N.: Synthesis and biological evaluation of novel pyrazolic chalcone derivatives as novel hepatocellular carcinoma therapeutics. Eur. J. Med. Chem. 129, 12–26 (2017). https://doi.org/10.1016/j.ejmech.2017.02.002
Hudson, E.A.; Dinh, P.A.; Kokubun, T.; Simmonds, M.S.; Gescher, A.: Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Cancer Epidemiol. Biomarkers Prev. 9(11), 1163–1170 (2000)
Siegers, C.-P.; Steffen, B.; Röbke, A.; Pentz, R.: The effects of garlic preparations against human tumor cell proliferation. Phytomedicine 6(1), 7–11 (1999)
Pisha, E.; Chai, H.; Lee, I.S.; Chagwedera, T.E.; Farnsworth, N.R.: Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis. Nat. Med. 1, 1046–1050, 1051 (1995)
Gottesman, M.M.: How cancer cells evade chemotherapy: sixteenth Richard and Hinda Rosenthal Foundation award lecture. Cancer Res. 53(4), 747–754 (1993)
Madhuri, S.; Pandey, G.: Some anticancer medicinal plants of foreign origin. Curr. Sci. 96(6), 779–783 (2009)
Aldomere, Y.A.: Synthesis, characterization, antibacterial activities of novel polydentate Schiff’s bases and their transition metal complexes. (2015)
Bhalodia, N.R.; Shukla, V.: Antibacterial and antifungal activities from leaf extracts of Cassia fistula l.: an ethnomedicinal plant. J. Adv. Pharm. Technol. Res. 2(2), 104–111 (2011)
Davies, K.; Pryor, W.: The evolution of free radical biology & medicine: a 20-year history. Free Radic. Biol. Med. 39(10), 1263–1264 (2005)
Hussein, A.I.A.: Modification of biologically active compounds from selected medicinal plants in Palestine (2009)
Havlickova, B.; Czaika, V.A.; Friedrich, M.: Epidemiological trends in skin mycoses worldwide. Mycoses 51, 2–15 (2008)
del Olmo, A.; Calzada, J.; Nuñez, M.: Nutrition: benzoic acid and its derivatives as naturally occurring compounds in foods and as additives: uses, exposure, and controversy. Crit. Rev. Food Sci. Nutr. 57(14), 3084–3103 (2017)
Pizzorno, J.E.; Murray, M.T.; Joiner-Bey, H.: The Clinician’s Handbook of Natural Medicine E-Book. Elsevier, Amsterdam (2016)
Rahman, A.-U.: Studies in Natural Products Chemistry/Edited by Atta-ur-Rahman. Elsevier, Amsterdam (2012)
Patrick, G.L.: An Introduction to Medicinal Chemistry. Oxford University Press, Oxford (2013)
Debnath, J.; Muthuswamy, S.K.; Brugge, J.S.: Morphogenesis and oncogenesis of MCF-10A mammary epithelial acini grown in three-dimensional basement membrane cultures. Methods 30(3), 256–268 (2003)
Nunez, R.: DNA measurement and cell cycle analysis by flow cytometry. Curr. Issues Mol. Biol. 3, 67–70 (2001)
Forbes, B.A.; Sahm, D.F.; Weissfeld, A.S.: Study Guide for Bailey and Scott’s Diagnostic Microbiology-E-Book. Elsevier, Amsterdam (2016)
Wikler, M.A.: Performance Standards for Antimicrobial Susceptibility Testing: Seventeenth Informational Supplement. Clinical and Laboratory Standards Institute, New York (2007)
Evans, B.A.J.; Griffiths, K.; Morton, M.: Inhibition of 5α-reductase in genital skin fibroblasts and prostate tissue by dietary lignans and isoflavonoids. J. Endocrinol. 147(2), 295–302 (1995)
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The authors would like to acknowledge the Faculty of Graduate Studies, Pharmaceutical Sciences Program, at An-Najah National University for facilitating the accomplishment of the current study.
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Jaradat, N., Khasati, A., Hawi, M. et al. In vitro Antitumor, Antibacterial, and Antifungal Activities of Phenylthio-Ethyl Benzoate Derivatives. Arab J Sci Eng 46, 5339–5344 (2021). https://doi.org/10.1007/s13369-020-05114-0
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DOI: https://doi.org/10.1007/s13369-020-05114-0