{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,17]],"date-time":"2026-01-17T11:00:50Z","timestamp":1768647650228,"version":"3.49.0"},"reference-count":34,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2022,10,7]],"date-time":"2022-10-07T00:00:00Z","timestamp":1665100800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Princess Nourah bint Abdulrahman University Researchers","award":["PNURSP2022R25"],"award-info":[{"award-number":["PNURSP2022R25"]}]},{"name":"Princess Nourah bint Abdulrahman University Researchers","award":["2\/113\/43"],"award-info":[{"award-number":["2\/113\/43"]}]},{"name":"Princess Nourah bint Abdulrahman University","award":["PNURSP2022R25"],"award-info":[{"award-number":["PNURSP2022R25"]}]},{"name":"Princess Nourah bint Abdulrahman University","award":["2\/113\/43"],"award-info":[{"award-number":["2\/113\/43"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>The combretastatins (cis-stilbenoid molecules) have received significant interest because of their simple chemical structures, excellent antiproliferative activity, and novel anti-tubulin molecular mechanism of action. Significant efforts have been carried out aiming at stabilizing the active cis-isomers. A new series of cis-vinylamide derivatives containing trimethoxyphenyl moiety were synthesized and characterized. Their anticancer activities were evaluated in vitro against MCF-7 breast cancer cell line. Compounds 2f, 3, and 5 displayed potent cytotoxic activity against the breast cancer cell line compared with CA-4 as the reference compound. The microtubule polymerization assay and flow cytometry analysis confirmed that the cytotoxic activity of compound 3 was related to inhibitory activity against tubulin polymerization. Compound 3 showed pro-apoptotic activity by inducting a significant increase in the percentage of pre-G1 phase in DNA flow cytometry compared to untreated control. The pro-apoptotic activity of compound 3 was inferred by a significant increase in the percentage of fluorescent annexin V\/PI positive apoptotic cells. It also increased the level of caspase 3 compared to the untreated control.<\/jats:p>","DOI":"10.3390\/sym14102088","type":"journal-article","created":{"date-parts":[[2022,10,11]],"date-time":"2022-10-11T03:32:56Z","timestamp":1665459176000},"page":"2088","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Design, Synthesis, and Investigation of Cytotoxic Activity of cis-Vinylamide-Linked Combretastatin Analogues as Potential Anticancer Agents"],"prefix":"10.3390","volume":"14","author":[{"given":"Tarfah","family":"Al-Warhi","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia"}]},{"given":"Leena S.","family":"Alqahtani","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, College of Science, University of Jeddah, Jeddah 23445, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0424-135X","authenticated-orcid":false,"given":"Ghadi","family":"Alsharif","sequence":"additional","affiliation":[{"name":"College of Clinical Laboratory Sciences, King Saud Bin Abdulaziz University for Health Sciences, Jeddah 21423, Saudi Arabia"}]},{"given":"Matokah","family":"Abualnaja","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Al Mukarrama 24381, Saudi Arabia"}]},{"given":"Ola A.","family":"Abu Ali","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7599-225X","authenticated-orcid":false,"given":"Safa H.","family":"Qahl","sequence":"additional","affiliation":[{"name":"Department of Biology, College of Science, University of Jeddah, P.O. Box 80327, Jeddah 21589, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0311-2975","authenticated-orcid":false,"given":"Hussam Awwadh E.","family":"Althagafi","sequence":"additional","affiliation":[{"name":"Biology Department, Faculty of Science and Arts, Al-Mikhwah, Al-Baha University, Al-Baha 1988, Saudi Arabia"}]},{"given":"Fahad","family":"Alharthi","sequence":"additional","affiliation":[{"name":"Department of Biology, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia"}]},{"given":"Ibrahim","family":"Jafri","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, College of Sciences, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7754-2524","authenticated-orcid":false,"given":"Fahmy G.","family":"Elsaid","sequence":"additional","affiliation":[{"name":"Biology Department, Science, College, King Khalid University, Abha 61421, Saudi Arabia"},{"name":"Zoology Department, Faculty of Science, Mansoura University, P.O. Box 70, Mansoura 35516, Egypt"}]},{"given":"Ali A.","family":"Shati","sequence":"additional","affiliation":[{"name":"Biology Department, Science, College, King Khalid University, Abha 61421, Saudi Arabia"}]},{"given":"Salman","family":"Aloufi","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, College of Sciences, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2916-0254","authenticated-orcid":false,"given":"Eman","family":"Fayad","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, College of Sciences, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2026-7373","authenticated-orcid":false,"given":"Islam","family":"Zaki","sequence":"additional","affiliation":[{"name":"Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Port Said University, Port Said 42526, Egypt"}]},{"given":"Martha M.","family":"Morcoss","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Nahda University, Beni-Suef 62513, Egypt"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4257","DOI":"10.1021\/acs.jmedchem.0c01799","article-title":"Small-Molecule Inhibitors Targeting the Canonical WNT Signaling Pathway for the Treatment of Cancer","volume":"64","author":"Liu","year":"2021","journal-title":"J. Med. 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