{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T02:33:47Z","timestamp":1760236427987,"version":"build-2065373602"},"reference-count":61,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2021,11,25]],"date-time":"2021-11-25T00:00:00Z","timestamp":1637798400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Previously, we reported the in vitro growth inhibitory effect of diarylpentanoid BP-M345 on human cancer cells. Nevertheless, at that time, the cellular mechanism through which BP-M345 exerts its growth inhibitory effect remained to be explored. In the present work, we report its mechanism of action on cancer cells. The compound exhibits a potent tumor growth inhibitory activity with high selectivity index. Mechanistically, it induces perturbation of the spindles through microtubule instability. As a consequence, treated cells exhibit irreversible defects in chromosome congression during mitosis, which induce a prolonged spindle assembly checkpoint-dependent mitotic arrest, followed by massive apoptosis, as revealed by live cell imaging. Collectively, the results indicate that the diarylpentanoid BP-M345 exerts its antiproliferative activity by inhibiting mitosis through microtubule perturbation and causing cancer cell death, thereby highlighting its potential as antitumor agent.<\/jats:p>","DOI":"10.3390\/molecules26237139","type":"journal-article","created":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T22:01:11Z","timestamp":1638309671000},"page":"7139","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["BP-M345, a New Diarylpentanoid with Promising Antimitotic Activity"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6483-9807","authenticated-orcid":false,"given":"Pedro","family":"Novais","sequence":"first","affiliation":[{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"Faculty of Sciences, University of Porto, Rua do Campo Alegre, s\/n, 4169-007 Porto, Portugal"},{"name":"ICBAS\u2014Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0694-7321","authenticated-orcid":false,"given":"Patr\u00edcia M. A.","family":"Silva","sequence":"additional","affiliation":[{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"},{"name":"TOXRUN\u2014Toxicology Research Unit, University Institute of Health Sciences, CESPU, CRL, 4585-116 Gandra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9883-8412","authenticated-orcid":false,"given":"Joana","family":"Moreira","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1391-2143","authenticated-orcid":false,"given":"Andreia","family":"Palmeira","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Isabel","family":"Amorim","sequence":"additional","affiliation":[{"name":"GreenUPorto (Sustainable Agrifood Production) Research Center, Faculty of Sciences, University of Porto, Rua do Campo Alegre, s\/n, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena","family":"Pinto","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0715-1779","authenticated-orcid":false,"given":"Honorina","family":"Cidade","sequence":"additional","affiliation":[{"name":"Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Edif\u00edcio do Terminal de Cruzeiros do Porto de Leix\u00f5es, Avenida General Norton de Matos, s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4006-5779","authenticated-orcid":false,"given":"Hassan","family":"Bousbaa","sequence":"additional","affiliation":[{"name":"UNIPRO\u2014Oral Pathology and Rehabilitation Research Unit, University Institute of Health Sciences (IUCS), CESPU, Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"64","DOI":"10.1016\/j.canlet.2018.10.005","article-title":"Mitosis inhibitors in anticancer therapy: When blocking the exit becomes a solution","volume":"440","author":"Henriques","year":"2019","journal-title":"Cancer Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1038\/nrc1317","article-title":"Microtubules as a target for anticancer drugs","volume":"4","author":"Jordan","year":"2004","journal-title":"Nat. Rev. Cancer"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1007\/978-1-4939-3542-0_25","article-title":"Anti-Microtubule Drugs","volume":"1413","author":"Florian","year":"2016","journal-title":"Methods Mol. Biol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2086","DOI":"10.1158\/1535-7163.MCT-09-0366","article-title":"Microtubule inhibitors: Differentiating tubulin-inhibiting agents based on mechanisms of action, clinical activity, and resistance","volume":"8","author":"Perez","year":"2009","journal-title":"Mol. Cancer Ther."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1111\/j.1365-2184.2011.00767.x","article-title":"Monitoring the fidelity of mitotic chromosome segregation by the spindle assembly checkpoint","volume":"44","author":"Silva","year":"2011","journal-title":"Cell Prolif."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/j.semcdb.2021.06.009","article-title":"Spindle assembly checkpoint activation and silencing at kinetochores","volume":"117","author":"Pines","year":"2021","journal-title":"Semin. Cell Dev. Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3265","DOI":"10.1016\/j.febslet.2014.07.011","article-title":"Dynein-dependent transport of spindle assembly checkpoint proteins off kinetochores toward spindle poles","volume":"588","author":"Silva","year":"2014","journal-title":"FEBS Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"R1002","DOI":"10.1016\/j.cub.2015.08.051","article-title":"The Molecular Biology of Spindle Assembly Checkpoint Signaling Dynamics","volume":"25","author":"Musacchio","year":"2015","journal-title":"Curr. Biol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"151075","DOI":"10.1016\/j.ejcb.2020.151075","article-title":"Microtubule-targeting agents and their impact on cancer treatment","volume":"99","year":"2020","journal-title":"Eur. J. Cell Biol."},{"key":"ref_10","first-page":"160","article-title":"An overview of microtubule targeting agents for cancer therapy","volume":"70","author":"Karahalil","year":"2019","journal-title":"Arch. Ind. Hyg. Toxicol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"790","DOI":"10.1038\/nrd3253","article-title":"Microtubule-binding agents: A dynamic field of cancer therapeutics","volume":"9","author":"Dumontet","year":"2010","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1080\/15384101.2018.1559557","article-title":"Mitotic slippage: An old tale with a new twist","volume":"18","author":"Sinha","year":"2019","journal-title":"Cell Cycle"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/j.ccr.2008.07.002","article-title":"Cancer Cells Display Profound Intra- and Interline Variation following Prolonged Exposure to Antimitotic Drugs","volume":"14","author":"Gascoigne","year":"2008","journal-title":"Cancer Cell"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Zhang, D., and Kanakkanthara, A. (2020). Beyond the Paclitaxel and Vinca Alkaloids: Next Generation of Plant-Derived Microtubule-Targeting Agents with Potential Anticancer Activity. Cancers, 12.","DOI":"10.3390\/cancers12071721"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1016\/j.ejmech.2017.11.062","article-title":"Recent advances in microtubule-stabilizing agents","volume":"143","author":"Cao","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1158\/1535-7163.MCT-13-0791","article-title":"Targeting Microtubules by Natural Agents for Cancer Therapy","volume":"13","author":"Mukhtar","year":"2014","journal-title":"Mol. Cancer Ther."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1016\/j.bmc.2014.12.027","article-title":"Natural antitubulin agents: Importance of 3,4,5-trimethoxyphenyl fragment","volume":"23","author":"Negi","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/0163-7258(91)90027-J","article-title":"Tubulin sulfhydryl groups as probes and targets for antimitotic and antimicrotubule agents","volume":"49","author":"Luduena","year":"1991","journal-title":"Pharmacol. Ther."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1080\/10286020.2016.1235562","article-title":"Synthesis and antioxidant activity of curcumin analogs","volume":"19","author":"Zheng","year":"2017","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"605","DOI":"10.4155\/fmc-2016-0223","article-title":"An overview of structure\u2013activity relationship studies of curcumin analogs as antioxidant and anti-inflammatory agents","volume":"9","author":"Arshad","year":"2017","journal-title":"Future Med. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"112177","DOI":"10.1016\/j.ejmech.2020.112177","article-title":"Diarylpentanoids with antitumor activity: A critical review of structure-activity relationship studies","volume":"192","author":"Moreira","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.toxlet.2017.07.212","article-title":"Inhibition of high glucose-induced inflammation and fibrosis by a novel curcumin derivative prevents renal and heart injury in diabetic mice","volume":"278","author":"Chen","year":"2017","journal-title":"Toxicol. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1080\/10408347.2014.948679","article-title":"Analytical Strategies for the Determination of Norepinephrine Reuptake Inhibitors in Pharmaceutical Formulations and Biological Fluids","volume":"46","author":"Saka","year":"2016","journal-title":"Crit. Rev. Anal. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"820","DOI":"10.1039\/C5MD00599J","article-title":"Curcumin inspired synthesis of unsymmetrical diarylpentanoids with highly potent anti-parasitic activities: In silico studies and DFT-based stereochemical calculation","volume":"7","author":"Din","year":"2016","journal-title":"Medchemcomm"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.bmc.2016.10.022","article-title":"Discovery of novel curcumin derivatives targeting xanthine oxidase and urate transporter 1 as anti-hyperuricemic agents","volume":"25","author":"Ao","year":"2017","journal-title":"Bioorganic Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3948","DOI":"10.3390\/molecules18043948","article-title":"Synthesis and biological evaluation of unsymmetrical curcumin analogues as tyrosinase inhibitors","volume":"18","author":"Jiang","year":"2013","journal-title":"Molecules"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3742","DOI":"10.1016\/j.bmc.2016.06.016","article-title":"2-Benzoyl-6-benzylidenecyclohexanone analogs as potent dual inhibitors of acetylcholinesterase and butyrylcholinesterase","volume":"24","author":"Leong","year":"2016","journal-title":"Bioorganic Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"302","DOI":"10.1016\/j.bmcl.2017.12.048","article-title":"In vitro and in silico evaluations of diarylpentanoid series as \u03b1-glucosidase inhibitor","volume":"28","author":"Leong","year":"2018","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1781","DOI":"10.1007\/s00044-013-0780-4","article-title":"Synthesis, docking, and in vitro studies of some substituted bischalcones on acid and alkaline phosphatases","volume":"23","author":"Singh","year":"2014","journal-title":"Med. Chem. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"849","DOI":"10.4314\/tjpr.v16i4.14","article-title":"Determination of activities of human carbonic anhydrase ii inhibitors from curcumin analogs","volume":"16","author":"Aditama","year":"2017","journal-title":"Trop. J. Pharm. Res."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1016\/j.fitote.2017.09.007","article-title":"Effects of curcumin and curcumin analogues on TRP channels","volume":"122","author":"Nalli","year":"2017","journal-title":"Fitoterapia"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/j.bcp.2014.12.012","article-title":"Heterocyclic cyclohexanone monocarbonyl analogs of curcumin can inhibit the activity of ATP-binding cassette transporters in cancer multidrug resistance","volume":"93","author":"Revalde","year":"2015","journal-title":"Biochem. Pharmacol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2969","DOI":"10.1002\/cmdc.202100337","article-title":"A Diarylpentanoid with Potential Activation of the p53 Pathway: Combination of in silico Screening Studies, Synthesis, and Biological Activity Evaluation","volume":"16","author":"Moreira","year":"2021","journal-title":"ChemMedChem"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.lfs.2015.10.015","article-title":"Enhanced cytotoxicity of prenylated chalcone against tumour cells via disruption of the p53-MDM2 interaction","volume":"142","author":"Soares","year":"2015","journal-title":"Life Sci."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4150","DOI":"10.1016\/j.arabjc.2016.04.015","article-title":"Design and synthesis of new inhibitors of p53\u2013MDM2 interaction with a chalcone scaffold","volume":"12","author":"Pereira","year":"2019","journal-title":"Arab. J. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"711","DOI":"10.1016\/j.ejmech.2018.07.037","article-title":"Targeting the MDM2-p53 protein-protein interaction with prenylchalcones: Synthesis of a small library and evaluation of potential antitumor activity","volume":"156","author":"Loureiro","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3947","DOI":"10.1111\/bph.14468","article-title":"Improving anticancer activity towards colon cancer cells with a new p53-activating agent","volume":"175","author":"Raimundo","year":"2018","journal-title":"Br. J. Pharmacol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/j.toxlet.2014.06.016","article-title":"Evaluation of 2\u2019,4\u2019-dihydroxy-3,4,5-trimethoxychalcone as antimitotic agent that induces mitotic catastrophe in MCF-7 breast cancer cells","volume":"229","author":"Masawang","year":"2014","journal-title":"Toxicol. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"111752","DOI":"10.1016\/j.ejmech.2019.111752","article-title":"Chalcone derivatives targeting mitosis: Synthesis, evaluation of antitumor activity and lipophilicity","volume":"184","author":"Pinto","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Fonseca, J., Marques, S., Silva, P., Brand\u00e3o, P., Cidade, H., Pinto, M., and Bousbaa, H. (2016). Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel. Molecules, 21.","DOI":"10.3390\/molecules21080982"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1763","DOI":"10.4161\/cc.7.12.6180","article-title":"Kinetochore-microtubule interactions \u201cin check\u201d by Bub1, Bub3 and BubR1: The dual task of attaching and signalling","volume":"7","author":"Logarinho","year":"2008","journal-title":"Cell Cycle"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1798","DOI":"10.1091\/mbc.e07-07-0633","article-title":"The human spindle assembly checkpoint protein Bub3 is required for the establishment of efficient kinetochore-microtubule attachments","volume":"19","author":"Logarinho","year":"2008","journal-title":"Mol. Biol. Cell"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1007\/BF00293368","article-title":"The structure of the cold-stable kinetochore fiber in metaphase PtK1 cells","volume":"84","author":"Rieder","year":"1981","journal-title":"Chromosoma"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1016\/j.ejmech.2018.04.011","article-title":"Recent advances in trimethoxyphenyl (TMP) based tubulin inhibitors targeting the colchicine binding site","volume":"151","author":"Li","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"102","DOI":"10.1016\/j.chempr.2016.12.005","article-title":"Structural Basis of cis- and trans-Combretastatin Binding to Tubulin","volume":"2","author":"Gaspari","year":"2017","journal-title":"Chem"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.1021\/acs.jnatprod.6b00428","article-title":"Structural and Biochemical Characterization of the Interaction of Tubulin with Potent Natural Analogues of Podophyllotoxin","volume":"79","author":"Barasoain","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1050","DOI":"10.1080\/14756366.2020.1753721","article-title":"Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors","volume":"35","author":"Fu","year":"2020","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1016\/j.ejmech.2019.01.033","article-title":"Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors","volume":"165","author":"Fu","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Novais, P., Silva, P.M.A., Amorim, I., and Bousbaa, H. (2021). Second-Generation Antimitotics in Cancer Clinical Trials. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13071011"},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Paulraj, F., Abas, F., Lajis, N.H., Othman, I., and Naidu, R. (2019). Molecular pathways modulated by curcumin analogue, diarylpentanoids in cancer. Biomolecules, 9.","DOI":"10.3390\/biom9070270"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2579","DOI":"10.1242\/jcs.039719","article-title":"How do anti-mitotic drugs kill cancer cells?","volume":"122","author":"Gascoigne","year":"2009","journal-title":"J. Cell Sci."},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Potapova, T., and Gorbsky, G. (2017). The Consequences of Chromosome Segregation Errors in Mitosis and Meiosis. Biology, 6.","DOI":"10.3390\/biology6010012"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2325","DOI":"10.1021\/ja00738a045","article-title":"Plant Antitumor Agents.VI.The Isolation and Structure of Taxol, a Novel Antileukemic and Antitumor Agent from Taxus brevifolia","volume":"93","author":"Wani","year":"1971","journal-title":"J. Am. Chem. Soc."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-021-83743-7","article-title":"Antagonizing the spindle assembly checkpoint silencing enhances paclitaxel and Navitoclax-mediated apoptosis with distinct mechanistic","volume":"11","author":"Henriques","year":"2021","journal-title":"Sci. Rep."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"10683","DOI":"10.1039\/C6OB01771A","article-title":"Reversibility of the thia-Michael reaction of cytotoxic C5-curcuminoid and structure-activity relationship of bis-thiol-adducts thereof","volume":"14","author":"Kohyama","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1765","DOI":"10.1002\/mc.22633","article-title":"Curcumin analog L48H37 induces apoptosis through ROS-mediated endoplasmic reticulum stress and STAT3 pathways in human lung cancer cells","volume":"56","author":"Feng","year":"2017","journal-title":"Mol. Carcinog."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Kudo, C., Yamakoshi, H., Sato, A., Nanjo, H., Ohori, H., Ishioka, C., Iwabuchi, Y., and Shibata, H. (2011). Synthesis of 86 species of 1,5-diaryl-3-oxo-1,4-pentadienes analogs of curcumin can yield a good lead in vivo. BMC Pharmacol., 11.","DOI":"10.1186\/1471-2210-11-4"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading","volume":"31","author":"Trott","year":"2009","journal-title":"J. Comput. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1848","DOI":"10.1016\/j.jmb.2014.02.005","article-title":"The novel microtubule-destabilizing drug BAL27862 binds to the colchicine site of tubulin with distinct effects on microtubule organization","volume":"426","author":"Prota","year":"2014","journal-title":"J. Mol. Biol."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1007\/s10822-010-9395-8","article-title":"Computer-aided drug design platform using PyMOL","volume":"25","author":"Lill","year":"2011","journal-title":"J. Comput. Aided. Mol. Des."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.2174\/156802608786786624","article-title":"Medicinal Chemistry and the Molecular Operating Environment (MOE): Application of QSAR and Molecular Docking to Drug Discovery","volume":"8","author":"Vilar","year":"2008","journal-title":"Curr. Top. Med. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7139\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:35:55Z","timestamp":1760168155000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7139"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,25]]},"references-count":61,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2021,12]]}},"alternative-id":["molecules26237139"],"URL":"https:\/\/doi.org\/10.3390\/molecules26237139","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2021,11,25]]}}}