{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T01:32:02Z","timestamp":1760059922201,"version":"build-2065373602"},"reference-count":53,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2025,7,18]],"date-time":"2025-07-18T00:00:00Z","timestamp":1752796800000},"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>A series of eleven new N-alkyl 3-(3-benzyloxyquinoxalin-2-yl) propanamides were prepared based on the azide coupling of 3-(3-benzyloxyquinoxalin-2-yl) propanhydrazide with a variety of primary and secondary amines and the consequent conjunction of a broad spectrum of lipophile and hydrophile characters to a quinoxaline ring system. 3-(3-benzyloxyquinoxalin-2-yl) propanhydrazide was produced in a two-step reaction of methyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl) propanoate with benzyl chloride followed by the hydrazinolysis of the corresponding ester. The antiproliferative activity of the compounds was tested in various cancer cell lines, including PC-3, Hela, HCT-116, and MCF-7; they showed a wide spectrum of activity for most of the tested compounds. Compound 6k exhibited the highest activity, which was comparable to that of doxorubicin, with IC50 (\u00b5M) values of 12.17 \u00b1 0.9, 9.46 \u00b1 0.7, 10.88 \u00b1 0.8, and 6.93 \u00b1 0.4 \u00b5M compared to 8.87 \u00b1 0.6, 5.57 \u00b1 0.4, 5.23 \u00b1 0.3, and 4.17 \u00b1 0.2 \u00b5M for doxorubicin against Hela, HCT-116, and MCF-7, respectively. The in silico mechanistic study revealed the inhibition of HDAC-6 through the binding of the unique zinc finger ubiquitin-binding domain (HDAC6 Zf-UBD). The docking results showed a specific binding pattern that emphasized the crucial role of the quinoxaline ring and its substituents. The newly developed derivatives were evaluated for antitumor effects against four cancer cell lines PC-3, HeLa, HCT-116, and MCF-7. This research led to the identification of a quinoxaline-based scaffold exhibiting broad-spectrum antiproliferative activity and a distinct mechanism involving binding to HDAC6 Zf-UBD. The findings highlight its potential for further optimization and preclinical studies to support future anticancer drug development.<\/jats:p>","DOI":"10.3390\/molecules30143025","type":"journal-article","created":{"date-parts":[[2025,7,18]],"date-time":"2025-07-18T13:33:27Z","timestamp":1752845607000},"page":"3025","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Novel N-Alkyl 3-(3-Benzyloxyquinoxalin-2-yl) Propanamides as Antiproliferative Agents: Design, Synthesis, In Vitro Testing, and In Silico Mechanistic Study"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2278-9738","authenticated-orcid":false,"given":"Samar A.","family":"Abubshait","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia"},{"name":"Basic and Applied Scientific Research Center, Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/j.bmc.2018.11.021","article-title":"An Insight into Medicinal Chemistry of Anticancer Quinoxalines","volume":"27","author":"Kaushal","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Patinote, C., Raevens, S., Baumann, A., Pellegrin, E., Bonnet, P.-A., and Deleuze-Masqu\u00e9fa, C. (2023). [1,2,4]Triazolo[4,3-a]Quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines. Molecules, 28.","DOI":"10.3390\/molecules28145478"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Kumar, A., Singh, A.K., Singh, H., Vijayan, V., Kumar, D., Naik, J., Thareja, S., Yadav, J.P., Pathak, P., and Grishina, M. (2023). Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective. Pharmaceuticals, 16.","DOI":"10.3390\/ph16020299"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Fan, D., Liu, P., Jiang, Y., He, X., Zhang, L., Wang, L., and Yang, T. (2022). Discovery and SAR Study of Quinoxaline-Arylfuran Derivatives as a New Class of Antitumor Agents. Pharmaceutics, 14.","DOI":"10.3390\/pharmaceutics14112420"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Bouali, N., Hammouda, M.B., Ahmad, I., Ghannay, S., Thouri, A., Dbeibia, A., Patel, H., Hamadou, W.S., Hosni, K., and Snoussi, M. (2022). Multifunctional Derivatives of Spiropyrrolidine Tethered Indeno-Quinoxaline Heterocyclic Hybrids as Potent Antimicrobial, Antioxidant and Antidiabetic Agents: Design, Synthesis, In Vitro and In Silico Approaches. Molecules, 27.","DOI":"10.3390\/molecules27217248"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"e202301401","DOI":"10.1002\/slct.202301401","article-title":"A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline","volume":"8","author":"Chawla","year":"2023","journal-title":"ChemistrySelect"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2395985","DOI":"10.1080\/14756366.2024.2395985","article-title":"Synthesis, Molecular Modelling, and Biological Evaluation of Novel Quinoxaline Derivatives for Treating Type II Diabetes","volume":"39","author":"Alasmary","year":"2024","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1556","DOI":"10.1080\/14756366.2022.2080205","article-title":"Triazoloquinoxalines-Based DNA Intercalators-Topo II Inhibitors: Design, Synthesis, Docking, ADMET and Anti-Proliferative Evaluations","volume":"37","author":"Elwan","year":"2022","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"101989","DOI":"10.1016\/j.rechem.2024.101989","article-title":"An Insight into the Therapeutic Impact of Quinoxaline Derivatives: Recent Advances in Biological Activities (2020\u20132024)","volume":"13","author":"Waseem","year":"2025","journal-title":"Results Chem."},{"key":"ref_10","unstructured":"Mamedov, V.A. (2016). Quinoxalines (Synthesis, Reactions, Mechanisms and Structure), Springer International Publishing."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"641","DOI":"10.3390\/70800641","article-title":"2,3-Bifunctionalized Quinoxalines: Synthesis, DNA Interactions and Evaluation of Anticancer, Anti-Tuberculosis and Antifungal Activity","volume":"7","author":"Waring","year":"2002","journal-title":"Molecules"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"e202400592","DOI":"10.1002\/cmdc.202400592","article-title":"Emerging Trends in Quinoxaline-Based Analogs as Protein Kinase Inhibitors: Structural Developments and SAR Insights","volume":"20","author":"Shivani","year":"2025","journal-title":"ChemMedChem"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"35400","DOI":"10.1039\/D4RA04292A","article-title":"Advances in Quinoxaline Derivatives: Synthetic Routes and Antiviral Efficacy against Respiratory Pathogens","volume":"14","author":"Dehnavi","year":"2024","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Buravchenko, G.I., and Shchekotikhin, A.E. (2023). Quinoxaline 1,4-Dioxides: Advances in Chemistry and Chemotherapeutic Drug Development. Pharmaceuticals, 16.","DOI":"10.3390\/ph16081174"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1107\/S090744490500137X","article-title":"Structures of Complexes between Echinomycin and Duplex DNA","volume":"61","author":"Sheldrick","year":"2005","journal-title":"Acta Crystallogr. D Biol. Crystallogr."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"9047","DOI":"10.1158\/0008-5472.CAN-05-1235","article-title":"Echinomycin, a Small-Molecule Inhibitor of Hypoxia-Inducible Factor-1 DNA-Binding Activity","volume":"65","author":"Kong","year":"2005","journal-title":"Cancer Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2566","DOI":"10.3390\/chemistry5040166","article-title":"Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines","volume":"5","author":"Zayed","year":"2023","journal-title":"Chemistry"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Suwanhom, P., Saetang, J., Khongkow, P., Nualnoi, T., Tipmanee, V., and Lomlim, L. (2021). Synthesis, Biological Evaluation, and In Silico Studies of New Acetylcholinesterase Inhibitors Based on Quinoxaline Scaffold. Molecules, 26.","DOI":"10.3390\/molecules26164895"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2820","DOI":"10.1039\/D0QO01575J","article-title":"Recent Advances in the Synthesis and Reactivity of Quinoxaline","volume":"8","author":"Yashwantrao","year":"2021","journal-title":"Org. Chem. Front."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1016\/j.ejmech.2014.06.058","article-title":"Quinoxaline, Its Derivatives and Applications: A State of the Art Review","volume":"97","author":"Pereira","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"195","DOI":"10.2174\/1871520617666170710182405","article-title":"Design and Discovery of Novel Quinoxaline Derivatives as Dual DNA Intercalators and Topoisomerase II Inhibitors","volume":"18","author":"Eissa","year":"2018","journal-title":"Anticancer Agents Med. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"El-Adl, K., El-Helby, A.-G.A., Sakr, H., and Elwan, A. (2020). Design, Synthesis, Molecular Docking and Anti-Proliferative Evaluations of [1,2,4]Triazolo[4,3-a]Quinoxaline Derivatives as DNA Intercalators and Topoisomerase II Inhibitors. Bioorg. Chem., 105.","DOI":"10.1016\/j.bioorg.2020.104399"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.ejmech.2018.06.004","article-title":"Design, Synthesis, Molecular Modeling and Anti-Proliferative Evaluation of Novel Quinoxaline Derivatives as Potential DNA Intercalators and Topoisomerase II Inhibitors","volume":"155","author":"Ibrahim","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"116360","DOI":"10.1016\/j.ejmech.2024.116360","article-title":"Quinoxaline Derivatives: Recent Discoveries and Development Strategies towards Anticancer Agents","volume":"271","author":"Montero","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Oyallon, B., Brachet-Botineau, M., Log\u00e9, C., Robert, T., Bach, S., Ibrahim, S., Raoul, W., Croix, C., Berthelot, P., and Guillon, J. (2021). New Quinoxaline Derivatives as Dual Pim-1\/2 Kinase Inhibitors: Design, Synthesis and Biological Evaluation. Molecules, 26.","DOI":"10.3390\/molecules26040867"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Kim, S.C., Boggu, P.R., Yu, H.N., Ki, S.Y., Jung, J.M., Kim, Y.S., Park, G.M., Ma, S.H., Kim, I.S., and Jung, Y.H. (2020). Synthesis and Biological Evaluation of Quinoxaline Derivatives as Specific C-Met Kinase Inhibitors. Bioorg. Med. Chem. Lett., 30.","DOI":"10.1016\/j.bmcl.2020.127189"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2414382","DOI":"10.1080\/14756366.2024.2414382","article-title":"Synthesis and Biological Evaluation of Quinoxaline Derivatives as ASK1 Inhibitors","volume":"39","author":"Han","year":"2024","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1111\/cbdd.13459","article-title":"Synthesis and Biological Evaluation of Quinoxaline Derivatives as Tubulin Polymerization Inhibitors That Elevate Intracellular ROS and Triggers Apoptosis via Mitochondrial Pathway","volume":"93","author":"Qi","year":"2019","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"El Newahie, A.M.S., Nissan, Y.M., Ismail, N.S.M., Abou El Ella, D.A., Khojah, S.M., and Abouzid, K.A.M. (2019). Design and Synthesis of New Quinoxaline Derivatives as Anticancer Agents and Apoptotic Inducers. Molecules, 24.","DOI":"10.3390\/molecules24061175"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Montero, V., Montana, M., Khoumeri, O., Correard, F., Est\u00e8ve, M.-A., and Vanelle, P. (2022). Synthesis, In Vitro Antiproliferative Activity, and In Silico Evaluation of Novel Oxiranyl-Quinoxaline Derivatives. Pharmaceuticals, 15.","DOI":"10.3390\/ph15070781"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"13439","DOI":"10.1002\/slct.202003024","article-title":"Synthesis and Anti Proliferative Activity of New N-Pentylquinoxaline Carboxamides and Their O-Regioisomer","volume":"5","author":"Aboelmagd","year":"2020","journal-title":"ChemistrySelect"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1039\/D0NJ03672B","article-title":"The Synthesis and Antiproliferative Activity of New N-Allyl Quinoxalinecarboxamides and Their O-Regioisomers","volume":"45","author":"Aboelmagd","year":"2021","journal-title":"New J. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2799","DOI":"10.1002\/jhet.3347","article-title":"Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-Yl)Oxy) Acetylamino Alkanoates","volume":"55","author":"Megahed","year":"2018","journal-title":"J. Heterocycl. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1007\/s10593-015-1661-1","article-title":"Chemoselective Synthesis of 3,6,7-Trisubstituted 2-(2,3:5,6-Di-O-Isopropylidene-\u03b2-D-Mannofuranosyloxy]- and 2-(2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-\u03b2-D-Glucopyranosyloxy)Quinoxaline Derivatives","volume":"51","author":"Fathalla","year":"2015","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"104","DOI":"10.24820\/ark.5550190.p009.947","article-title":"Synthesis of Methyl [3-Alkyl-2-(2,4-Dioxo-3,4-Dihydro-2H-Quinazolin-1-Yl)-Acetamido] Alkanoate","volume":"2017","author":"Ismail","year":"2017","journal-title":"Arkivoc"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1002\/hc.20203","article-title":"N1-Allyl-3-Substituted-6,7-Dimethyl-1,2-Dihydro-2-Quinoxalinone as Key Intermediate for New Acyclonucleosides and Their Regioisomer O-Analogues","volume":"17","author":"Ali","year":"2006","journal-title":"Heteroat. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"179","DOI":"10.3998\/ark.5550190.0009.d20","article-title":"Convenient Syntheses of Methyl 2-[2-(3-Acetyl-4-Methyl-2-Oxo-1,2-Dihydroquinolin-1-Yl)Acetamido] Alkanoates and Their O-Regioisomers","volume":"2008","author":"Ali","year":"2008","journal-title":"Arkivoc"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"130004","DOI":"10.1016\/j.molstruc.2021.130004","article-title":"Synthesis, Crystal Structure, DFT Calculations, Hirshfeld Surface Analysis, Energy Frameworks, Molecular Dynamics and Docking Studies of Novel Isoxazolequinoxaline Derivative (IZQ) as Anti-Cancer Drug","volume":"1232","author":"Abad","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2401","DOI":"10.1021\/acs.jmedchem.6b01759","article-title":"High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators","volume":"60","author":"Son","year":"2017","journal-title":"J. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"7029","DOI":"10.1021\/acs.jafc.2c01898","article-title":"Synthesis, Anti-Potato Virus Y Activities, and Interaction Mechanisms of Novel Quinoxaline Derivatives Bearing Dithioacetal Moiety","volume":"70","author":"Sun","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1371","DOI":"10.1007\/s00706-014-1193-x","article-title":"Synthesis of Quinoxaline Reverse Ribofuranosides and Their O-Regioisomers","volume":"145","author":"Ali","year":"2014","journal-title":"Monatsh. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"9090","DOI":"10.1021\/acs.jmedchem.7b00933","article-title":"Small Molecule Antagonists of the Interaction between the Histone Deacetylase 6 Zinc-Finger Domain and Ubiquitin","volume":"60","author":"Harding","year":"2017","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/0022-1759(86)90368-6","article-title":"Rapid Colorimetric Assay for Cell Growth and Survival. Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability","volume":"89","author":"Denizot","year":"1986","journal-title":"J. Immunol. Methods"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1021\/acs.molpharmaceut.6b01115","article-title":"Inclusion Complexation of Etodolac with Hydroxypropyl-Beta-Cyclodextrin and Auxiliary Agents: Formulation Characterization and Molecular Modeling Studies","volume":"14","author":"Sherje","year":"2017","journal-title":"Mol. Pharm."},{"key":"ref_46","first-page":"D271","article-title":"The RCSB Protein Data Bank: Integrative View of Protein, Gene and 3D Structural Information","volume":"45","author":"Rose","year":"2017","journal-title":"Nucleic Acids Res."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"D437","DOI":"10.1093\/nar\/gkaa1038","article-title":"RCSB Protein Data Bank: Powerful New Tools for Exploring 3D Structures of Biological Macromolecules for Basic and Applied Research and Education in Fundamental Biology, Biomedicine, Biotechnology, Bioengineering and Energy Sciences","volume":"49","author":"Burley","year":"2021","journal-title":"Nucleic Acids Res."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"4291","DOI":"10.1021\/acs.jctc.1c00302","article-title":"OPLS4: Improving Force Field Accuracy on Challenging Regimes of Chemical Space","volume":"17","author":"Lu","year":"2021","journal-title":"J. Chem. Theory Comput."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Gomaa, M.S., Alturki, M.S., Tawfeeq, N., Hussein, D.A., Pottoo, F.H., Al Khzem, A.H., Sarafroz, M., and Abubshait, S. (2024). Discovery of Non-Peptide GLP-1 Positive Allosteric Modulators from Natural Products: Virtual Screening, Molecular Dynamics, ADMET Profiling, Repurposing, and Chemical Scaffolds Identification. Pharmaceutics, 16.","DOI":"10.20944\/preprints202412.0085.v1"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"141456","DOI":"10.1016\/j.molstruc.2025.141456","article-title":"Design, Synthesis and Antiproliferative Activity against Colorectal Cancer Cells of Methyl 2-(3-(2-Oxo-3-Phenylquinoxalin-1(2H)-Yl)Propanamido)Alkanoates and Related Compounds","volume":"1330","author":"Gomaa","year":"2025","journal-title":"J. Mol. Struct."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Jaundoo, R., Bohmann, J., Gutierrez, G.E., Klimas, N., Broderick, G., and Craddock, T.J.A. (2018). Using a Consensus Docking Approach to Predict Adverse Drug Reactions in Combination Drug Therapies for Gulf War Illness. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19113355"},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Salam, M.A., Al-Amin, M.Y., Salam, M.T., Pawar, J.S., Akhter, N., Rabaan, A.A., and Alqumber, M.A.A. (2023). Antimicrobial Resistance: A Growing Serious Threat for Global Public Health. Healthcare, 11.","DOI":"10.20944\/preprints202305.0555.v1"},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Chen, Z., Chen, Y., Fang, Y., Wang, X., Chen, Y., Qi, Q., Huang, F., and Xiao, X. (2015). Meta-Analysis of Colistin for the Treatment of Acinetobacter Baumannii Infection. Sci. Rep., 5.","DOI":"10.1038\/srep17091"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/14\/3025\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:12:12Z","timestamp":1760033532000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/14\/3025"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,18]]},"references-count":53,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2025,7]]}},"alternative-id":["molecules30143025"],"URL":"https:\/\/doi.org\/10.3390\/molecules30143025","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2025,7,18]]}}}