{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,30]],"date-time":"2026-05-30T01:59:37Z","timestamp":1780106377404,"version":"3.54.0"},"reference-count":52,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2022,5,21]],"date-time":"2022-05-21T00:00:00Z","timestamp":1653091200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"SIRIC OncoLille","award":["Cancer 2015-2020"],"award-info":[{"award-number":["Cancer 2015-2020"]}]},{"name":"SATT Nord","award":["Cancer 2015-2020"],"award-info":[{"award-number":["Cancer 2015-2020"]}]},{"name":"Contrat de Plan Etat R\u00e9gion CPER","award":["Cancer 2015-2020"],"award-info":[{"award-number":["Cancer 2015-2020"]}]},{"name":"Institut pour la Recherche sur le Cancer de Lille","award":["Cancer 2015-2020"],"award-info":[{"award-number":["Cancer 2015-2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Small molecules targeting the PD-1\/PD-L1 checkpoint are actively searched to complement the anticancer arsenal. Different molecular scaffolds have been reported, including phenyl-pyrazolone derivatives which potently inhibit binding of PD-L1 to PD-1. These molecules are structurally close to antioxidant drug edaravone (EDA) used to treat amyotrophic lateral sclerosis. For this reason, we investigated the capacity of five PD-L1-binding phenyl-pyrazolone compounds (1\u20135) to scavenge the formation of oxygen free radicals using electron spin resonance spectroscopy with DPPH\/DMPO probes. In addition, the reactivity of the compounds toward the oxidized base 5-formyluracil (5fU) was assessed using chromatography coupled to mass spectrometry and photodiode array detectors. The data revealed that the phenyl-pyrazolone derivatives display antioxidant properties and exhibit a variable reactivity toward 5fU. Compound 2 with a N-dichlorophenyl-pyrazolone moiety cumulates the three properties, being a potent PD-L1 binder, a robust antioxidant and an aldehyde-reactive compound. On the opposite, the adamantane derivative 5 is a potent PD-L1 binding with a reduced antioxidant potential and no aldehyde reactivity. The nature of the substituent on the phenyl-pyrazolone core modulates the antioxidant capacity and reactivity toward aromatic aldehydes. The molecular signature of the compound can be adapted at will, to confer additional properties to these PD-L1 binders.<\/jats:p>","DOI":"10.3390\/molecules27103316","type":"journal-article","created":{"date-parts":[[2022,5,21]],"date-time":"2022-05-21T09:18:08Z","timestamp":1653124688000},"page":"3316","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Antioxidant Properties and Aldehyde Reactivity of PD-L1 Targeted Aryl-Pyrazolone Anticancer Agents"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3904-4815","authenticated-orcid":false,"given":"Natascha","family":"Leleu-Chavain","sequence":"first","affiliation":[{"name":"Univ. Lille, Inserm, CHU Lille, U1286\u2014INFINITE\u2014Lille Inflammation Research International Center, ICPAL, 3 Rue du Professeur Laguesse, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Romain","family":"Regnault","sequence":"additional","affiliation":[{"name":"Univ. Lille, CHU Lille, ULR 7365\u2014GRITA\u2014Groupe de Recherche sur les Formes Injectables et les Technologies Associ\u00e9es, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hania","family":"Ahouari","sequence":"additional","affiliation":[{"name":"LASIRE Laboratoire Avanc\u00e9 de Spectroscopie pour les Int\u00e9ractions la R\u00e9activit\u00e9 et l\u2032Environnement, 59655 Villeneuve d\u2032Ascq, France"},{"name":"Univ. Lille, FR 2638\u2014IMEC\u2014Institut Michel-Eug\u00e8ne Chevreul, 59655 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rapha\u00ebl","family":"Le Biannic","sequence":"additional","affiliation":[{"name":"Univ. Lille, Inserm, CHU Lille, U1286\u2014INFINITE\u2014Lille Inflammation Research International Center, ICPAL, 3 Rue du Professeur Laguesse, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2034-800X","authenticated-orcid":false,"given":"Mostafa","family":"Kouach","sequence":"additional","affiliation":[{"name":"Univ. Lille, CHU Lille, ULR 7365\u2014GRITA\u2014Groupe de Recherche sur les Formes Injectables et les Technologies Associ\u00e9es, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fr\u00e9d\u00e9rique","family":"Klupsch","sequence":"additional","affiliation":[{"name":"Univ. Lille, Inserm, CHU Lille, U1286\u2014INFINITE\u2014Lille Inflammation Research International Center, ICPAL, 3 Rue du Professeur Laguesse, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1882-8469","authenticated-orcid":false,"given":"Romain","family":"Magnez","sequence":"additional","affiliation":[{"name":"Univ. Lille, CHU Lille, CNRS, Inserm, UMR9020\u2014UMR1277\u2014Canther\u2014Cancer Heterogeneity, Plasticity and Resistance to Therapies, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7282-2703","authenticated-orcid":false,"given":"Herv\u00e9","family":"Vezin","sequence":"additional","affiliation":[{"name":"LASIRE Laboratoire Avanc\u00e9 de Spectroscopie pour les Int\u00e9ractions la R\u00e9activit\u00e9 et l\u2032Environnement, 59655 Villeneuve d\u2032Ascq, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0998-4160","authenticated-orcid":false,"given":"Xavier","family":"Thuru","sequence":"additional","affiliation":[{"name":"Univ. Lille, CHU Lille, CNRS, Inserm, UMR9020\u2014UMR1277\u2014Canther\u2014Cancer Heterogeneity, Plasticity and Resistance to Therapies, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2973-9357","authenticated-orcid":false,"given":"Christian","family":"Bailly","sequence":"additional","affiliation":[{"name":"Oncowitan, Scientific Consulting Office, 59290 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8551-0899","authenticated-orcid":false,"given":"Jean-Fran\u00e7ois","family":"Goossens","sequence":"additional","affiliation":[{"name":"Univ. Lille, CHU Lille, ULR 7365\u2014GRITA\u2014Groupe de Recherche sur les Formes Injectables et les Technologies Associ\u00e9es, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R\u00e9gis","family":"Millet","sequence":"additional","affiliation":[{"name":"Univ. Lille, Inserm, CHU Lille, U1286\u2014INFINITE\u2014Lille Inflammation Research International Center, ICPAL, 3 Rue du Professeur Laguesse, 59000 Lille, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1186\/s12943-021-01489-2","article-title":"Combination strategies with PD-1\/PD-L1 blockade: Current advances and future directions","volume":"21","author":"Yi","year":"2022","journal-title":"Mol. Cancer"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"zcaa002","DOI":"10.1093\/narcan\/zcaa002","article-title":"Combined cytotoxic chemotherapy and immunotherapy of cancer: Modern times","volume":"2","author":"Bailly","year":"2020","journal-title":"NAR Cancer"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Pandey, P., Khan, F., Qari, H.A., Upadhyay, T.K., Alkhateeb, A.F., and Oves, M. (2022). Revolutionization in Cancer Therapeutics via Targeting Major Immune Checkpoints PD-1, PD-L1 and CTLA-4. Pharmaceuticals, 15.","DOI":"10.3390\/ph15030335"},{"key":"ref_4","first-page":"1","article-title":"Small Molecule Inhibitors of Programmed Cell Death Ligand 1 (PD-L1): A Patent Review (2019\u20132021)","volume":"10","author":"Deng","year":"2022","journal-title":"Expert. Opin. Ther. Pat."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"72167","DOI":"10.18632\/oncotarget.20050","article-title":"Small-molecule inhibitors of PD-1\/PD-L1 immune checkpoint alleviate the PD-L1-induced exhaustion of T-cells","volume":"8","author":"Skalniak","year":"2017","journal-title":"Oncotarget"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1080\/13543776.2018.1512706","article-title":"A patent review on PD-1\/PD-L1 antagonists: Small molecules, peptides, and macrocycles (2015\u20132018)","volume":"28","author":"Shaabani","year":"2018","journal-title":"Expert. Opin. Ther. Pat."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"764","DOI":"10.3389\/fchem.2019.00764","article-title":"Computational insight into the small molecule intervening PD-L1 dimerization and the potential structure-activity relationship","volume":"7","author":"Shi","year":"2019","journal-title":"Front. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"12392","DOI":"10.1038\/s41598-019-48826-6","article-title":"Comprehensive in vitro characterization of PD-L1 small molecule inhibitors","volume":"9","author":"Ganesan","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Guo, Y., Jin, Y., Wang, B., and Liu, B. (2021). Molecular mechanism of small-molecule inhibitors in blocking the PD-1\/PD-L1 pathway through PD-L1 dimerization. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22094766"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"105034","DOI":"10.1016\/j.bioorg.2021.105034","article-title":"Design, synthesis, and biological evaluation of 1-methyl-1H-pyrazolo[4,3-b]pyridine derivatives as novel small-molecule inhibitors targeting the PD-1\/PD-L1 interaction","volume":"114","author":"Dai","year":"2021","journal-title":"Bioorg. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"113001","DOI":"10.1016\/j.ejmech.2020.113001","article-title":"Design, synthesis, evaluation, and SAR of 4-phenylindoline derivatives, a novel class of small-molecule inhibitors of the programmed cell death-1\/ programmed cell death-ligand 1 (PD-1\/PD-L1) interaction","volume":"211","author":"Yang","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"16020","DOI":"10.1021\/acs.jmedchem.1c01409","article-title":"Interfering with the tumor-immune interface: Making way for triazine-based small molecules as novel PD-L1 inhibitors","volume":"64","author":"Russomanno","year":"2021","journal-title":"J. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Zhang, H., Xia, Y., Yu, C., Du, H., Liu, J., Li, H., Huang, S., Zhu, Q., Xu, Y., and Zou, Y. (2021). Discovery of novel small-molecule inhibitors of PD-1\/PD-L1 interaction via structural simplification strategy. Molecules, 26.","DOI":"10.3390\/molecules26113347"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"97","DOI":"10.4155\/fmc-2021-0256","article-title":"Advances of biphenyl small-molecule inhibitors targeting PD-1\/PD-L1 interaction in cancer immunotherapy","volume":"14","author":"Chen","year":"2022","journal-title":"Future Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"100","DOI":"10.2174\/1574892813666181029142812","article-title":"Novel small molecule inhibitors of programmed cell death (PD)-1, and its ligand, PD-L1 in cancer immunotherapy: A review update of patent literature","volume":"14","author":"Kopalli","year":"2019","journal-title":"Recent Pat. Anticancer Drug Discov."},{"key":"ref_16","unstructured":"Thuru, X., Quesnel, M., Magnez, R., Millet, R., Leleu, N., and Klupsch, F. Novel pyrazolone derivatives as PD-1\/PD-L1 interaction inhibitors. EP3766544, PCT\/EP2020\/070478 (WO\/2021\/009384)."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"114343","DOI":"10.1016\/j.ejmech.2022.114343","article-title":"Pyrazolones as inhibitors of immune checkpoint blocking the PD-1\/PD-L1 interaction","volume":"236","author":"Magnez","year":"2022","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1080\/14737175.2019.1581610","article-title":"Edaravone for the treatment of amyotrophic lateral sclerosis","volume":"19","author":"Yoshino","year":"2019","journal-title":"Expert Rev. Neurother."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"907","DOI":"10.1111\/jcpt.13392","article-title":"Clinical effects and safety of edaravone in treatment of acute ischaemic stroke: A meta-analysis of randomized controlled trials","volume":"46","author":"Chen","year":"2021","journal-title":"J. Clin. Pharm. Ther."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"105967","DOI":"10.1016\/j.intimp.2019.105967","article-title":"Potential use of edaravone to reduce specific side effects of chemo-, radio- and immuno-therapy of cancers","volume":"77","author":"Bailly","year":"2019","journal-title":"Int. Immunopharmacol."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Cha, S.J., and Kim, K. (2022). Effects of the edaravone, a drug approved for the treatment of amyotrophic lateral sclerosis, on mitochondrial function and neuroprotection. Antioxidants, 11.","DOI":"10.3390\/antiox11020195"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"555","DOI":"10.3109\/00207454.2014.959121","article-title":"Edaravone\u2019s free radical scavenging mechanisms of neuroprotection against cerebral ischemia: Review of the literature","volume":"125","author":"Ren","year":"2015","journal-title":"Int. J. Neurosci."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Ahmadinejad, F., Geir M\u00f8ller, S., Hashemzadeh-Chaleshtori, M., Bidkhori, G., and Jami, M.S. (2017). Molecular mechanisms behind free radical scavengers function against oxidative stress. Antioxidants, 6.","DOI":"10.3390\/antiox6030051"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1124\/jpet.107.131391","article-title":"The radical scavenger edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) reacts with a pterin derivative and produces a cytotoxic substance that induces intracellular reactive oxygen species generation and cell death","volume":"324","author":"Arai","year":"2008","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1093\/nass\/nrn287","article-title":"Reactive oxygen species generation through NADH oxidation by pterin derivatives","volume":"52","author":"Nonogawa","year":"2008","journal-title":"Nucleic Acids Symp. Ser."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.freeradbiomed.2021.05.002","article-title":"Properties and reactivity of the folic acid and folate photoproduct 6-formylpterin","volume":"171","author":"Goossens","year":"2021","journal-title":"Free Radic. Biol. Med."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"115463","DOI":"10.1016\/j.bmc.2020.115463","article-title":"Chemical reactivity and uses of 1-phenyl-3-methyl-5-pyrazolone (PMP), also known as edaravone","volume":"28","author":"Bailly","year":"2020","journal-title":"Bioorg. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Regnault, R., Kouach, M., Goossens, L., Thuru, X., Bailly, C., and Goossens, J.F. (2022). Mono- and bis-edaravone adducts formed in the presence of vanillin in an aqueous solution. Sep. Sci. Plus, 1\u201312.","DOI":"10.1002\/sscp.202270055"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5702","DOI":"10.3390\/s90705702","article-title":"Antioxidant activity and total phenolic and flavonoid contents of Hieracium pilosella L.","volume":"9","author":"Tumbas","year":"2009","journal-title":"Extr. Sens."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1016\/j.carres.2009.09.038","article-title":"Chitosan gallate as a novel potential polysaccharide antioxidant: An EPR study","volume":"345","author":"Pasanphan","year":"2010","journal-title":"Carbohydr. Res."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1376","DOI":"10.1016\/j.bmcl.2014.01.045","article-title":"A multiple free-radical scavenging (MULTIS) study on the antioxidant capacity of a neuroprotective drug, edaravone as compared with uric acid, glutathione, and trolox","volume":"24","author":"Kamogawa","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1248\/cpb.52.186","article-title":"The reaction rate of edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with hydroxyl radical","volume":"52","author":"Abe","year":"2004","journal-title":"Chem. Pharm. Bull."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1204","DOI":"10.1016\/S0021-9258(19)57287-8","article-title":"The transition metal-mediated formation of the hydroxyl free radical during the reduction of molecular oxygen by ferredoxin-ferredoxin:NADP+ oxidoreductase","volume":"263","author":"Morehouse","year":"1988","journal-title":"J. Biol. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1016","DOI":"10.1021\/acs.accounts.8b00543","article-title":"Detection and Application of 5-Formylcytosine and 5-Formyluracil in DNA","volume":"52","author":"Wang","year":"2019","journal-title":"Acc. Chem. Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"15445","DOI":"10.1021\/acs.analchem.1c03339","article-title":"Sequencing 5-formyluracil in genomic DNA at single-base resolution","volume":"93","author":"Yang","year":"2021","journal-title":"Anal. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"10243","DOI":"10.1021\/acs.analchem.1c01644","article-title":"ISFrag: De novo recognition of in-source fragments for liquid chromatography-mass spectrometry data","volume":"93","author":"Guo","year":"2021","journal-title":"Anal. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"579","DOI":"10.1080\/10715760600606374","article-title":"Electron spin resonance and spin trapping technique provide direct evidence that edaravone prevents acute ischemia-reperfusion injury of the liver by limiting free radical-mediated tissue damage","volume":"40","author":"Kono","year":"2006","journal-title":"Free Radic. Res."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1269\/jrr.10060","article-title":"Pulse radiolysis study on free radical scavenger edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one). 2: A comparative study on edaravone derivatives","volume":"52","author":"Hata","year":"2011","journal-title":"J. Radiat. Res."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"117403","DOI":"10.1016\/j.lfs.2020.117403","article-title":"Regulation of PD-L1 expression on cancer cells with ROS-modulating drugs","volume":"246","author":"Bailly","year":"2020","journal-title":"Life Sci."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"106759","DOI":"10.1016\/j.intimp.2020.106759","article-title":"Inhibition of programmed death ligand 1 (PD-L1) expression in breast cancer cells by sesamin","volume":"86","author":"Kongtawelert","year":"2020","journal-title":"Int. Immunopharmacol."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Sp, N., Kang, D.Y., Lee, J.M., and Jang, K.J. (2021). Mechanistic Insights of Anti-Immune Evasion by Nobiletin through Regulating miR-197\/STAT3\/PD-L1 Signaling in Non-Small Cell Lung Cancer (NSCLC) Cells. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22189843"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Mendonca, P., Hill, L., and Soliman, K.F.A. (2022). Effects of Cardamonin on PD-1\/PD-L1 Checkpoint in Triple-Negative Breast Cancer. FASEB J., 36.","DOI":"10.1096\/fasebj.2022.36.S1.R2273"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Evans, J., Mendonca, P., and Soliman, K.F.A. (2022). Hesperetin modulation of oxidative stress and inflammatory mediators in LPS-Activated BV-2 Microglial Cells. FASEB J., 36.","DOI":"10.1096\/fasebj.2022.36.S1.R2269"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/j.ijbiomac.2022.03.122","article-title":"Comparison of the immune activation capacities of fucoidan and laminarin extracted from Laminaria japonica","volume":"208","author":"An","year":"2022","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"995","DOI":"10.7150\/ijbs.67329","article-title":"Ascorbic acid induced TET2 enzyme activation enhances cancer immunotherapy efficacy in renal cell carcinoma","volume":"18","author":"Peng","year":"2022","journal-title":"Int. J. Biol. Sci."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"112835","DOI":"10.1016\/j.jep.2020.112835","article-title":"Curcumol inhibits the expression of programmed cell death-ligand 1 through crosstalk between hypoxia-inducible factor-1\u03b1 and STAT3 (T705) signaling pathways in hepatic cancer","volume":"257","author":"Zuo","year":"2020","journal-title":"J. Ethnopharmacol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"110588","DOI":"10.1016\/j.biopha.2020.110588","article-title":"Vitamin C: A stem cell promoter in cancer metastasis and immunotherapy","volume":"131","author":"Fu","year":"2020","journal-title":"Biomed. Pharmacother."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"112553","DOI":"10.1016\/j.biopha.2021.112553","article-title":"The potential role of vitamin C in empowering cancer immunotherapy","volume":"146","author":"Bedhiafi","year":"2022","journal-title":"Biomed. Pharmacother."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6212935","DOI":"10.1155\/2020\/6212935","article-title":"Selective Targeting of Cancerous Mitochondria and Suppression of Tumor Growth Using Redox-Active Treatment Adjuvant","volume":"2020","author":"Bakalova","year":"2020","journal-title":"Oxid. Med. Cell Longev."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"101780","DOI":"10.1016\/j.redox.2020.101780","article-title":"Regulation of PD-L1 expression in K-ras-driven cancers through ROS-mediated FGFR1 signaling","volume":"38","author":"Glorieux","year":"2021","journal-title":"Redox Biol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"647472","DOI":"10.3389\/fchem.2021.647472","article-title":"Synthesis of herbicide candidate through optimization of quinclorac with 3-methyl-1H-pyrazol-5-yl","volume":"9","author":"Luo","year":"2021","journal-title":"Front. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"17623","DOI":"10.1038\/s41598-017-17963-1","article-title":"PD-1\/PD-L1 binding studies using microscale thermophoresis","volume":"7","author":"Magnez","year":"2017","journal-title":"Sci. Rep."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3316\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:16:09Z","timestamp":1760138169000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3316"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,21]]},"references-count":52,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["molecules27103316"],"URL":"https:\/\/doi.org\/10.3390\/molecules27103316","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,21]]}}}