{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T05:02:40Z","timestamp":1787029360015,"version":"build-2736575974"},"reference-count":66,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,7,23]],"date-time":"2023-07-23T00:00:00Z","timestamp":1690070400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Centre, Poland","award":["2017\/27\/N\/NZ7\/02423"],"award-info":[{"award-number":["2017\/27\/N\/NZ7\/02423"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceutics"],"abstract":"<jats:p>Sonodynamic therapy (SDT) is a non-invasive therapeutic modality in cancer treatment that combines low-intensity ultrasound (US) and sonosensitizers. Tumor cells are destroyed through the synergistic effects of ultrasound and a chemical sonosensitizer. This study focused on the synthesis and in vitro evaluation of the sonodynamic effect of natural curcumin, triterpene oleanolic acid, and their semi-synthetic derivatives on tongue cancer SCC-25 and hypopharyngeal FaDu cell lines. The combination of the tested compounds with sonication showed a synergistic increase in cytotoxicity. In the group of oleanolic acid derivatives, oleanoyl hydrogen succinate (6) showed the strongest cytotoxic effect both in the SCC-25 and FaDu cell lines. Comparing curcumin (4) and its pyrazole derivative (5), curcumin showed a better cytotoxic effect on SCC-25 cells, while curcumin pyrazole was more potent on FaDu cells. The highest sonotherapeutic activity, compared to its individual components, was demonstrated by a structural linker mode hybrid containing both curcumin pyrazole-oleanoyl hydrogen succinate units within one complex molecule (7). This study can be beneficial in the context of new perspectives in the search for effective sonosensitizers among derivatives of natural organic compounds.<\/jats:p>","DOI":"10.3390\/pharmaceutics15072008","type":"journal-article","created":{"date-parts":[[2023,7,24]],"date-time":"2023-07-24T01:08:11Z","timestamp":1690160891000},"page":"2008","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Curcumin\u2013Triterpene Type Hybrid as Effective Sonosensitizers for Sonodynamic Therapy in Oral Squamous Cell Carcinoma"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7419-945X","authenticated-orcid":false,"given":"Katarzyna","family":"Sowa-Kasprzak","sequence":"first","affiliation":[{"name":"Chair and Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6 Str., 60-780 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ma\u0142gorzata","family":"J\u00f3zkowiak","sequence":"additional","affiliation":[{"name":"Department of Toxicology, Poznan University of Medical Sciences, Dojazd 30 Str., 61-131 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8320-5201","authenticated-orcid":false,"given":"Dorota","family":"Olender","sequence":"additional","affiliation":[{"name":"Chair and Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6 Str., 60-780 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4108-6499","authenticated-orcid":false,"given":"Anna","family":"Pawe\u0142czyk","sequence":"additional","affiliation":[{"name":"Chair and Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6 Str., 60-780 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hanna","family":"Piotrowska-Kempisty","sequence":"additional","affiliation":[{"name":"Department of Toxicology, Poznan University of Medical Sciences, Dojazd 30 Str., 61-131 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1121-6272","authenticated-orcid":false,"given":"Lucjusz","family":"Zaprutko","sequence":"additional","affiliation":[{"name":"Chair and Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6 Str., 60-780 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4169","DOI":"10.1002\/adma.201500323","article-title":"Red-Emissive Carbon Dots for Fluorescent, Photoacoustic, and Thermal Theranostics in Living Mice","volume":"27","author":"Ge","year":"2015","journal-title":"Adv. Mater."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1021\/jacs.8b08714","article-title":"Self-Assembled Copper\u2013Amino Acid Nanoparticles for in Situ Glutathione \u201cAND\u201d H2O2 Sequentially Triggered Chemodynamic Therapy","volume":"141","author":"Ma","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"124212","DOI":"10.1016\/j.cej.2020.124212","article-title":"Lysosome-targetable carbon dots for highly efficient photothermal\/photodynamic synergistic cancer therapy and photoacoustic\/two-photon excited fluorescence imaging","volume":"388","author":"Zhao","year":"2020","journal-title":"Chem. Eng. J."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6527","DOI":"10.1021\/jacs.9b10228","article-title":"Ultrafine Titanium Monoxide (TiO1+x) Nanorods for Enhanced Sonodynamic Therapy","volume":"142","author":"Wang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1801733","DOI":"10.1002\/advs.201801733","article-title":"Nanocatalytic Tumor Therapy by Biomimetic Dual Inorganic Nanozyme-Catalyzed Cascade Reaction","volume":"6","author":"Gao","year":"2019","journal-title":"Adv. Sci."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"331","DOI":"10.4155\/tde-2016-0080","article-title":"Synergistic efficacy of ultrasound, sonosensitizers and chemotherapy: A review","volume":"8","author":"Hirschberg","year":"2017","journal-title":"Ther. Deliv."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"214087","DOI":"10.1016\/j.ccr.2021.214087","article-title":"Advances and perspectives in organic sonosensitizers for sonodynamic therapy","volume":"445","author":"Xing","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"325","DOI":"10.20892\/j.issn.2095-3941.2016.0068","article-title":"Recent advances of sonodynamic therapy in cancer treatment","volume":"13","author":"Wan","year":"2016","journal-title":"Cancer Biol. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.ultras.2012.06.005","article-title":"The ABCG2 transporter is a key molecular determinant of the efficacy of sonodynamic therapy with Photofrin in glioma stem-like cells","volume":"53","author":"Xu","year":"2013","journal-title":"Ultrasonics"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"99","DOI":"10.4236\/jct.2011.22011","article-title":"Sonodynamic Antitumor Effect of Benzoporphyrin Derivative Monoacid Ring A on KLN205 Cells","volume":"02","author":"Osaki","year":"2011","journal-title":"J. Cancer Ther."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1016\/j.ultras.2011.10.013","article-title":"Apoptosis induced by sonodynamic treatment by protoporphyrin IX on MDA-MB-231 cells","volume":"52","author":"Li","year":"2012","journal-title":"Ultrasonics"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Zheng, L., Sun, X., Zhu, X., Lv, F., Zhong, Z., Zhang, F., Guo, W., Cao, W., Yang, L., and Tian, Y. (2014). Apoptosis of THP-1 Derived Macrophages Induced by Sonodynamic Therapy Using a New Sonosensitizer Hydroxyl Acetylated Curcumin. PLoS ONE, 9.","DOI":"10.1371\/journal.pone.0093133"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"40967","DOI":"10.1038\/srep40967","article-title":"Antiproliferative and Apoptosis-inducing Effect of exo-Protoporphyrin IX based Sonodynamic Therapy on Human Oral Squamous Cell Carcinoma","volume":"7","author":"Lv","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_14","first-page":"3673","article-title":"Sonodynamic Therapy of Cancer Using Novel Sonosensitizers","volume":"27","author":"Kuroki","year":"2007","journal-title":"Anticancer Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1933","DOI":"10.1016\/j.ultrasmedbio.2010.06.022","article-title":"Role of Autophagy in Sonodynamic Therapy-Induced Cytotoxicity in S180 Cells","volume":"36","author":"Wang","year":"2010","journal-title":"Ultrasound Med. Biol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1586","DOI":"10.1021\/acsnano.9b06689","article-title":"Fluorinated Chitosan To Enhance Transmucosal Delivery of Sonosensitizer-Conjugated Catalase for Sonodynamic Bladder Cancer Treatment Post-intravesical Instillation","volume":"14","author":"Li","year":"2020","journal-title":"ACS Nano"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"14926","DOI":"10.1021\/la503929c","article-title":"Polymeric Microbubbles as Delivery Vehicles for Sensitizers in Sonodynamic Therapy","volume":"30","author":"McEwan","year":"2014","journal-title":"Langmuir"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2000560","DOI":"10.1002\/adhm.202000560","article-title":"An Ultrasound-Excitable Aggregation-Induced Emission Dye for Enhanced Sonodynamic Therapy of Tumors","volume":"9","author":"Zeng","year":"2020","journal-title":"Adv. Healthc. Mater."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"7312","DOI":"10.1021\/acsnano.8b03674","article-title":"Ultrasound Triggered Conversion of Porphyrin\/Camptothecin-Fluoroxyuridine Triad Microbubbles into Nanoparticles Overcomes Multidrug Resistance in Colorectal Cancer","volume":"12","author":"Chen","year":"2018","journal-title":"ACS Nano"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6178","DOI":"10.7150\/thno.29569","article-title":"Nanosonosensitizers for Highly Efficient Sonodynamic Cancer Theranostics","volume":"8","author":"Huang","year":"2018","journal-title":"Theranostics"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1039\/C9TB02198A","article-title":"Dual ultrasound-activatable nanodroplets for highly-penetrative and efficient ovarian cancer theranostics","volume":"8","author":"Yang","year":"2020","journal-title":"J. Mater. Chem. B"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10415","DOI":"10.1007\/s13277-016-4931-3","article-title":"Hyperthermotherapy enhances antitumor effect of 5-aminolevulinic acid-mediated sonodynamic therapy with activation of caspase-dependent apoptotic pathway in human glioma","volume":"37","author":"Ju","year":"2016","journal-title":"Tumor Biol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1211\/0022357022412","article-title":"Sonodynamic antitumour effect of chloroaluminum phthalocyanine tetrasulfonate on murine solid tumour","volume":"56","author":"Yumita","year":"2010","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3023","DOI":"10.1016\/j.bmc.2016.05.015","article-title":"Comparing the efficacy of photodynamic and sonodynamic therapy in non-melanoma and melanoma skin cancer","volume":"24","author":"McEwan","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9355","DOI":"10.1021\/acsami.8b21968","article-title":"Mitochondria-Targeted and Ultrasound-Activated Nanodroplets for Enhanced Deep-Penetration Sonodynamic Cancer Therapy","volume":"11","author":"Zhang","year":"2019","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1111\/j.1349-7006.2004.tb02192.x","article-title":"Enhanced antitumor activity of ultrasonic irradiation in the presence of new quinolone antibiotics in vitro","volume":"95","author":"Huang","year":"2004","journal-title":"Cancer Sci."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1016\/j.saa.2010.11.054","article-title":"Spectroscopic investigation on protein damage by ciprofloxacin under ultrasonic irradiation","volume":"78","author":"Liu","year":"2011","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1016\/j.ultrasmedbio.2009.09.007","article-title":"Hypocrellin B Enhances Ultrasound-Induced Cell Death of Nasopharyngeal Carcinoma Cells","volume":"36","author":"Wang","year":"2010","journal-title":"Ultrasound Med. Biol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"10528","DOI":"10.1039\/C8RA09172B","article-title":"Berberine nanoparticles for promising sonodynamic therapy of a HeLa xenograft tumour","volume":"9","author":"Liu","year":"2019","journal-title":"RSC Adv."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2101976","DOI":"10.1002\/smll.202101976","article-title":"Organic Sonosensitizers for Sonodynamic Therapy: From Small Molecules and Nanoparticles toward Clinical Development","volume":"17","author":"Li","year":"2021","journal-title":"Small"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"8181","DOI":"10.1016\/j.tet.2012.07.072","article-title":"Novel pyrazoline and pyrazole porphyrin derivatives: Synthesis and photophysical properties","volume":"68","author":"Moura","year":"2012","journal-title":"Tetrahedron"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"579","DOI":"10.2174\/1871520615666150907095756","article-title":"Oleanolic Acid A-lactams Inhibit the Growth of HeLa, KB, MCF-7 and Hep-G2 Cancer Cell Lines at Micromolar Concentrations","volume":"16","author":"Ruszkowski","year":"2016","journal-title":"Anticancer Agents Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1016\/j.bmcl.2006.03.009","article-title":"Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase","volume":"16","author":"Chen","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1681","DOI":"10.1248\/cpb.48.1681","article-title":"Chemical Modification of Oleanene Type Triterpenes and Their Inhibitory Activity against HIV-1 Protease Dimerization","volume":"48","author":"Ma","year":"2000","journal-title":"Chem. Pharm. Bull."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.molstruc.2013.09.006","article-title":"Beckmann rearrangement of oxime obtained from oleanolic acid. Structure elucidation of the initial oxime","volume":"1053","author":"Zaprutko","year":"2013","journal-title":"J. Mol. Struct."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2894","DOI":"10.1016\/j.bmc.2007.12.054","article-title":"Synthesis and exploration of novel curcumin analogues as anti-malarial agents","volume":"16","author":"Mishra","year":"2008","journal-title":"Bioorganic Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"108876","DOI":"10.1016\/j.steroids.2021.108876","article-title":"Type and position of linkage govern the cytotoxicity of oleanolic acid rhodamine B hybrids","volume":"172","author":"Heise","year":"2021","journal-title":"Steroids"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Sowa-Kasprzak, K., Toto\u0144, E., Kujawski, J., Olender, D., Lisiak, N., Zaprutko, L., Rubi\u015b, B., Kaczmarek, M., and Pawe\u0142czyk, A. (2023). Synthesis, Cytotoxicity and Molecular Docking of New Hybrid Compounds by Combination of Curcumin with Oleanolic Acid. Biomedicines, 11.","DOI":"10.3390\/biomedicines11061506"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"470","DOI":"10.1097\/00001813-199706000-00010","article-title":"Antiproliferative effect of curcumin (diferuloylmethane) against human breast tumor cell lines","volume":"8","author":"Mehta","year":"1997","journal-title":"Anticancer Drugs"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Tomeh, M., Hadianamrei, R., and Zhao, X. (2019). A Review of Curcumin and Its Derivatives as Anticancer Agents. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20051033"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Uro\u0161evi\u0107, M., Nikoli\u0107, L., Gaji\u0107, I., Nikoli\u0107, V., Dini\u0107, A., and Miljkovi\u0107, V. (2022). Curcumin: Biological Activities and Modern Pharmaceutical Forms. Antibiotics, 11.","DOI":"10.3390\/antibiotics11020135"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Adamczak, A., O\u017carowski, M., and Karpi\u0144ski, T.M. (2020). Curcumin, a Natural Antimicrobial Agent with Strain-Specific Activity. Pharmaceuticals, 13.","DOI":"10.3390\/ph13070153"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1177\/1534735410377197","article-title":"Ultrasound-Induced Cell Death of Nasopharyngeal Carcinoma Cells in the Presence of Curcumin","volume":"10","author":"Wang","year":"2011","journal-title":"Integr. Cancer Ther."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"103326","DOI":"10.1016\/j.bioorg.2019.103326","article-title":"Oleanolic acid oxime derivatives and their conjugates with aspirin modulate the NF-\u03baB-mediated transcription in HepG2 hepatoma cells","volume":"93","author":"Paluszczak","year":"2019","journal-title":"Bioorganic Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1016\/j.cbi.2010.01.034","article-title":"Antioxidant activities of oleanolic acid in vitro: Possible role of Nrf2 and MAP kinases","volume":"184","author":"Wang","year":"2010","journal-title":"Chem. Biol. Interact."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.mce.2013.06.014","article-title":"Oleanolic acid improves hepatic insulin resistance via antioxidant, hypolipidemic and anti-inflammatory effects","volume":"376","author":"Wang","year":"2013","journal-title":"Mol. Cell. Endocrinol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"620472","DOI":"10.1155\/2015\/620472","article-title":"Antimicrobial Activity of Oleanolic and Ursolic Acids: An Update","volume":"2015","author":"Jesus","year":"2015","journal-title":"Evid. Based Complement. Alternat. Med."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3615","DOI":"10.3390\/molecules18033615","article-title":"Efficient Synthesis and Anti-Fungal Activity of Oleanolic Acid Oxime Esters","volume":"18","author":"Zhao","year":"2013","journal-title":"Molecules"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Ayeleso, T., Matumba, M., and Mukwevho, E. (2017). Oleanolic Acid and Its Derivatives: Biological Activities and Therapeutic Potential in Chronic Diseases. Molecules, 22.","DOI":"10.3390\/molecules22111915"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"153788","DOI":"10.1016\/j.phymed.2021.153788","article-title":"A nanosensitizer self-assembled from oleanolic acid and chlorin e6 for synergistic chemo\/sono-photodynamic cancer therapy","volume":"93","author":"Zheng","year":"2021","journal-title":"Phytomedicine"},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Pawe\u0142czyk, A., Sowa-Kasprzak, K., Olender, D., and Zaprutko, L. (2018). Molecular Consortia\u2014Various Structural and Synthetic Concepts for More Effective Therapeutics Synthesis. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19041104"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1509","DOI":"10.2174\/1389557521666210105110848","article-title":"Structure and Activity of Pentacyclic Triterpenes Codrugs. A Review","volume":"21","author":"Olender","year":"2021","journal-title":"Mini-Rev. Med. Chem."},{"key":"ref_53","first-page":"202","article-title":"Strong and Long-Lasting Antinociceptive and Anti-inflammatory Conjugate of Naturally Occurring Oleanolic Acid and Aspirin","volume":"7","author":"Wachowiak","year":"2016","journal-title":"Front. Pharmacol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"20839","DOI":"10.3390\/molecules191220839","article-title":"Hybrid curcumin compounds: A new strategy for cancer treatment","volume":"19","author":"Teiten","year":"2014","journal-title":"Molecules."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3","DOI":"10.2174\/1568026621666211105101231","article-title":"Recent Progress in Oleanolic Acid: Structural Modification and BiologicalActivity","volume":"22","author":"Wang","year":"2022","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.cbi.2013.11.009","article-title":"Methyl 3-hydroxyimino-11-oxoolean-12-en-28-oate (HIMOXOL), a synthetic oleanolic acid derivative, induces both apoptosis and autophagy in MDA-MB-231 breast cancer cells","volume":"208","author":"Lisiak","year":"2014","journal-title":"Chem. Biol. Interact."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"e1800366","DOI":"10.1002\/cbdv.201800366","article-title":"Recent Updates in Curcumin Pyrazole and Isoxazole Derivatives: Synthesis and Biological Application","volume":"16","author":"Mishra","year":"2019","journal-title":"Chem. Biodivers."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Lozada-Garc\u00eda, M., Enr\u00edquez, R., Ram\u00edrez-Ap\u00e1n, T., Nieto-Camacho, A., Palacios-Espinosa, J., Custodio-Galv\u00e1n, Z., Soria-Arteche, O., and P\u00e9rez-Villanueva, J. (2017). Synthesis of Curcuminoids and Evaluation of Their Cytotoxic and Antioxidant Properties. Molecules, 22.","DOI":"10.3390\/molecules22040633"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1590\/1679-775720130317","article-title":"Oral squamous cell carcinoma: Clinicopathological features from 346 cases from a single Oral Pathology service during an 8-year period","volume":"21","author":"Pires","year":"2013","journal-title":"J. Appl. Oral Sci."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"401","DOI":"10.2174\/1381612825666190123114107","article-title":"Photo- and Sono-Dynamic Therapy: A Review of Mechanisms and Considerations for Pharmacological Agents Used in Therapy Incorporating Light and Sound","volume":"25","author":"Yang","year":"2019","journal-title":"Curr. Pharm. Des."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1177\/1534735409343693","article-title":"Sonodynamic and Photodynamic Therapy in Advanced Breast Carcinoma: A Report of 3 Cases","volume":"8","author":"Wang","year":"2009","journal-title":"Integr. Cancer Ther."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1667\/RR3510.1","article-title":"Mechanism of Porphyrin-Induced Sonodynamic Effect: Possible Role of Hyperthermia","volume":"165","author":"Kinoshita","year":"2006","journal-title":"Radiat. Res."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1","DOI":"10.13189\/nn.2016.040101","article-title":"Combination of Sonodynamic and Photodynamic Therapy against Cancer Would Be Effective through Using a Regulated Size of Nanoparticles","volume":"4","author":"Miyoshi","year":"2016","journal-title":"Nanosci. Nanoeng."},{"key":"ref_64","first-page":"737264","article-title":"The Sonodynamic Effect of Curcumin on THP-1 Cell-Derived Macrophages","volume":"2013","author":"Wang","year":"2013","journal-title":"BioMed Res. Int."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1016\/j.ultsonch.2004.03.004","article-title":"Sonodynamic therapy\u2013\u2013A review of the synergistic effects of drugs and ultrasound","volume":"11","author":"Rosenthal","year":"2004","journal-title":"Ultrason. Sonochem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1016\/j.ultsonch.2005.10.001","article-title":"Comparison between sonodynamic effect and photodynamic effect with photosensitizers on free radical formation and cell killing","volume":"13","author":"Hiraoka","year":"2006","journal-title":"Ultrason. Sonochem."}],"container-title":["Pharmaceutics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1999-4923\/15\/7\/2008\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:17:28Z","timestamp":1760127448000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1999-4923\/15\/7\/2008"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,23]]},"references-count":66,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2023,7]]}},"alternative-id":["pharmaceutics15072008"],"URL":"https:\/\/doi.org\/10.3390\/pharmaceutics15072008","relation":{},"ISSN":["1999-4923"],"issn-type":[{"value":"1999-4923","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,23]]}}}