Rational design, synthesis, and pharmacological characterisation of dicarbonyl curcuminoid analogues with improved stability against lung cancer via ROS and ER stress mediated cell apoptosis and pyroptosis

References

• Zou Y, Hu Y, Jiang Z, et al. Exhaled metabolic markers and relevant dysregulated pathways of lung cancer: a pilot study. Ann Med 2022;54:790–802.
   PubMed Web of Science ®Google Scholar
• Wang J, Zhang Y, Zhang G, et al. Radiotherapy-induced enrichment of EGF-modified doxorubicin nanoparticles enhances the therapeutic outcome of lung cancer. Drug Deliv 2022;29:588–99.
   PubMed Web of Science ®Google Scholar
• Noorafshan A, Ashkani-Esfahani S. A review of therapeutic effects of curcumin. Curr Pharm Des 2013;19:2032–46.
   PubMed Web of Science ®Google Scholar
• Soltani B, Bodaghabadi N, Ghaemi N, Sadeghizadeh M. Radiation-induced surge of macrophage foam cell formation, oxidative damage, and cytokine release is attenuated by a nanoformulation of curcumin. Int J Radiat Biol 2017;93:303–14.
   PubMed Web of Science ®Google Scholar
• Kasi PD, Tamilselvam R, Skalicka-Wozniak K, et al. Molecular targets of curcumin for cancer therapy: an updated review. Tumour Biol 2016;37:13017–28.
   PubMed Web of Science ®Google Scholar
• Mirzaei H, Shakeri A, Rashidi B, et al. Phytosomal curcumin: a review of pharmacokinetic, experimental and clinical studies. Biomed Pharmacother 2017;85:102–12.
   PubMed Web of Science ®Google Scholar
• Sharma RA, Euden SA, Platton SL, et al. Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin Cancer Res 2004;10:6847–54.
   PubMed Web of Science ®Google Scholar
• Dhillon N, Aggarwal BB, Newman RA, et al. Phase II trial of curcumin in patients with advanced pancreatic cancer. Clin Cancer Res 2008;14:4491–9.
   PubMed Web of Science ®Google Scholar
• Wang YJ, Pan MH, Cheng AL, et al. Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal 1997;15:1867–76.
   PubMed Web of Science ®Google Scholar
• Heger M, van Golen RF, Broekgaarden M, Michel MC. The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer. Pharmacol Rev 2014;66:222–307.
   PubMed Web of Science ®Google Scholar
• Priyadarsini KI. The chemistry of curcumin: from extraction to therapeutic agent. Molecules 2014;19:20091–112.
   PubMed Web of Science ®Google Scholar
• Zhao C, Liu Z, Liang G. Promising curcumin-based drug design: mono-carbonyl analogues of curcumin (MACs). Curr Pharm Des 2013;19:2114–35.
   PubMed Web of Science ®Google Scholar
• Wang Y, Xiao J, Zhou H, et al. A novel monocarbonyl analogue of curcumin, (1E,4E)-1,5-bis(2,3-dimethoxyphenyl)penta-1,4-dien- 3-one, induced cancer cell H460 apoptosis via activation of endoplasmic reticulum stress signaling pathway. J Med Chem 2011;54:3768–78.
   PubMed Web of Science ®Google Scholar
• Chen L, Li Q, Weng B, et al. Design, synthesis, anti-lung cancer activity, and chemosensitization of tumor-selective MCACs based on ROS-mediated JNK pathway activation and NF-κB pathway inhibition. Eur J Med Chem 2018;151:508–19.
   PubMed Web of Science ®Google Scholar
• Wu J, Wu S, Shi L, et al. Design, synthesis, and evaluation of asymmetric EF24 analogues as potential anti-cancer agents for lung cancer. Eur J Med Chem 2017;125:321–1331.
   Web of Science ®Google Scholar
• Wu J, Cai Z, Wei X, et al. Anti-Lung Cancer Activity of the Curcumin Analog JZ534 In Vitro. Biomed Res Int 2015;2015:504529.
   PubMed Web of Science ®Google Scholar
• Xia Y, Weng B, Wang Z, et al. W346 inhibits cell growth, invasion, induces cycle arrest and potentiates apoptosis in human gastric cancer cells in vitro through the NF-kappaB signaling pathway. Tumour Biol 2016;37:4791–801.
   PubMedGoogle Scholar
• Chen L, Li Q, Zheng Z, et al. Design and optimize N-substituted EF24 as effective and low toxicity NF-kappaB inhibitor for lung cancer therapy via apoptosis-to-pyroptosis switch. Chem Biol Drug Des 2019;94:1368–77.
   PubMed Web of Science ®Google Scholar
• Winter E, Neuenfeldt PD, Chiaradia-Delatorre LD, et al. Symmetric bis-chalcones as a new type of breast cancer resistance protein inhibitors with a mechanism different from that of chromones. J Med Chem 2014;57:2930–41.
   PubMed Web of Science ®Google Scholar
• Svetnik V, Liaw A, Tong C, et al. Random forest: a classification and regression tool for compound classification and QSAR modeling. J Chem Inf Comput Sci 2003;42:1947–58.
   Google Scholar
• Wang YP, Gao WQ, Shi XY, et al. Chemotherapy drugs induce pyroptosis through caspase-3 cleavage of a gasdermin. Nature 2017;547:99–103.
   PubMed Web of Science ®Google Scholar
• Debatin KM. Apoptosis pathways in cancer and cancer therapy. Cancer Immunol Immunother 2004;53:153–9.
   PubMed Web of Science ®Google Scholar
• Sabharwal SS, Schumacker PT. Mitochondrial ROS in cancer: initiators, amplifiers or an Achilles' heel? Nat Rev Cancer 2014;14:709–21.
   PubMed Web of Science ®Google Scholar
• Raj L, Ide T, Gurkar AU, et al. Selective killing of cancer cells by a small molecule targeting the stress response to ROS. Nature 2011;475:231–4.
   PubMed Web of Science ®Google Scholar
• Thayyullathil F, Chathoth S, Hago A, et al. Rapid reactive oxygen species (ROS) generation induced by curcumin leads to caspase-dependent and -independent apoptosis in L929 cells. Free Radic Biol Med 2008;45:1403–12.
   PubMed Web of Science ®Google Scholar
• Lindholm D, Korhonen L, Eriksson O, Kõks S. Recent insights into the role of unfolded protein response in ER stress in health and disease. Front Cell Dev Biol 2017;5:48.
   PubMed Web of Science ®Google Scholar
• Zeeshan HM, Lee GH, Kim HR, Chae HJ. Endoplasmic reticulum stress and associated ROS. Int J Mol Sci 2016;17:327.
   PubMed Web of Science ®Google Scholar
• Senft D, Ronai ZA. UPR, autophagy, and mitochondria crosstalk underlies the ER stress response. Trends Biochem Sci 2015;40:141–8.
   PubMed Web of Science ®Google Scholar
• Bertolotti A, Zhang Y, Hendershot LM, et al. Dynamic interaction of BiP and ER stress transducers in the unfolded-protein response. Nat Cell Biol 2000;2:326–32.
   PubMed Web of Science ®Google Scholar
• Khan I, Tang E, Arany P. Molecular pathway of near-infrared laser phototoxicity involves ATF-4 orchestrated ER stress. Sci Rep 2015;5:10581.
   PubMed Web of Science ®Google Scholar
• Lee AH, Iwakoshi NN, Glimcher LH. XBP-1 regulates a subset of endoplasmic reticulum resident chaperone genes in the unfolded protein response. Mol Cell Biol 2003;23:7448–59.
   PubMed Web of Science ®Google Scholar
• Oyadomari S, Mori M. Roles of CHOP/GADD153 in endoplasmic reticulum stress. Cell Death Differ 2004;11:381–9.
   PubMed Web of Science ®Google Scholar
• Xu X, Huang L, Zhang Z, et al. Targeting non-oncogene ROS pathway by alantolactone in B cell acute lymphoblastic leukemia cells. Life Sci 2019;227:153–65.
   PubMed Web of Science ®Google Scholar
• Wu JZ, Du XJ, Li WL, et al. A novel non-ATP competitive FGFR1 inhibitor with therapeutic potential on gastric cancer through inhibition of cell proliferation, survival and migration. Apoptosis 2017;22:852–64.
   PubMed Web of Science ®Google Scholar
• Cai CY, Rao L, Rao Y, et al. Analogues of xanthones–Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates. Eur J Med Chem 2017;130:51–9.
   PubMed Web of Science ®Google Scholar
• Blanksby SJ, Ellison GB. Bond dissociation energies of organic molecules. Acc Chem Res 2003;36:255–63.
   PubMed Web of Science ®Google Scholar
• Kozlowski D, Trouillas P, Calliste C, et al. Density functional theory study of the conformational, electronic, and antioxidant properties of natural chalcones. J Phys Chem A 2007;111:1138–45.
   PubMed Web of Science ®Google Scholar
• Tønnesen HH, Karlsen J, van Henegouwen GB. Studies on curcumin and curcuminoids. VIII. Photochemical stability of curcumin. Z Lebensm Unters Forsch 1986;183:116–22.
   PubMedGoogle Scholar
• Agnihotri N, Mishra PC. Scavenging mechanism of curcumin toward the hydroxyl radical: a theoretical study of reactions producing ferulic acid and vanillin. J Phys Chem A 2011;115:14221–32.
   PubMed Web of Science ®Google Scholar
• Khurana A, Ho CT. High performance liquid chromatographic analysis of curcuminoids and their photo-oxidative decomposition compounds in curcuma Longa L. J Liq Chromatogr 1988;11:2295–304.
   Web of Science ®Google Scholar
• Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 1994;98:11623–7.
   Web of Science ®Google Scholar
• Wright JS, Carpenter DJ, McKay DJ, Ingold KU. Theoretical calculation of substituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E. J Am Chem Soc 1997;119:4245–52.
   Web of Science ®Google Scholar
• Silva ER, Queiroz AN, Almeida ED, Borges RS. A DFT study of aminophenol stability. J Comput Thero Nanos 2009;6:1–3.
   Google Scholar
• Wei T, Wu J, Zhu W, et al. Characterization of nitrogen-bridged 1,2,4,5-tetrazine-, furazan-, and 1H-tetrazole-based polyheterocyclic compounds: heats of formation, thermal stability, and detonation properties. J Mol Model 2012;18:3467–79.
   PubMed Web of Science ®Google Scholar
• Amrita J, Satish S, Sunil KY, Kapil K. Stability indicating assay methods and its progression in analytical chemistry. Asian J Biomater Res 2018;1:1–11.
   Google Scholar
• Jorgensen I, Rayamajhi M, Miao EA. Programmed cell death as a defence against infection. Nat Rev Immunol 2017;17:151–64.
   PubMed Web of Science ®Google Scholar
• Fang Y, Tian S, Pan Y, et al. Pyroptosis: a new frontier in cancer. Biomed Pharmacother 2020;121:109595.
   PubMed Web of Science ®Google Scholar
• Li J, Yang C, Li YG, et al. LncRNA GAS5 suppresses ovarian cancer by inducing inflammasome formation. Biosci Rep 2018;38:BSR20171150–69.
   PubMed Web of Science ®Google Scholar
• Won CH, Jong-Baeck L. Role of the tumor microenvironment in the pathogenesis of gastric carcinoma. World J Gastroenterol 2014;20:1667–82.
   PubMed Web of Science ®Google Scholar
• Liu JL, Yao L, Zhang MY, et al. Downregulation of LncRNA-XIST inhibited development of non-small cell lung cancer by activating miR-335/SOD2/ROS signal pathway mediated pyroptotic cell death. Aging (Albany NY) 2019;11:7830–46.
   PubMedGoogle Scholar
• Zhang CC, Li CG, Wang YF, et al. Chemotherapeutic paclitaxel and cisplatin differentially induce pyroptosis in A549 lung cancer cells via caspase-3/GSDME activation. Apoptosis 2019;24:312–25.
   PubMed Web of Science ®Google Scholar
• Chen LP, Weng BX, Li HM, et al. A thiopyran derivative with low murine toxicity with therapeutic potential on lung cancer acting through a NF-kappaB mediated apoptosis-to-pyroptosis switch. Apoptosis 2019;24:74–82.
   PubMed Web of Science ®Google Scholar
• Zhu M, Wang JB, Xie JW, et al. Design, synthesis, and evaluation of chalcone analogues incorporate alpha, beta-unsaturated ketone functionality as anti-lung cancer agents via evoking ROS to induce pyroptosis. Eur J Med Chem 2018;157:1395–405.
   PubMed Web of Science ®Google Scholar
• Long KL, Gu LL, Li LL, et al. Small-molecule inhibition of APE1 induces apoptosis, pyroptosis, and necroptosis in non-small cell lung cancer. Cell Death Dis 2021;12:503.
   PubMed Web of Science ®Google Scholar
• Yuan RYK, Zhao WT, Wang QQ, et al. Cucurbitacin B inhibits non-small cell lung cancer in vivo and in vitro by triggering TLR4/NLRP3/GSDMD-dependent pyroptosis. Pharmacol Res 2021;170:105748.
   PubMed Web of Science ®Google Scholar
• Lebeaupin C, Proics E, de Bieville CH, et al. ER stress induces NLRP3 inflammasome activation and hepatocyte death. Cell Death Dis 2015;6:e1879.
   PubMed Web of Science ®Google Scholar
• Le X, Mu JH, Peng WY, et al. DNA methylation downregulated ZDHHC1 suppresses tumor growth by altering cellular metabolism and inducing oxidative/ER stress-mediated apoptosis and pyroptosis. Theranostics 2020;10:9495–511.
   PubMed Web of Science ®Google Scholar