The luminescent Chalcones. Its potential use as a luminescent and antitumoral agents
DOI:
https://doi.org/10.17533/udea.vitae.v29n3a347295Keywords:
2’-hydroxychalcones, Anticancer agent, Luminescent biomarker, Cytotoxic effectsAbstract
BACKGROUND: Hepatocellular carcinoma (HCC) is one of the most diagnosed cancers worldwide. Chemoprevention of HCC can be achieved using natural or synthetic compounds that reverse, suppress, detect, or prevent cancer progression. OBJECTIVES: In this study, both the antiproliferative effects and luminescent properties of 2’-hydroxychalcones were evaluated. METHODS: Cell viability was evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay, spectroscopy assays, and density functional theory (DFT) calculations were used to determine the luminescent properties of 2´-hydroxychalcones. RESULTS: Cytotoxic effects of 2´-hydroxychalcones were observed over the HepG2 and EA.hy926 cells. Since the chalcone moiety could be used as a fluorescent probe, these compounds may be helpful in cancer diagnosis and tumor localization. They may enable tumor observation and regression through the fluorescence during treatment; therefore, the compounds are a potential candidate as novel anticancer agents acting on human hepatomas. CONCLUSIONS: This report describes the chalcones’ use as a specific luminescent biomarker in tumor cells. We also report the cellular uptake of 2’-hydroxychalcones, their cellular distribution, and the mechanisms that may be responsible for their cytotoxic effects.
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References
Rahman MA, Chalcone : A Valuable Insight into the Recent Advances and Potential. Chem. Sci. 2011, 2011, 1–16, DOI: https://doi.org/10.4172/2150-3494.1000021
Kumar V, Kumar S, Hassan M, Wu H, Thimmulappa RK, Kumar A, Sharma SK, Parmar VS, Biswal S, Malhotra S V Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells. J. Med. Chem. 2011, 54, 4147–59, DOI: https://doi.org/10.1021/jm2002348.
Marquina S, Maldonado-Santiago M, Sánchez-Carranza J N, Antúnez-Mojica M, González-Maya L, Razo-Hernández RS, Alvarez L, Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway. Bioorganic Med. Chem. 2019, 27, 43–54, DOI: https://doi.org/10.1016/J.BMC.2018.10.045.
Tadigoppula N, Korthikunta V, Gupta S, Kancharla P, Khaliq T, Soni, A, Srivastava RK, Srivastava K, Puri S K, Raju K S R, et al. Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents. J. Med. Chem. 2013, 56, 31–45, DOI: https://doi.org/10.1021/jm300588j.
Shenvi S, Kumar K, Hatti K S Rijesh K, Diwakar L, Reddy G C, Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: structure-activity relationship. Eur. J. Med. Chem. 2013, 62, 435–42, DOI: https://doi.org/10.1016/j.ejmech.2013.01.018.
Zarate X, Schott E, Escobar C A, Lopez-Castro R, Echeverria C, Alvarado-Soto L, Interaction of Chalcones with CT-DNA by Spectrophotometric Analysis and Theoretical Simulations. Quim. Nova 2016, 39, 914–918.
Dickson J, Flores L, Stewart M, LeBlanc R, Pati H N, Lee M, Holt H, Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology. J. Chem. Educ. 2006, 83, 934, DOI: https://doi.org/10.1021/ed083p934.
Echeverria C, Santibañez J F, Donoso-Tauda O, Escobar C , Ramirez-Tagle R , Structural antitumoral activity relationships of synthetic chalcones. Int. J. Mol. Sci. 2009, 10, 221–31, DOI: https://doi.org/10.3390/ijms10010221.
Detsi A, Majdalani M, Kontogiorgis C, Hadjipavlou-Litina D, Kefalas P, Natural and synthetic 2’-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorg. Med. Chem. 2009, 17, 8073–85, DOI: https://doi.org/10.1016/j.bmc.2009.10.002.
Boumendjel A, Boccard J, Carrupt P A, Nicolle E, Blanc M, Geze A, Choisnard L, Wouessidjewe D, Matera E L, Dumontet C, Antimitotic and antiproliferative activities of chalcones: forward structure-activity relationship. J. Med. Chem. 2008, 51, 2307–10, DOI: https://doi.org/10.1021/jm0708331.
Ramirez-Tagle R, Escobar C, Romero V, Montorfano I, Armisén R, Borgna V, Jeldes E, Pizarro L, Simon F, Echeverria C, Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells. Int. J. Mol. Sci. 2016, 17, 260, DOI: https://doi.org/10.3390/ijms17020260.
Suwito H, Jumina M, Pudjiastuti P, Fanani M Z, Kimata-Ariga Y, Katahira R, Kawakami T, Fujiwara T, Hase T, et al. Design and synthesis of chalcone derivatives as inhibitors of the ferredoxin - Ferredoxin-NADP+ reductase interaction of Plasmodium falciparum: Pursuing new antimalarial agents. Molecules 2014, 19, 21473–21488, DOI: https://doi.org/10.3390/MOLECULES191221473.
Jagtap AR, Satam VS, Rajule RN, Kanetkar VR, Synthesis of highly fluorescent coumarinyl chalcones derived from 8-acetyl-1,4-diethyl-1,2,3,4-tetrahydro-7H-pyrano(2,3-g)quinoxalin-7-one and their spectral characteristics. Dye. Pigment. 2011, 91, 20–25, DOI: https://doi.org/10.1016/j.dyepig.2011.01.011.
Asiri A, Marwani H, Green Synthesis, Characterization, Photophysical and Electrochemical Properties of Bis-chalcones. Int. J. Electrochem. 2014, 9, 799–809.
Xue Y, Mou J, Liu Y, Gong X, Yang Y, An L, An ab initio simulation of the UV/Visible spectra of substituted chalcones. Cent. Eur. J. Chem. 2010, 8, 928–936, DOI: https://doi.org/10.2478/s11532-010-0058-3.
Zarate X, Schott E, Escobar CA, Lopez-Castro R, Echeverria C, Alvarado-Soto L, Ramirez-Tagle, R. Interaction of chalcones with CT-DNA by spectrophotometric analysis and theoretical simulations. Quim. Nova 2016, 39, DOI: https://doi.org/10.5935/0100-4042.20160114.
Javitt B, Hep G2 as a resource cholesterol, for metabolic and bile studies: lipoprotein , acids. FASEB 1990, 4, 161–168, DOI: https://doi.org/10.1096/fasebj.4.2.2153592
Mosmann T, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55–63.
te Velde G , Bickelhaupt F M, Baerends E J, Fonseca Guerra C, van Gisbergen S J A , Snijders J G , Ziegler T, Chemistry with ADF, Journal of Comp Chem , 2001, 22, 931–967, DOI: https://doi.org/10.1002/jcc.1056.
van Lenthe E, Baerends E J, Snijders J G , Van Relativistic total energy using regular approximations. J. Chem. Phys. 1994, 101, DOI: https://doi.org/10.1063/1.467943
Snijders J G, Vernooijs P, Baerends E J , Roothaan-Hartree-Fock-Slater atomic wave functions: Single-zeta, double-zeta, and extended Slater-type basis sets for 87Fr-103Lr. Atomic Data and Nuclear Data Tables 26, (6) 1981, 26, 483–509, DOI: https://doi.org/10.1016/0092-640X(81)90004-8
Casida M E, Huix-Rotllant M, Progress in time-dependent density-functional theory. Annu. Rev. Phys. Chem. 2012, 63, 287–323, DOI: https://doi.org/10.1146/annurev-physchem-032511-143803.
Pye C C, Ziegler T, van Lenthe E, Louwen J N, An implementation of the conductor-like screening model of solvation within the Amsterdam density functional package — Part II. COSMO for real solvents 1. Can. J. Chem. 2009, 87, 790–797, DOI: https://doi.org/10.1139/V09-008.
Choi Y E, Kwak J W, Park J W, Nanotechnology for early cancer detection. Sensors (Basel). 2010, 10, 428–55, DOI: https://doi.org/10.3390/s100100428.
Sharma R, Kumar R, Kodwani R, Kapoor S, Khare A, Bansal R, Khurana S, Singh S, Thomas J, Roy B, et al. A Review on Mechanisms of Anti Tumor Activity of Chalcones. Anticancer. Agents Med. Chem. 2015, 16, 200–211, DOI: https://doi.org/10.2174/1871520615666150518093144.
Ramirez-Tagle R, Escobar C A, Romero V, Montorfano I, Armisén R, Borgna V, Jeldes E, Pizarro L, Simon F, Echeverria C, Chalcone-induced apoptosis through caspase-dependent intrinsic pathways in human hepatocellular carcinoma cells. Int. J. Mol. Sci. 2016, 17, DOI: https://doi.org/10.3390/ijms17020260.
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