Anticancer Activity of Natural and Synthetic Chalcones

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2021 Nov 13

PMID 34768736

Citations 40

Authors

Teodora Constantinescu

Claudiu N Lungu

Affiliations

Soon will be listed here.

Abstract

Cancer is a condition caused by many mechanisms (genetic, immune, oxidation, and inflammatory). Anticancer therapy aims to destroy or stop the growth of cancer cells. Resistance to treatment is theleading cause of the inefficiency of current standard therapies. Targeted therapies are the most effective due to the low number of side effects and low resistance. Among the small molecule natural compounds, flavonoids are of particular interest for theidentification of new anticancer agents. Chalcones are precursors to all flavonoids and have many biological activities. The anticancer activity of chalcones is due to the ability of these compounds to act on many targets. Natural chalcones, such as licochalcones, xanthohumol (XN), panduretin (PA), and loncocarpine, have been extensively studied and modulated. Modification of the basic structure of chalcones in order to obtain compounds with superior cytotoxic properties has been performed by modulating the aromatic residues, replacing aromatic residues with heterocycles, and obtaining hybrid molecules. A huge number of chalcone derivatives with residues such as diaryl ether, sulfonamide, and amine have been obtained, their presence being favorable for anticancer activity. Modification of the amino group in the structure of aminochalconesis always favorable for antitumor activity. This is why hybrid molecules of chalcones with different nitrogen hetercycles in the molecule have been obtained. From these, azoles (imidazole, oxazoles, tetrazoles, thiazoles, 1,2,3-triazoles, and 1,2,4-triazoles) are of particular importance for the identification of new anticancer agents.

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References

Yun C, Kim H, Lim J, Lee S . Heat Shock Proteins: Agents of Cancer Development and Therapeutic Targets in Anti-Cancer Therapy. Cells. 2019; 9(1). PMC: 7017199. DOI: 10.3390/cells9010060. View

Hao Y, Zhang C, Sun Y, Xu H . Licochalcone A inhibits cell proliferation, migration, and invasion through regulating the PI3K/AKT signaling pathway in oral squamous cell carcinoma. Onco Targets Ther. 2019; 12:4427-4435. PMC: 6556467. DOI: 10.2147/OTT.S201728. View

Tagousop C, Tamokou J, Ekom S, Ngnokam D, Voutquenne-Nazabadioko L . Antimicrobial activities of flavonoid glycosides from Graptophyllum grandulosum and their mechanism of antibacterial action. BMC Complement Altern Med. 2018; 18(1):252. PMC: 6139119. DOI: 10.1186/s12906-018-2321-7. View

Qiu C, Zhang T, Zhang W, Zhou L, Yu B, Wang W . Licochalcone A Inhibits the Proliferation of Human Lung Cancer Cell Lines A549 and H460 by Inducing G2/M Cell Cycle Arrest and ER Stress. Int J Mol Sci. 2017; 18(8). PMC: 5578150. DOI: 10.3390/ijms18081761. View

Qi S, Guo L, Yan S, Lee R, Yu S, Chen S . Hypocrellin A-based photodynamic action induces apoptosis in A549 cells through ROS-mediated mitochondrial signaling pathway. Acta Pharm Sin B. 2019; 9(2):279-293. PMC: 6437636. DOI: 10.1016/j.apsb.2018.12.004. View

de Mello M, Abrahim-Vieira B, Souza Domingos T, de Jesus J, de Sousa A, Rodrigues C . A comprehensive review of chalcone derivatives as antileishmanial agents. Eur J Med Chem. 2018; 150:920-929. DOI: 10.1016/j.ejmech.2018.03.047. View

Mohamed M, Abuo-Rahma G . Molecular targets and anticancer activity of quinoline-chalcone hybrids: literature review. RSC Adv. 2022; 10(52):31139-31155. PMC: 9056499. DOI: 10.1039/d0ra05594h. View

Zha J, Wu X, Gong G, Koffas M . Pathway enzyme engineering for flavonoid production in recombinant microbes. Metab Eng Commun. 2019; 9:e00104. PMC: 6838514. DOI: 10.1016/j.mec.2019.e00104. View

Saito K, Matsuo Y, Imafuji H, Okubo T, Maeda Y, Sato T . Xanthohumol inhibits angiogenesis by suppressing nuclear factor-κB activation in pancreatic cancer. Cancer Sci. 2017; 109(1):132-140. PMC: 5765302. DOI: 10.1111/cas.13441. View

10.

Abou-Zied H, Youssif B, Mohamed M, Hayallah A, Abdel-Aziz M . EGFR inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and docking studies of novel xanthine derivatives carrying chalcone moiety as hybrid molecules. Bioorg Chem. 2019; 89:102997. DOI: 10.1016/j.bioorg.2019.102997. View

11.

Xue Y, Li H, Zhang Y, Han X, Zhang G, Li W . Natural and synthetic flavonoids, novel blockers of the volume-regulated anion channels, inhibit endothelial cell proliferation. Pflugers Arch. 2018; 470(10):1473-1483. DOI: 10.1007/s00424-018-2170-8. View

12.

Wang J, Liao A, Thakur K, Zhang J, Huang J, Wei Z . Licochalcone B Extracted from Glycyrrhiza uralensis Fisch Induces Apoptotic Effects in Human Hepatoma Cell HepG2. J Agric Food Chem. 2019; 67(12):3341-3353. DOI: 10.1021/acs.jafc.9b00324. View

13.

Ng Z, Koick Y, Yong P . Comparative analyses on radical scavenging and cytotoxic activity of phenolic and flavonoid content from selected medicinal plants. Nat Prod Res. 2020; 35(23):5271-5276. DOI: 10.1080/14786419.2020.1749617. View

14.

Chen W, Luo G, Zhang X . Recent Advances in Subcellular Targeted Cancer Therapy Based on Functional Materials. Adv Mater. 2018; 31(3):e1802725. DOI: 10.1002/adma.201802725. View

15.

Davies K, Jibran R, Zhou Y, Albert N, Brummell D, Jordan B . The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective. Front Plant Sci. 2020; 11:7. PMC: 7010833. DOI: 10.3389/fpls.2020.00007. View

16.

Seo J, Choi H, Oh H, Lee M, Kim E, Yoon G . Licochalcone D directly targets JAK2 to induced apoptosis in human oral squamous cell carcinoma. J Cell Physiol. 2018; 234(2):1780-1793. DOI: 10.1002/jcp.27050. View

17.

Siwach A, Verma P . Synthesis and therapeutic potential of imidazole containing compounds. BMC Chem. 2021; 15(1):12. PMC: 7893931. DOI: 10.1186/s13065-020-00730-1. View

18.

Song M, Yoon G, Choi J, Kim E, Liu X, Oh H . Janus kinase 2 inhibition by Licochalcone B suppresses esophageal squamous cell carcinoma growth. Phytother Res. 2020; 34(8):2032-2043. DOI: 10.1002/ptr.6661. View

19.

Pugazhendhi A, Edison T, Karuppusamy I, Kathirvel B . Inorganic nanoparticles: A potential cancer therapy for human welfare. Int J Pharm. 2018; 539(1-2):104-111. DOI: 10.1016/j.ijpharm.2018.01.034. View

20.

Munteanu A, Notaro A, Jakubaszek M, Cowell J, Tharaud M, Goud B . Synthesis, Characterization, Cytotoxic Activity, and Metabolic Studies of Ruthenium(II) Polypyridyl Complexes Containing Flavonoid Ligands. Inorg Chem. 2020; 59(7):4424-4434. DOI: 10.1021/acs.inorgchem.9b03562. View