Anticancer Activity of Chalcones and Its Derivatives: Review and In Silico Studies

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 May 27

PMID 37241750

Authors

Fernando Ferreira Leite

Natalia Ferreira de Sousa

Bruno Hanrry Melo de Oliveira

Gabrielly Diniz Duarte

Maria Denise Leite Ferreira

Marcus Tullius Scotti

Jose Maria Barbosa Filho

Luis Cezar Rodrigues

Ricardo Olimpio de Moura

Francisco Jaime Bezerra Mendonca-Junior

Luciana Scotti

Affiliations

Soon will be listed here.

Abstract

Chalcones are direct precursors in the biosynthesis of flavonoids. They have an α,β-unsaturated carbonyl system which gives them broad biological properties. Among the biological properties exerted by chalcones, their ability to suppress tumors stands out, in addition to their low toxicity. In this perspective, the present work explores the role of natural and synthetic chalcones and their anticancer activity in vitro reported in the last four years from 2019 to 2023. Moreover, we carried out a partial least square (PLS) analysis of the biologic data reported for colon adenocarcinoma lineage HCT-116. Information was obtained from the Web of Science database. Our in silico analysis identified that the presence of polar radicals such as hydroxyl and methoxyl contributed to the anticancer activity of chalcones derivatives. We hope that the data presented in this work will help researchers to develop effective drugs to inhibit colon adenocarcinoma in future works.

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References

Al-Hamashi A, Koranne R, Dlamini S, Alqahtani A, Karaj E, Rashid M . A new class of cytotoxic agents targets tubulin and disrupts microtubule dynamics. Bioorg Chem. 2021; 116:105297. PMC: 8530978. DOI: 10.1016/j.bioorg.2021.105297. View

Nanjala C, Odago W, Rono P, Waswa E, Mutinda E, Oulo M . A review on ethnobotany, phytochemistry, and pharmacology of the genus Didymocarpus wall. (Gesneriaceae). J Ethnopharmacol. 2022; 295:115404. DOI: 10.1016/j.jep.2022.115404. View

Wang D, Liang J, Zhang J, Wang Y, Chai X . Natural Chalcones in Chinese Materia Medica: Licorice. Evid Based Complement Alternat Med. 2020; 2020:3821248. PMC: 7102474. DOI: 10.1155/2020/3821248. View

Chan E, Wong S, Tangah J, Inoue T, Chan H . Phenolic constituents and anticancer properties of Morus alba (white mulberry) leaves. J Integr Med. 2020; 18(3):189-195. DOI: 10.1016/j.joim.2020.02.006. View

Dandawate P, Ahmed K, Padhye S, Ahmad A, Biersack B . Anticancer Active Heterocyclic Chalcones: Recent Developments. Anticancer Agents Med Chem. 2020; 21(5):558-566. DOI: 10.2174/1871520620666200705215722. View

Shaik A, Prasad Y, Nissankararao S, Shahanaaz S . Synthesis, Biological and Computational Evaluation of Novel 2,3-dihydro-2-aryl-4-(4- isobutylphenyl)-1,5-benzothiazepine Derivatives as Anticancer and Anti-EGFR Tyrosine Kinase Agents. Anticancer Agents Med Chem. 2020; 20(9):1115-1128. DOI: 10.2174/1871520620666200130091142. View

Seba V, de Lima G, Pereira B, Silva G, Reinhardt L, Arantes P . Development, Characterization and Cell Viability Inhibition of PVA Spheres Loaded with Doxorubicin and 4'-Amino-1-Naphthyl-Chalcone (D14) for Osteosarcoma. Polymers (Basel). 2021; 13(16). PMC: 8401585. DOI: 10.3390/polym13162611. View

Mourad A, Mourad M, Jones P . Novel HDAC/Tubulin Dual Inhibitor: Design, Synthesis and Docking Studies of α-Phthalimido-Chalcone Hybrids as Potential Anticancer Agents with Apoptosis-Inducing Activity. Drug Des Devel Ther. 2020; 14:3111-3130. PMC: 7425103. DOI: 10.2147/DDDT.S256756. View

Escribano-Ferrer E, Queralt Regue J, Garcia-Sala X, Boix Montanes A, Lamuela-Raventos R . In Vivo Anti-inflammatory and Antiallergic Activity of Pure Naringenin, Naringenin Chalcone, and Quercetin in Mice. J Nat Prod. 2019; 82(2):177-182. DOI: 10.1021/acs.jnatprod.8b00366. View

10.

Mastachi-Loza S, Ramirez-Candelero T, Benitez-Puebla L, Fuentes-Benites A, Gonzalez-Romero C, Vazquez M . Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions. Chem Asian J. 2022; 17(20):e202200706. DOI: 10.1002/asia.202200706. View

11.

Xiao J, Gao M, Diao Q, Gao F . Chalcone Derivatives and their Activities against Drug-resistant Cancers: An Overview. Curr Top Med Chem. 2020; 21(5):348-362. DOI: 10.2174/1568026620666201022143236. View

12.

Othman E, Fayed E, Husseiny E, Abulkhair H . Apoptosis induction, PARP-1 inhibition, and cell cycle analysis of leukemia cancer cells treated with novel synthetic 1,2,3-triazole-chalcone conjugates. Bioorg Chem. 2022; 123:105762. DOI: 10.1016/j.bioorg.2022.105762. View

13.

Gao F, Huang G, Xiao J . Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure-activity relationship. Med Res Rev. 2020; 40(5):2049-2084. DOI: 10.1002/med.21698. View

14.

Josephs S, Ichim T, Prince S, Kesari S, Marincola F, Escobedo A . Unleashing endogenous TNF-alpha as a cancer immunotherapeutic. J Transl Med. 2018; 16(1):242. PMC: 6119315. DOI: 10.1186/s12967-018-1611-7. View

15.

Verza F, Das U, Fachin A, Dimmock J, Marins M . Roles of Histone Deacetylases and Inhibitors in Anticancer Therapy. Cancers (Basel). 2020; 12(6). PMC: 7352721. DOI: 10.3390/cancers12061664. View

16.

Han Y, Dong W, Guo Q, Li X, Huang L . The importance of indole and azaindole scaffold in the development of antitumor agents. Eur J Med Chem. 2020; 203:112506. DOI: 10.1016/j.ejmech.2020.112506. View

17.

Huang X, Liu Z, Wang M, Yin X, Wang Y, Dai L . Platinum(IV) complexes conjugated with chalcone analogs as dual targeting anticancer agents: In vitro and in vivo studies. Bioorg Chem. 2020; 105:104430. DOI: 10.1016/j.bioorg.2020.104430. View

18.

Hassan S, Sudomova M . Molecular Mechanisms of Flavonoids against Tumor Gamma-Herpesviruses and Their Correlated Cancers-A Focus on EBV and KSHV Life Cycles and Carcinogenesis. Int J Mol Sci. 2023; 24(1). PMC: 9820319. DOI: 10.3390/ijms24010247. View

19.

Wang Y, Li L, Ma T, Cheng X, Liu D . Design, Synthesis, and Apoptosis-Promoting Effect Evaluation of Chalcone Derivatives Containing Aminoguanidine Units. Anticancer Agents Med Chem. 2021; 22(11):2116-2124. DOI: 10.2174/1871520621666211026091226. View

20.

de Souza P, Biba G, Melo E, Frazao Muzitano M . Chalcones against the hallmarks of cancer: a mini-review. Nat Prod Res. 2021; 36(18):4809-4826. DOI: 10.1080/14786419.2021.2000980. View