Derivatization of Curcumin and the Effect of Resultant Derivatives on BRC-9 Breast Cancer Cells

Document Type : Research Article

Authors

1 Department of Chemistry, Faculty of Science, Khorramabad Branch, Islamic Azad University, Khorramabad, I.R. IRAN

2 Department of biology, Faculty of Science, Arak University, Arak, I.R. IRAN

Abstract

Medicinal herbs have been taken into consideration for cancer treatment because of the high prevalence of cancer and the severe consequences of chemotherapy. Turmeric, the common name of the Curcuma longa plant, is one of these herbs as Indian spices being applicable for food spices as well as treatment of various diseases. The medicinal and biological effects of turmeric are actually associated with the main component of its rhizome, i.e. curcumin. Curcumin has antioxidant, antibacterial, anticancer, antifungal, and antiviral properties. In this research, curcumin derivatives were synthesized via a condensation reaction of some aromatic amines (aniline, 2-nitroaniline, 4-ethyl aniline) with curcumin. The effects of the molar ratio of amine: to curcumin on the type of products were also examined. The structure of the products was characterized by FT-IR, 1HNMR, and 13CNMR spectroscopy. The anticancer activities of compounds were investigated by the MTT assay (4,5-dimethylthiazol-2-yl) - 2,5 - diphenyltetrazoliu bromide test). It was evaluated with different dosages of curcumin derivatives at different times against BRC-9 breast cancer cells which exhibited the most potent anticancer activity.

Keywords

Main Subjects


[2] Siegel RL., Miller KD., Jemal A., Cancer Statistics  CA. Cancer. J. Clin, 69: 7-34(2019).
[3] Pishgar F., Ebrahimi H., Saeedi Moghaddam S., Fitzmaurice C ., Amini E.,  Global, Regional and National Burden of Prostate Cancer, 1990 to 2015: Results from the Global Burden of Disease Study 2015. J. Urol, 199: 1224-32(2018).
[4] Mcaloon CJ., Boylan LM., Hamborg T., Hamborg T., Stallard N., Osman F., Lim P B, Hayat S A.,  The Changing Face of Cardiovascular Disease 2000-2012: an Analysis of the World Health Organisation Global Health Estimates Data, Int. J. Cardiol, 224: 256-64(2016).
[5] Maruthappu M., Watkins J., Noor A.M., Williams C., Ali R., Sullivan R., Zeltner T., Atun R., Economic Downturns, Universal Health Coverage, and Cancer Mortality in High-Income and Middle-Income Countries, 1990-2010: A Longitudinal Analysis,
The Lancet, 388(10045): 684-95 (2016).
[6] Johnston WW.,  Cytologic Diagnosis of Lung Cancer. Principles and Problems, Path. Rese.Prac, 181: 1-36 (1986).
[7] Sikora E., Bielak-Zmijewska A., Mosieniak G., Targeting Normal and Cancer Senescent Cells as a Strategy of Senotherapy, Ageing. Res. Rev, 55: 100941 (2019).
[8] Chávez J.P., Gürbüz B., Pinto C.M.A., The Effect of Aggressive Chemotherapy in a Model for HIV/AIDS-Cancer Dynamics, Comm. Nonlin. Scie. Nume. Simul, 75: 109-20 (2019).
[9] Lachance J.C., Radhakrishnan S., Madiwale G., Guerrier S., Vanamala J.K.P., Targeting Hallmarks of Cancer with a Food System-based Approach, Nutrition, 69: 110563 (2019).
[10] Blaes A., Prizment A., Koene RJ., Konety S., Cardio-oncology Related to Heart Failure: Common Risk Factors Between Cancer and Cardiovascular Disease, Heart. Fail. Clin., 13: 367-380 (2017).
[11] Riscal R., Skuli N., Simon MC., Even Cancer Cells Watch their Cholesterol, Mol. Cell. 76: 220-31 (2019).
[12] Zhou M., Zhang X., Yu C., Nan X., Chen X., Zhang X., Shape Regulated Anticancer Activities and Systematic Toxicities of Drug Nanocrystals in Vivo, Nanomedicine, 12: 181-9 (2016).
[13] Agarwal N., Majee C., Chakraborthy G.S., Natural Herbs as Anticancer Drugs, Inter. J. Pharm.Tech. Res., 4: 1142-53 (2012).
[14] Guldiken B., Ozkan G., Catalkaya G., Ceylan F.D., Ekin Yalcinkaya I., Capanoglu E., Phytochemicals of Herbs and Spices: Health Versus Toxicological Effects, Food. Chem. Tox, 119: 37-49 (2018).
[15] Amjad S., Jafri A., Sharma A.K., Serajuddin M.,
A Novel Strategy of Nanosized Herbal Drugs and their Delivery in the Treatment of Diabetes: Present Status and Future Prospects. J. Herb. Medic. In press, Corrected Proof, 100279 (2019).
[16] Harwansh R.K., Deshmukh R., Rahman M.A., Nanoemulsion: Promising Nanocarrier System for Delivery of Herbal Bioactives, J. Drug. Deli. Sci. Tech., 51: 224-33 (2019).
[17] Dadashpour M., Firouzi-Amandi A., Pourhassan-Moghaddam M., Maleki M.J., Soozangar N., Jeddi F., Nouri M., Zarghami N., Pilehvar-Soltanahmadi Y., Biomimetic Synthesis of Silver Nanoparticles Using Matricaria Chamomilla Extract and their Potential Anticancer Activity Against Human Lung Cancer Cells, Mater. Sci. Eng. C Mater. Biol. Appl, 92: 902-12(2018).
[18] Rocha-Guzmán N.E., González-Laredo R.F., Vázquez-Cabral B.D., Moreno-Jiménez M.R., Gallegos-Infante J.A., Gamboa-Gómez C.I.., Flores-Rueda A.G., Oak Leaves as a New Potential Source for Functional Beverages: Their Antioxidant Capacity and Monomer Flavonoid Composition. Funct. Medic. Beve, 381-411 (2019).
[19] Mansoori B., Mohammadi A., Amin Doustvandi M., Mohammadnejad F., Kamari F., Gjerstorff M.F., Baradaran B., Hamblin M.R., Photodynamic Therapy for Cancer: Role of Natural Products, Photo. Photodyn. Ther., 26: 395-404 (2019).
[21] Sheikh E.B.M., Tripathi M., Role of Nano-Curcumin: A Treatment for Cancer. J. Medic. Plant. Stud, 5: 394-7 (2017).
[22] Vogel A.P.J., Examen Chimique de La Racine de Curcuma. J. Pharm., 1: 289-300 (1815).
[23] Ravindran J., Prasad S., Aggarwal B.B., Curcumin and Cancer Cells: How Many Ways Can Curry Kill Tumor Cells Selectively? AAPS. J., 11: 495-510 (2009).
[24] Wilken R., Veena M.S., Wang M.B., Srivatsan E.S., Curcumin: A Review of Anti-Cancer Properties and Therapeutic Activity in Head and Neck Squamous Cell Carcinoma, Mol. Cancer, 10: 12 (2011).
[25] Tonnesen H.H., Karlsen J., Studies on Curcumin and Curcuminoids. VI. Kinetics of Curcumin Degradation in Aqueous Solution, Z. Lebensm. Unter. Forsch., 180: 402-4 (1985).
[26] Doosthosseini H., Salehi Z., Rezaei M., Ghelich P., Optimized Method for Curcumin Separation from Turmeric Oleoresin. Iran. J. Chem. Chem. Eng. (IJCCE), 38: 141-148 (2019).
[27] Toda S., Miyase T., Arichi H., Tanizawa H., Takino Y., Natural Antioxidants. III. Antioxidative Components Isolated from Rhizome of Curcuma Longa L, Chem. Pharm. Bull. (Tokyo), 33: 1725-1728 (1985).
[29] Desantis C.E., Ma J., Gaudet MM., Newman L.A., Miller K.D., Goding Sauer A., Jemal A., Siegel R L., Breast Cancer Statistics, 2019, CA. Cancer. J. Clin, 69: 211-33 (2019).
[30] Sadjadi A., Nouraie M., Ghorbani A., Alimohammadian M., Malekzadeh R., Epidemiology of Breast Cancer in the Islamic Republic of Iran: First Results from a Population-Based Cancer Registry, East. Mediter. Health. J, 15: 1426-1431 (2009).
[32] Basile V.F.E., Lazzari S., Belluti S., Pignedoli F., Imbriano C., Curcumin Derivatives: Molecular Basis of their Anti-Cancer Activity, Biochem. Pharmacol. 78: 1305-15 (2009).
[34] Lal J., Gupta SK., Thavaselvam D., Agarwal DD., Synthesis and Pharmacological Activity Evaluation of Curcumin Derivatives, Chin. Chem. Lett, 27: 1067-72 (2016).
[35] Datta S., K. Misra S., Lal Saha M., Lahiri N., Louie J., Pan D., J. Stang P., Orthogonal Self-Assembly of an Organoplatinum(II) Metallacycle and Cucurbit[8]uril that Delivers Curcumin to Cancer Cells, Proce. Nati. Acad. Scien, 115 (32): 8087-8092 (2018).