A Caffeic Acid Derivative Potential for Anticancer Drug: Synthesis of N-(piperidinyl)caffeamide and Its Activity against P388 Leukemia Murine Cells
DOI:
https://doi.org/10.20956/ica.v13i2.10962Keywords:
anticancer, caffeamide, caffeic acid, piperidine, P388Abstract
Some esters and amide derivatives of p-hydroxycinnamic acid have anticancer activity. However, the amide compound is more stable to metabolic reactions compared to its ester derivative. In this research, the synthesis of a new compound, namely N-(piperidinyl)caffeamide (M5) and its anticancer activity assay, has been conducted. The compound M5 was synthesized using p-hydroxycinnamic acid and piperidine as starting materials, and the activity assay was carried out against P388 Leukemia Murine Cells by the MTT method. By these methods, the compound M5 was obtained a yellowish crystalline with a melting point of 212-214°C, and it was very active as an anticancer with an IC50 value of 0.861 μg/mL. This compound was more active than the analog compounds previously synthesized.References
Angelino, D., Cossua, M., Martic, A., Zanolettic, M., Chiavarolia, L., Brighentia, F., … Martini, D. (2017). Bioaccessibility and bioavailability of phenolic compounds in bread: a review. Food Funct. https://doi.org/10.1039/C7FO00574A
Catchpole, O., Mitchell, K., Bloor, S., Davis, P., & Suddes, A. (2015). Fitoterapia Antiproliferative activity of New Zealand propolis and phenolic compounds vs human colorectal adenocarcinoma cells. Fitoterapia, 106, 167–174. https://doi.org/10.1016/j.fitote.2015.09.004
Chiang, E. I., Tsai, S., Kuo, Y., Pai, M., Chiu, H., Rodriguez, R. L., & Tang, F. (2014). Caffeic Acid Derivatives Inhibit the Growth of Colon Cancer : Involvement of the PI3-K / Akt and AMPK Signaling Pathways, 9(6). https://doi.org/10.1371/journal.pone.0099631
Damasceno, S. S., Dantas, B. B., & Ribeiro-filho, J. (2017). Chemical Properties of Caffeic and Ferulic Acids in Biological System: Implications in Cancer Therapy. A Review, 3015–3023. https://doi.org/10.2174/1381612822666161208145508
De, P., Baltas, M., & Bedos-Belval, F. (2011). Cinnamic Acid Derivatives as Anticancer Agents-A Review. Current Medicinal Chemistry, 18, 1672–1703.
Farah, A., & Donangelo, C. M. (2006). Phenolic compounds in coffee 1, 18(1), 23–36.
Firdaus, H., Naid, T., Soekamto, N., Sumarna, S., & Islam, M. (2017). Synthesis of piperidine and morpholine amides of ferrulic acid and their bioactivity against P-388 Leukemia cells. International Journal of ChemTech Reseaerch, 10(1), 27–33.
Firdaus, Seniwati, Alamsyah, N., & Paramita, S. (2019). Synthesis and activity of N-(o-tolyl)caffeamide and N-(o-tolyl)-p-coumaramide against P388 leukemia murine cells. Journal of Physics: Conference Series, 1341(3). https://doi.org/10.1088/1742-6596/1341/3/032005
Firdaus, Soekamto, N. H., Permatasari, N. U., Seniwati, Sukarti, Makmun, & Agustiningsih, A. (2012). SINTESIS SENYAWA TURUNAN SEKUNDER DAN TERSIER p -KUMARAMIDA DAN UJI AKTIVITASNYA SEBAGAI ANTI TUMOR SEL LEUKIMIA P388. Indonesia Chimica Acta, 5(2), 10–16.
Firdaus, Soekamto, N. H., Seniwati, Islam, M. F., & Sultan. (2018). Phenethyl ester and amide of Ferulic Acids: Synthesis and bioactivity against P388 Leukemia Murine Cells. Journal of Physics: Conference Series, 979(1). https://doi.org/10.1088/1742-6596/979/1/012016
Gajek, G., Marciniak, B., & Kontek, R. (2020). Antagonistic Effects of CAPE ( a Component of Propolis ) on the Cytotoxicity and Genotoxicity of Irinotecan and SN38 in Human Gastrointestinal Cancer Cells In Vitro. https://doi.org/10.3390/molecules25030658
Georgiev, L., Chochkova, M., Ivanova, G., Najdenski, H., Ninova, M., & Milkova, T. (2012). Radical scavenging and antimicrobial activities of cinnamoyl amides of biogenic monoamines. Rivista Italiana Delle Sostanze Grasse, 89(2), 91–102.
Guzman, J. D. (2014). Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity. https://doi.org/10.3390/molecules191219292
Hadi Kuncoro, Rijai, L., Julaeha, E., & Supratman, U. (2003). CYTOTOXIC ACTIVITY AGAINST P-388 MURINE LEUKEMIA CELL FROM Lygodium microphyllum HERB. Jurnal Farmasi Galenika, 3(1), 147–173.
Huang, Q., Lin, Y., & Yan, Y. (2013). Caffeic Acid Production Enhancement by Engineering a Phenylalanine Over-Producing Escherichia coli Strain, 9999(xxx), 1–9. https://doi.org/10.1002/bit.24988
Magnani, C., Isaac, V. L. B., Correa, M. A., & Salgado, H. R. N. (2014). Caffeic acid: a review of its potential use in medications and cosmetics. Anal. Methods, 6, 3203–3210. https://doi.org/10.1039/c3ay41807c
Nakamura, K., Nakajima, T., Aoyama, T., Okitsu, S., & Koyama, M. (2014). One-pot esterification and amidation of phenolic acids. Tetrahedron, 1–11.
Rosa, L. S., Silva, N. J. A., Soares, N. C. P., Monteiro, M. C., & Teodoro, A. J. (2016). Anticancer Properties of Phenolic Acids in Colon Cancer – A Review. Journal of Nutrition & Food Sciences, 6(2), 1–7. https://doi.org/10.4172/2155-9600.1000468
Russell, W., & Duthie, G. (2011). Symposium on ‘ Nutrition : getting the balance right in 2010 ’ Session 3 : Influences of food constituents on gut health Plant secondary metabolites and gut health : the case for phenolic acids Proceedings of the Nutrition Society HO Proceedings of the Nu, (May), 389–396. https://doi.org/10.1017/S0029665111000152
Sharma, P. (2011). Cinnamic acid derivatives: A new chapter of various pharmacological activities. J. Chem. Pharm. Res., 3(2), 403–423.
Sidoryk, K., Jaromin, A., Filipczak, N., Cmoch, P., & Cybulski, M. (2018). Synthesis and Antioxidant Activity of Caffeic Acid Derivatives. Molecules, 23, 1–12. https://doi.org/10.3390/molecules23092199
Silva, T., Oliveira, C., & Borges, F. (2014). Caffeic acid derivatives , analogs and applications : a patent review, 1–14. https://doi.org/10.1517/13543776.2014.959492
Tošović, J. (2017). SPECTROSCOPIC FEATURES OF CAFFEIC ACID : THEORETICAL STUDY. Kragujevac J Sci, 39, 99–108.
Touaibia, M., & Doiron, J. (2011). Caffeic Acid , A Versatile Pharmacophore : An Overview, 695–713.
Widiyarti, G., Hanafi, M., Kosela, S., & Budianto, E. (2016). Cytotoxic Activity of Citronellyl Caproate on Murine Leukemia ( P388 ) Cells, 12(3), 209–220.
Downloads
Published
Issue
Section
License
Copyright (c) 2020 Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta)
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
This is an open access journal which means that all contents is freely available without charge to the user or his/her institution. Users are allowed to read, download, copy, distribute, print, search, or link to the full texts of the articles in this journal without asking prior permission from the publisher or the author.
Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta) operates a CC BY-SA 4.0 © license for journal papers. Copyright remains with the author, but Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta) is licensed to publish the paper, and the author agrees to make the article available with the CC BY-SA 4.0 license. Reproduction as another journal article in whole or in part would be plagiarism. Jurnal Akta Kimia Indonesia (Indonesia Chimica Acta) reserves all rights except those granted in this copyright notice.