Anticancer agents derived from natural cinnamic acids

Anti-Cancer Agents in Medicinal Chemistry

Volumn 15, Issue 8, 2015, Pages 980-987

  Su, Ping ^a   Shi, Yaling ^a   Wang, Jinfeng ^a   Shen, Xiuxiu ^a   Zhang, Jie ^a  

^a XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Anticancer candidates; Caffeic acid; Ferulic acid; Sinapic acid

Indexed keywords

ANTINEOPLASTIC AGENT; ARTEPILLIN C; BACCHARIN; CAFFEIC ACID; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; CISPLATIN; DRUPANIN; EPIDERMAL GROWTH FACTOR RECEPTOR; FERULIC ACID; GELATINASE A; GELATINASE B; HISTONE DEACETYLASE; ISOFERULIC ACID; JANUS KINASE; N BENZYL 2 CYANO 3 (3,4 DIHYDROXYPHENYL)ACRYLAMIDE; NATURAL PRODUCT; SINAPIC ACID; STAT PROTEIN; UNCLASSIFIED DRUG; VORINOSTAT; BIOLOGICAL PRODUCT; CAFFEIC ACID DERIVATIVE; COUMARIC ACID;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BRAIN INFARCTION; CLINICAL TRIAL (TOPIC); COLORECTAL CANCER; CUTANEOUS T CELL LYMPHOMA; HUMAN; IC50; IMMUNOMODULATION; LIVER CELL CARCINOMA; NEOPLASM; OXIDATIVE STRESS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; ISOLATION AND PURIFICATION; NEOPLASMS; PATHOLOGY;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CAFFEIC ACIDS; CINNAMATES; COUMARIC ACIDS; HUMANS; NEOPLASMS;

EID: 84940934696     PISSN: 18715206     EISSN: 18755992     Source Type: Journal    
DOI: 10.2174/1871520615666150130111120     Document Type: Article

References (39)

1. [1] Jing, L, Yi, H, David, L. W, Junfeng, W, Qingsong, L. Natural products as kinase inhibitors. Nat. Prod. Rep., 2012, 29, 392.
2. [2] Takahashi, T, Miyazawa, M. Tyrosinase inhibitory activities of cinnamic acid analogues. Pharmazie., 2010, 65(12), 913-918.
3. [3] Rao, P.V; Gan, S.H. Cinnamon: A multifaceted medicinal plant. Evid. Based Complement. Alternat. Med., 2014.
4. [4] Cabello, C.M, Bair, W.B, Lamore, S.D. The cinnamon-derived ichael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth. Free Radic. Biol. Med., 2009, 46(2), 220-231.
5. [5] Song, F, Li, H, Sun, J, Wang, S. Protective effects of cinnamic acid and cinnamic aldehyde on isoproterenol-induced acute myocardial ischemia in rats. J. Ethnopharmacol., 2013, 150(1), 125-130.
6. [6] Touaibia, M, Jean-François, J, Doiron, J. Caffeic Acid, a versatile pharmacophore: An overview. Mini Rev. Med. Chem., 2011, 11(8), 695-713.
7. [7] Chuu, C.P, Lin, H.P, Ciaccio, M.F, Kokontis, J.M, Hause, R.J Jr, Hiipakka, R.A, Liao, S, Jones, R.B. Caffeic acid phenethyl ester suppresses the proliferation of human prostate cancer cells through inhibition of p70S6K and Akt signaling networks. Cancer Prev. Res. (Phila.), 2012, 5(5), 788-797.
8. [8] Natarajan, K, Singh, S, Burke, T.R Jr, Grunberger, D, Aggarwal, B.B. Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B. Proc. Natl. Acad. Sci. USA, 1996, 93, 9090-9095.
9. [9] Li, W, Li, N, Tang, Y, Li, B, Liu, L, Zhang, X, Fu, H, Duan, J.A. Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer. Bioorg. Med. Chem. Lett., 2012, 22(19), 6085-6088.
10. [10] Bailly, F, Toillon, R.A, Tomavo, O, Jouy, N, Hondermarck, H, Cotelle P. Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breastcancer cells. Bioorg. Med. Chem. Lett., 2013, 23(2), 574-578.
11. [11] Koseki, T, Fushinobu, S, Ardiansyah; Shirakawa, H, Komai, M. Occurrence, properties, and applications of feruloyl esterases. Appl. Microbiol. Biotechnol., 2009, 84(5), 803-810.
12. [12] Lin, M.C, Wang, F.Y, Kuo, Y.H, Tang, F.Y. Cancer chemopreventive effects of lycopene: suppression of MMP-7 expression and cell invasion in human colon cancer cells. J. Agric. Food Chem., 2011, 59(20), 11304-11318.
13. [13] Mao, J.L, Ran, X.K, Tian, J.Z, Jiao, B, Zhou, H.L, Chen, L.; Wang, Z.G. Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives. Bioorg. Med. Chem. Lett., 2011, 21(5), 1549-1553.
14. [14] Ferulic acid. Available at: http://baike.so.com/doc/3521742.html. (Accessed July 3, 2014).
15. [15] Zhang, L.W, Al-Suwayeh, S.A, Hsieh, P.W, Fang, J.Y. A comparison of skin delivery of ferulic acid and its derivatives: Evaluation of their efficacy and safety. Int. J. Pharm., 2010, 399(1-2), 44-51.
16. [16] Yun, K.J, Koh, D.J, Kim, S.H, Park, S.J.; Ryu, J.H, Kim, D.G, Lee, J.Y, Lee, K.T. Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. J. Agric. Food Chem., 2008, 56(21), 10265-10272.
17. [17] Milkowski, C, Strack, D. Sinapate esters in brassicaceous plants: Biochemistry, molecular biology, evolution and metabolic engineering. Planta. 2010, 232(1), 19-35.
18. [18] Tsai, C.M, Yen, G.C, Sun, F.M, Yang, S.F, Weng, C.J. Assessment of the anti-invasion potential and mechanism of select cinnamic acid derivatives on human lungadenocarcinoma cells. Mol. Pharm.,2013, 10(5), 1890-900.
19. [19] Niero, E.L, Machado-Santelli, G.M. Cinnamic acid induces apoptotic cell death and cytoskeleton disruption in human melanoma cells. J. Exp. Clin. Cancer Res., 2013, 32, 31.
20. [20] Luo, Y, Qiu, K.M, Lu, X, Liu, K, Fu, J, Zhu, H.L. Synthesis, biological evaluation, and molecular modeling of cinnamic acyl sulfonamide derivatives as novel antitubulin agents. Bioorg. Med. Chem., 2011, 19(16), 4730-4738.
21. [21] Yang, X.H, Wen, Q, Zhao, T.T, Sun, J, Li, X, Xing, M, Lu, X, Zhu, H.L. Synthesis, biological evaluation,and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amidederivatives as novel antitubulin agents. Bioorg. Med. Chem., 2012, 20(3), 1181-1187.
22. [22] Li, D.D, Lv, P.C, Zhang, H, Zhang, H.J, Hou, Y.P, Liu, K, Ye, Y.H, Zhu, H.L. The combination of 4-anilinoquinazoline and cinnamic acid: A novel mode of binding to the epidermal growthfactor receptor tyrosine kinase. Bioorg. Med. Chem., 2011, 19(16), 5012-5022.
23. [23] Qian, Y, Zhang, H.J, Zhang, H, Xu, C, Zhao, J, Zhu, H.L. Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives asnovel anticancer agents. Bioorg. Med. Chem., 2010, 18(14), 4991-4996.
24. [24] Yen, G.C, Chen, Y.L, Sun, F.M, Chiang, Y.L, Lu, S.H, Weng, C.J. A comparative study on the effectiveness of cis-and trans-form of cinnamic acid treatments for inhibiting invasiveactivity of human lung adenocarcinoma cells. Eur. J. Pharm. Sci., 2011, 44(3), 281-287.
25. [25] Xia, Z, Correa, R.G, Das, J.K, Farhana, L, Castro, D.J, Yu, J, Oshima, R.G, Fontana, J.A, Reed, J.C, Dawson, M.I. Analogues of orphan nuclear receptor small heterodimer partner ligand and Received: August 26, 2014 Revised: September 27, 2014 Accepted: November 20, 2014 Anti-Cancer Agents in Medicinal Chemistry, 2015, Vol. 15, No. 8 987 apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3- chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of leukemia and cancer cell lines. J. Med. Chem., 2012, 55(1), 233-249.
26. [26] Kumazaki, M, Shinohara, H, Taniguchi, K, Yamada, N, Ohta, S, Ichihara, K, Akao, Y. Propolis cinnamic acid derivatives induce apoptosis through both extrinsic and intrinsic apoptosis signaling pathways and modulate of miRNA expression. Phytomedicine, 2014, 21(8-9), 1070-1077.
27. [27] Zou, H, Wu, H, Zhang, X, Zhao Y, Stöckigt, J, Lou, Y, Yu, Y. Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acidderivatives. Bioorg. Med. Chem., 2010, 18(17), 6351-6359.
28. [28] Schlageter, M, Terracciano, L.M, D'Angelo, S, Sorrentino, P. Histopathology of hepatocellular carcinoma. World J. Gastroenterol., 2014, 20(43), 15955-15964.
29. [29] Guerriero, E, Sorice, A, Capone, F, Costantini, S, Palladino, P, D'ischia, M, Castello, G. Effects of lipoic acid, caffeic acid and a synthesized lipoyl-caffeic conjugate on human hepatoma cell lines. Molecules, 2011, 16(8), 6365-6377.
30. [30] Endo, S, Matsunaga, T, Mamiya, H, Ohta, C, Soda, M, Kitade, Y, Tajima, K, Zhao, H.T, El-Kabbani, O, Hara, A. Kinetic studies of AKR1B10, human aldose reductase-like protein: Endogenous substrates and inhibition by steroids. Arch. Biochem. Biophys., 2009, 487(1), 1-9.
31. [31] Soda, M, Hu, D, Endo, S, Takemura, M, Li, J, Wada, R, Ifuku, S, Zhao, H.T, El-Kabbani O, Ohta, S, Yamamura, K, Toyooka, N, Hara, A, Matsunaga, T. Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10. Eur. J. Med. Chem., 2012, 48, 321-329.
32. [32] Hajmohamad Ebrahim Ketabforoosh S, Amini, M, Vosooghi, M, Shafiee, A, Azizi, E, Kobarfard, F. Synthesis, evaluation of anticancer activity and QSAR study of heterocyclic esters of caffeic Acid. Iran. J. Pharm. Res., 2013, 12(4), 705-719.
33. [33] Chiang, E.P, Tsai, S.Y, Kuo, Y.H, Pai, M.H, Chiu, H.L, Rodriguez, R.L, Tang, F.Y. Caffeic Acid Derivatives Inhibit the Growth of colon cancer: Involvement of the PI3-K/Akt and AMPK signaling pathways. PLoS. One., 2014, 9(6), e99631.
34. [34] Swiatek-Machado, K, Mieczkowski, J, Ellert-Miklaszewska, A, Swierk, P, Fokt, I, Szymanski, S, Skora, S, Szeja, W, Grynkiewicz, G, Lesyng, B, Priebe, W, Kaminska, B. Novel small molecular inhibitors disrupt the JAK/STAT3 and FAK signaling pathways and exhibit a potentantitumor activity in glioma cells. Cancer Biol. Ther., 2012, 13(8), 657-670.
35. [35] Sanderson, J.T, Clabault, H, Patton, C, Lassalle-Claux, G, Jean-François, J, Paré, A.F, Hebert, M J, Surette, M.E, Touaibia, M. Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells. Bioorg. Med. Chem., 2013, 21(22), 7182-7193.
36. [36] Lee, S.J, Kang, M.S, Oh, J.S, Na, H.S, Lim, Y.J, Jeong, Y.I, Lee, H.C. Caffeic acid-conjugated chitosan derivatives and their anti-tumor activity. Arch. Pharm. Res., 2013, 36(12), 1437-1446
37. [37] Serafim, T.L, Carvalho, F.S, Marques, M.P, Calheiros, R, Silva, T, Garrido, J, Milhazes, N, Borges, F, Roleira, F, Silva, E.T, Holy, J, Oliveira, P.J. Lipophilic caffeic and ferulic acid derivatives presenting cytotoxicity against human breast cancer cells. Chem. Res. Toxicol., 2011, 24(5), 763-774.
38. [38] Lu, W, Wang, F, Zhang, T, Dong, J, Gao, H, Su, P, Shi, Y, Zhang, J. Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives. Bioorg. Med. Chem., 2014, 22(9), 2707-2713
39. [39] Zeng, X, Zheng, J, Fu, C, Su, H, Sun, X, Zhang, X, Hou, Y, Zhu, Y. A newly synthesized sinapic acid derivative inhibits endothelial activation in vitro and in vivo. Mol. Pharmacol., 2013, 83(5), 1099-1108.