Synthesis of Caffeic Acid Phenethyl Ester Analogues and Their Cytotoxicities Against Human Cancer Cells

Yan-Hui Wang; Qu-Sheng Li; Peng-Long Wang; Kuo Xu; Ya-Tao Cheng; Xin Xu; Qiang Li; Yu-Zhong Zhang; Hai-Min Lei

doi:10.14233/ajchem.2014.15974

Issue

Vol. 26 No. 9 (2014): Vol 26 Issue 9

Issue Published : April 28, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Caffeic Acid Phenethyl Ester Analogues and Their Cytotoxicities Against Human Cancer Cells

https://doi.org/10.14233/ajchem.2014.15974

Yan-Hui Wang

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Qu-Sheng Li

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Peng-Long Wang

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Kuo Xu

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Ya-Tao Cheng

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Xin Xu

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Qiang Li

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Yu-Zhong Zhang

School of Basic Medical Sciences, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Hai-Min Lei

School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, P.R. China

Corresponding Author(s) : Hai-Min Lei

hm_lei@126.com

Asian Journal of Chemistry, Vol. 26 No. 9 (2014): Vol 26 Issue 9
Article Published : April 29, 2014

Abstract

Although caffeic acid phenethyl ester exhibits strong antitumor property, but its pharmacophore has not been elaborated clearly as yet. Seventeen caffeic acid phenethyl ester analogues were synthesized via simple and easy procedures and their antiproliferative effects were evaluated toward Bel-7402 and MCF-7 cancer cell lines. Compared to compounds 1-11, 12, 13, 14, 15 showed cytotoxic effects. The IC₅₀ values (μM) of compound 14 (41.87, 51.98) were about equal to caffeic acid phenethyl ester’s (34.60, 42.26). Structure-activity relationship analysis demonstrated that the a, b-unsaturated double bond and the phenolic hydroxyl group in caffeic acid phenethyl ester were essential for the antitumor activities. Besides, the cytotoxic properties of these compounds were determined by the methoxy groups on the phenyl ring and the location of aromatic hydroxyl groups. These results may be of great benefit to people in screening new anticancer drug candidates.

Keywords

Caffeic acid phenethyl ester analogues Pharmacophore Cytotoxic properties

Wang, Y.-H., Li, Q.-S., Wang, P.-L., Xu, K., Cheng, Y.-T., Xu, X., … Lei, H.-M. (2014). Synthesis of Caffeic Acid Phenethyl Ester Analogues and Their Cytotoxicities Against Human Cancer Cells. Asian Journal of Chemistry, 26(9), 2686–2690. https://doi.org/10.14233/ajchem.2014.15974

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References

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D. Grunberger, R. Banerjee, K. Eisinger, E.M. Oltz, L. Efros, M. Caldwell, V. Estevez and K. Nakanishi, Experientia, 44, 230 (1988); doi:10.1007/BF01941717.

B.H. Ackerman, R.E. Guilday, C.L. Reigart, M.L. Patton and L.R. Haith, J. Burn Care Res., 34, 1 (2013); doi:10.1097/BCR.0b013e31827e4ee9.

S. Akyol, G. Ozturk, Z. Ginis, F. Armutcu, M.R. Yigitoglu and O. Akyol, Nutr. Cancer, 65, 515 (2013); doi:10.1080/01635581.2013.776693.

J.H. Park, J.K. Lee, H.S. Kim, S.T. Chung, J.H. Eom, K.A. Kim, S.J. Chung, S.Y. Paik and H.Y. Oh, Int. Immunopharmacol., 4, 429 (2004); doi:10.1016/j.intimp.2004.01.013.

H. Göçer and I. Gülçin, Int. J. Food Sci. Nutr., 62, 821 (2011); doi:10.3109/09637486.2011.585963.

J. Wu, C. Omene, J. Karkoszka, M. Bosland, J. Eckard, C.B. Klein and K. Frenkel, Cancer Lett., 308, 43 (2011); doi:10.1016/j.canlet.2011.04.012.

K.W. Lee, N.J. Kang, J.H. Kim, K.M. Lee, D.E. Lee, H.J. Hur and H.J. Lee, J. Genes Nutr., 2, 319 (2008); doi:10.1007/s12263-007-0067-9.

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J. Lin, D. Grunberger and P.B. Fisher, Cell. Mol. Biol., 38, 513 (1992).

H.-P. Lin, C.-Y. Lin, C.-C. Liu, L.-C. Su, C. Huo, Y.-Y. Kuo, J.-C. Tseng, J.-M. Hsu, C.-K. Chen and C.-P. Chuu, Int. J. Mol. Sci., 14, 5264 (2013); doi:10.3390/ijms14035264.

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T. Nagaoka, A.H. Banskota, Y. Tezuka, I. Saiki and S. Kadota, Bioorg. Med. Chem., 10, 3351 (2002); doi:10.1016/S0968-0896(02)00138-4.

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O.K. Mirzoeva, G.F. Sud’ina, M.A. Pushkareva, G.A. Korshunova, N.V. Sumbatian and S.D. Varfolomeev, Bioorg. Khim., 21, 143 (1995).

T.R.J. Burke, M. Fesen, A. Mazumder, J. Yung, J. Wang, A.M. Carothers, D. Grunberger, J. Driscoll, Y. Pommier and K. Kohn, Med. Chem., 38, 4171 (1995); doi:10.1021/jm00021a006.

C.-C. Lo and P.-M. Chao, J. Chem. Ecol., 16, 3245 (1990); doi:10.1007/BF00982095.

Issue

Vol. 26 No. 9 (2014): Vol 26 Issue 9

Synthesis of Caffeic Acid Phenethyl Ester Analogues and Their Cytotoxicities Against Human Cancer Cells

Corresponding Author(s) : Hai-Min Lei

Abstract

Keywords

Full Article

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References

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