Generic placeholder image

Letters in Organic Chemistry

Author(s): Luu Xuan Hieu, Tran Thi Hong Ha, Hoang Kim Chi, Tran Khac Vu, Pham Van Chung, Truong Ngoc Hung* and Luu Van Chinh*

DOI: 10.2174/1570178619666220325140413

DownloadDownload PDF Flyer Cite As
Novel Derivatives Based on Zerumbone Scaffold as Potential Anticancer Inhibitors

Page: [1062 - 1069] Pages: 8

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

A two-step procedure was applied to couple zerumbone, a natural sesquiterpene, with thiols 8a-k to obtain a small library of ten novel zerumbone derivatives 9a-k with full-length library data of spectra including 1H-, 13C-NMR, and HRMS. The tautomerization of 9a, 9b, and 9c was revealed in DMSO and discussed in the case of 9c. The series of 9a-k together with zerumbone 1 was evaluated for their in vitro cytotoxic activity using three human cancer cell lines, HepG2, A549 and HeLa. The results revealed that all zerumbone derivatives had cytotoxic activity against HepG2, A549, and HeLa cells that was 4-20 times stronger than zerumbone.

Keywords: Zerumbone, mercapto, S-alkylation, cytotoxicity, tautomerization, cancer cells.

Graphical Abstract

[1]
Girisa, S.; Shabnam, B.; Monisha, J.; Fan, L.; Halim, C.E.; Arfuso, F.; Ahn, K.S.; Sethi, G.; Kunnumakkara, A.B. Molecules, 2019, 24(4), 734.
[http://dx.doi.org/10.3390/molecules24040734] [PMID: 30781671]
[2]
Cumming, J.N.; Ploypradith, P.; Posner, G.H. Adv. Pharmacol., 1997, 37, 253-297.
[http://dx.doi.org/10.1016/S1054-3589(08)60952-7] [PMID: 8891104]
[3]
Li, Q.; Wang, Z.; Xie, Y.; Hu, H. Biomed. Pharmacother., 2020, 125109955
[http://dx.doi.org/10.1016/j.biopha.2020.109955] [PMID: 32014691]
[4]
Liu, J.; Yang, Z.; Kong, Y.; He, Y.; Xu, Y.; Cao, X. J. Food Biochem., 2019, 43(9)e12972
[http://dx.doi.org/10.1111/jfbc.12972] [PMID: 31489665]
[5]
Zhang, X.; Xia, Y.; Yang, L.; He, J.; Li, Y.; Xia, C. Viruses, 2019, 11(9), 835.
[http://dx.doi.org/10.3390/v11090835] [PMID: 31500389]
[6]
Elsebai, M.F.; Mocan, A.; Atanasov, A.G. Front. Pharmacol., 2016, 7, 472.
[http://dx.doi.org/10.3389/fphar.2016.00472] [PMID: 28008316]
[7]
Dung, N.X.; Chinh, T.D.; Rang, D.D.; Leclereq, P.A. J. Essent. Oil Res., 1993, 5(5), 553-555.
[http://dx.doi.org/10.1080/10412905.1993.9698277]
[8]
Elsohly, H.N.; Croom, E.M., Jr; El-Feraly, F.S.; El-Sherei, M.M. J. Nat. Prod., 1990, 53(6), 1560-1564.
[http://dx.doi.org/10.1021/np50072a026]
[9]
Tse, E.G.; Korsik, M.; Todd, M.H. Malar. J., 2019, 18(1), 93.
[http://dx.doi.org/10.1186/s12936-019-2724-z] [PMID: 30902052]
[10]
Murakami, A.; Takahashi, D.; Kinoshita, T.; Koshimizu, K.; Kim, H.W.; Yoshihiro, A.; Nakamura, Y.; Jiwajinda, S.; Terao, J.; Ohigashi, H. Carcinogenesis, 2002, 23(5), 795-802.
[http://dx.doi.org/10.1093/carcin/23.5.795] [PMID: 12016152]
[11]
Giang, P.M.; Son, P.T.; Jin, H.Z.; Lee, J.H.; Lee, J.J. Sci. Pharm., 2009, 77(3), 589-595.
[http://dx.doi.org/10.3797/scipharm.0907-16]
[12]
Takada, Y.; Murakami, A.; Aggarwal, B.B. Oncogene, 2005, 24(46), 6957-6969.
[http://dx.doi.org/10.1038/sj.onc.1208845] [PMID: 16007145]
[13]
Hoffman, A.; Spetner, L.M.; Burke, M. Carcinogenesis, 2002, 23(11), 1961-1972.
[http://dx.doi.org/10.1093/carcin/23.11.1961] [PMID: 12419847]
[14]
Dermani, F.K.; Amini, R.; Saidijam, M.; Pourjafar, M.; Saki, S.; Najafi, R. J. Cell. Physiol., 2018, 233(12), 9538-9547.
[http://dx.doi.org/10.1002/jcp.26874] [PMID: 29943808]
[15]
Abdelwahab, S.I.; Abdul, A.B.; Mohan, S.; Taha, M.M.E.; Syam, S.; Ibrahim, M.Y.; Mariod, A.A. Leuk. Res., 2011, 35(2), 268-271.
[http://dx.doi.org/10.1016/j.leukres.2010.07.025] [PMID: 20708800]
[16]
Ma, S.; Lei, Y.; Zhang, L.; Wang, J. Oncol. Lett., 2018, 16(4), 4379-4383.
[http://dx.doi.org/10.3892/ol.2018.9184] [PMID: 30197671]
[17]
Truong, V.V.; Nam, T.D.; Hung, T.N.; Nga, N.T.; Quan, P.M.; Chinh, L.V.; Jung, S.H. Bioorg. Med. Chem. Lett., 2015, 25(22), 5182-5185.
[http://dx.doi.org/10.1016/j.bmcl.2015.09.069] [PMID: 26459207]
[18]
Vu, V.V.; Vu, T.K. Curr. Bioact. Compd., 2021, 17(4), 331-338.
[http://dx.doi.org/10.2174/1573407216999200630133625]
[19]
Kitayama, T.; Nikahama, M.; Yamasaki, K.; Inoue, H.; Imada, C.; Yonekura, Y.; Awata, M.; Takaya, H.; Kawai, Y.; Onishi, K.; Murakami, A. Tetrahedron, 2013, 69(47), 10152-10160.
[http://dx.doi.org/10.1016/j.tet.2013.09.026]
[20]
Utaka, Y.; Kashiwazaki, G.; Tajima, S.; Fujiwara, Y.; Sumi, K.; Itoh, T.; Kitayama, T. Tetrahedron, 2019, 75(10), 1343-1350.
[http://dx.doi.org/10.1016/j.tet.2019.01.038]
[21]
Kalesh, K.A.; Clulow, J.A.; Tate, E.W. Chem. Commun. (Camb.), 2015, 51(25), 5497-5500.
[http://dx.doi.org/10.1039/C4CC09527H] [PMID: 25598414]
[22]
Azam, M.A.; Suresh, B.; Kalsi, S.S.; Antony, A.S. S. Afr. J. Chem., 2010, 63, 114-122.
[23]
Amer, H.H.; Ali, O.M. Orient. J. Chem., 2017, 33(5), 2303-2310.
[http://dx.doi.org/10.13005/ojc/330519]
[24]
Yu, Q.M.; Yan, X.; Du, R.; Xiao, G.Y.; Yu, X.L.; Gao, Y.; Wen, L.L. Lett. Drug Des. Discov., 2016, 13(6), 570-576.
[http://dx.doi.org/10.2174/1570180812666150821003536]
[25]
Mavrova, A.T.; Dimov, S.; Yancheva, D.; Rangelov, M.; Wesselinova, D.; Tsenov, J.A. Eur. J. Med. Chem., 2016, 123, 69-79.
[http://dx.doi.org/10.1016/j.ejmech.2016.07.022] [PMID: 27474924]
[26]
Nishiguchi, S.; Izumi, T.; Kuono, T.; Sukegawa, J.; Ilies, L.; Nakamura, E. ACS Catal., 2018, 8(10), 9738-9743.
[http://dx.doi.org/10.1021/acscatal.8b02610]
[27]
Claramunt, R.M.; López, C.; Alkorta, I.; Elguero, J.; Yang, R.; Schulman, S. Magn. Reson. Chem., 2004, 42(8), 712-714.
[http://dx.doi.org/10.1002/mrc.1409] [PMID: 15248261]
[28]
Likhitwitayawuid, K.; Angerhofer, C.K.; Cordell, G.A.; Pezzuto, J.M.; Ruangrungsi, N. J. Nat. Prod., 1993, 56(1), 30-38.
[http://dx.doi.org/10.1021/np50091a005] [PMID: 8450319]
[29]
Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R.J. J. Natl. Cancer Inst., 1990, 82(13), 1107-1112.
[http://dx.doi.org/10.1093/jnci/82.13.1107]
[30]
Nadzri, N.M.; Abdul, A.B.; Sukari, M.A.; Abdelwahab, S.I.; Eid, E.E.M.; Mohan, S.; Kamalidehghan, B.; Anasamy, T.; Beng Ng, K.; Syam, S.; Arbab, I.A.; Rahman, H.S.; Ali, H.M. eCAM, 2013, 2013, 810632.
[31]
Al-Zubairi, A.S. Online J. Biol. Sci., 2018, 18(2), 123-129.
[32]
Fusi, F.; Durante, M.; Sgaragli, G.; Khanh, P.N.; Son, N.T.; Huong, T.T.; Huong, V.N.; Cuong, N.M. Planta Med., 2015, 81(4), 298-304.
[http://dx.doi.org/10.1055/s-0034-1396307] [PMID: 25714723]