Design, synthesis and biological activity of piperlongumine derivatives as selective anticancer agents

European Journal of Medicinal Chemistry

Volumn 82, Issue , 2014, Pages 545-551

  Wu, Yuelin ^a,b   Min, Xiao ^a   Zhuang, Chunlin ^a   Li, Jin ^a   Yu, Zhiliang ^a   Dong, Guoqiang ^a   Yao, Jiangzhong ^a   Wang, Shengzheng ^a   Liu, Yang ^a   Wu, Shanchao ^a   Zhu, Shiping ^a   Sheng, Chunquan ^a   Wei, Yunyang ^b   Zhang, Huojun ^c   Zhang, Wannian ^a   Miao, Zhenyuan ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Anticancer agent; Biological activity; Piperlongumine; Selectivity

Indexed keywords

(E) 1 [2 ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDROPYRIDIN 2(1H) ONE; (E) 1 [2 METHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDROPYRIDIN 2(1H) ONE; (E) 2 BUTYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLIC ACID; (E) 2 ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLIC ACID; (E) 2 PROPYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLIC ACID; (E) 3 BROMO 1 [2 BUTYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 BROMO 1 [2 ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 BROMO 1 [2 METHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DI HYDROPYRIDIN 2(1H) ONE; (E) 3 BROMO 1 [2 PROPYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 BROMO 1 [3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDROPYRIDIN 2(1H) ONE; (E) 3 CLORO 1 [2 BUTYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 CLORO 1 [2 ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 CLORO 1 [2 METHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 CLORO 1 [2 PROPYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) 3 CLORO 1 [3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) MORPHOLINO 1 [2 ETHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; (E) MORPHOLINO 1 [2 METHYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DI HYDROPYRIDIN 2(1H) ONE; (E) MORPHOLINO 1 [2 PROPYL 3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DI HYDROPYRIDIN 2(1H) ONE; (E) MORPHOLINO 1 [3 (3,4,5 TRIMETHOXYPHENYL)ACRYLOYL] 5,6 DIHYDRO PYRIDIN 2(1H) ONE; ALKALOID DERIVATIVE; ANTINEOPLASTIC AGENT; PIPERLONGUMINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; 1,3 DIOXOLANE DERIVATIVE; PIPERLONGUMININE;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; BREAST CARCINOMA; CANCER CELL; CANCER CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; COLORECTAL CARCINOMA; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LUNG CARCINOMA; MOUSE; MTT ASSAY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; TUMOR GROWTH; CELL LINE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HCT116 CELL LINE; METABOLISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL LINE; CELL PROLIFERATION; DIOXOLANES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HUMANS; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84902686663     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.070     Document Type: Article

References (23)

1. C.Y. Duh, Y.C. Wu, and S.K. Wang Cytotoxic pyridone alkaloids from the leaves of piper-aborescens J. Nat. Prod. 53 1990 1575 1577
2. D. Jyothi, P. Vanathi, P.M. Gowri, V.R.S. Rao, J.M. Rao, and A.S. Sreedhar Diferuloylmethane augments the cytotoxic effects of piplartine isolated from Piper chaba Toxicol. In Vitro 23 2009 1085 1091
3. K.V. Golovine, P.B. Makhov, E. Teper, A. Kutikov, D. Canter, R.G. Uzzo, and V.M. Kolenko Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells Prostate 73 2013 23 30
4. S. Ginzburg, K.V. Golovine, P.B. Makhov, R.G. Uzzo, A. Kutikov, and V.M. Kolenko Piperlongumine inhibits NF-kappaB activity and attenuates aggressive growth characteristics of prostate cancer cells Prostate 74 2014 177 186
5. J.M. Liu, F. Pan, L. Li, Q.R. Liu, Y. Chen, X.X. Xiong, K. Cheng, S.B. Yu, Z. Shi, A.C. Yu, and X.Q. Chen Piperlongumine selectively kills glioblastoma multiforme cells via reactive oxygen species accumulation dependent JNK and p38 activation Biochem. Biophys. Res. Commun. 437 2013 87 93
6. S.S. Han, V.S. Tompkins, D.J. Son, N.L. Kamberos, L.L. Stunz, A. Halwani, G.A. Bishop, and S. Janz Piperlongumine inhibits LMP1/MYC-dependent mouse B-lymphoma cells Biochem. Biophys. Res. Commun. 436 2013 660 665
7. M. Jarvius, M. Fryknas, P. D'Arcy, C. Sun, L. Rickardson, J. Gullbo, C. Haglund, P. Nygren, S. Linder, and R. Larsson Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells Biochem. Biophys. Res. Commun. 431 2013 117 123
8. V.R. Rao, P. Muthenna, G. Shankaraiah, C. Akileshwari, K.H. Babu, G. Suresh, K.S. Babu, R.S.C. Kumar, K.R. Prasad, P.A. Yadav, J.M. Petrash, G.B. Reddy, and J.M. Rao Synthesis and biological evaluation of new piplartine analogues as potent aldose reductase inhibitors (ARIs) Eur. J. Med. Chem. 57 2012 344 361
9. I.L. Tsai, F.P. Lee, C.C. Wu, C.Y. Duh, T. Ishikawa, J.J. Chen, Y.C. Chen, H. Seki, and I.S. Chen New cytotoxic cyclobutanoid amides, a new furanoid lignan and anti-platelet aggregation constituents from Piper arborescens Planta Med. 71 2005 535 542 (Pubitemid 40910600)
10. B.S. Park, D.J. Son, Y.H. Park, T.W. Kim, and S.E. Lee Antiplatelet effects of acidamides isolated from the fruits of Piper longum L. Phytomedicine 14 2007 853 855 (Pubitemid 350017877)
11. J.B. Fontenele, L. Leal, E.R. Silveira, F.H. Felix, C.F.B. Felipe, and G.S.B. Viana Antiplatelet effects of piplartine, an alkamide isolated from Piper tuberculatum: possible involvement of cyclooxygenase blockade and antioxidant activity J. Pharm. Pharmacol. 61 2009 511 515
12. D.J. Son, S.Y. Kim, S.S. Han, C.W. Kim, S. Kumar, B.S. Park, S.E. Lee, Y.P. Yun, H. Jo, and Y.H. Park Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling Biochem. Biophys. Res. Commun. 427 2012 349 354
13. H.M.D. Navickiene, A.C. Alecio, M.J. Kato, V.D. Bolzani, M.C.M. Young, A.J. Cavalheiro, and M. Furlan Antifungal amides from Piper hispidum and Piper tuberculatum Phytochemistry 55 2000 621 626
14. R.V. da Silva, H.M.D. Navickiene, M.J. Kato, V.D.S. Bolzania, C.I. Meda, M.C.M. Young, and M. Furlan Antifungal amides from Piper arboreum and Piper tuberculatum Phytochemistry 59 2002 521 527
15. L. Raj, T. Ide, A.U. Gurkar, M. Foley, M. Schenone, X. Li, N.J. Tolliday, T.R. Golub, S.A. Carr, A.F. Shamji, A.M. Stern, A. Mandinova, S.L. Schreiber, and S.W. Lee Selective killing of cancer cells by a small molecule targeting the stress response to ROS Nature 475 2011 231 234
16. D.P. Bezerra, C. Pessoa, M.O. de Moraes, N. Saker-Neto, E.R. Silveira, and L.V. Costa-Lotufo Overview of the therapeutic potential of piplartine (piperlongumine) Eur. J. Pharm. Sci. 48 2012 453 463
17. D.J. Adams, Z.V. Boskovic, J.R. Theriault, A.J. Wang, A.M. Stern, B.K. Wagner, A.F. Shamji, and S.L. Schreiber High-throughput screening identifies small-molecule enhancers of reactive oxygen species that are nontoxic or cause genotype-selective cell death ACS Chem. Biol. 8 2013 923 929
18. D. Trachootham, J. Alexandre, and P. Huang Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat. Rev. Drug. Discov. 8 2009 579 591
19. Z.V. Boskovic, M.M. Hussain, D.J. Adams, M. Dai, and S.L. Schreiber Synthesis of piperlogs and analysis of their effects on cells Tetrahedron 69 2013
20. H. Randhawa, K. Kibble, H. Zeng, M.P. Moyer, and K.M. Reindl Activation of ERK signaling and induction of colon cancer cell death by piperlongumine Toxicol. In Vitro 27 2013 1626 1633
21. D.J. Adams, M. Dai, G. Pellegrino, B.K. Wagner, A.M. Stern, A.F. Shamji, and S.L. Schreiber Synthesis, cellular evaluation, and mechanism of action of piperlongumine analogs Proc. Natl. Acad. Sci. U. S. A. 109 2012 15115 15120
22. P.M. Boll, J. Hansen, O. Simonsen, and N. Thorup Synthesis and molecular-structure of piplartine (=Piperlongumine) Tetrahedron 40 1984 171 175
23. J.L. Richards, S.M. Myhre, and J.I. Jay Total synthesis of piplartine, 13-desmethylpiplartine, and cenocladamide: three compounds isolated from Piper cenocladum Abstr. Pap. Am. Chem. Soc. 221 2001 U188-U188