Synthetic cyclohexenyl chalcone natural products possess cytotoxic activities against prostate cancer cells and inhibit cysteine cathepsins in vitro

Biochemical and Biophysical Research Communications

Volumn 416, Issue 3-4, 2011, Pages 397-402

  Deb Majumdar, Ishita ^a   Devanabanda, Arvind ^a   Fox, Benjamin ^a   Schwartzman, Jacob ^a   Cong, Huan ^b   Porco, John A ^b   Weber, Horst C ^a  

^a BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Boston University   (United States)

Author keywords

Cathepsin inhibitor; Cyclohexenyl chalcone; Cysteine cathepsin protease; Diels Alder natural products; Prostate cancer

Indexed keywords

CATHEPSIN; CATHEPSIN L; CHALCONE DERIVATIVE; CYCLOHEXENYL CHALCONE; CYSTEINE CATHEPSIN; CYSTEINE PROTEINASE; NATURAL PRODUCT; NICOLAIOIDESIN C; PANDURATIN A; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER INVASION; CELL CYCLE ARREST; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL FREE SYSTEM; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG INHIBITION; ENZYME ASSAY; GENE EXPRESSION PROFILING; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; METASTASIS; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN ANALYSIS; PROTEIN FUNCTION; TUMOR GROWTH;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BIOLOGICAL AGENTS; CATHEPSINS; CELL CYCLE; CELL LINE, TUMOR; CHALCONE; CHALCONES; CYCLOHEXANES; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; HUMANS; MALE; PROSTATIC NEOPLASMS;

ALNUS;

EID: 84855886881     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2011.11.052     Document Type: Article

References (39)

1. Tuntiwachwuttikul P., Pancharoen O., Reutrakul V., Byrne L.T. (l'RS,2'SR,6'RS)-(2,6-Dihydroxy-4-methoxypheny∼)-[3'-methyl-2'-(3'-methylbut-2'-enyl)-6'-phenylcyclohex-3'-enyllmethanone (Panduratin A)-a Constituent of the Red Rhizomes of a Variety of Boesenbergia pandurata. Aust. J. Chem. 1984, 37:449-453.
2. Gu J.Q., Park E.J., Vigo J.S., Graham J.G., Fong H.H., Pezzuto J.M., Kinghorn A.D. Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase. J. Nat. Prod. 2002, 65:1616-1620.
3. Win N.N., Awale S., Esumi H., Tezuka Y., Kadota S. Bioactive secondary metabolites from Boesenbergia pandurata of Myanmar and their preferential cytotoxicity against human pancreatic cancer PANC-1 cell line in nutrient-deprived medium. J. Nat. Prod. 2007, 70:1582-1587.
4. Cheenpracha S., Karalai C., Ponglimanont C., Subhadhirasakul S., Tewtrakul S. Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata. Bioorg. Med. Chem. 2006, 14:1710-1714.
5. Kiat T.S., Pippen R., Yusof R., Ibrahim H., Khalid N., Rahman N.A. Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease. Bioorg. Med. Chem. Lett. 2006, 16:3337-3340.
6. Morikawa T., Funakoshi K., Ninomiya K., Yasuda D., Miyagawa K., Matsuda H., Yoshikawa M. Medicinal foodstuffs. XXXIV. Structures of new prenylchalcones prenylflavanones with TNF-alpha aminopeptidase N inhibitory activities from Boesenbergia rotunda. Chem. Pharm. Bull. (Tokyo) 2008, 56:956-962.
7. Yun J.M., Kweon M.H., Kwon H., Hwang J.K., Mukhtar H. Induction of apoptosis and cell cycle arrest by a chalcone panduratin A isolated from Kaempferia pandurata in androgen-independent human prostate cancer cells PC3 and DU145. Carcinogenesis 2006, 27:1454-1464.
8. Cheah S.C., Appleton D.R., Lee S.T., Lam M.L., Hadi A.H., Mustafa M.R. Panduratin A inhibits the growth of A549 cells through induction of apoptosis and inhibition of NF-kappaB translocation. Molecules 2011, 16:2583-2598.
9. Yun J.M., Kwon H., Mukhtar H., Hwang J.K. Induction of apoptosis by Panduratin A isolated from Kaempferia pandurata in human colon cancer HT-29 cells. Planta Med. 2005, 71:501-507.
10. Lopez-Otin C., Matrisian L.M. Emerging roles of proteases in tumour suppression. Nat. Rev. Cancer 2007, 7:800-808.
11. Mohamed M.M., Sloane B.F. Cysteine cathepsins: multifunctional enzymes in cancer. Nat. Rev. Cancer 2006, 6:764-775.
12. Palermo C., Joyce J.A. Cysteine cathepsin proteases as pharmacological targets in cancer. Trends Pharmacol. Sci. 2008, 29:22-28.
13. Brubaker K.D., Vessella R.L., True L.D., Thomas R., Corey E. Cathepsin K mRNA and protein expression in prostate cancer progression. J. Bone Miner. Res. 2003, 18:222-230.
14. Lankelma J.M., Voorend D.M., Barwari T., Koetsveld J., Van der Spek A.H., De Porto A.P., Van Rooijen G., Van Noorden C.J. Cathepsin L, target in cancer treatment?. Life Sci. 2010, 86:225-233.
15. Alvarez-Diaz S., Valle N., Garcia J.M., Pena C., Freije J.M., Quesada V., Astudillo A., Bonilla F., Lopez-Otin C., Munoz A. Cystatin D is a candidate tumor suppressor gene induced by vitamin D in human colon cancer cells. J. Clin. Invest. 2009, 119:2343-2358.
16. Gocheva V., Joyce J.A. Cysteine cathepsins and the cutting edge of cancer invasion. Cell Cycle 2007, 6:60-64.
17. Gocheva V., Zeng W., Ke D., Klimstra D., Reinheckel T., Peters C., Hanahan D., Joyce J.A. Distinct roles for cysteine cathepsin genes in multistage tumorigenesis. Genes Dev. 2006, 20:543-556.
18. Goulet B., Sansregret L., Leduy L., Bogyo M., Weber E., Chauhan S.S., Nepveu A. Increased expression and activity of nuclear cathepsin L in cancer cells suggests a novel mechanism of cell transformation. Mol. Cancer Res. 2007, 5:899-907.
19. Jedeszko C., Sloane B.F. Cysteine cathepsins in human cancer. Biol. Chem. 2004, 385:1017-1027.
20. Joyce J.A., Baruch A., Chehade K., Meyer-Morse N., Giraudo E., Tsai F.Y., Greenbaum D.C., Hager J.H., Bogyo M., Hanahan D. Cathepsin cysteine proteases are effectors of invasive growth and angiogenesis during multistage tumorigenesis. Cancer Cell 2004, 5:443-453.
21. Sullivan S., Tosetto M., Kevans D., Coss A., Wang L., O'Donoghue D., Hyland J., Sheahan K., Mulcahy H., O'Sullivan J. Localization of nuclear cathepsin L and its association with disease progression and poor outcome in colorectal cancer. Int. J. Cancer 2009, 125:54-61.
22. Colella R., Jackson T., Goodwyn E. Matrigel invasion by the prostate cancer cell lines, PC3 and DU145, and cathepsin L+B activity. Biotech. Histochem. 2004, 79:121-127.
23. Friedrich B., Jung K., Lein M., Turk I., Rudolph B., Hampel G., Schnorr D., Loening S.A. Cathepsins B, H, L and cysteine protease inhibitors in malignant prostate cell lines, primary cultured prostatic cells and prostatic tissue. Eur. J. Cancer 1999, 35:138-144.
24. Miyake H., Hara I., Eto H. Serum level of cathepsin B and its density in men with prostate cancer as novel markers of disease progression. Anticancer Res. 2004, 24:2573-2577.
25. Nagler D.K., Kruger S., Kellner A., Ziomek E., Menard R., Buhtz P., Krams M., Roessner A., Kellner U. Up-regulation of cathepsin X in prostate cancer and prostatic intraepithelial neoplasia. Prostate 2004, 60:109-119.
26. Nalla A.K., Gorantla B., Gondi C.S., Lakka S.S., Rao J.S. Targeting MMP-9, uPAR, and cathepsin B inhibits invasion, migration and activates apoptosis in prostate cancer cells. Cancer Gene Ther. 2010, 17:599-613.
27. Podgorski I., Linebaugh B.E., Sameni M., Jedeszko C., Bhagat S., Cher M.L., Sloane B.F. Bone microenvironment modulates expression and activity of cathepsin B in prostate cancer. Neoplasia 2005, 7:207-223.
28. Sinha A.A., Quast B.J., Korkowski J.C., Wilson M.J., Reddy P.K., Ewing S.L., Sloane B.F., Gleason D.F. The relationship of cathepsin B and stefin A mRNA localization identifies a potentially aggressive variant of human prostate cancer within a Gleason histologic score. Anticancer Res. 1999, 19:2821-2829.
29. Cong H., Becker C.F., Elliott S.J., Grinstaff M.W., Porco J.A. Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones. J. Am. Chem. Soc. 2010, 132:7514-7518.
30. Chee C.F., Abdullah I., Buckle M.J.C., Rahman N.A. An efficient synthesis of (±)-panduratin A and (±)-isopanduratin A, inhibitors of dengue-2 viral activity. Tetrahedron Lett. 2010, 51:495-498.
31. Cong H., Ledbetter D., Rowe G.T., Caradonna J.P., Porco J.A. Electron transfer-initiated Diels-Alder cycloadditions of 2'-hydroxychalcones. J. Am. Chem. Soc. 2008, 130:9214-9215.
32. Qanungo S., Das M., Haldar S., Basu A. Epigallocatechin-3-gallate induces mitochondrial membrane depolarization and caspase-dependent apoptosis in pancreatic cancer cells. Carcinogenesis 2005, 26:958-967.
33. Benitez D.A., Pozo-Guisado E., Alvarez-Barrientos A., Fernandez-Salguero P.M., Castellon E.A. Mechanisms involved in resveratrol-induced apoptosis and cell cycle arrest in prostate cancer-derived cell lines. J. Androl. 2007, 28:282-293.
34. Tang Y.Q., Jaganath I.B., Sekaran S.D. Phyllanthus spp. induces selective growth inhibition of PC-3 MeWo human cancer cells through modulation of cell cycle and induction of apoptosis. PLoS One 2010, 5.
35. 2/M arrest by modulating expression of p21waf1/cip1, cdc25C and cyclin B in human prostate carcinoma PC-3 cells. Life Sci. 2007, 81:1323-1331.
36. Wan S.B., Chen D., Dou Q.P., Chan T.H. Study of the green tea polyphenols catechin-3-gallate (CG) and epicatechin-3-gallate (ECG) as proteasome inhibitors. Bioorg. Med. Chem. 2004, 12:3521-3527.
37. Smith D.M., Wang Z., Kazi A., Li L.H., Chan T.H., Dou Q.P. Synthetic analogs of green tea polyphenols as proteasome inhibitors. Mol. Med. 2002, 8:382-392.
38. Kwan J.C., Eksioglu E.A., Liu C., Paul V.J., Luesch H. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 2009, 52:5732-5747.
39. Murata R.M., Yatsuda R., dos Santos M.H., Kohn L.K., Martins F.T., Nagem T.J., Alencar S.M., de Carvalho J.E., Rosalen P.L. Antiproliferative effect of benzophenones and their influence on cathepsin activity. Phytother. Res. 2010, 24:379-383.