Chalcones in cancer: Understanding their role in terms of QSAR. II part

Mini-Reviews in Medicinal Chemistry

Volumn 13, Issue 7, 2013, Pages 952-970

  Repanas, A ^a   Katsori, A M ^a   Hadjipavlou Litina, D ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Anticancer activity; Chalcones; Cytoprotection; Lipophilicity; QSAR; Steric factors

Indexed keywords

BETA IONONE; CHALCONE; ETHCHLORVYNOL; TANGERETIN;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST CARCINOMA; COMPARATIVE STUDY; DRUG FORMULATION; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; IC 50; MATHEMATICAL PARAMETERS; NEOPLASM; NONHUMAN; PHYSICAL CHEMISTRY; PROSTATE CANCER; QUANTITATIVE STRUCTURE ACTIVITY RELATION; UTERINE CERVIX CARCINOMA; VALIDATION PROCESS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CHALCONES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84878667613     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/1389557511313070002     Document Type: Article

References (65)

1. V. Kostanecki, Tambor, J. Über die sechs isomeren Monooxybenzalacetophenone (Monooxychalkone). Ber. Dtsch. Chem. Ges., 1899, 32(2), 1921-1926.
2. Bohm, B.A. In The Flavonoids, 1st ed. Harborne, J.B., Mabry, T. J. Harborne, H., Ed.; Chapman and Hall: London, 1975, pp 442-504.
3. Patil, C.B.; Mahajan, S.K.; Katti, S.A. Chalcone: A Versatile Molecule. J. Pharm. Sci. & Res., 2010, 1(3), 11-22.
4. Go, M.L.; Wu, X.; Liu, X.L. Chalcones: an update on cytotoxic and chemoprotective properties. Curr. Med. Chem., 2005, 12(4), 481-499.
5. Katsori, A.M.; Hadjipavlou-Litina, D. Chalcones in cancer: understanding their role in terms of QSAR. Curr. Med. Chem., 2009,16(9), 1062-1081.
6. Ducki, S.; Forrest, R.; Hadfield, J.A.; Kendall, A.; Lawrence, N.J.; McGown, A.T.; Rennison, D. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg. Med. Chem. Lett., 1998, 8(9), 1051-1056.
7. Dimmock, J.; Elias, D.; Beazely, M.; Kandepu, N. Bioactivities of chalcones. Curr. Med. Chem., 1999, 6(12), 1125-1149.
8. Rahman, M. Chalcone: A Valuable Insight into the Recent Advances and Potential Pharmacological Activities. Chem. Sci. J., 2011, 29, 1-16.
9. Orlikova, B.; Tasdemir, D.; Golais, F.; Dicato, M.; Diederich, M. Dietary chalcones with chemopreventive and chemotherapeutic potential. Genes Nutr., 2011, 6(2), 125-147.
10. Katsori, A.M.; Hadjipavlou-Litina, D. Recent progress in therapeutic applications of chalcones. Expert Opin. Ther. Pat., 2011, 21(10), 1575-1596.
11. Liu, H.L.; Jiang, W.B.; Xie, M.X. Flavonoids: recent advances as anticancer drugs. Recent Pat. Anticancer Drug Discov., 2010, 5(2), 152-164.
12. Batovska, D.I.; Todorova, I.T. Trends in utilization of the pharmacological potential of chalcones. Curr. Clin. Pharmacol, 2010,5(1), 1-29.
13. Batovska, D.I.; Parushev, S.P. An Update on the Anticancer Effects of Chalcones. Int. J. Curr. Chem., 2010, 1(4), 217-236.
14. Ducki, S. Antimitotic Chalcones and Related Compounds as Inhibitors of Tubulin Assembly. Anticancer Agents Med. Chem., 2009,9(3), 336-347.
15. Boumendjel, A.; Ronot, X.; Boutonnat, J. Chalcones Derivatives Acting as Cell Cycle Blockers: Potential Anti Cancer Drugs? Curr. Drug Targets, 2009, 10(4), 363-371.
16. Mojzis, J.; Varinska, L.; Mojzisova, G.; Kostova, I.; Mirossay, L. Antiangiogenic effects of flavonoids and chalcones. Pharmacol. Res., 2008, 57(4), 259-265.
17. Kontogiorgis, C; Mantzanidou, M.; Hadjipavlou-Litina, D. Chalcones and their potential role in inflammation. Mini Rev. Med. Chem., 2008, 8(12), 1224-1242.
18. Zdzislawa, N. A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem., 2007, 42(2), 125-137.
19. Lawrence, N.J.; McGown, A.T. The chemistry and biology of antimitotic chalcones and related enone systems. Curr. Pharm. Des., 2005, 11(13), 1679-1693.
20. Ni, L.; Meng, C.Q.; Sikorski, J.A. Recent advances in therapeutic chalcones. Expert Opin. Ther. Pat., 2004, 14(12), 1669-1691.
21. Hanahan, D.; Weinberg, Robert A. Hallmarks of Cancer: The Next Generation. Cell, 2011, 144(5), 646-674.
22. Ben-Neriah, Y.; Karin, M. Inflammation meets cancer, with NF-[kappa]B as the matchmaker. Nat. Immunol, 2011, 12(8), 715-723.
23. Colotta, F.; Allavena, P.; Sica, A.; Garlanda, C; Mantovani, A. Cancer-related inflammation, the seventh hallmark of cancer: links to genetic instability. Carcinogenesis, 2009, 30(7), 1073-1081.
24. Jemal, A.; Bray, F.; Center, M.M.; Ferlay, J.; Ward, E.; Forman, D. Global cancer statistics. CA Cancer J. Clin., 2011, 61(2), 69-90.
25. Piazza, G.A.; Keeton, A.B.; Tinsley, H.N.; Whitt, J.D.; Gary, B.D.; Mathew, B.; Singh, R.; Grizzle, W.E.; Reynolds, R.C. NSAIDs: Old Drugs Reveal New Anticancer Targets. Pharmaceuticals, 2010, 3(5), 1652-1667.
26. Kashfi, K.; Enna, S.J.; Michael, W. Anti-Inflammatory Agents as Cancer Therapeutics. Adv. Pharmacol, 2009, 57, 31-89.
27. Puntoni, M.; Marra, D.; Zanardi, S.; Decensi, A. Inflammation and cancer prevention. Ann. Oncol, 2008, 19 Suppl 7, vii, 225-229.
28. Delmulle, L.; Bellahcène, A.; Dhooge, W.; Comhaire, F.; Roelens, F.; Huvaere, K.; Heyerick, A.; Castronovo, V.; De Keukeleire, D. Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine, 2006, 13(9-10), 732-734.
29. Zhang, X.; Yeung, E.D.; Wang, J.; Panzhinskiy, E.E.; Tong, C; Li, W.; Li, J. Isoliquiritigenin, a natural anti-oxidant, selectively inhibits the proliferation of prostate cancer cells. Clin. Exp. Pharmacol. Physiol, 2010, 37(8), 841-847.
30. Tu, H.-Y.; Huang, A.M.; Hour, T.-C; Yang, S.-C; Pu, Y.-S.; Lin, C.-N. Synthesis and biological evaluation of 2',5'-dimethoxy chalcone derivatives as microtubule-targeted anticancer agents. Bioorganic & Medicinal Chemistry, 2010, 18(6), 2089-2098.
31. Zhou, J.; Geng, G.; Batist, G.; Wu, J.H. Syntheses and potential anti-prostate cancer activities of ionone-based chalcones. Bio organic & Medicinal Chemistry Letters, 2009, 19(4), 1183-1186.
32. Sharma, A.; Chakravarti, B.; Gupt, M.P.; Siddiqui, J.A.; Konwar, R.; Tripathi, R.P. Synthesis and anti breast cancer activity of biphenyl based chalcones. Bioorganic & amp; Medicinal Chemistry, 2010, 18(13), 4711-4720.
33. Hayat, F.; Salahuddin, A.; Umar, S.; Azam, A. Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail. Eur. J. Med. Chem., 2010, 45(10), 4669-4675.
34. Rao, G.V.; Swamy, B.N.; Chandregowda, V.; Reddy, G.C. Synthesis of (±)Abyssinone I and related compounds: Their antioxidant and cytotoxic activities. Eur. J. Med. Chem., 2009, 44(5), 2239-2245.
35. Kim, T.-H.; Seo, W.D.; Ryu, H.W.; Seo, H.R.; Jin, Y.B.; Lee, M.; Ji, Y.-H.; Park, K.H.; Lee, Y.-S. Anti-tumor effects by a synthetic chalcone compound is mediated by c-Myc-mediated reactive oxygen species production. Chem. Biol. Interact, 2010, 188(1), 111-118.
36. Bhat, B.A.; Dhar, K.L.; Puri, S.C.; Saxena, A.K.; Shanmugavel, M.; Qazi, G.N. Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents. Bioorg. Med. Chem. Lett, 2005, 15(12), 3177-3180.
37. Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity. Bioorg. Med. Chem., 2008, 16(8), 4286-4293.
38. Reddy, M.V.R.; Pallela, V.R.; Cosenza, S.C.; Mallireddigari, M.R.; Patti, R.; Bonagura, M.; Truongcao, M.; Akula, B.; Jatiani, S.S.; Reddy, E.P. Design, synthesis and evaluation of (E)-a-benzylthio chalcones as novel inhibitors of BCR-ABL kinase. Bioorg. Med. Chem., 2010, 18(6), 2317-2326.
39. de Carvalho Tavares, L.; Johann, S.; Maria de Almeida Alves, T.; Guerra, J.C.; Maria de Souza-Fagundes, E.; Cisalpino, P.S.; Bortoluzzi, A.J.; Caramori, G.F.; de Mattos Piccoli, R.; Braibante, H.T.S.; Braibante, M.E.F.; Pizzolatti, M.G. Quinolinyl and quinolinyl N-oxide chalcones: Synthesis, antifungal and cytotoxic activities. Eur. J. Med. Chem., 2011, 46(9), 4448-4456.
40. Chaturvedi, M.M.; Sung, B.; Yadav, V.R.; Kannappan, R.; Aggarwal, B.B. NF-[kappa]B addiction and its role in cancer: 'one size does not fit all'. Oncogene, 2011, 30(14), 1615-1630.
41. Gupta, S.C.; Sundaram, C; Reuter, S.; Aggarwal, B.B. Inhibiting NF-[kappa]B activation by small molecules as a therapeutic strategy. Biochimica et Biophysica Acta (BBA) - Gene Regulatory Mechanisms, 2010, 1799(10-12), 775-787.
42. Yadav, V.R.; Prasad, S.; Sung, B.; Aggarwal, B.B. The role of chalcones in suppression of NF-KB-mediated inflammation and cancer. Int. Immunopharmacol, 2011, 11(3), 295-309.
43. Szliszka, E.; Czuba, Z.; Mazur, B.; Sedek, L.; Paradysz, A.; Krol, W. Chalcones Enhance TRAIL-Induced Apoptosis in Prostate Cancer Cells. Int. J. Mol. Sci., 2009, 11(1), 1-13.
44. Kim, N. Butein sensitizes human leukemia cells to apoptosis induced by tumor necrosis factor-related apoptosis inducing ligand (TRAIL). Arch. Pharm. Res., 2008, 31(9), 1179-1186.
45. Szliszka, E.; Czuba, Z.P.; Mazur, B.; Paradysz, A.; Krol, W. Chalcones and Dihydrochalcones Augment TRAIL-Mediated Apoptosis in Prostate Cancer Cells. Molecules, 2010, 15(8), 5336-5353.
46. Klein, T.; Bischoff, R. Physiology and pathophysiology of matrix metalloproteases. Amino Acids, 2011, 41(2), 271-290.
47. Rodrigues, J.; Abramjuk, C; Vásquez, L.; Gamboa, N.; Domínguez, J.; Nitzsche, B.; Höpfner, M.; Georgieva, R.; Bäumler, H.; Stephan, C; Jung, K.; Lein, M.; Rabien, A. New 4-Maleamic Acid and 4-Maleamide Peptidyl Chalcones as Potential Multitarget Drugs for Human Prostate Cancer. Pharm. Res., 2011, 28(4), 907-919.
48. Ngameni, B.; Touaibia, M.; Patnam, R.; Belkaid, A.; Sonna, P.; Ngadjui, B.T.; Annabi, B.; Roy, R. Inhibition of MMP-2 secretion from brain tumor cells suggests chemopreventive properties of a furanocoumarin glycoside and of chalcones isolated from the twigs of Dorstenia turbinata. Phytochemistry, 2006, 67(23), 2573-2579.
49. BioByte Corporation, C.-Q.d., 201 W Fourth str., Suite # 204, Claremont, CA 91711-4707, USA.
50. Hansch Corwin; Albert, L. Exploring QSAR: Fundamentals and Applications in Chemistry and Biology. American Chemical Society: Washington, D.C., 1995.
51. Hansch, C; Leo, A.; Hoekman, D. Exploring QSAR: Hydrophobic, electronic, and steric constants. American Chemical Society: Washington, DC, 1995.
52. Cramer, R.D.; Bunce, J.D.; Patterson, D.E.; Frank, I.E. Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies. Quantitative Structure-Activity Relationships, 1988, 7(1), 18-25.
53. Golbraikh, A.; Tropsha, A. Beware of q2! J. Mol. Graph. Model, 2002, 20(4), 269-276.
54. Ivanova, Y.; Momekov, G.; Petrov, O.; Karaivanova, M.; Kalcheva, V. Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones. Eur. J. Med. Chem., 2007, 42(11-12), 1382-1387.
55. Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Cruz-Lopez, O.; Cara, C.L.; Balzarini, J.; Hamel, E.; Canella, A.; Fabbri, E.; Gambari, R.; Basso, G.; Viola, G. Hybrid a-bromoacryloylamido chalcones. Design, synthesis and biological evaluation. Bioorg. Med. Chem. Lett, 2009, 19(7), 2022-2028.
56. Henmi, K.; Hiwatashi, Y.; Hikita, E.; Toyama, N.; Hirano, T. Methoxy- and fluoro-chalcone derivatives arrest cell cycle progression and induce apoptosis in human melanoma cell A375. Biol. Pharm. Bull, 2009, 32(6), 1109-1113.
57. Quintin, J.; Desrivot, J.; Thoret, S.; Menez, P.L.; Cresteil, T.; Lewin, G. Synthesis and biological evaluation of a series of tangeretin-derived chalcones. Bioorg. Med. Chem. Lett, 2009, 19(1), 167-169.
58. Bandgar, B.P.; Gawande, S.S. Synthesis and biological screening of a combinatorial library of p-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents. Bioorg. Med. Chem., 2010, 18(5), 2060-2065.
59. Tatman, D.; Mo, H. Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells. Cancer Lett, 2002, 175(2), 129-139.
60. Janakiram, N.B.; Cooma, I.; Mohammed, A.; Steele, V.E.; Rao, C.V. p-Ionone inhibits colonic aberrant crypt foci formation in rats, suppresses cell growth, and induces retinoid X receptor-a in human colon cancer cells. Mol. Cancer Ther., 2008, 7(1), 181-190.
61. Boumendjel, A.; Boccard, J.; Carrupt, P.-A.; Nicolle, E.; Blanc, M.; Geze, A.; Choisnard, L.; Wouessidjewe, D.; Matera, E.-L.; Dumontet, C. Antimitotic and Antiproliferative Activities of Chalcones: Forward Structure-Activity Relationship. J. Med. Chem., 2008, 51(7), 2307-2310.
62. Dimmock, J.R.; Kandepu, N.M.; Hetherington, M.; Quail, J.W.; Pugazhenthi, U.; Sudom, A.M.; Chamankhah, M.; Rose, P.; Pass, E.; Allen, T.M.; Halleran, S.; Szydlowski, J.; Mutus, B.; Tannous, M.; Manavathu, E.K.; Myers, T.G.; De Clercq, E.; Balzarini, J. Cytotoxic Activities of Mannich Bases of Chalcones and Related Compounds. J. Med. Chem., 1998, 41(7), 1014-1026.
63. Hsieh, H.K.; Tsao, L.T.; Wang, J.P.; Lin, C.N. Synthesis and antiinflammatory effect of chalcones. J. Pharm. Pharmacol, 2000, 52(2), 163-171.
64. Hansch, C; Kurup, A.; Garg, R.; Gao, H. Chem-Bioinformatics and QSAR: A Review of QSAR Lacking Positive Hydrophobic Terms. Chem. Rev., 2001, 101(3), 619-672.
65. Hansch, C; Klein, T.E. Molecular graphics and QSAR in the study of enzyme-ligand interactions. On the definition of bioreceptors. Acc. Chem. Res., 1986, 19(12), 392-400.