Potential cytotoxic and apoptosis inducing agents: Synthesis and evaluation of methoxy-substituted chalcones against human lung and cervical cancers

Medicinal Chemistry Research

Volumn 22, Issue 11, 2013, Pages 5408-5417

  Ethiraj, K R ^a   Aranjani, Jesil Mathew ^b   Nawaz Khan, F ^a  

^a VIT UNIVERSITY   (India)

^b MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

Apoptosis; Cytotoxicity; Flow cytometry; HeLa; Methoxy substituted chalcones; MTT assay

Indexed keywords

1 (2 FLUORO 4 METHOXYPHENYL) 3 (2,3,4 TRIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUORO 4 METHOXYPHENYL) 3 (2,4 DIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUORO 4 METHOXYPHENYL) 3 (2,4,5 TRIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUORO 4 METHOXYPHENYL) 3 (2,4,6 TRIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUORO 4 METHOXYPHENYL) 3 (3,4,5 TRIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUORO 4 METHOXYPHENYL) 3 (3,5 DIMETHOXYPHENYL)PROP 2 ENE 1 ONE; 1 (2 FLUOROPHENYL) 3 (2,4 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2 FLUOROPHENYL) 3 (2,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2 FLUOROPHENYL) 3 (2,4,6 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2 FLUOROPHENYL) 3 (2,5 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2 FLUOROPHENYL) 3 (3,4,5 TRIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 (2 FLUOROPHENYL) 3 (3,5 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; ACETOPHENONE DERIVATIVE; APOPTOSIS INDUCING FACTOR; BENZALDEHYDE DERIVATIVE; CHALCONE DERIVATIVE; CYTOTOXIC AGENT; DOXORUBICIN; FLUORINE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ADENOCARCINOMA; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE S PHASE; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; FLOW CYTOMETRY; HIGH RESOLUTION MOLECULAR SPECTROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; LUNG CANCER; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SUBSTITUTION REACTION; UTERINE CERVIX CANCER;

EID: 84887447473     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0520-9     Document Type: Article

References (34)

1. Aarnio M, Sankila R, Pukkala E, Salovaara R, Aaltonen LA, de la Chapelle A, Peltomäki P, Mecklin JP, Järvinen HJ (1999) Cancer risk in mutation carriers of DNA-mismatch-repair genes. Int J Cancer 81(2):214-218
2. Bandgar BP, Gawande SS (2010) Synthesis and biological screening of a combinatorial library of [beta]-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents. Bioorg Med Chem 18(5):2060-2065
3. Bandgar BP, Gawande SS, Bodade RG, Totre JV, Khobragade CN (2010) Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg Med Chem 18(3):1364-1370
4. Bhat BA, Dhar KL, Puri SC, Saxena AK, Shanmugavel M, Qazi GN (2005) Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents. Bioorg Med Chem Lett 15(12):3177-3180
5. Brown JM, Attardi LD (2005) The role of apoptosis in cancer development and treatment response. Nat Rev Cancer 5(3):231-237
6. Dhar DN, Barton S (1981) The chemistry of chalcones and related compounds. Wiley, New York
7. Farce A, Loge C, Gallet S, Lebegue N, Carato P, Chavatte P, Berthelot P, Lesieur D (2004) Docking study of ligands into the colchicine binding site of tubulin. J Enzyme Inhib Med Chem 19(6):541-547
8. Hathwar VR, Roopan SM, Subashini R, Khan FN, Guru Row TN (2010) Analysis of Cl Cl and CH Cl intermolecular interactions involving chlorine in substituted 2-chloroquinoline derivatives. J Chem Sci 122:677-685
9. Hsu YL, Kuo PL, Tzeng WS, Lin CC (2006) Chalcone inhibits the proliferation of human breast cancer cell by blocking cell cycle progression and inducing apoptosis. Food Chem Toxicol 44(5):704-713
10. Igney FH, Krammer PH (2002) Death and anti-death: tumour resistance to apoptosis. Nat Rev Cancer 2(4):277-288
11. Khan FN, Mohana Roopan S, Hathwar VR, Ng SW (2009a) 2-Chloro-3- hydroxymethyl-6-methoxyquinoline. Acta Crystallogr Sect E 66:o201
12. Khan FN, Mohana Roopan S, Hathwar VR, Ng SW (2009b) 2-Chloro-3- hydroxymethyl-7-dimethylquinoline. Acta Crystallogr Sect E 66:o200
13. Khan FN, Manivel P, Prabakaran K, Hathwar VR, Ng SW (2010) 5-Phenyl-3-(2-thienyl)-1, 2, 4-triazolo [3, 4-a] isoquinoline. Acta Crystallogr Sect E 66:o488
14. Kini SG, Bhat AR, Bryant B, Williamson JS, Dayan FE (2009) Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives. Eur J Med Chem 44(2):492-500
15. Lam KW, Uddin R, Liew CY, Tham CL, Israf DA, Syahida A, Rahman MBA, Ul-Haq Z, Lajis NH (2011) Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent. Med Chem Res 19:1-14
16. LeBlanc R, Dickson J, Brown T, Stewart M, Pati HN, VanDerveer D, Arman H, Harris J, Pennington W, Holt HL Jr (2005) Synthesis and cytotoxicity of epoxide and pyrazole analogs of the combretastatins. Bioorg Med Chem 13(21):6025-6034
17. Lou C, Wang M, Yang G, Cai H, Li Y, Zhao F, Yang H, Tong L, Cai B (2009) Preliminary studies on anti-tumor activity of 2′,4′- dihydroxychalcone isolated from herba oxytropis in human gastric cancer MGC-803 cells. Toxicol In Vitro 23(5):906-910
18. Mizuno CS, Paul S, Suh N, Rimando AM (2010) Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth. Bioorg Med Chem Lett 20(24):7385-7387
19. Mojzis J, Varinska L, Mojzisova G, Kostova I, Mirossay L (2008) Antiangiogenic effects of flavonoids and chalcones. Pharmacol Res 57(4):259-265
20. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65(1-2):55-63
21. Nawaz Khan F, Jayakumar R, Pillai CN (2003) Electrocatalytic oxidative cleavage by electrogenerated periodate. J Mol Catal A 195:139-145
22. Ormerod MG, Orr RM, Peacock JH (1994) The role of apoptosis in cell killing by cisplatin: a flow cytometric study. Br J Cancer 69(1):93
23. Patel JR, Dholakiya BZ (2012) Synthesis of 1-(4-((E)-3-arylacryloyl) phenyl)-3,4-dibromo-1H-pyrrole-2,5-diones and screening for anti-Candida and antituberculosis activity. Med Chem Res 21(8):1977-1983
24. Patil NT, Nawaz Khan F, Yamamoto Y (2004) Microwave-enhanced Pd(0)/acetic acid catalyzed allylation reactions of C, N, O pronucleophiles with alkynes. Tetrahedron Lett 45:8497-8499
25. Pilatova M, Varinska L, Perjesi P, Sarissky M, Mirossay L, Solar P, Ostro A, Mojzis J (2010) In vitro antiproliferative and antiangiogenic effects of synthetic chalcone analogues. Toxicol In Vitro 24(5):1347-1355
26. 2/Ruphos-catalyzed Sonogashira coupling of 1-chloroisoquinolines in the formation of 1-alkynyl-3-substituted isoquinolines. Tetrahedron Lett 52:2566-2570
27. Riccardi C, Nicoletti I (2006) Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat Protoc 1(3):1458-1461
28. Sasayama T, Tanaka K, Mizukawa K, Kawamura A, Kondoh T, Hosoda K, Kohmura E (2007) Trans-4-lodo,4-boranyl-chalcone induces antitumor activity against malignant glioma cell lines in vitro and in vivo. J Neurooncol 85(2):123-132
29. Subashini R, Mohana Roopan S, Nawaz Khan F (2010) Synthesis and free radical scavenging property of some quinoline derivatives. J Chil Chem Soc 55:317-319
30. Tajudeen SS, Khan FN (2007) Synthesis of some 3-substituted isochromen-1-ones. Synth Commun 37:3649-3656
31. Vanhoecke BW, Delporte F, Van Braeckel E, Heyerick A, Depypere HT, Nuytinck M, De Keukeleire D, Bracke ME (2005) A safety study of oral tangeretin and xanthohumol administration to laboratory mice. In Vivo 19(1):103
32. Vogel S, Barbic M, Jürgenliemk G, Heilmann J (2010) Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect. Eur J Med Chem 45(6):2206-2213
33. Ye C-L, Liu J-W, Wei D-Z, Lu Y-H, Qian F (2004) In vitro anti-tumor activity of 2′,4′-dihydroxy-6′-methoxy-3′,5′- dimethylchalcone against six established human cancer cell lines. Pharmacol Res 50(5):505-510
34. Ye CL, Liu JW, Wei DZ, Lu YH, Qian F (2005) In vivo antitumor activity by 2,4-dihydroxy-6-methoxy-3,5-dimethylchalcone in a solid human carcinoma xenograft model. Cancer Chemother Pharmacol 55(5):447-452