Biological evaluation of synthetic analogues of curcumin: Chloro-substituted-20-hydroxychalcones as potential inhibitors of tubulin polymerization and cell proliferation

Medicinal Chemistry Research

Volumn 20, Issue 4, 2011, Pages 503-510

  Aryapour, Hassan ^a   Riazi, Gholam Hossein ^a   Foroumadi, Alireza ^b   Ahmadian, Shahin ^a   Shafiee, Abbas ^b   Karima, Oveis ^a   Mahdavi, Majid ^a   Emami, Saeed ^c   Sorkhi, Maedeh ^b   Khodadady, Sirus ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Chalcone; Curcumin; K562; Microtubule; SK N MC

Indexed keywords

1 (5 CHLORO 2 HYDROXYPHENYL) 3 (3 CHLOROPHENYL)PROP 2 EN 1 ONE; CURCUMIN; TUBULIN MODULATOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CIRCULAR DICHROISM; DISSOCIATION CONSTANT; DRUG CYTOTOXICITY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

EID: 80052038529     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9344-z     Document Type: Article

References (29)

1. Aggarwal BB, Sundaram C, Malani N, Ichikawa H (2007) Curcumin: the Indian solid gold. Adv Exp Med Biol 595:1-75
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
3. Brown T, Holt H Jr, Lee M (2006) Synthesis of biologically active heterocyclic stilbene and chalcone analogs of combretastatin. Top Heterocycl Chem 2:1-51
4. Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ et al (1998) Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg Med Chem Lett 8:1051-1056 (Pubitemid 28216282)
5. Gupta K, Panda D (2002) Perturbation of microtubule polymerization by quercetin through tubulin binding: a novel mechanism of its antiproliferative activity. Biochemistry 41:13029-13038 (Pubitemid 35215787)
6. Gupta KK, Bharne SS, Rathinasamy K, Naik NR, Panda D (2006) Dietary antioxidant curcumin inhibits microtubule assembly through tubulin binding. FEBS J 273:5320-5332 (Pubitemid 44772390)
7. Gururaj AE, Belakavadi M, Venkatesh DA, Marme D, Salimath BP (2002) Molecular mechanisms of anti-angiogenic effect of curcumin. Biochem Biophys Res Commun 297:934-942 (Pubitemid 35230341)
8. Hoehle SI, Pfeiffer E, Solyom AM, Metzler M (2006) Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver. J Agric Food Chem 54:756-764 (Pubitemid 43274111)
9. Jiang JD, Davis AS, Middleton K, Ling YH, Perez-Soler R et al (1998) 3-(Iodoacetamido)-benzoylurea: a novel cancericidal tubulin ligand that inhibits microtubule polymerization, phosphorylates bcl-2, and induces apoptosis in tumor cells. Cancer Res 58:5389-5395 (Pubitemid 28551121)
10. Jordan MA, Wilson L (1998) Microtubules and actin filaments: dynamic targets for cancer chemotherapy. Curr Opin Cell Biol 10:123-130 (Pubitemid 28066130)
11. Jordan MA, Wilson L (2004) Microtubules as a target for anticancer drugs. Nat Rev Cancer 4:253-265 (Pubitemid 38525281)
12. Legraverend M, Tunnah P, Noble M, Ducrot P, Ludwig O et al (2000) Cyclin-dependent kinase inhibition by new C-2 alkynylated purine derivatives and molecular structure of a CDK2-inhibitor complex. J Med Chem 43:1282-1292 (Pubitemid 30212570)
13. Ma R, Song G, You W, Yu L, Su W et al (2008) Anti-microtubule activity of tubeimoside I and its colchicine binding site of tubulin. Cancer Chemother Pharmacol 62:559-568
14. Mayer TU, Kapoor TM, Haggarty SJ, King RW, Schreiber SL et al (1999) Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286:971-974
15. Murphy DB, Johnson KA, Borisy GG (1977) Role of tubulinassociated proteins in microtubule nucleation and elongation. J Mol Biol 117:33-52 (Pubitemid 8227743)
16. Panchatcharam M, Miriyala S, Gayathri VS, Suguna L (2006) Curcumin improves wound healing by modulating collagen and decreasing reactive oxygen species. Mol Cell Biochem 290:87-96 (Pubitemid 44473238)
17. Rai D, Singh JK, Roy N, Panda D (2008) Curcumin inhibits FtsZ assembly: an attractive mechanism for its antibacterial activity. Biochem J 410:147-155 (Pubitemid 351300334)
18. Robinson TP, Ehlers T, Hubbard IR, Bai X, Arbiser JL et al (2003) Design, synthesis, and biological evaluation of angiogenesis inhibitors: aromatic enone and dienone analogues of curcumin. Bioorg Med Chem Lett 13:115-117 (Pubitemid 35447696)
19. Rowinsky EK, Donehower RC (1991) The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics. Pharmacol Ther 52:35-84
20. Roy M, Chakraborty S, Siddiqi M, Bhattacharya RK (2002) Induction of apoptosis in tumor cells by natural phenolic compounds. Asian Pac J Cancer Prev 3:61-67
21. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R (1995) Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94:79-83
22. Scatchard G (1949) The attractions of proteins for small molecules ions. Ann N Y Acad Sci 51:660-672
23. Scudiero DA, Shoemaker RH, Paull KD, Monks A, Tierney S et al (1988) Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res 48:4827-4833
24. Sengupta S, Smitha SL, Thomas NE, Santhoshkumar TR, Devi SK et al (2005) 4-Amino-5-benzoyl-2-(4-methoxyphenylamino)thiazole (DAT1): a cytotoxic agent towards cancer cells and a probe for tubulin-microtubule system. Br J Pharmacol 145:1076-1083. (Pubitemid 43079980)
25. Med Chem Res (2011) 20:503-510 509
26. Tishler RB, Lamppu DM, Park S, Price BD (1995) Microtubuleactive drugs taxol, vinblastine, and nocodazole increase the levels of transcriptionally active p53. Cancer Res 55:6021-6025
27. Wang YJ, Pan MH, Cheng AL, Lin LI, Ho YS et al (1997) Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal 15:1867-1876
28. Yoshida D, Hoshino S, Shimura T, Takahashi H, Teramoto A (2000) Drug-induced apoptosis by anti-microtubule agent, estramustine phosphate on human malignant glioma cell line, U87MG; in vitro study. J Neurooncol 47:133-140 (Pubitemid 30665324)
29. Zhang J, Li GB, Jun MA (2003) Effects of chlorine content and position of chlorinated phenols on their oxidation kinetics by potassium permanganate. J Environ Sci (China) 15:342-345 (Pubitemid 36947274)