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Research Article

Brine shrimp lethality assay ‘an effective prescreen’: Microwave-assisted synthesis, BSL toxicity and 3DQSAR studies-based designing, docking and antitumor evaluation of potent chalcones

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Pages 1091-1103 | Received 18 Oct 2012, Accepted 16 Feb 2013, Published online: 07 Jun 2013

References

  • Aryapour H, Riazi GH, Ahmadian S, et al. (2012). Induction of apoptosis through tubulin inhibition in human cancer cells by new chromene based chalcones. Pharm Biol 50:1551–60
  • Ahsanullah Ansari FL, Nazir S, et al. (2007). Combinatorial synthesis and antitumour studies on an aryl and heteroaryl chalcone library using positional scanning method. Chem Biodiv 4:203–14
  • Aldaz H, Rice LM, Stearns T, Agard DA. (2005). Insights into microtubule nucleation from the crystal structure of human gamma-tubulin. Nature 435:523–7
  • Anderson JE, Goetz CM, McLaughlin JL, Suffness M. (1991). A blind comparison of simple bench-top bioassays and human tumour cell cytotoxicities as antitumor prescreens. Phytochem Anal 2:107–11
  • Ansari FL, Nazir S, Naureen H, Mirza B. (2005). Combinatorial synthesis and antibacterial studies on an indexed chalcone library. Chem Biodivers 2:1656–64
  • Ansari FL, Baseer M, Iftikhar F, et al. (2009). Microwave assisted synthesis, antibacterial activity against Bordetellabronchiseptica of a library of 3′-hydroxyaryl and heteroaryl chalcones and molecular descriptors-based SAR. ARKIVOC X:318–32
  • Atta-ur-Rahman Choudhary MI, Thomsen WJ. (2001). Bioassay Techniques for Drug Development. Amsterdam, The Netherlands: Harwood Academic Publishers
  • Basili S, Bergen A, DallAcqua F, et al. (2007). Relationship between the structure and the DNA binding properties of diazoniapolycyclic duplex- and triplex-DNA binders: Efficiency, selectivity, and binding mode. Biochem US 46:12721–36
  • Boeck P, Falcào CAB, Leal PC, et al. (2006). Synthesis of chalcone analogues with increased antileishmanial activity. Bioorg Med Chem 14:1538–45
  • Bowen JP, Robinson TP, Ehlers T, et al. (2005). Synthesis and biological evaluation of aromatic enones related to curcumin. US Patent 6,906,105
  • Cai SX, Reddy PS, Drewe JA, et al. (2007). Multifluoro-substituted chalcones and analogs as activators of caspases and inducers of apoptosis and the use thereof. US Patent 72,56,219
  • Clark M, Cramer RD III, Jones DM, et al. (1990). Comparative molecular field analysis (CoMFA). 2. Toward its use with 3D structural databases. Tetrahedron Comput Meth 3:47–59
  • Clark M. Crammer RD III, Opdenbosh V. (1989). Validation of the general purpose Tripos 5.2 force field. J Comput Chem 10:982–1012
  • Damazio RG, Zanatta AP, Cazarolli LH, et al. (2010). Antihyperglycemic activity of naphthylchalcones. Eur J Med Chem 45:1332–7
  • Deng J, Sanchez T, Al-Mawsawi LQ, et al. (2007). Synthesis and biological activities of aryl-ether-, biaryl-, and fluorene-aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT-2. Bioorg Med Chem 15:4985–8
  • Dobbs K, Hehre WJ. (1987). Molecular orbital theory of the properties of inorganic and organometallic compounds. Comput Chem 8:880–93
  • Dominguez JN, Leon C, Rodrigues J, et al. (2005a). Synthesis and evaluation of new antimalarial phenylurenyl chalcone derivatives. Med Chem 48:3654–8
  • Dominguez JN, León C, Rodrigues J, et al. (2005b). Synthesis and antimalarial activity of sulfonamide chalcone derivatives: II. Farmaco 60:307–21
  • Ducki S. (2009). Antimitotic chalcones and related compounds as inhibitors of tubulin assembly. Anticancer Agents Med Chem 9:336–47
  • Dyrager C, Wickstrom M, Friden SM, et al. (2011). Inhibitors and promoters of tubulin polymerization: Synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents. Bioorg Med Chem 19:2659–65
  • Furusawa J, Funakoshi TM, Mashino T, et al. (2009). Chalcones from Myracrodruonurundeuva are efficacious in guinea pig ovalbumin-induced allergic conjunctivitis. Int J Immunopharmacol 9:499–507
  • Gasteiger J, Marsili M. (1980). Iterative partial equalization of orbital electronegativity – A rapid access to atomic charges. Tetrahedron 36:3219–28
  • Geyer JA, Keenan SM, Woodard CL, et al. (2009). Selective inhibition of Pfmrk, a Plasmodium falciparum CDK, by antimalarial 1,3-diaryl-2-propenones. Bioorg Med Chem Lett 19:1982–5
  • Gacche RN, Dhole NA, Kamble SG, Bandgar BP. (2008). In vitro evaluation of selected chalcones for antioxidant activity. J Enzyme Inhib Med Chem 23:28–31
  • Ghosh A, Mandal S, Banerji A, et al. (2009). A new chalcone from Pongamiapinnata and its antioxidant properties. Nat Prod Commun 4:209–10
  • Huang YT, Huang DM, Guh JH, et al. (2005). CIL-102 interacts with microtubule polymerization and causes mitotic arrest following apoptosis in the human prostate cancer PC-3 cell line. J Biol Chem 280:2771–9
  • Jordan MA, Wilson L. (1998). Microtubules and actin filaments: Dynamic targets for cancer chemotherapy. Curr Option Cell Biol 10:123–30
  • Kayser O, Kiderlen AF. (2001). In vitro leishmanicidal activity of naturally occurring chalcones. Phytother Res 15:148–52
  • Keepers YP, Pizao PE, Peters GJ, et al. (1991). Comparison of the sulforhodamine B protein and tetrazolium (MTT) assays for in vitro chemosensitivity testing. Eur J Cancer 27:897–900
  • Kiat TS, Pippen R, Yusof R, et al. (2006). Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease. Bioorg Med Chem Lett 16:3337–40
  • Kong Y, Wang K, Edler MC, et al. (2010). A boronic acid chalcone analog of combretastatin A-4 as a potent antiproliferation agent. Bioorg Med Chem 18:971–7
  • Kim MY, Park BY, Kim KM, et al. (2003). Pharmaceutical composition containing chalcone or its derivatives for matrix metalloproteinase. Patent WO/2003/037315
  • Lee JC, Timasheff SN. (1977). Tubulin polymerization assay using >99% pure tubulin, OD based – Porcine (BK006P) N. Biochemistry 16:1754–62
  • Lin YM, Zhou Y, Flavin MT, et al. (2002). Chalcones and flavonoids as anti-tuberculosis agents. Bioorg Med Chem 10:2795–802
  • Liu X, Go ML. (2006). Antiproliferative properties of piperidinylchalcones. Bioorg Med Chem 14:153–63
  • Liu M, Wilairat P, Croft SL, et al. (2003). Structure--activity relationships of antileishmanial and antimalarial chalcones. Bioorg Med Chem 11:2729–38
  • Manilal A, Sujith S, Kiran S, et al. (2009). Cytotoxic potentials of red alga, Laurencia brandenii collected from the Indian coast. Global J Pharmacol 3:90–4
  • Mozziconacci J, Sandblad L, Wachsmuth M, et al. (2008). Tubulin dimers oligomerize before their incorporation into microtubules. PLoS ONE 3:e3821 . doi:10.1371/journal.pone.0003821
  • Na Y, Cha J, Yoon H, Kwon Y. (2009). A concise synthesis of licochalcone E and its regio-isomer, licochalcone. Chem Pharm Bull 57:607–9
  • Sivakumar PM, Priya S, Doble M. (2009). Synthesis, biological evaluation, mechanism of action and quantitative structure–activity relationship studies of chalcones as antibacterial agents. Chem Biol Drug Dis 73:403–15
  • Sivakumar PM, Seenivasan SP, Kumar V, Doble M. (2007). Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives. Bioorg Med Chem Lett 17:1695–700
  • SYBYL. (2004). Ligand-Based Design Manual, version 7.0. TriposInc, St. Louis (MO): SYBYL, Tripos Inc
  • Tuma, AMC, Malikzay A, Ouyang X, et al. (2010). Antitumor activity of IMC-038525, a novel oral tubulin polymerization inhibitor. Translational Oncol 3:318–25
  • Won SJ, Liu CT, Tsao LT, et al. (2005). Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents. Eur J Med Chem 40:103–12
  • Yang HM, Shin HR, Cho SH, et al. (2007). Structural requirement of chalcones for the inhibitory activity of interleukin-5. Bioorg Med Chem 15:104–11
  • Zhou J, Geng G, Batist G, Wu J H. (2009). Synthesis and potential anti-prostate cancer activities of ionone-based chalcones. Bioorg Med Chem Lett 19:1183–96

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