Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields

European Journal of Medicinal Chemistry

Volumn 46, Issue 8, 2011, Pages 3265-3273

  Drakulić, Branko J ^a   Stanojković, Tatjana P ^b   Žižak, Željko S ^b   Dabović, Milan M ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b INSTITUTE FOR ONCOLOGY AND RADIOLOGY OF SERBIA   (Serbia)

Author keywords

4 aryl 4 oxo 2 butenoic acids; Antiproliferative activity; Human tumors; Molecular interaction fields

Indexed keywords

ACRYLIC ACID DERIVATIVE; ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; AROYLACRYLIC ACID DERIVATIVE; NSC 143; NSC 145150; NSC 25331; NSC 30659; NSC 31589; NSC 321477; NSC 32875; NSC 329366; NSC 39971; NSC 672120; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL CYCLE S PHASE; CELL GROWTH; CELL PROLIFERATION; CELL STRAIN K 562; CONTROLLED STUDY; COVALENT BOND; DRUG POTENCY; HELA CELL; HUMAN; HUMAN CELL; IC 50; MOLECULAR INTERACTION; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ACRYLATES; CELL CYCLE; CELL LINE, TUMOR; CELL SURVIVAL; COLONIC NEOPLASMS; CROTONIC ACIDS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE; MODELS, MOLECULAR; PHENOLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; THERMODYNAMICS; UTERINE CERVICAL NEOPLASMS;

EID: 79958247946     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.04.043     Document Type: Article

References (58)

1. H. von Peschman Ueber Condensationsprodukte zweibasischer Fettsäuren Ber. Dtsch. Chem. Ges 15 1882 881 892
2. H. Rinderknecht, J.L. Ward, F. Bergel, and A.L. Morrison Studies on antibiotics. II. Bacteriological activity and possible mode of action of certain nonnitrogenous natural and synthetic antibiotics Biochem. J. 41 1947 463 469
3. B.J. Cramer, W. Schroeder, W.J. Moran, C.H. Nield, M. Edwards, C.I. Jarowski, and B. Puetzer The antibacterial activity of some β-aroyl-acrylic acids, esters, and amides J. Am. Pharm. Assoc. Sci. 37 1948 439 449
4. F.K. Kirchner, J.H. Bailey, and C.J. Cavallito Ring substituted benzoylacrylic acids as antibacterial agents J. Amer. Chem. Soc. 71 1949 1210 1213
5. N.H. Cromwell, P.L. Creger, and K.E. Cook Studies with the amine adducts of β-benzoylacrylic acid and its methyl ester J. Amer. Chem. Soc. 78 1956 4412 4416
6. A. Dal Pozzo, M. Acquasaliante, G. Donezzeli, P. De Maria, and C. Nicoli 3-Carbonylacrylic derivatives as potential antimicrobial agents. Correlations between activity and reactivity toward cysteine J. Med. Chem. 30 1987 1674 1677 (Pubitemid 17135917)
7. K. Bowden, M.S. Dixon, and J.R. Runson Structure-activity relations. Part 4. Reactivity and anti-bacterial activity of 3-aroylacrylic acids and their methyl esters J. Chem. Res. Synopses 1979 8
8. K. Bowden, A. Dal Pozzo, and C.K. Duah Structure-activity relations. Part 5. Antibacterial activity of a series of substituted (E)-3-(4-phenylbenzoyl) acrylic acids, -chalcones, -2-hydroxychalcones and -α-bromochalcones; addition of cysteine to substituted 3-benzoylacrylic acids and related compounds J. Chem. Res. Synopses 1990 2801 2830
9. K. Bowden, and M.P. Henry Structure-activity relations. II. Antibacterial activity of 3-benzoylacrylic acids and esters, ACS Advances in Chemistry Series Biol. Correl.-Hansch Approach, Symp. 114 1972 130 140
10. B.M. Anderson, M.L. Tanhcoo, and A. Dal Pozzo Selective enzyme inactivation by benzoylacrylic acid derivatives Biochem. Biophys. Acta 703 1982 204 211
11. B.M. Anderson, C.D. Anderson, G. Donzzeli, and A. Dal Pozzo Sulfhydryl enzyme inactivation by nicotinoylacrylates Biochem. Biophys. Acta 787 1984 215 220
12. O. Dvorak, J. Venta, and M. Semonsky Report on treatment of advanced carcinoma of genitals with the preparation mbba Neoplasma 12 1965 93 100
13. O. Dvorak Cytembena treatment of advanced gynaecological carcinomas Neoplasma 18 1971 461 464
14. O. Dvorak, and J. Bauer Cytembena treatment of advances and relapsing uterine cervix carcinoma Neoplasma 18 1971 465 466
15. Z. Matejovsky Effects of Cytembena in the treatment of malignant musculoskeletal tumours Neoplasma 18 1971 473 480
16. Z. Juranić, Lj. Stevović, B. Drakulić, T. Stanojković, S. Radulović, and I. Juranić Substituted (E)-β-(benzoyl)acrylic acids suppressed survival of neoplastic human HeLa cells J. Serb. Chem. Soc. 64 1999 505 512
17. S. Amslinger The tunable functionality of α,β-unsaturated carbonyl compounds enables their differential application in biological systems ChemMedChem 5 2010 351 356
18. D.L. Buckley, T.W. Corson, N. Aberle, and C.M. Crews Hiv Protease-mediated activation of sterically capped proteasome inhibitors and substrates J. Am. Chem. Soc. 133 2011 698 700
19. S.K. Rabindran, C.M. Discafani, E.C. Rosfjord, M. Baxter, M.B. Floyd, J. Golas, W.A. Hallett, B.D. Johnson, R. Nilakantan, E. Overbeek, M.F. Reich, R. Shen, X. Shi, H.-R. Tsou, Y.-F. Wang, and A. Wissner Antitumor Activity of HKI-272, an orally active, irreversible inhibitor of the HER-2 tyrosine kinase Cancer Res. 64 2004 3958 3965 (Pubitemid 38697310)
20. L.V. Sequist, B. Besse, T.J. Lynch, V.A. Miller, K.K. Wong, B. Gitlitz, K. Eaton, C. Zacharchuk, A. Freyman, C. Powell, R. Ananthakrishnan, S. Quinn, and J.-C. Soria Neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor: results of a phase II trial in patients with advanced non-small-cell lung cancer J. Clin. Oncol. 28 2010 3076 3083
21. A. Wissner, E. Overbeek, M.F. Reich, M.B. Floyd, B.D. Johnson, N. Mamuya, E.C. Rosfjord, C. Discafani, R. Davis, X. Shi, S.K. Rabindran, B.C. Gruber, F. Ye, W.A. Hallett, R. Nilakantan, R. Shen, Y.-F. Wang, L.M. Greenberger, and H.-R. Tsou Synthesis and structure-activity relationships of 6,7-disubstituted 4-anilinoquinoline-3-carbonitriles. The design of an orally active, irreversible inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor-2 (HER-2) J. Med. Chem. 46 2003 49 63 (Pubitemid 36043786)
22. D.G. Covell, A. Wallqvist, R. Huang, N. Thanki, and A.A. Rabow X-Jun Lu, Analysis of gene expression, small-molecule screening and structural databases Proteins 59 2005 403 433
23. R.H. Shoemaker The NCI60 human tumour cell line anticancer drug screen Nat. Rev. Cancer 6 2006 813 823 (Pubitemid 44450469)
24. A.-M. Katsori, and D. Hadjipavlou-Litina Chalcones in cancer: understanding their role in terms of QSAR Curr. Med. Chem. 16 2009 1062 1081
25. J.R. Dimmock, G.A. Zello, E.O. Oloo, J.W. Quail, H.-B. Kraatz, P. Perjesi, F. Aradi, K. Takacs-Novak, T.M. Allen, C.L. Santos, J. Balzarini, E. De Clercq, and J.P. Stables Correlations between cytotoxicity and topography of some 2-arylidenebenzocycloalkanones determined by X-ray crystallography J. Med. Chem. 45 2002 3103 3111 (Pubitemid 34721532)
26. st Conference of the Serbian Chemical Society, Book of Abstracts, p. 191, Belgrade 2003.
27. S.B. Novaković, G.A. Bogdanović, B.J. Drakulić, A. Spasojević-de Biré, I.O. Juranić, Electronic and topological properties of the non-covalent interactions in derivative of benzoylacrylic acid, Second Humboldt Conference on Noncovalent Interactions, Book of abstracts, p. 45, Vršac, Serbia, 2009. Full article in preparation.
28. N. Sugiyama, H. Kataoka, C. Kashima, and K. Yamada The photoreaction of β-benoylacrylic acid Bull. Chem. Soc. Jpn. 42 1969 1353 1356
29. B.J. Drakulić, Synthesis, Epoxidation and Photoisomerization of Ar-aroylacrylic Acids, Graduate thesis, Faculty of Chemistry, University of Belgrade, February 1996, Belgrade.
30. H.N. Patia, U. Dasa, R.K. Sharmab, and J.R. Dimmock Cytotoxic thiol alkylators Mini-Rev. Med. Chem. 7 2007 131 139 (Pubitemid 46592176)
31. F. Fontaine, M. Pastor, and F. Sanz Incorporating molecular shape into the alignment-free GRid-INdependent descriptors J. Med. Chem. 47 2004 2805 2815 (Pubitemid 38656733)
32. M. Pastor, G. Cruciani, I. McLay, S. Pickett, and S. Clementi GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors J. Med.Chem. 43 2000 3233 3243
33. A. Durán, G. Comesaña, and M. Pastor Development and validation of AMANDA, a new algorithm for selecting highly relevant regions in molecular interaction fields J. Chem. Inf. Mod. 48 2008 1813 1823
34. Pentacle v. 1.0.5, Molecular Discovery Ltd, http://www.moldiscovery.com (accessed on 03.04.11).
35. P. Gaillard, P.A. Carrupt, B. Testa, and A. Boudon Molecular lipophilicity potential, a tool in 3D QSAR: method and applications J. Comput. Aid. Mol. Des 8 1994 83 96
36. B.J. Drakulić, Z.D. Juranić, T.P. Stanojković, and I.O. Juranić 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids selectively suppressed proliferation of neoplastic human HeLa cells. A SAR/QSAR study J. Med. Chem. 48 2005 5600 5603 (Pubitemid 41209257)
37. M.D. Vitorović-Todorović, I.O. Juranić, L.M. Mandić, and B.J. Drakulić 4-Aryl-4-oxo-N-phenyl-2- aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields Bioorg. Med. Chem. 18 2010 1181 1193
38. B.J. Drakulić, unpublised results;
39. B.J. Drakulić, M.D. Vitorović-Todorović, I.N. Cvijetić, unpublised results.
40. A.T. Dinkova-Kostova, M.A. Massiah, R.E. Bozak, R.J. Hicks, and P. Talalay Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups Proc. Natl. Acad. Sci. USA 98 2001 3404 3409 (Pubitemid 32220858)
41. A. Duran, I. Zamora, and M. Pastor Suitability of GRIND-Based principal properties for the description of molecular similarity and ligand-based virtual screening J. Chem. Inf. Model. 49 2009 2129 2138
42. W.J. Houlihan, J. Nadelson, for Sandoz Inc. patent, US 4083997, 1978.
43. D. Papa, E. Schwenk, F. Villani, and E. Klingsberg β-Aroylacrylic acids J. Am. Chem. Soc. 70 1948 3356 3360
44. Haung-Minlon A simple modification of the Wolff-Kishner reduction J. Am. Chem. Soc. 68 1946 2487 2488
45. N.J. Kim, K.H. Chung, and E.K. Ryu Friedel-Crafts cyclohexylation of arenes with 1,3-dicyclohexylcarbodiimide (DCC) Tetrahedron Lett. 35 1994 903 904 (Pubitemid 24073920)
46. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
47. M. Ohno, and T. Abe Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6) J. Immunol. Methods 145 1991 199 203
48. M. Carbonari, T. Tedesco, and M. Fiorilli A unified procedure for conservative (morphology) and integral (DNA and immunophenotype) cell staining for flow cytometry Cytometry 44 2001 120 125
49. J. Boström Reproducing the conformations of protein-bound ligands: a critical evaluation of several popular conformational searching tools J. Comput. Aid. Mol. Des. 15 2001 1137 1152 (Pubitemid 34778180)
50. T.A. Halgren Merck molecular force field. I. Basis, Form, Scope, Parameterization, performance MMFF94 J. Comput. Chem. 17 1996 490 519 (Pubitemid 126567067)
51. J.J.P. Stewart Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements J. Mol. Mod. 13 2007 1173 1213 (Pubitemid 47629446)
52. A. Klamt, and G. Schüümann COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient J. Chem. Soc. Perkin Trans. 2 1993 799 805
53. A. Pedretti, L. Villa, and G. Vistoli VEGA - An open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming J. Comput. Aid. Mol. Des 18 2004 167 173 http://www.ddl.unimi.it VegaZZ 2.4.0 (accessed on 03.04.11) (Pubitemid 39069412)
54. P.J. Goodford A computational procedure for determining energetically favorable binding sites on biologically important macromolecules J. Med. Chem. 28 1985 849 857 http://www.moldiscovery.com GRID v.22b Molecular Discovery Ltd. (assessed on 03.04.11) (Pubitemid 15012490)
55. G. Cruciani Molecular Interaction Fields. Applications in Drug Discovery and ADME Prediction 2006 Wiley-VCH Zurich, Switzerland
56. G. Caron, A. Nurisso, and G. Ermondi How to extend the use of grid-based interaction energy maps from chemistry to biotopics ChemMedChem 4 2009 29 36 www.casmedchem.unito.it (assessed on 03.04.11)
57. Jmol v11.2.10, an open-source Java viewer for chemical structures in 3D. http://www.jmol.org/ (assessed on 03.04.11).
58. H. Kubinyi Non-linear dependence of biological activity on hydrophobic character: the bilinear model J. Med. Chem. 20 1977 625 629 http://www.kubinyi. de/bilin-program.html (assessed on 03.04.11)