Multivariate SAR and QSAR of cucurbitacin derivatives as cytotoxic compounds in a human lung adenocarcinoma cell line

Journal of Molecular Graphics and Modelling

Volumn 48, Issue , 2014, Pages 70-79

  Lang, Karen L ^a   Silva, Izabella T ^b   Machado, Vanessa R ^b   Zimmermann, Lara A ^b   Caro, Miguel S B ^b   Simões, Cláudia M O ^b   Schenkel, Eloir P ^b   Durán, Fernando J ^c   Bernardes, Lílian S C ^b   De Melo, Eduardo B ^d  

^a FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^d UNIVERSIDADE ESTADUAL DO OESTE DO PARANÁ   (Brazil)

Author keywords

Cucurbitacins; Lung cancer; OPS; PLS; PLS DA; QSAR

Indexed keywords

CUCURBITACINS; LUNG CANCER; OPS; PLS; PLS-DA; QSAR;

CELL CULTURE; DISCRIMINANT ANALYSIS; LEAST SQUARES APPROXIMATIONS; RESPIRATORY SYSTEM;

CYTOTOXICITY;

CUCURBITACIN DERIVATIVE; CYTOTOXIC AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; DISCRIMINANT ANALYSIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LUNG ADENOCARCINOMA; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION;

CUCURBITACINS; LUNG CANCER; OPS; PLS; PLS-DA; QSAR;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CUCURBITACINS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MULTIVARIATE ANALYSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891502657     PISSN: 10933263     EISSN: 18734243     Source Type: Journal    
DOI: 10.1016/j.jmgm.2013.12.004     Document Type: Article

References (81)

1. A. Ganesan The impact of natural products upon modern drug discovery Curr. Opin. Chem. Biol. 12 2008 306 317
2. D.J. Newman, and G.M. Cragg Natural products as sources of new drugs over the 30 years from 1981 to 2010 J. Nat. Prod. 75 2012 311 335
3. K.L. Lang, I.T. Silva, L.A. Zimmermann, V.R. Machado, M.R. Teixeira, M.I. Lapuh, M.A. Galetti, J.A. Palermo, G.M. Cabrera, L.S.C. Bernardes, C.M.O. Simões, E.P. Schenkel, M.S.B. Caro, and F.J. Durán Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives Bioorg. Med. Chem. 20 2012 3016 3030
4. M. Miró Cucurbitacins and their pharmacological effects Phytother. Res. 9 1995 159 168
5. J.C. Chen, M.H. Chiu, R.L. Nie, G.A. Cordel, and S.X. Qiu Cucurbitacins and cucurbitane glycosides: structures and biological activities Nat. Prod. Rep. 22 2005 386 399 (Pubitemid 40885718)
6. J.L. Ríos, J.M. Escandell, M.C. Recio, and R. Atta Ur New insights into the bioactivity of cucurbitacins Stud. Nat. Prod. Chem. 32 2005 429 469
7. D.H. Lee, G.B. Iwanski, and N.H. Thoennissen Cucurbitac: ancient compound shedding new light on cancer treatment Sci. World J. 10 2010 413 418
8. K.L.K. Duncan, M.D. Duncan, M.C. Alley, and E.A. Sausville Cucurbitacin E-induced disruption of the actin and vimentin cytoskeleton in prostate carcinoma cells Biochem. Pharmacol. 52 1996 1553 1560 (Pubitemid 26375461)
9. J.M. Escandell, P. Kaler, M.C. Recio, T. Sasazuki, S. Shirasawa, L. Augenlicht, J.L. Ríos, and L. Klampfer Activated kRas protects colon cancer cells from cucurbitacin-induced apoptosis: the role of p53 and p21 Biochem. Pharmacol. 76 2008 198 207
10. N. Wakimoto, D. Yin, J. O'Kelly, T. Haritunians, B. Karlan, J. Said, H. Xing, and H.P. Koeffler Cucurbitacin B has a potent antiproliferative effect on breast cancer cells in vitro and in vivo Cancer Sci. 99 2008 1793 1797
11. X. Shi, B. Franko, C. Frantz, H.M. Amin, and R. Lai JSI-124 (cucurbitacin I) inhibits Janus kinase-3/signal transducer and activator of transcription-3 signalling, downregulates nucleophosmin-anaplastic lymphoma kinase (ALK), and induces apoptosis in ALK-positive anaplastic large cell lymphoma cells Br. J. Haematol. 135 2006 26 32 (Pubitemid 44337660)
12. T. Tannin-Spitz, S. Grossman, S. Dovrat, H.E. Gottlieb, and M. Bergman Growth inhibitory activity of cucurbitacin glucosides isolated from Citrullus colocynthis on human breast cancer cells Biochem. Pharmacol. 73 2007 56 67 (Pubitemid 44853933)
13. N.H. Thoennissen, G.B. Iwanski, N.B. Doan, R. Okamoto, P. Lin, S. Abbassi, J.H. Song, D. Yin, M. Toh, W.D. Xie, J.W. Said, and H.P. Koeffler Cucurbitacin B induces apoptosis by inhibition of the JAK/STAT pathway and potentiates antiproliferative effects of gemcitabine on pancreatic cancer cells Cancer Res. 69 2009 5876 5884
14. K.T. Chan, F.Y. Meng, Q. Li, C.Y. Ho, T.S. Lam, Y. To, W.H. Lee, M. Li, K.H. Chu, and M. Toh Cucurbitacin B induces apoptosis and S phase cell cycle arrest in BEL-7402 human hepatocellular carcinoma cells and is effective via oral administration Cancer Lett. 294 2010 118 124
15. L. Yang, S. Wu, Q. Zhang, F. Liu, and P. Wu 23,24-Dihydrocucurbitacin B induces G2/M cell-cycle arrest and mitochondria-dependent apoptosis in human breast cancer cells (Bcap37) Cancer Lett. 256 2007 267 278 (Pubitemid 47418353)
16. J. Sun, M.A. Blaskovich, R. Jove, S.K. Livingston, D. Coppola, and S.M. Sebti Cucurbitacin Q: a selective STAT3 activation inhibitor with potent antitumor activity Oncogene 27 2008 1344
17. M.A. Blaskovich, J. Sun, A. Cantor, J. Turkson, R. Jove, and S. Sebti Discovery of JSI-124 (Cucurbitacin I), a selective Janus kinase/signal transducer and activator of transcription 3 signaling pathway inhibitor with potent antitumor activity against human and murine cancer cells in mice Cancer Res. 63 2003 1270 1279 (Pubitemid 36348705)
18. B. Jayaprakasam, N.P. Seeram, and M.G. Nair Anticancer and antiinflammatory activities of cucurbitacins from Cucurbita andreana Cancer Lett. 189 2003 11 16 (Pubitemid 35351514)
19. M.D. Duncan, and K.L.K. Duncan Cucurbitacin E targets proliferating endothelia J. Surg. Res. 69 1997 55 60 (Pubitemid 27265827)
20. C. Nantasenamat, C. Isarankura-Na-Ayudhya, T. Naenna, and V. Prachayasittikul A practical overview of quantitative structure-activity relationship EXCLI J. 8 2009 74 88
21. F.A. Molfetta, A.T. Bruni, F.P. Rosseli, and A.B.F. Silva A partial least squares and principal component regression study of quinone compounds with trypanocidal activity Struct. Chem. 18 2007 49 57 (Pubitemid 46202924)
22. Y. Qin, H. Deng, H. Yan, and R. Zhong An accurate nonlinear QSAR model for the antitumor activities of chloroethylnitrosoureas using neural networks J. Mol. Graph. Model. 29 2011 826 833
23. A. Speck-Planche, V.V. Kleandrova, F. Luan, and M.N.D.S. Cordeiro Chemoinformatics in multi-target drug discovery for anti-cancer therapy: in silico design of potent and versatile anti-brain tumor agents Anticancer Agents Med. Chem. 12 2012 678 685
24. A. Speck-Planche, V.V. Kleandrova, F. Luan, and M.N.D.S. Cordeiro Chemoinformatics in anti-cancer chemotherapy: multi-target QSAR model for the in silico discovery of anti-breast cancer agents Eur. J. Pharm. Sci. 47 2012 273 279
25. U. Lahl, and U. Gundert-Remy The use of (Q)SAR methods in the context of REACH Toxicol. Mech. Meth. 18 2008 149 158 (Pubitemid 351414976)
26. G.V. Dang, B.M. Rode, and H. Stuppner Quantitative electronic structure-activity relationship (QESAR) of natural cytotoxic compounds: maytansinoids, quassinoids and cucurbitacins Eur. J. Pharm. Sci. 2 1994 331 350
27. J. Bartalis, and F.T. Halaweish In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines Bioorg. Med. Chem. 19 2011 2757 2766
28. K.L. Lang, T.R. Guimarães, V.R. Machado, L.A. Zimmermann, I.T. Silva, M.R. Teixeira, F.J. Durán, J.A. Palermo, C.M.O. Simões, M.S.B. Caro, and E.P. Schenkel New cytotoxic cucurbitacins from Wilbrandia ebracteata Cogn. Planta Med. 77 2011 1648 1651
29. V.R. Machado Semi-síntese de derivados glicosilados de dihidrocucurbitacina B, isolada de Wilbrandia ebracteata Cogn Dissertation 2012 Pharmacy School, Universidade Federal de Santa Catarina
30. M.R. Farias, E.P. Schenkel, R. Mayer, and G. Rucker Cucurbitacins as constituents of Wilbrandia ebracteata Planta Med. 59 1993 272 275 (Pubitemid 23168780)
31. 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)
32. M. Barker, and W. Rayens Partial least squares for determination J. Chemom. 17 2003 166 173
33. S. Wold, M. Sjöström, and L. Eriksson PLS-regression: a basic tool of chemometrics Chemom. Intell. Lab. Syst. 58 2001 109 130 (Pubitemid 33033283)
34. ChemOffice Ultra, version 8.0 2004 Cambridge Soft Corporation Cambridge, USA
35. Gaussian 09W, version 7.0 2009 Gaussian Inc. Wallingford, USA
36. N.M. O'Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, and G.R. Hutchison Open Babel: an open chemical toolbox J. Cheminform. 3 2011 33
37. Gauss View, version 5.0 2009 Gaussian Inc. Wallingford, USA
38. R. Todeschini, and V. Consonni Molecular Descriptors for Chemoinformatics 2nd ed. 2009 Wiley-VCH Weinheim
39. Dragon User Guide, version 6.0 2011 Talete srl. Italy
40. J.P.A. Martins, and M.M.C. Ferreira QSAR modeling: a new open source computational package to generate and validate QSAR models Quim. Nova 26 2013 554 560
41. M.P. González, C. Terán, L. Saíz-Urra, and M. Teijeira Variable selection methods in QSAR: an overview Curr. Top. Med. Chem. 8 2008 1606 1627
42. R.F. Teófilo, J.P. Martins, and M.M.C. Ferreira Sorting variables by using informative vectors as a strategy for feature selection in multivariate regression J. Chemom. 23 2009 32 48
43. P.P. Roy, J.T. Leonard, and K. Roy Exploring the impact of size of training sets for the development of predictive QSAR models Chemom. Intell. Lab. Syst. 90 2008 31 42 (Pubitemid 350213175)
44. P.P. Roy, and K. Roy On some aspects of variable selection for partial least squares regression models QSAR Comb. Sci. 27 2008 302 313
45. L.T.F.M. Camargo, M.M. Sena, and A.J. Camargo A quantum chemical and chemometrical study of indolo[2,1-b]quinazoline and their analogues with cytotoxic activity against breast cancer cells SAR QSAR Environ. Res. 20 2009 537 549
46. B. Dejaegher, L. Dhooghe, M. Goodarzi, S. Apers, L. Pieters, and Y.V. Heyden Classification models for neocryptolepine derivatives as inhibitors of the beta-haematin formation Anal. Chim. Acta 705 2011 98 110
47. S. Askjaer, and M. Langgård Combining pharmacophore fingerprints and PLS-discriminant analysis for virtual screening and SAR elucidation J. Chem. Inf. Model. 48 2008 476 488 (Pubitemid 351535417)
48. I. Mitra, A. Saha, and K. Roy Chemometric QSAR modeling and in silico design of antioxidant NO donor phenols Sci. Pharm. 79 2011 31 57
49. A.C. Gaudio, and E. Zandonade Proposition, validation and analysis of QSAR models Quim. Nova 24 2001 658 671 (Pubitemid 33680135)
50. R. Kiralj, and M.M.C. Ferreira Basic validation procedures for regression models in QSAR and QSPR studies: theory and application J. Braz. Chem. Soc. 20 2009 770 787
51. L. Eriksson, J. Jaworska, A.P. Worth, M.T.D. Cronin, R.M. McDowell, and P. Gramatica Methods for reliability and uncertainty assessment and for applicability evaluations of classification and regression-based QSARs Environ. Health Perspect. 111 2003 1361 1375 (Pubitemid 37021142)
52. A. Golbraikh, M. Shen, Z. Xiao, Y. Xiao, K. Lee, and A. Tropsha Rational selection of training and test set for the development of validated QSAR models QSAR Comb. Chem. 17 2003 241 253 (Pubitemid 37062785)
53. P.K. Ojha, I. Mitra, R.N. Das, and K. Roy Further exploring rm2 metrics for validation of QSPR models Chemom. Intell. Lab. Syst. 107 2011 194 205
54. Pirouette, version 4 2007 Informetrix Inc. USA
55. P. Gramatica Principles of QSAR models validation: internal and external QSAR Comb. Chem. 26 2007 694 701 (Pubitemid 46932857)
56. S. Wold, L. Eriksson, and S. Clementi Statistical validation of QSAR results H. van de Waterbeemd, Chemometric Methods in Molecular Design 1998 Wiley-VCH Weinheim 309 318
57. V. Consonni, D. Ballabio, and R. Todeschini Evaluation of model predictive ability by external validation techniques J. Chemom. 24 2010 194 201
58. F. Luan, A. Melo, F. Borges, and M.N.L.D.S. Cordeiro Affinity prediction on A3 adenosine receptor antagonists: the chemometric approach Bioorg. Med. Chem. 19 2011 6853 6859
59. M.B.C. Leão, A.C. Pavão, V.A.A. Espinoza, C.A. Taft, and E.P. Bulnes A multivariate model of chemical carcinogenesis J. Mol. Struct. Theochem. 719 2005 129 135 (Pubitemid 40444674)
60. A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, and O. Igglessi-Markopoulou A novel QSAR model for predicting induction of apoptosis by 4-aryl-4H-chromenes Bioorg. Med. Chem. 14 2006 6686 6694 (Pubitemid 44233302)
61. A. Takano, K.E.N. Hashimoto, M. Ogawa, J. Koyanagi, T. Kurihara, H. Wakabayashi, H. Kikuchi, Y. Nakamura, N. Motohashi, H. Sakagami, K. Yamamoto, and A. Tanaka Tumor-specific cytotoxicity and type of cell death induced by naphtho[2,3-b]furan-4,9-diones and related compounds in human tumor cell lines: relationship to electronic structure Anticancer Res. 29 2009 455 464
62. C. Hansch, B. Bonavida, A. Jazirehi, J.J. Cohen, C. Milliron, and A. Kurup Quantitative structure-activity relationships of phenolic compounds causing apoptosis Bioorg. Med. Chem. 11 2003 617 620 (Pubitemid 36132239)
63. C. Hansch, A. Jazirehi, S.B. Mekapati, R. Garga, and B. Bonavida QSAR of apoptosis induction in various cancer cells Bioorg. Med. Chem. 11 2003 3015 3019 (Pubitemid 36683018)
64. A.O. de Souza, M.T.C. Pedrosa, J.B. Alderete, A.F. Cruz, M.A.F. Prado, R.B. Alves, and C.L. Silva Cytotoxicity, antitumoral and antimycobacterial activity of tetrazole and oxadiazole derivatives Pharmazie 60 2005 396 397 (Pubitemid 40684469)
65. F.F.P. Arantes, L.C.A. Barbosa, C.R.A. Maltha, A.J. Demunera, P.H. Fidêncio, and J.W.M. Carneiro A quantum chemical and chemometric study of sesquiterpene lactones with cytotoxicity against tumor cells J. Chemom. 25 2011 401 407
66. J.F. Bromberg, M.H. Wrzeszczynska, G. Devgan, Y. Zhao, R.G. Pestell, C. Albanese, and J.E. Darnell Jr. STAT3 as an oncogene Cell 98 1999 295 303 (Pubitemid 29380565)
67. I.R. Silva, M.R. Teixeira, K.L. Lang, T.R. Guimarães, S.E. Dudek, F.J. Durán, S. Ludwig, M.S.B. Caro, E.P. Schenkel, and C.M.O. Simões Proliferative inhibition and apoptotic mechanism on human non-small-cell lung cancer (A549 cells) of a novel cucurbitacin from Wilbrandia ebracteata Cogn. Int. J. Cancer Res. 9 2013 54 68
68. R.M.V. Abreu, C.F.R. Ferreira, and M.J.R.P. Queiroz QSAR model for predicting radical scavenging activity of di(hetero)arylamines derivatives of benzo[b]thiophenes Eur. J. Med. Chem. 44 2009 1952 1958
69. P. Gramatica, E. Papa, A. Marrocchi, L. Minuti, and A. Taticchi Quantitative structure-activity relationship modeling of polycyclic aromatic hydrocarbon mutagenicity by classification methods based on holistic theoretical molecular descriptors Ecotoxicol. Environ. Saf. 66 2007 353 361 (Pubitemid 46204888)
70. R.A. Gupta, A.K. Gupta, L.K. Soni, and S.G. Kaskhedikar Study of physicochemical properties-antitubercular activity relationship of naphthalene-1,4-dione analogs: a QSAR approach Chem. Pap. 63 2009 723
71. M. Nakhjiri, M. Safavi, E. Alipour, S. Emami, A.F. Atash, M. Jafari-Zavareh, S.K. Ardestani, M. Khoshneviszadeh, A. Foroumadi, and A. Shafiee Asymmetrical 2,6-bis(benzylidene)cyclohexanones: synthesis, cytotoxic activity and QSAR study Eur. J. Med. Chem. 50 2012 113 123
72. X. Liu, J. Chen, H. Yu, J. Zhao, J.P. Giesy, and X. Wang Quantitative structure activity relationship (QSAR) for toxicity of chlorophenols on L929 cells in vitro Chemosphere 64 2006 1619 1626 (Pubitemid 44067172)
73. W. Zhou, Z. Dai, Y. Chen, and Z. Yuan Computational QSAR models with high-dimensional descriptor selection improve antitumor activity design of ARC-111 analogues Med. Chem. Res. 22 2013 278 286
74. B. Bhhatarai, and P. Gramatica Oral LD50 toxicity modeling and prediction of per- and polyfluorinated chemicals on rat and mouse Mol. Divers. 15 2011 467 476
75. A.M. Helguera, M. Natália, D.S. Cordeiro, M.A.C. Pérez, R.D. Combes, and M.P. González QSAR modeling of the rodent carcinogenicity of nitrocompounds Bioorg. Med. Chem. 16 2008 3395 3407 (Pubitemid 351444819)
76. B.F. Rasulev, N.D. Abdullaev, V.N. Syrov, and J. Leszczynski A Qqantitative structure-activity relationship (QSAR) study of the antioxidant activity of flavonoids QSAR Comb. Sci. 24 2005 1056 1065 (Pubitemid 41736471)
77. G. Ramírez-Galicia, H. Martínez-Pacheco, R. Garduño-Juárez, and O. Deeb Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO Med. Chem. Res. 21 2012 2501 2516
78. A.P. Hartmann, D.H. Jornada, and E.B. Melo A new fully validated and interpreted quantitative structure-activity relationship model of p-aminosalicylic acid derivatives as neuraminidase inhibitors Chem. Pap. 67 2013 556 567
79. E.B. Melo, and M.M.C. Ferreira A 4D structure-activity relationship model to predict HIV-1 integrase strand transfer inhibition using the LQTA-QSAR methodology J. Chem. Inf. Mod. 52 2012 1722 1732
80. S. Wold PLS for multivariate linear modeling H. van de Waterbeemd, Chemometric Methods in Molecular Design 1998 Wiley-VCH Weinheim 195 218
81. L.B. Kier, and L.H. Hall The electrotopological state: structure modeling for QSAR and database analysis J. Devillers, A.T. Balaban, Topological Indices and Related Descriptors in QSAR and QSPR 1999 Gordon and Breach United Kingdom 491 562