Published October 12, 2018 | Version v1

In vitro cytotoxicity and structure-activity relationship approaches of entkaurenoic acid derivatives against human breast carcinoma cell line

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da Costa, Ricardo M., Bastos, Jairo K., Costa, Maria C.A., Ferreira, Márcia M.C., Mizuno, Cássia S., Caramori, Giovanni F., Nagurniak, Gláucio R., Simão, Marília R., dos Santos, Raquel A., Veneziani, Rodrigo C.S., Ambrósio, Sérgio R., Parreira, Renato L.T. (2018): In vitro cytotoxicity and structure-activity relationship approaches of entkaurenoic acid derivatives against human breast carcinoma cell line. Phytochemistry 156: 214-223, DOI: 10.1016/j.phytochem.2018.10.005, URL: http://dx.doi.org/10.1016/j.phytochem.2018.10.005

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urn:lsid:plazi.org:pub:FFD0FFBAF97F8325A804FFCD5E462D43

References

  • Batista, R., Garcia, P.A., Castro, M.A., del Corral, J.M.M., Speziali, N.L., Varotti, F.D., de Paula, R.C., Garcia-Fernandez, L.F., Francesch, A., Feliciano, A.S., de Oliveira, A.B., 2013. Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives. Eur. J. Med. Chem. 62, 168-176.
  • Batista, R., Humberto, J.L., Chiari, E., de Oliveira, A.B., 2007. Synthesis and trypanocidal activity of ent- kaurane glycosides. Bioorg. Med. Chem. 15, 381-391. Baumann, K., Stiefl, N., 2004. Validation tools for variable subset regression. J. Comput. Aided Mol. Des. 18, 549-562
  • Becke, A.D., 1993. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
  • Braga, R.S., Barone, P.M.V.B., Galvao, D.S., 2000. Identifying carcinogenic activity of methylated and non-methylated polycyclic aromatic hydrocarbons (PAHs) through electronic and topological indices. Braz. J. Phys. 30, 560-568.
  • Carman, R.M., 1964. Agathis microstachya oleoresin. Aust. J. Chem. 17, 393-394.
  • Clark, R.D., Fox, P.C., 2004. Statistical variation in progressive scrambling. J. Comput. Aided Mol. Des. 18, 563-576.
  • Costa-Lotufo, L.V., Cunha, G.M.A., Farias, P.A.M., Viana, G.S.B., Cunha, K.M.A., Pessoa, C., Moraes, M.O., Silveira, E.R., Gramosa, N.V., Rao, V.S.N., 2002. The cytotoxic and embryotoxic effects of kaurenoic acid, a diterpene isolated from Copaifera langsdorffii oleo-resin. Toxicon 40, 1231-1234.
  • Danishuddin, Khan, A.U., 2016. Descriptors and their selection methods in QSAR analysis: paradigm for drug design. Drug Discov. Today 21, 1291-1302.
  • De Andrade, B.B., Moreira, M.R., Ambrosio, S.R., Furtado, N.A.J.C., Cunha, W.R., Martins, C.H.G., Veneziani, R.C.S., 2011. Evaluation of ent -kaurenoic acid derivatives for their anticariogenic activity. Nat. Prod. Commun. 6, 777-780.
  • Do Nascimento, A.M., De Oliveira, D.C.R., 2001. Kaurene diterpenes and other chemical constituents from Mikania stipulacea (M. Vahl) willd. J. Braz. Chem. Soc. 12, 552-555.
  • dos Santos, G.F., da Silva Lima, G., Pereira de Oliveira, G., de Souza Filho, J.D., da Silva Amaral, L., Rodrigues-Filho, E., Takahashi, J.A., 2018. New AChE inhibitors from microbial transformation of trachyloban-19-oic acid by Syncephalastrum racemosum. Bioorg. Chem. 79, 60-63.
  • Duarte, N., Jardanhazy, A., Molnar, J., Hilgeroth, A., Ferreira, M.J.U., 2008. Synergistic interaction between p-glycoprotein modulators and epirubicine on resistant cancer cells. Bioorg. Med. Chem. 16, 9323-9330.
  • Eriksson, L., Jaworska, J., Worth, A.P., Cronin, M.T.D., McDowell, R.M., Gramatica, P., 2003. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ. Health Perspect. 111, 1361-1375.
  • Ferreira, M.M.C., 2015. Quimiometria: Conceitos, Metodos e Aplicacoes. Editora UNICAMP, Campinas, pp. 496.
  • Foye, W.O., Lemke, T.L., Williams, D.A., 1995. Principles of Medicinal Chemistry. Williams & Wilkins, Philadelphia, pp. 1489.
  • Fraga, B.M., Bressa, C., Gonzalez-Vallejo, V., Gonzalez, P., Guillermo, R., 2012. Biotransforrnation of ent-kaur-16-ene and ent-trachylobane 7 beta-acetoxy derivatives by the fungus Gibberella fujikuroi (Fusarium fujikuroi). Phytochemistry 81, 60-70.
  • Fraga, B.M., Bressa, C., Gonzalez-Vallejo, V., Suarez, S., Guillermo, R., 2011. Neighbouring group participation in the reaction of 7-oxo-ent-kaur-16-ene derivatives with diacetoxyiodobenzene. Synthesis of gibberellin analogues. Tetrahedron Lett. 52, 7138-7140.
  • Golbraikh, A., Tropsha, A., 2002. Beware of q(2)!. J. Mol. Graph. Model. 20, 269-276.
  • Hadda, T.B., Karagoz Genc, Z., Masand, V.H., Nebbache, N., Warad, I., Jodeh, S., Genc, M., Mabkhot, Y.N., Barakat, A., Zamora, H.S., 2015. Computational POM and DFT evaluation of experimental in-vitro cancer inhibition of staurosporine-ruthenium(II) complexes: the power force of organometallics in drug design. Acta Chim. Slov. 62, 679-688.
  • Hansch, C., Sammes, P.G., Taylor, J.B., 1990. Comprehensive Medicinal Chemistry: the Rational Design, Mechanistic Study & Therapeutic Applications of Chemical Compounds. Pergamon Press, Oxford, pp. 6000.
  • Hilgeroth, A., Molnar, A., Molnar, J., Voigt, B., 2006. Correlation of calculated molecular orbital energies of some phenothiazine compounds with MDR reversal properties. Eur. J. Med. Chem. 41, 548-551.
  • Hueso-Falcon, I., Giron, N., Velasco, P., Amaro-Luis, J.M., Ravelo, A.G., de las Heras, B., Hortelano, S., Estevez-Braun, A., 2010. Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives. Bioorg. Med. Chem. 18, 1724-1735.
  • Jackson, M., Karwowski, J.P., Humphrey, P.E., Kohl, W.L., Barlow, G.J., Tanaka, S.K., 1993. Calbistrins, novel antifungal agents produced by penicillium-restrictum .1. Production, taxonomy of the producing organism and biological-activity. J. Antibiot. 46, 34-38.
  • Kiralj, R., Ferreira, M.M.C., 2009. Basic validation procedures for regression models in QSAR and QSPR studies: theory and application. J. Braz. Chem. Soc. 20, 770-787.
  • Kiralj, R., Ferreira, M.M.C., 2010. Is your QSAR/QSPR descriptor real or trash? J. Chemometr. 24, 681-693.
  • Krishnan, R., Binkley, J.S., Seeger, R., Pople, J.A., 1980. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys. 72, 650-654.
  • Kubinyi, H., 1979. Progress in Drug Research. Birkhauer Verlag, Basel, pp. 101.
  • Kubinyi, H., 2008. QSAR: Hansch Analysis and Related Approaches. VCH Verlagsgesellschaft mbH, New York, pp. 240.
  • Lizarte Neto, F.S., Tirapelli, D.P.C., Ambrosio, S.R., Tirapelli, C.R., Oliveira, F.M., Novais, P.C., Peria, F.M., Oliveira, H.F., Carlotti Junior, C.G., Tirapelli, L.F., 2013. Kaurene diterpene induces apoptosis in U87 human malignant glioblastoma cells by suppression of anti-apoptotic signals and activation of cysteine proteases. Braz. J. Med. Biol. Res. 46, 71-78.
  • Marquina, S., Parra, J.L., Gonzalez, M., Zamilpa, A., Escalante, J., Trejo-Hernandez, M.R., Alvarez, L., 2009. Hydroxylation of the diterpenes ent- kaur-16-en-19-oic and entbeyer-15-en-19-oic acids by the fungus Aspergillus niger. Phytochemistry 70, 2017-2022.
  • Martinez, J.C.G., Andrada, M.F., Vega-Hissi, E.G., Garibotto, F.M., Nogueras, M., Rodriguez, R., Cobo, J., Enriz, R.D., Estrada, M.R., 2017. Dihydrofolate reductase inhibitors: a quantitative structure-activity relationship study using 2D-QSAR and 3D-QSAR methods. Med. Chem. Res. 26, 247-261.
  • Martins, J.P.A., Ferreira, M.C.M., 2013. QSAR modeling: um novo pacote computacional open source para gerar e validar modelos QSAR. Quim. Nova 36.
  • Misra, S.K., Ghoshal, G., Gartia, M.R., Wu, Z., De, A.K., Ye, M., Bromfield, C.R., Williams, E.M., Singh, K., Tangella, K.V., Rund, L., Schulten, K., Schook, L.B., Ray, P.S., Burdette, E.C., Pan, D., 2015. Trimodal therapy: combining hyperthermia with repurposed bexarotene and ultrasound for treating liver cancer. ACS Nano 9, 10695-10718.
  • Mizokami, S.S., Arakawa, N.S., Ambrosio, S.R., Zarpelon, A.C., Casagrande, R., Cunha, T.M., Ferreira, S.H., Cunha, F.Q., Verri, W.A., 2012. Kaurenoic acid from Sphagneticola trilobata inhibits inflammatory pain: effect on cytokine production and activation of the NO-Cyclic GMP-Protein kinase G-ATP-Sensitive potassium channel signaling pathway. J. Nat. Prod. 75, 896-904.
  • Moreira, M.R., Souza, A.B., Soares, S., Bianchi, T.C., de Souza Eugenio, D., Lemes, D.C., Martins, C.H., da Silva Moraes, T., Tavares, D.C., Ferreira, N.H., Ambrosio, S.R., Veneziani, R.C., 2016. ent -Kaurenoic acid-rich extract from Mikania glomerata: in vitro activity against bacteria responsible for dental caries. Fitoterapia 112, 211-216.
  • Newman, D.J., Cragg, G.M., 2016. Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod. 79, 629-661.
  • OECD, O.F.E.C.-O.A.D., 2007. Guidance document on validation of (quantitative structure-activity relationship [QSAR] models. In: OECD. vol. 69 OECD, Paris.
  • Parshikov, I.A., Sutherland, J.B., 2014. The use of Aspergillus niger cultures for biotransformation of terpenoids. Process Biochem. 49, 2086-2100.
  • Porto, T.S., Simao, M.R., Carlos, L.Z., Martins, C.H.G., Furtado, N.A.J.C., Said, S., Arakawa, N.S., dos Santos, R.A., Veneziani, R.C.S., Ambrosio, S.R., 2013. Pimaranetype diterpenes obtained by biotransformation: antimicrobial properties against clinically isolated gram-positive multidrug-resistant bacteria. Phytother Res. 27, 1502-1507.
  • Pratim, R.P., Kunal, R., 2008. On some aspects of variable selection for partial least squares regression models. QSAR Comb. Sci. 27, 302-313.
  • Roy, P.P., Leonard, J.T., Roy, K., 2008. Exploring the impact of size of training sets for the development of predictive QSAR models. Chemometr. Intell. Lab. Syst. 90, 31-42.
  • Rucker, C., Rucker, G., Meringer, M., 2007. y-Randomization and its variants in QSPR/ QSAR. J. Chem. Inf. Model. 47, 2345-2357.
  • Rudolf, J.D., Dong, L.B., Manoogian, K., Shen, B., 2016. Biosynthetic origin of the ether ring in platensimycin. J. Am. Chem. Soc. 138, 16711-16721.
  • Severiano, M.E., Simao, M.R., Ramos, H.P., Parreira, R.L., Arakawa, N.S., Said, S., Furtado, N.A., de Oliveira, D.C., Gregorio, L.E., Tirapelli, C.R., Veneziani, R.C., Ambrosio, S.R., 2013. Biotransformation of ent-pimaradienoic acid by cell cultures of