Allyl Dibenzoylmethane Derivative: Antimelanoma Activity and Study of Its Molecular Mechanism of Interaction with DNA
In this study, we assessed the cytotoxic effect of 1,3-diphenyl-2-allyl-1,3-propanedione (DPAP) on B16F10 and Tm5 melanoma cells and investigated its interaction with DNA (deoxyribonucleic acid) using optical tweezers. The compound showed to be effective against B16F10 cells with selectivity index (...
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Published in | Journal of the Brazilian Chemical Society Vol. 32; no. 7; pp. 1491 - 1497 |
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Main Authors | , , , , , , , |
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Language | English |
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Sociedade Brasileira de Química
01.07.2021
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Abstract | In this study, we assessed the cytotoxic effect of 1,3-diphenyl-2-allyl-1,3-propanedione (DPAP) on B16F10 and Tm5 melanoma cells and investigated its interaction with DNA (deoxyribonucleic acid) using optical tweezers. The compound showed to be effective against B16F10 cells with selectivity index (SI) of 7.92 and interaction to the outer surface of the double helix, probably at the minor groove of DNA. This likely induced a bending deformation of the polymer chain, decreasing persistence length, and indicated that each DPAP molecule occupies a single base pair upon binding to the double helix. |
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AbstractList | In this study, we assessed the cytotoxic effect of 1,3-diphenyl-2-allyl-1,3-propanedione (DPAP) on B16F10 and Tm5 melanoma cells and investigated its interaction with DNA (deoxyribonucleic acid) using optical tweezers. The compound showed to be effective against B16F10 cells with selectivity index (SI) of 7.92 and interaction to the outer surface of the double helix, probably at the minor groove of DNA. This likely induced a bending deformation of the polymer chain, decreasing persistence length, and indicated that each DPAP molecule occupies a single base pair upon binding to the double helix. |
Author | Oliveira, Rayane Diaz, Marisa Santos, Anésia Rocha, Márcio Oliveira, Leandro Diaz-Muñoz, Gaspar Andrade, Ulisses Baeta, Jefferson |
AuthorAffiliation | Universidade Federal de Viçosa Centro Federal de Educação Tecnológica de Minas Gerais Universidade Federal de Minas Gerais |
AuthorAffiliation_xml | – sequence: 0 name: Centro Federal de Educação Tecnológica de Minas Gerais – sequence: 0 name: Universidade Federal de Viçosa – sequence: 0 name: Universidade Federal de Minas Gerais |
Author_xml | – sequence: 1 givenname: Jefferson surname: Baeta fullname: Baeta, Jefferson – sequence: 2 givenname: Ulisses surname: Andrade fullname: Andrade, Ulisses – sequence: 3 givenname: Rayane surname: Oliveira fullname: Oliveira, Rayane – sequence: 4 givenname: Leandro surname: Oliveira fullname: Oliveira, Leandro – sequence: 5 givenname: Anésia surname: Santos fullname: Santos, Anésia – sequence: 6 givenname: Gaspar surname: Diaz-Muñoz fullname: Diaz-Muñoz, Gaspar – sequence: 7 givenname: Márcio surname: Rocha fullname: Rocha, Márcio – sequence: 8 givenname: Marisa orcidid: 0000-0002-3370-4149 surname: Diaz fullname: Diaz, Marisa |
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Keywords | Tm5 cells optical tweezers DPAP DNA B16F10 cells dacarbazine |
Language | English |
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References | Shain, A. H.; Bastian, B. C. 2016; 16 Magalhães, A. F.; Tozzi, A. M. A.; Magalhães, E. G.; Blanco, I. S.; Nogueira, M. A. 1997; 46 Sischka, A.; Toensing, K.; Eckel, R.; Wilking, S. D.; Sewald, N.; Ros, R.; Anselmetti, D. 2005; 88 Jones, H. P.; Maragò, O. M.; Volpe, G. 2015 McGhee, J. D.; Von Hippel, P. H. 1974; 88 Oliveira, L.; Rocha, M. S. 2017; 96 Chaurasiya, K. R.; Paramanathan, T.; McCauley, M. J.; Williams, M. C. 2010; 7 Rocha, M. S. 2015; 7 Mort, R. L.; Jackson, I. J.; Patton, E. E. 2015; 142 Fukai, T.; Nishizawa, J.; Nomura, T. 1994; 35 Moura, T. A.; Oliveira, L.; Rocha, M. S. 2019; 130 Alves, P. S.; Mesquita, O. N.; Rocha, M. S. 2020; 124 Marko, J. F.; Siggia, E. D. 1995; 28 Siegel, R. L.; Miller, K. D.; Jemal, A. 2018; 68 Nogueira, M. A.; Magalhães, E. G.; Magalhães, A. F.; Biloti, D. N.; Laverde, A.; Pessine, F. B.; Marsaioli, A. J. 2003; 58 2007 Carvalho, C. A.; da Cunha, M. E.; Guigliani, R.; Bakos, L.; Ashton-Prolla, P. 2004; 79 Alexander, M. M.; Eggermont, A. S.; Robert, C. 2014; 383 2013 Silva, E. F.; Bazoni, R. F.; Ramos, E. B.; Rocha, M. S. 2016; 107 Nascimento, F. R.; Moura, T. A.; Baeta, J. V. P. B.; Publio, B. C.; Ferreira, P. M. F.; Santos, A. A.; França, A. A. P.; Rocha, M. S.; Diaz-Muñoz, G.; Diaz, M. A. N. 2018; 239 Oba-Shinjo, S. M.; Correa, M.; Ricca, T. I.; Molognoni, F.; Pinhal, M. A.; Neves, I. A.; Marie, S. K. N.; Sampaio, L. O.; Nader, H. B.; Chammas, R.; Jasiulonis, M. G. 2006; 8 |
References_xml | – volume: 107 year: 2016 publication-title: Biopolymers contributor: fullname: Silva, E. F.; Bazoni, R. F.; Ramos, E. B.; Rocha, M. S. – volume: 16 start-page: 345 year: 2016 end-page: 345 publication-title: Nat. Rev. Cancer contributor: fullname: Shain, A. H.; Bastian, B. C. – volume: 79 start-page: 53 year: 2004 end-page: 53 publication-title: An. Bras. Dermatol. contributor: fullname: Carvalho, C. A.; da Cunha, M. E.; Guigliani, R.; Bakos, L.; Ashton-Prolla, P. – volume: 58 start-page: 1163 year: 2003 end-page: 1163 publication-title: Il Farmaco contributor: fullname: Nogueira, M. A.; Magalhães, E. G.; Magalhães, A. F.; Biloti, D. N.; Laverde, A.; Pessine, F. B.; Marsaioli, A. J. – volume: 142 start-page: 620 year: 2015 end-page: 620 publication-title: Development contributor: fullname: Mort, R. L.; Jackson, I. J.; Patton, E. E. – volume: 35 start-page: 515 year: 1994 end-page: 515 publication-title: Phytochem. contributor: fullname: Fukai, T.; Nishizawa, J.; Nomura, T. – volume: 96 start-page: 032408 year: 2017 end-page: 032408 publication-title: Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. contributor: fullname: Oliveira, L.; Rocha, M. S. – year: 2015 publication-title: Optical Tweezers: Principles and Applications contributor: fullname: Jones, H. P.; Maragò, O. M.; Volpe, G. – volume: 28 start-page: 8759 year: 1995 end-page: 8759 publication-title: Macromolecules contributor: fullname: Marko, J. F.; Siggia, E. D. – volume: 7 start-page: 299 year: 2010 end-page: 299 publication-title: Phys. Life Rev. contributor: fullname: Chaurasiya, K. R.; Paramanathan, T.; McCauley, M. J.; Williams, M. C. – volume: 88 start-page: 469 year: 1974 end-page: 469 publication-title: J. Mol. Biol. contributor: fullname: McGhee, J. D.; Von Hippel, P. H. – volume: 383 start-page: 816 year: 2014 end-page: 816 publication-title: Lancet contributor: fullname: Alexander, M. M.; Eggermont, A. S.; Robert, C. – year: 2007 publication-title: GraphPad Prism 5.0 – volume: 7 start-page: 967 year: 2015 end-page: 967 publication-title: Integr. Biol. contributor: fullname: Rocha, M. S. – volume: 88 start-page: 404 year: 2005 end-page: 404 publication-title: Biophys. J. contributor: fullname: Sischka, A.; Toensing, K.; Eckel, R.; Wilking, S. D.; Sewald, N.; Ros, R.; Anselmetti, D. – volume: 239 start-page: 1 year: 2018 end-page: 1 publication-title: Biophys. Chem. contributor: fullname: Nascimento, F. R.; Moura, T. A.; Baeta, J. V. P. B.; Publio, B. C.; Ferreira, P. M. F.; Santos, A. A.; França, A. A. P.; Rocha, M. S.; Diaz-Muñoz, G.; Diaz, M. A. N. – volume: 130 start-page: 1018 year: 2019 end-page: 1018 publication-title: Int. J. Biol. Macromol. contributor: fullname: Moura, T. A.; Oliveira, L.; Rocha, M. S. – volume: 124 start-page: 1020 year: 2020 end-page: 1020 publication-title: J. Phys. Chem. B contributor: fullname: Alves, P. S.; Mesquita, O. N.; Rocha, M. S. – volume: 46 start-page: 1029 year: 1997 end-page: 1029 publication-title: Phytochemistry contributor: fullname: Magalhães, A. F.; Tozzi, A. M. A.; Magalhães, E. G.; Blanco, I. S.; Nogueira, M. A. – volume: 8 start-page: 231 year: 2006 end-page: 231 publication-title: Neoplasia contributor: fullname: Oba-Shinjo, S. M.; Correa, M.; Ricca, T. I.; Molognoni, F.; Pinhal, M. A.; Neves, I. A.; Marie, S. K. N.; Sampaio, L. O.; Nader, H. B.; Chammas, R.; Jasiulonis, M. G. – year: 2013 publication-title: Microsoft Office Excel 2013 – volume: 68 start-page: 7 year: 2018 end-page: 7 publication-title: Cancer J. Clin. contributor: fullname: Siegel, R. L.; Miller, K. D.; Jemal, A. |
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Title | Allyl Dibenzoylmethane Derivative: Antimelanoma Activity and Study of Its Molecular Mechanism of Interaction with DNA |
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