Structural, biological and computational study of oxamide derivative Scientific paper

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Ignjat P. Filipović
https://orcid.org/0000-0003-1307-6242
Emina M. Mrkalić
https://orcid.org/0000-0002-9708-2326
Giorgio Pelosi
https://orcid.org/0000-0002-7946-0602
Vesna Kojić
https://orcid.org/0000-0002-2399-0807
Dimitar Jakimov
https://orcid.org/0000-0002-1747-4718
Dejan Baskić
https://orcid.org/0000-0002-6152-0742
Zoran D. Matović
https://orcid.org/0000-0002-5937-4424

Abstract

A dicarboxylato-diamide-type compound 2,2'-[(1,2-dioxoethane-1,2-diyl)diimino]dibenzoic acid (H4obbz) (1) was synthesized and characterized. The crystal structure of K2H2obbz·2H2O (2) was determined by X-ray diffract­tion analysis. The cytotoxic activities of the compounds were tested against four different cancer cell lines MCF-7, A549, HT-29, HeLa and a human nor­mal cell line MRC-5. The results indicate reasonable dose-dependent cytotox­icity of the ligands that show selectivity against the tested carcinoma and healthy cell lines. Flow cytometric analysis and fluorescence microscopy showed that the most active compound, H4obbz, induced apoptosis and G0/G1 cell cycle arrest, indicating blockage of DNA synthesis as a possible mech­anism that trig­gers apoptosis. Docking and molecular dynamics simulations gave similar res­ponses regarding interactions (binding) between their ligands and chaperon Grp78. The MMGBSA determined ΔG binding energies were in the range from –104 to –140 kJ mol-1.

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How to Cite
[1]
I. P. Filipović, “Structural, biological and computational study of oxamide derivative: Scientific paper”, J. Serb. Chem. Soc., vol. 87, no. 5, pp. 545–559, Feb. 2022.
Section
Organic Chemistry

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References

Z. D. Matović, E. Mrkalić, G. Bogdanović, V. Kojić, A. Meetsma, R. Jelić, J. Inorg. Biochem. 121 (2013) 134 (https://doi.org/10.1016/j.jinorgbio.2013.01.006)

E. M. Mrkalić, R. M. Jelić, O. R. Klisurić, Z. D. Matović, J. Chem. Soc. Dalt. Trans. 43 (2014) 15126 (https://doi.org/10.1039/c3dt53384k)

S. Kumar, Cell Death Differ. 14 (2007) 32 (https://doi.org/10.1038/sj.cdd.4402060)

C. M. Palermo, C. A. Bennett, A. C. Winters, C. S. Hemenway, Leuk. Res. 32 (2008) 633 (https://doi.org/10.1016/j.leukres.2007.08.002)

C. Assunção Guimarães, R. Linden, Eur. J. Biochem. 271 (2004) 1638 (https://doi.org/10.1111/j.1432-1033.2004.04084.x)

L. Galluzzi, O. Kepp, G. Kroemer, Oncogene 31 (2012) 2805 (https://doi.org/10.1038/onc.2011.459)

Y. Qiao, C. Dsouza, A. A. Matthews, Y. Jin, W. He, J. Bao, F. Jiang, R. Chandna, R. Ge, L. Fu, Eur. J. Med. Chem. 193 (2020) 112228 (https://doi.org/10.1016/j.ejmech.2020.112228)

K. Nakatani, J. Y. Carriat, Y. Journaux, O. Kahn, F. Lloret, J. P. Renard, Y. Pei, J. Sletten, M. Verdaguer, J. Am. Chem. Soc. 111 (1989) 5739 (https://doi.org/10.1021/ja00197a036)

G.M. Sheldrick, SADABS, Siemens Area Detector Absorption Correction Software, University of Göttingen, Göttingen, 1996

G.M. Sheldrick, SHELXL97, Program for Structure Refinement, University of Göttingen, Göttingen, 1997

L. J. Farrugia, J. Appl. Crystallogr. 32 (1999) 837 (https://doi.org/10.1107/S0021889899006020)

W. Schmitz, Krist. Und Tech. 10 (1975) K120 (https://doi.org/10.1002/crat.19750101116)

M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for crystal structure illustrations, Oak Ridge, TN, 1996 (https://doi.org/10.2172/369685)

Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2016

A. D. Becke, Phys. Rev., A 38 (1988) 3098 (https://doi.org/10.1103/PhysRevA.38.3098)

C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 37 (1988) 785 (https://doi.org/10.1103/PhysRevB.37.785)

A. D. Becke, J. Chem. Phys. 98 (1993) 5648 (https://doi.org/10.1063/1.464913)

M. F. Peintinger, D. V. Oliveira, T. Bredow, J. Comput. Chem. 34 (2013) 451 (https://doi.org/10.1002/jcc.23153)

A. T. Macias, D. S. Williamson, N. Allen, J. Borgognoni, A. Clay, Z. Daniels, P. Dokurno, M. J. Drysdale, G. L. Francis, C. J. Graham, R. Howes, N. Matassova, J. B. Murray, R. Parsons, T. Shaw, A. E. Surgenor, L. Terry, Y. Wang, M. Wood, A. J. Massey, J. Med. Chem. 54 (2011) 4034 (https://doi.org/10.1021/jm101625x)

G. Jones, P. Willett, R. C. Glen, A. R. Leach, R. Taylor, J. Mol. Biol. 267 (1997) 727 (https://doi.org/10.1006/jmbi.1996.0897)

O. Trott, A. J. Olson, J. Comput. Chem. 31 (2010) 455 (https://doi.org/10.1002/jcc.21334)

Amber 2021, University of California, San Francisco, CA, 2021

W. L. Jorgensen, J. Chandrasekhar, J. D. Madura, R. W. Impey, M. L. Klein, J. Chem. Phys. 79 (1983) 926 (https://doi.org/10.1063/1.445869)

W. L. Jorgensen, J. D. Madura, Mol. Phys. 56 (1985) 1381 (https://doi.org/10.1080/00268978500103111)

P. Li, L. F. Song, K. M. Merz, J. Chem. Theory Comput. 11 (2015) 1645 (https://doi.org/10.1021/ct500918t)

A. W. Götz, M. J. Williamson, D. Xu, D. Poole, S. Le Grand, R. C. Walker, J. Chem. Theory Comput. 8 (2012) 1542 (https://doi.org/10.1021/ct200909j)

R. Salomon-Ferrer, A. W. Götz, D. Poole, S. Le Grand, R. C. Walker, J. Chem. Theory Comput. 9 (2013) 3878 (https://doi.org/10.1021/ct400314y)

S. Le Grand, A. W. Götz, R. C. Walker, Comput. Phys. Commun. 184 (2013) 374 (https://doi.org/10.1016/j.cpc.2012.09.022)

M. S. Jeremić, H. Wadepohl, V. V. Kojić, D. S. Jakimov, R. Jelić, S. Popović, Z. D. Matović, P. Comba, RSC Adv. 7 (2017) 5282 (https://doi.org/10.1039/C6RA26199J)

T. Mosmann, J. Immunol. Methods 65 (1983) 55 (https://doi.org/10.1016/0022-1759(83)90303-4)

N. Khanna, H. Jayaram, N. Singh, Life Sci. 75 (2004) 179 (https://doi.org/10.1016/j.lfs.2003.11.026)

S. Zinkel, A. Gross, E. Yang, Cell Death Differ. 13 (2006) 1351 (https://doi.org/10.1038/sj.cdd.4401987)

R. Kim, M. Emi, K. Tanabe, Y. Uchida, K. Arihiro, Eur. J. Surg. Oncol. 32 (2006) 269 (https://doi.org/10.1016/j.ejso.2005.12.006)

G. Kroemer, S. J. Martin, Nat. Med. 11 (2005) 725 (https://doi.org/10.1038/nm1263)

J. Peng, X. Chen, Q. Hu, M. Yang, H. Liu, W. Wei, S. Liu, H. Wang, Mol. Med. Rep. 10 (2014) 2271 (https://doi.org/10.3892/mmr.2014.2489)

E. Rosati, R. Sabatini, G. Rampino, F. De Falco, M. Di Ianni, F. Falzetti, K. Fettucciari, A. Bartoli, I. Screpanti, P. Marconi, Blood 116 (2010) 2713 (https://doi.org/10.1182/blood-2010-03-275628)

Y. Wang, J. Hu, Y. Cai, S. Xu, B. Weng, K. Peng, X. Wei, T. Wei, H. Zhou, X. Li, and Guang Liang, J. Med. Chem 56 (2013) 9601 (https://doi.org/10.1021/jm4016312)

C. Girdlestone, S. Hayward, J. Comput. Biol. 23 (2016) 21 (https://doi.org/10.1089/cmb.2015.0143).

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