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Investigation of Potential Antibacterial Properties of Some Azo Compounds by Molecular Docking Method

Yıl 2019, Cilt: 14 Sayı: 1, 150 - 154, 31.05.2019
https://doi.org/10.29233/sdufeffd.544174

Öz

In
this study, molecular docking studies were applied to three azo dyes,
2-[(3,5-diamino-1H-pyrazol-4-yl)diazenyl]-5-nitrobenzoic acid (A),
2-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]-5-nitrobenzoic acid (B) and
2-[(5-amino-3-methyl-1H-pyrazol-4-yl)diazenyl]-5-nitrobenzoic acid (C), which
synthesized in our previous studies, to investigate their potential
antibacterial properties. Modelling was performed on SwissDock web server using
EADock DSS algorithm. Docking simulations of ligands (A, B and C) were
performed into the
E. coli beta-ketoacyl-acyl
carrier protein synthase III (KAS III) active site to determine the probable
binding conformations and inhibitory effects. Docking results were also
compared with triclosan used as a commercial antibacterial agent and it was
found that compound B had the best antibacterial property.

Kaynakça

  • J. Lee, S. Kim, J. Sim, D. Lee, H. H. Kim, J. S. Hwang, D. G. Lee, Z. Y. Park, and J. I. Kim, “A potent antibacterial activity of new short D-enantiomeric lipopeptide against multi drug resistant bacteria,” Biochim Biophys Acta Biomembr., 1861, 34-42, 2019.
  • S. Tahir, T. Mahmood, F. Dastgir, I. Haq, A. Waseem, and U. Rashid, “Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria,” Eur J Med Chem., 166, 224-231, 2019.
  • M. Caniçaa, V. Manageiro, H. Abriouel, J. Moran-Giladd, and C.M.A.P. Franzg, “Antibiotic resistance in foodborne bacteria,” Trends Food Sci. Technol., 84, 41-44, 2019.
  • I.J. Schalk, “Siderophoreeantibiotic conjugates: exploiting iron uptake to deliver drugs into bacteria,” Clin. Microbiol. Infect., 24, 801-802, 2018.
  • F. R. Fields, S. W. Lee, and M. J. McConnell, “Using bacterial genomes and essential genes for the development of new antibiotics,” Biochem. Pharmacol., 134, 74–86, 2017.
  • Ç. Karabacak Atay, T. Tilki, and B. Dede, “Design and synthesis of novel ribofuranose nucleoside analogues as antiproliferative agents: A molecular docking and DFT study,” J. Mol. Liq., 269, 315–326, 2018.
  • P. Sledz, and A. Caflisch, “Protein structure-based drug design: from docking to molecular Dynamics,” Curr. Opin. Struc. Biol., 48, 93–102, 2018.
  • S. Kumar, and S. Kumar, “Chapter 6: Molecular Docking: A Structure-Based Approach for Drug Repurposing,” In Silico Drug Design, 161-189, 2019.
  • K. A. Ramsbottoma, D. F. Carrb, A. R. Jonesa, and D. J. Rigdena, “Critical assessment of approaches for molecular docking to elucidate associations of HLA alleles with adverse drug reactions,” Mol. Immunol., 101, 488-499, 2018.
  • Ç. Karabacak Atay, M. Gokalp, S. Ozdemir Kart, and T. Tilki, “Mono azo dyes derived from 5-nitroanthranilic acid: Synthesis, absorption properties and DFT calculations,” J. Mol. Struct., 1141, 237-244, 2017.
  • A. Grosdidier, V. Zoete, and O. Michielin, “SwissDock, a protein-small molecule docking web service based on EADock DSS,” Nucleic Acids Res., 39, 270-277, 2011.
  • Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N., Bourne, P.E., (2000). The Protein Data Bank. Nucleic Acids Res., 28(1), 235–242.
  • Gaussian 09, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
  • E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin, “UCSF Chimera--a visualization system for exploratory research and analysis,” J. Comput. Chem., 13, 1605-1612, 2004.
  • A.D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Phys. Rev. A, 38, 3098-3100, 1988.
  • C. Lee, W. Yang, and R.G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B, 37, 785-789, 1988.

Moleküler Docking Yöntemi ile Bazı Azo Bileşiklerinin Potansiyel Antibakteriyel Özelliklerinin İncelenmesi

Yıl 2019, Cilt: 14 Sayı: 1, 150 - 154, 31.05.2019
https://doi.org/10.29233/sdufeffd.544174

Öz

Bu
çalışmada, önceki çalışmalarımızda sentezlediğimiz 
üç azo boyarmaddenin, 2 -
[(3,5-diamino-1H-pirazol-4-il)diazenil]-5-nitrobenzoik asit (A),
2-[(3,5)-dimetil-1H-pirazol-4-il) diazenil]-5-nitrobenzoik asit (B) ve
2-[(5-amino-3-metil-1H-pirazol-4-il) diazenil]-5-nitrobenzoik asit (C),
potansiyel antibakteriyel özelliklerini araştırmak için moleküler doking
çalışmaları yapıldı.
Modelleme,
SwissDock web sunucusunda EADock DSS algoritması kullanılarak gerçekleştirildi.
Olası
bağlanma konformasyonları ve inhibe edici etkileri belirlemek için
E. coli beta-ketoaçil-açil taşıyıcı
protein sentaz III (KAS III) aktif bölgesine ligandların (A, B ve C) bağlanma
simülasyonları yapıldı.

Doking sonuçları ayrıca ticari bir antibakteriyel madde olarak
kullanılan triklosan ile karşılaştırıldı ve B bileşiğinin en iyi antibakteriyel
özelliğe sahip olduğu bulundu.

Kaynakça

  • J. Lee, S. Kim, J. Sim, D. Lee, H. H. Kim, J. S. Hwang, D. G. Lee, Z. Y. Park, and J. I. Kim, “A potent antibacterial activity of new short D-enantiomeric lipopeptide against multi drug resistant bacteria,” Biochim Biophys Acta Biomembr., 1861, 34-42, 2019.
  • S. Tahir, T. Mahmood, F. Dastgir, I. Haq, A. Waseem, and U. Rashid, “Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria,” Eur J Med Chem., 166, 224-231, 2019.
  • M. Caniçaa, V. Manageiro, H. Abriouel, J. Moran-Giladd, and C.M.A.P. Franzg, “Antibiotic resistance in foodborne bacteria,” Trends Food Sci. Technol., 84, 41-44, 2019.
  • I.J. Schalk, “Siderophoreeantibiotic conjugates: exploiting iron uptake to deliver drugs into bacteria,” Clin. Microbiol. Infect., 24, 801-802, 2018.
  • F. R. Fields, S. W. Lee, and M. J. McConnell, “Using bacterial genomes and essential genes for the development of new antibiotics,” Biochem. Pharmacol., 134, 74–86, 2017.
  • Ç. Karabacak Atay, T. Tilki, and B. Dede, “Design and synthesis of novel ribofuranose nucleoside analogues as antiproliferative agents: A molecular docking and DFT study,” J. Mol. Liq., 269, 315–326, 2018.
  • P. Sledz, and A. Caflisch, “Protein structure-based drug design: from docking to molecular Dynamics,” Curr. Opin. Struc. Biol., 48, 93–102, 2018.
  • S. Kumar, and S. Kumar, “Chapter 6: Molecular Docking: A Structure-Based Approach for Drug Repurposing,” In Silico Drug Design, 161-189, 2019.
  • K. A. Ramsbottoma, D. F. Carrb, A. R. Jonesa, and D. J. Rigdena, “Critical assessment of approaches for molecular docking to elucidate associations of HLA alleles with adverse drug reactions,” Mol. Immunol., 101, 488-499, 2018.
  • Ç. Karabacak Atay, M. Gokalp, S. Ozdemir Kart, and T. Tilki, “Mono azo dyes derived from 5-nitroanthranilic acid: Synthesis, absorption properties and DFT calculations,” J. Mol. Struct., 1141, 237-244, 2017.
  • A. Grosdidier, V. Zoete, and O. Michielin, “SwissDock, a protein-small molecule docking web service based on EADock DSS,” Nucleic Acids Res., 39, 270-277, 2011.
  • Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N., Bourne, P.E., (2000). The Protein Data Bank. Nucleic Acids Res., 28(1), 235–242.
  • Gaussian 09, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
  • E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin, “UCSF Chimera--a visualization system for exploratory research and analysis,” J. Comput. Chem., 13, 1605-1612, 2004.
  • A.D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Phys. Rev. A, 38, 3098-3100, 1988.
  • C. Lee, W. Yang, and R.G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B, 37, 785-789, 1988.
Toplam 16 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Makaleler
Yazarlar

Çiğdem Karabacak Atay 0000-0001-7226-9971

Tahir Tilki 0000-0002-1040-2375

Bülent Dede 0000-0003-1416-7373

Yayımlanma Tarihi 31 Mayıs 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 14 Sayı: 1

Kaynak Göster

IEEE Ç. Karabacak Atay, T. Tilki, ve B. Dede, “Investigation of Potential Antibacterial Properties of Some Azo Compounds by Molecular Docking Method”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, c. 14, sy. 1, ss. 150–154, 2019, doi: 10.29233/sdufeffd.544174.