234
Views
4
CrossRef citations to date
0
Altmetric
Special Issue: 9th International Symposium on Computational Methods in Toxicology and Pharmacology Integrating Internet Resources (CMTPI-2017) - Part 2. Guest Editors: A.K. Saxena and M. Saxena

Synthesis and investigation of binding interactions of 1,4-benzoxazine derivatives on topoisomerase IV in Acinetobacter baumanniiFootnote$

, , , &
Pages 941-956 | Received 25 Oct 2017, Accepted 09 Nov 2017, Published online: 05 Dec 2017

References

  • D.E. Ehmann and S.D. Lahiri, Novel compounds targeting bacterial DNA topoisomerase/DNA gyrase, Curr. Opin. Pharmacol. 18 (2014), pp. 76–83.
  • H.W. Boucher, G.H. Talbot, J.S. Bradley, J.E. Edwards, D. Gilbert, L.B. Rice, M. Scheld, B. Spellberg, and J. Bartlett, Bad bugs, no drugs: No ESKAPE! An update from the Infectious Diseases Society of America, Clin. Infect. Dis. 48 (2009), pp. 1–12.
  • S. Park, K.M. Lee, Y.S. Yoo, J.S. Yoo, J.I. Yoo, H.S. Kim, Y.S. Lee, and G.T. Chung, Alterations of gyrA, gyrB, and parC and activity of efflux pump in fluoroquinolone-resistant Acinetobacter baumannii, Osong. Public Health Res. Perspect. 2 (2011), pp. 164–70.
  • J. Vila, J. Ruiz, P. Goni, A. Marcos, and T.J. De Anta, Mutation in the gyrA gene of quinolone-resistant clinical isolates of Acinetobacter baumannii, Antimicr. Agents Chemother. 39 (1995), pp. 1201–1203.
  • S. Yilmaz, G. Altinkanat-Gelmez, K. Bolelli, D. Guneser-Merdan, M.U. Over-Hasdemir, I. Yildiz, E. Aki-Yalcin, and I. Yalcin, Pharmacophore generation of 2-substituted benzothiazoles as AdeABC efflux pump inhibitors in A. baumannii, SAR QSAR Environ. Res. 25 (2014), pp. 551–563.
  • T. Tomasic and L.P. Masic, Prospects for developing new antibacterials targeting bacterial type IIA topoisomerases, Curr. Top. Med. Chem. 14 (2014), pp. 130–151.
  • F. Collin, S. Karkare, and A. Maxwell, Exploiting bacterial DNA gyrase as a drug target: Current state and perspectives, Appl. Microbiol. Biotechnol. 92 (2011), pp. 479–497.
  • M.A. Azam and J. Thathan, Pharmacophore generation, atom-based 3D-QSAR and molecular dynamics simulation analyses of pyridine-3-carboxamide-6-yl-urea analogues as potential gyrase B inhibitors, SAR QSAR Environ. Res. 28 (2017), pp. 275–296.
  • J.J. Perez, C.S. Lupala, and P. Gomez-Gutierrez, Designing type II topoisomerase inhibitors: A molecular modeling approach, Curr. Top. Med. Chem. 14 (2014), pp. 40–50.
  • L. Aravind, D.D. Leipe, and E.V. Koonin, Toprim—a conserved catalytic domain in type IA and II topoisomerases, DnaG-type primases, OLD family nucleases and RecR proteins, Nucleic Acids Res. 26 (1998), pp. 4205–4213.
  • R. Dutta and M. Inouye, GHKL, an emergent ATPase/kinase superfamily, Trends Biochem. Sci. 25 (2000), pp. 24–28.
  • G.M. Harami, M. Gyimesi, and M. Kovacs, From keys to bulldozers: Expanding roles for winged helix domains in nucleic-acid-binding proteins, Trends Biochem. Sci. 38 (2013), pp. 364–371.
  • B.D. Bax, P.F. Chan, D.S. Eggleston, A. Fosberry, D.R. Gentry, F. Gorrec, I. Giordano, M.M. Hann, A. Hennessy, M. Hibbs, J. Huang, E. Jones, J. Jones, K.K. Brown, C.J. Lewis, E.W. May, M.R. Saunders, O. Singh, C.E. Spitzfaden, C. Shen, A. Shillings, A.J. Theobald, A. Wohlkonig, N.D. Pearson, and M.N. Gwynn, Type IIA topoisomerase inhibition by a new class of antibacterial agents, Nature 466 (2010), pp. 935–940.
  • J.G. Heddle, S. Mitelheiser, A. Maxwell, and N.H. Thomson, Nucleotide binding to DNA gyrase causes loss of DNA wrap, J. Mol. Biol. 337 (2004), pp. 597–610.
  • A.D. Bates and A. Maxwell, Energy coupling in type II topoisomerases: Why do they hydrolyze ATP?, Biochemistry 46 (2007), pp. 7929–7941.
  • N.L. Williams and A. Maxwell, Probing the two-gate mechanism of DNA gyrase using cysteine cross-linking, Biochemistry 38 (1999), pp. 13502–13511.
  • L.M. Oppegard, H.A. Schwanz, T.R. Towle, R.J. Kerns, and H. Hiasa, Fluoroquinolones stimulate the DNA cleavage activity of topoisomerase IV by promoting the binding of Mg(2+) to the second metal binding site, Biochim. Biophys. Acta 2016 (1860), pp. 569–575.
  • B.H. Schmidt, A.B. Burgin, J.E. Deweese, N. Osheroff, and J.M. Berger, A novel and unified two-metal mechanism for DNA cleavage by type II and IA topoisomerases, Nature 465 (2010), pp. 641–644.
  • S.L. Pitts, G.F. Liou, L.A. Mitchenall, A.B. Burgin, A. Maxwell, K.C. Neuman, and N. Osheroff, Use of divalent metal ions in the DNA cleavage reaction of topoisomerase IV, Nucleic Acids Res. 39 (2011), pp. 4808–4817.
  • L.C. Axford, P.K. Agarwal, K.H. Anderson, L.N. Andrau, J. Atherall, S. Barker, J.M. Bennett, M. Blair, I. Collins, L.G. Czaplewski, D.T. Davies, C.T. Gannon, D. Kumar, P. Lancett, A. Logan, C.J. Lunniss, D.R. Mitchell, D.A. Offermann, J.T. Palmer, N. Palmer, G.R. Pitt, S. Pommier, D. Price, B. Narasinga Rao, R. Saxena, T. Shukla, A.K. Singh, M. Singh, A. Srivastava, C. Steele, N.R. Stokes, H.B. Thomaides-Brears, E.M. Tyndall, D. Watson, and D.J. Haydon, Design, synthesis and biological evaluation of alpha-substituted isonipecotic acid benzothiazole analogues as potent bacterial type II topoisomerase inhibitors, Bioorg. Med. Chem. Lett. 23 (2013), pp. 6598–6603.
  • K. Drlica, Mechanism of fluoroquinolone action, Curr. Op. Microbiol. 2 (1999), pp. 504–508.
  • I. Laponogov, M.K. Sohi, D.A. Veselkov, X.S. Pan, R. Sawhney, A.W. Thompson, K.E. McAuley, L.M. Fisher, and M.R. Sanderson, Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases, Nat. Struct. Mol. Biol. 16 (2009), pp. 667–669.
  • I. Laponogov, X.S. Pan, D.A. Veselkov, K.E. McAuley, L.M. Fisher, and M.R. Sanderson, Structural basis of gate-DNA breakage and resealing by type II topoisomerases, PLoS One 5 (2010), p. e11338.
  • A. Wohlkonig, P.F. Chan, A.P. Fosberry, P. Homes, J. Huang, M. Kranz, V.R. Leydon, T.J. Miles, N.D. Pearson, R.L. Perera, A.J. Shillings, M.N. Gwynn, and B.D. Bax, Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance, Nat. Struct. Mol. Biol. 17 (2010), pp. 1152–1153.
  • S. Alper-Hayta, E. Aki-Sener, B. Tekiner-Gulbas, I. Yildiz, O. Temiz-Arpaci, I. Yalcin, and N. Altanlar, Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones, Eur. J. Med. Chem. 41 (2006), pp. 1398–1404.
  • Discovery Studio 3.5, Accelrys Software Inc., San Diego 2013; software available at http://accelrys.com/products/discoverystudio.
  • S. Yilmaz, G. Altinkanat-Gelmez, K. Bolelli, D. Guneser-Merdan, M. Ufuk Over-Hasdemir, E. Aki-Yalcin, and I. Yalcin, Binding site feature description of 2-substituted benzothiazoles as potential AcrAB-TolC efflux pump inhibitors in E. coli, SAR QSAR Environ. Res. 26 (2015), pp. 853–871.
  • I. Yalcin, B.P. Tekiner, I.Y. Oren, O.T. Arpaci, E. Aki-Sener, and N. Altanlar, Synthesis and antimicrobial activity of some novel 2, 6, 7-trisubstituted-2H-3, 4-dihydro-1, 4-benzoxazin-3-one derivatives, Indian J. Chem. 42B (2003), pp. 905–909.
  • T. Kumonaka, T. Hase, T. Aotsuka, T. Kurihara, Y. Nakamura, T. Matsui, H. Ishikawa, and F. Kobayashi, 1,4-benzoxazine-2-acetic acid compound, method for production thereof and use thereof, Google Patents, 1997.
  • P. Barraja, P. Diana, A. Montalbano, A. Martorana, A. Carbone, and G. Cirrincione, Synthesis of the new ring system 2-oxo-[1,4]oxazino[3,2-e]indole, heteroanalogue of Angelicin, Tetrahedron Lett. 50 (2009), pp. 4182–4184.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.