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Novel tricyclics (e.g., GSK945237) as potent inhibitors of bacterial type IIA topoisomerases.

Miles TJ, Hennessy AJ, Bax B, Brooks G, Brown BS, Brown P, Cailleau N, Chen D, Dabbs S, Davies DT, Esken JM, Giordano I, Hoover JL, Jones GE, Kusalakumari Sukmar SK, Markwell RE, Minthorn EA, Rittenhouse S, Gwynn MN, Pearson ND
Bioorg Med Chem Lett 26 2464-2469 (2016)
Cited: 24 times
EuropePMC logo PMID: 27055939

Abstract

During the course of our research on the lead optimisation of the NBTI (Novel Bacterial Type II Topoisomerase Inhibitors) class of antibacterials, we discovered a series of tricyclic compounds that showed good Gram-positive and Gram-negative potency. Herein we will discuss the various subunits that were investigated in this series and report advanced studies on compound 1 (GSK945237) which demonstrates good PK and in vivo efficacy properties.

Reviews - 5iwm mentioned but not cited (1)

  1. DNA Topoisomerase Inhibitors: Trapping a DNA-Cleaving Machine in Motion. Bax BD, Murshudov G, Maxwell A, Germe T. J Mol Biol 431 3427-3449 (2019)

Articles - 5iwm mentioned but not cited (4)

  1. Cryo-EM structure of the complete E. coli DNA gyrase nucleoprotein complex. Vanden Broeck A, Lotz C, Ortiz J, Lamour V. Nat Commun 10 4935 (2019)
  2. GC-MS analysis of phytoconstituents from Amomum nilgiricum and molecular docking interactions of bioactive serverogenin acetate with target proteins. Konappa N, Udayashankar AC, Krishnamurthy S, Pradeep CK, Chowdappa S, Jogaiah S. Sci Rep 10 16438 (2020)
  3. A 2.8 Å Structure of Zoliflodacin in a DNA Cleavage Complex with Staphylococcus aureus DNA Gyrase. Morgan H, Lipka-Lloyd M, Warren AJ, Hughes N, Holmes J, Burton NP, Mahenthiralingam E, Bax BD. Int J Mol Sci 24 1634 (2023)
  4. Nybomycin inhibits both types of E. coli DNA gyrase - fluoroquinolone-sensitive and fluoroquinolone-resistant. Shiriaev DI, Sofronova AA, Berdnikovich EA, Lukianov DA, Komarova ES, Marina VI, Zakalyukina YV, Biryukov MV, Maviza TP, Ivanenkov YA, Sergiev PV, Osterman IA, Dontsova OA. Antimicrob Agents Chemother 95 AAC.00777-20 (2023)


Reviews citing this publication (4)

  1. Topoisomerases as anticancer targets. Delgado JL, Hsieh CM, Chan NL, Hiasa H. Biochem J 475 373-398 (2018)
  2. Two Decades of Successful SAR-Grounded Stories of the Novel Bacterial Topoisomerase Inhibitors (NBTIs). Kolarič A, Anderluh M, Minovski N. J Med Chem 63 5664-5674 (2020)
  3. The search for novel treatment strategies for Streptococcus pneumoniae infections. Cools F, Delputte P, Cos P. FEMS Microbiol Rev 45 fuaa072 (2021)
  4. A review on the synthesis of heteroannulated quinolones and their biological activities. Elshaier YAMM, Aly AA, El-Aziz MA, Fathy HM, Brown AB, Ramadan M. Mol Divers 26 2341-2370 (2022)

Articles citing this publication (15)

  1. Mechanistic and Structural Basis for the Actions of the Antibacterial Gepotidacin against Staphylococcus aureus Gyrase. Gibson EG, Bax B, Chan PF, Osheroff N. ACS Infect Dis 5 570-581 (2019)
  2. Producing irreversible topoisomerase II-mediated DNA breaks by site-specific Pt(II)-methionine coordination chemistry. Wang YR, Chen SF, Wu CC, Liao YW, Lin TS, Liu KT, Chen YS, Li TK, Chien TC, Chan NL. Nucleic Acids Res 45 10861-10871 (2017)
  3. Thiophene antibacterials that allosterically stabilize DNA-cleavage complexes with DNA gyrase. Chan PF, Germe T, Bax BD, Huang J, Thalji RK, Bacqué E, Checchia A, Chen D, Cui H, Ding X, Ingraham K, McCloskey L, Raha K, Srikannathasan V, Maxwell A, Stavenger RA. Proc Natl Acad Sci U S A 114 E4492-E4500 (2017)
  4. Novel Bacterial Topoisomerase Inhibitors with Potent Broad-Spectrum Activity against Drug-Resistant Bacteria. Charrier C, Salisbury AM, Savage VJ, Duffy T, Moyo E, Chaffer-Malam N, Ooi N, Newman R, Cheung J, Metzger R, McGarry D, Pichowicz M, Sigerson R, Cooper IR, Nelson G, Butler HS, Craighead M, Ratcliffe AJ, Best SA, Stokes NR. Antimicrob Agents Chemother 61 e02100-16 (2017)
  5. Novel 3-fluoro-6-methoxyquinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase IV. Mitton-Fry MJ, Brickner SJ, Hamel JC, Barham R, Brennan L, Casavant JM, Ding X, Finegan S, Hardink J, Hoang T, Huband MD, Maloney M, Marfat A, McCurdy SP, McLeod D, Subramanyam C, Plotkin M, Reilly U, Schafer J, Stone GG, Uccello DP, Wisialowski T, Yoon K, Zaniewski R, Zook C. Bioorg Med Chem Lett 27 3353-3358 (2017)
  6. Research Support, Non-U.S. Gov't Novel bacterial topoisomerase inhibitors: challenges and perspectives in reducing hERG toxicity. Kolarič A, Minovski N. Future Med Chem 10 2241-2244 (2018)
  7. Potent DNA gyrase inhibitors bind asymmetrically to their target using symmetrical bifurcated halogen bonds. Kolarič A, Germe T, Hrast M, Stevenson CEM, Lawson DM, Burton NP, Vörös J, Maxwell A, Minovski N, Anderluh M. Nat Commun 12 150 (2021)
  8. Rapid Evolution of Reduced Susceptibility against a Balanced Dual-Targeting Antibiotic through Stepping-Stone Mutations. Szili P, Draskovits G, Révész T, Bogár F, Balogh D, Martinek T, Daruka L, Spohn R, Vásárhelyi BM, Czikkely M, Kintses B, Grézal G, Ferenc G, Pál C, Nyerges Á. Antimicrob Agents Chemother 63 e00207-19 (2019)
  9. A Robust Pneumonia Model in Immunocompetent Rodents to Evaluate Antibacterial Efficacy against S. pneumoniae, H. influenzae, K. pneumoniae, P. aeruginosa or A. baumannii. Hoover JL, Lewandowski TF, Mininger CL, Singley CM, Sucoloski S, Rittenhouse S. J Vis Exp (2017)
  10. Bimodal Actions of a Naphthyridone/Aminopiperidine-Based Antibacterial That Targets Gyrase and Topoisomerase IV. Gibson EG, Oviatt AA, Cacho M, Neuman KC, Chan PF, Osheroff N. Biochemistry 58 4447-4455 (2019)
  11. Novel Bacterial Topoisomerase Inhibitors Exploit Asp83 and the Intrinsic Flexibility of the DNA Gyrase Binding Site. Franco-Ulloa S, La Sala G, Miscione GP, De Vivo M. Int J Mol Sci 19 E453 (2018)
  12. Pharmacophore generation, atom-based 3D-QSAR and molecular dynamics simulation analyses of pyridine-3-carboxamide-6-yl-urea analogues as potential gyrase B inhibitors. Azam MA, Thathan J. SAR QSAR Environ Res 28 275-296 (2017)
  13. Antibacterial small molecules targeting the conserved TOPRIM domain of DNA gyrase. Walker SS, Labroli M, Painter RE, Wiltsie J, Sherborne B, Murgolo N, Sher X, Mann P, Zuck P, Garlisi CG, Su J, Kargman S, Xiao L, Scapin G, Salowe S, Devito K, Sheth P, Buist N, Tan CM, Black TA, Roemer T. PLoS One 12 e0180965 (2017)
  14. Structurally Optimized Potent Dual-Targeting NBTI Antibacterials with an Enhanced Bifurcated Halogen-Bonding Propensity. Kokot M, Weiss M, Zdovc I, Hrast M, Anderluh M, Minovski N. ACS Med Chem Lett 12 1478-1485 (2021)
  15. 1,3-Dioxane-Linked Novel Bacterial Topoisomerase Inhibitors: Expanding Structural Diversity and the Antibacterial Spectrum. Lu Y, Mann CA, Nolan S, Collins JA, Parker E, Papa J, Vibhute S, Jahanbakhsh S, Thwaites M, Hufnagel D, Hazbón MH, Moreno J, Stedman TT, Wittum T, Wozniak DJ, Osheroff N, Yalowich JC, Mitton-Fry MJ. ACS Med Chem Lett 13 955-963 (2022)


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