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Inhibitors of bacterial enoyl acyl carrier protein reductase (FabI): 2,9-disubstituted 1,2,3,4-tetrahydropyrido[3,4-b]indoles as potential antibacterial agents.

Seefeld MA, Miller WH, Newlander KA, Burgess WJ, Payne DJ, Rittenhouse SF, Moore TD, DeWolf WE, Keller PM, Qiu X, Janson CA, Vaidya K, Fosberry AP, Smyth MG, Jaworski DD, Slater-Radosti C, Huffman WF
Bioorg Med Chem Lett 11 2241-4 (2001)
Cited: 34 times
EuropePMC logo PMID: 11527706

Abstract

An SAR study of a screening lead has led to the identification of 2,9-disubstituted 1,2,3,4-tetrahydropyrido[3,4-b]indoles as inhibitors of Staphylococcus aureus enoyl acyl carrier protein reductase (FabI).

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  2. Current progress in the fatty acid metabolism in Cryptosporidium parvum. Zhu G. J Eukaryot Microbiol 51 381-388 (2004)
  3. The reductase steps of the type II fatty acid synthase as antimicrobial targets. Zhang YM, Lu YJ, Rock CO. Lipids 39 1055-1060 (2004)
  4. 'FAS't inhibition of malaria. Surolia A, Ramya TN, Ramya V, Surolia N. Biochem J 383 401-412 (2004)
  5. Novel targets for the future development of antibacterial agents. McDevitt D, Payne DJ, Holmes DJ, Rosenberg M. J Appl Microbiol 92 Suppl 28S-34S (2002)
  6. Recent advances in inhibitors of bacterial fatty acid synthesis type II (FASII) system enzymes as potential antibacterial agents. Wang Y, Ma S. ChemMedChem 8 1589-1608 (2013)
  7. Facilitating Compound Entry as a Means to Discover Antibiotics for Gram-Negative Bacteria. Muñoz KA, Hergenrother PJ. Acc Chem Res 54 1322-1333 (2021)

Articles citing this publication (21)

  1. Mode of action, in vitro activity, and in vivo efficacy of AFN-1252, a selective antistaphylococcal FabI inhibitor. Kaplan N, Albert M, Awrey D, Bardouniotis E, Berman J, Clarke T, Dorsey M, Hafkin B, Ramnauth J, Romanov V, Schmid MB, Thalakada R, Yethon J, Pauls HW. Antimicrob Agents Chemother 56 5865-5874 (2012)
  2. Validation of antibacterial mechanism of action using regulated antisense RNA expression in Staphylococcus aureus. Ji Y, Yin D, Fox B, Holmes DJ, Payne D, Rosenberg M. FEMS Microbiol Lett 231 177-184 (2004)
  3. Implementation of permeation rules leads to a FabI inhibitor with activity against Gram-negative pathogens. Parker EN, Drown BS, Geddes EJ, Lee HY, Ismail N, Lau GW, Hergenrother PJ. Nat Microbiol 5 67-75 (2020)
  4. Identification and characterization of inhibitors of bacterial enoyl-acyl carrier protein reductase. Ling LL, Xian J, Ali S, Geng B, Fan J, Mills DM, Arvanites AC, Orgueira H, Ashwell MA, Carmel G, Xiang Y, Moir DT. Antimicrob Agents Chemother 48 1541-1547 (2004)
  5. Discovery of a novel and potent class of F. tularensis enoyl-reductase (FabI) inhibitors by molecular shape and electrostatic matching. Hevener KE, Mehboob S, Su PC, Truong K, Boci T, Deng J, Ghassemi M, Cook JL, Johnson ME. J Med Chem 55 268-279 (2012)
  6. Crystal structure of enoyl-acyl carrier protein reductase (FabK) from Streptococcus pneumoniae reveals the binding mode of an inhibitor. Saito J, Yamada M, Watanabe T, Iida M, Kitagawa H, Takahata S, Ozawa T, Takeuchi Y, Ohsawa F. Protein Sci 17 691-699 (2008)
  7. Design and synthesis of aryl ether inhibitors of the Bacillus anthracis enoyl-ACP reductase. Tipparaju SK, Mulhearn DC, Klein GM, Chen Y, Tapadar S, Bishop MH, Yang S, Chen J, Ghassemi M, Santarsiero BD, Cook JL, Johlfs M, Mesecar AD, Johnson ME, Kozikowski AP. ChemMedChem 3 1250-1268 (2008)
  8. Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases. Aiello D, Barnes MH, Biswas EE, Biswas SB, Gu S, Williams JD, Bowlin TL, Moir DT. Bioorg Med Chem 17 4466-4476 (2009)
  9. AG205, a novel agent directed against FabK of Streptococcus pneumoniae. Takahata S, Iida M, Osaki Y, Saito J, Kitagawa H, Ozawa T, Yoshida T, Hoshiko S. Antimicrob Agents Chemother 50 2869-2871 (2006)
  10. 4-Pyridone derivatives as new inhibitors of bacterial enoyl-ACP reductase FabI. Kitagawa H, Kumura K, Takahata S, Iida M, Atsumi K. Bioorg Med Chem 15 1106-1116 (2007)
  11. Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors. Takhi M, Sreenivas K, Reddy CK, Munikumar M, Praveena K, Sudheer P, Rao BN, Ramakanth G, Sivaranjani J, Mulik S, Reddy YR, Narasimha Rao K, Pallavi R, Lakshminarasimhan A, Panigrahi SK, Antony T, Abdullah I, Lee YK, Ramachandra M, Yusof R, Rahman NA, Subramanya H. Eur J Med Chem 84 382-394 (2014)
  12. The effects of triclosan on uropathogen susceptibility to clinically relevant antibiotics. Wignall GR, Goneau LW, Chew BH, Denstedt JD, Cadieux PA. J Endourol 22 2349-2356 (2008)
  13. An Iterative Approach Guides Discovery of the FabI Inhibitor Fabimycin, a Late-Stage Antibiotic Candidate with In Vivo Efficacy against Drug-Resistant Gram-Negative Infections. Parker EN, Cain BN, Hajian B, Ulrich RJ, Geddes EJ, Barkho S, Lee HY, Williams JD, Raynor M, Caridha D, Zaino A, Shekhar M, Muñoz KA, Rzasa KM, Temple ER, Hunt D, Jin X, Vuong C, Pannone K, Kelly AM, Mulligan MP, Lee KK, Lau GW, Hung DT, Hergenrother PJ. ACS Cent Sci 8 1145-1158 (2022)
  14. Rational questing for potential novel inhibitors of FabK from Streptococcus pneumoniae by combining FMO calculation, CoMFA 3D-QSAR modeling and virtual screening. Zhang Q, Yu C, Min J, Wang Y, He J, Yu Z. J Mol Model 17 1483-1492 (2011)
  15. Phenylimidazole derivatives as new inhibitors of bacterial enoyl-ACP reductase FabK. Kitagawa H, Ozawa T, Takahata S, Iida M. Bioorg Med Chem Lett 17 4982-4986 (2007)
  16. Phenylimidazole derivatives as specific inhibitors of bacterial enoyl-acyl carrier protein reductase FabK. Ozawa T, Kitagawa H, Yamamoto Y, Takahata S, Iida M, Osaki Y, Yamada K. Bioorg Med Chem 15 7325-7336 (2007)
  17. Pharmacophore and molecular docking guided 3D-QSAR study of bacterial enoyl-ACP reductase (FabI) Inhibitors. Lu X, Lv M, Huang K, Ding K, Ding K, You Q. Int J Mol Sci 13 6620-6638 (2012)
  18. Characterization of protein-ligand binding interactions of enoyl-ACP reductase (FabI) by native MS reveals allosteric effects of coenzymes and the inhibitor triclosan. Joyner PM, Tran DP, Zenaidee MA, Loo JA. Protein Sci 31 568-579 (2022)
  19. Crystallization and preliminary X-ray analysis of enoyl-acyl carrier protein reductase (FabK) from Streptococcus pneumoniae. Saito J, Yamada M, Watanabe T, Kitagawa H, Takeuchi Y. Acta Crystallogr Sect F Struct Biol Cryst Commun 62 576-578 (2006)
  20. Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus. Lenin HH, Lauro FV, Marcela RN, Socorro HM, Maria LR, Francisco DC, Elodia GC, Eduardo PG, Josefa PE, Regina CC, Saidy EH. J Chem Biol 10 159-177 (2017)
  21. Studies of Staphylococcus aureus FabI inhibitors: fragment-based approach based on holographic structure-activity relationship analyses. Kronenberger T, Asse LR, Wrenger C, Trossini GH, Honorio KM, Maltarollo VG. Future Med Chem 9 135-151 (2017)


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