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Pyridone-conjugated monobactam antibiotics with gram-negative activity.

Brown MF, Mitton-Fry MJ, Arcari JT, Barham R, Casavant J, Gerstenberger BS, Han S, Hardink JR, Harris TM, Hoang T, Huband MD, Lall MS, Lemmon MM, Li C, Lin J, McCurdy SP, McElroy E, McPherson C, Marr ES, Mueller JP, Mullins L, Nikitenko AA, Noe MC, Penzien J, Plummer MS, Schuff BP, Shanmugasundaram V, Starr JT, Sun J, Tomaras A, Young JA, Zaniewski RP
J Med Chem 56 5541-52 (2013)
Cited: 18 times
EuropePMC logo PMID: 23755848

Abstract

Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monobactam analogues with in vitro antibacterial activity against clinically relevant Gram-negative species including Pseudomonas aeruginosa , Klebsiella pneumoniae , and Escherichia coli . Rat pharmacokinetic studies with compound 17 demonstrate low clearance and low plasma protein binding. In addition, evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

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Reviews citing this publication (8)

  1. New β-Lactamase Inhibitors in the Clinic. Papp-Wallace KM, Bonomo RA. Infect Dis Clin North Am 30 441-464 (2016)
  2. Bifunctional antimicrobial conjugates and hybrid antimicrobials. Klahn P, Brönstrup M. Nat Prod Rep 34 832-885 (2017)
  3. Antibacterial and β-Lactamase Inhibitory Activity of Monocyclic β-Lactams. Decuyper L, Jukič M, Sosič I, Žula A, D'hooghe M, Gobec S. Med Res Rev 38 426-503 (2018)
  4. Antimicrobial molecular nanocarrier-drug conjugates. Skwarecki AS, Milewski S, Schielmann M, Milewska MJ. Nanomedicine 12 2215-2240 (2016)
  5. Microbial siderophore-based iron assimilation and therapeutic applications. Li K, Chen WH, Bruner SD. Biometals 29 377-388 (2016)
  6. Signed, Sealed, Delivered: Conjugate and Prodrug Strategies as Targeted Delivery Vectors for Antibiotics. Cheng AV, Wuest WM. ACS Infect Dis 5 816-828 (2019)
  7. Siderophore conjugates to combat antibiotic-resistant bacteria. Rayner B, Verderosa AD, Ferro V, Blaskovich MAT. RSC Med Chem 14 800-822 (2023)
  8. Translational deficiencies in antibacterial discovery and new screening paradigms. Dunman PM, Tomaras AP. Curr Opin Microbiol 27 108-113 (2015)

Articles citing this publication (9)

  1. The Role of Iron and Siderophores in Infection, and the Development of Siderophore Antibiotics. Page MGP. Clin Infect Dis 69 S529-S537 (2019)
  2. Pharmacodynamic Profiling of a Siderophore-Conjugated Monocarbam in Pseudomonas aeruginosa: Assessing the Risk for Resistance and Attenuated Efficacy. Kim A, Kutschke A, Ehmann DE, Patey SA, Crandon JL, Gorseth E, Miller AA, McLaughlin RE, Blinn CM, Chen A, Nayar AS, Dangel B, Tsai AS, Rooney MT, Murphy-Benenato KE, Eakin AE, Nicolau DP. Antimicrob Agents Chemother 59 7743-7752 (2015)
  3. Thienopyrimidinone Derivatives That Inhibit Bacterial tRNA (Guanine37-N1)-Methyltransferase (TrmD) by Restructuring the Active Site with a Tyrosine-Flipping Mechanism. Zhong W, Pasunooti KK, Balamkundu S, Wong YH, Nah Q, Gadi V, Gnanakalai S, Chionh YH, McBee ME, Gopal P, Lim SH, Olivier N, Buurman ET, Dick T, Liu CF, Lescar J, Dedon PC. J Med Chem 62 7788-7805 (2019)
  4. Synthetic studies of cystobactamids as antibiotics and bacterial imaging carriers lead to compounds with high in vivo efficacy. Testolin G, Cirnski K, Rox K, Prochnow H, Fetz V, Grandclaudon C, Mollner T, Baiyoumy A, Ritter A, Leitner C, Krull J, van den Heuvel J, Vassort A, Sordello S, Hamed MM, Elgaher WAM, Herrmann J, Hartmann RW, Müller R, Brönstrup M. Chem Sci 11 1316-1334 (2019)
  5. SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of Pseudomonas aeruginosa PBP3. Murphy-Benenato KE, Dangel B, Davis HE, Durand-Réville TF, Ferguson AD, Gao N, Jahić H, Mueller JP, Manyak EL, Quiroga O, Rooney M, Sha L, Sylvester M, Wu F, Zambrowski M, Zhao SX. ACS Med Chem Lett 6 537-542 (2015)
  6. Design, synthesis and microbiological evaluation of ampicillin-tetramic acid hybrid antibiotics. Cherian PT, Deshpande A, Cheramie MN, Bruhn DF, Hurdle JG, Lee RE. J Antibiot (Tokyo) 70 65-72 (2017)
  7. Biofilm-specific uptake of a 4-pyridone-based iron chelator by Pseudomonas aeruginosa. Houshmandyar S, Eggleston IM, Bolhuis A. Biometals 34 315-328 (2021)
  8. In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria. Decuyper L, Deketelaere S, Vanparys L, Jukič M, Sosič I, Sauvage E, Amoroso AM, Verlaine O, Joris B, Gobec S, D'hooghe M. Chemistry 24 15254-15266 (2018)
  9. Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)-H bonds. Wu F, Han X, Li X, Shen X, Wang C, Tian Z, Cheng B, Zhang J, Sheng L, Zhai H. Commun Chem 4 46 (2021)


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