Lactimidomycin

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Lactimidomycin is a glutarimide antibiotic derived from the bacteria Streptomyces amphibiosporus.[1][2] It has antifungal, antiviral and anti-cancer properties, acting as a direct inhibitor of protein translation in ribosomes.[3][4][5] Antiviral activity is seen against a variety of RNA viruses including flaviviruses such as dengue fever, Kunjin virus and Modoc virus, as well as vesicular stomatitis virus and poliovirus.[6] As lactimidomycin is a natural product containing an unusual unsaturated 12-membered lactone ring, it has been the subject of numerous total synthesis approaches.[7][8][9][10]

References[edit | edit source]

  1. ↑ Sugawara K, Nishiyama Y, Toda S, Komiyama N, Hatori M, Moriyama T, Sawada Y, Kamei H, Konishi M, Oki T. Lactimidomycin, a new glutarimide group antibiotic. Production, isolation, structure and biological activity. J Antibiot (Tokyo). 1992 Sep;45(9):1433-41. PMID 1429229
  2. ↑ Ju J, Seo JW, Her Y, Lim SK, Shen B. New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus. Org Lett. 2007 Dec 6;9(25):5183-6. PMID 17997563
  3. ↑ Schneider-Poetsch T, Ju J, Eyler DE, Dang Y, Bhat S, Merrick WC, Green R, Shen B, Liu JO. Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. Nat Chem Biol. 2010 Mar;6(3):209-217. PMID 20118940
  4. ↑ Micoine K, Persich P, Llaveria J, Lam MH, Maderna A, Loganzo F, Fürstner A. Total syntheses and biological reassessment of lactimidomycin, isomigrastatin and congener glutarimide antibiotics. Chemistry. 2013 Jun 3;19(23):7370-83. doi: 10.1002/chem.201300393. PMID 23595541
  5. ↑ Garreau de Loubresse N, Prokhorova I, Holtkamp W, Rodnina MV, Yusupova G, Yusupov M. Structural basis for the inhibition of the eukaryotic ribosome. Nature. 2014 Sep 25;513(7519):517-22. doi: 10.1038/nature13737. PMID 25209664
  6. ↑ Carocci M, Yang PL. Lactimidomycin is a broad-spectrum inhibitor of dengue and other RNA viruses. Antiviral Res. 2016 Apr;128:57-62. doi: 10.1016/j.antiviral.2016.02.005 PMID 26872864
  7. ↑ Micoine K, Fürstner A. Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin. J Am Chem Soc. 2010 Oct 13;132(40):14064-6. doi: 10.1021/ja107141p. PMID 20831202
  8. ↑ Larsen BJ, Sun Z, Nagorny P. Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization. Org Lett. 2013 Jun 21;15(12):2998-3001. doi: 10.1021/ol401186f. PMID 23731327
  9. ↑ Nagasawa T, Kuwahara S. Formal total synthesis of lactimidomycin. Org Lett. 2013 Jun 21;15(12):3002-5. doi: 10.1021/ol401214f. PMID 23731346
  10. ↑ Larsen BJ, Sun Z, Lachacz E, Khomutnyk Y, Soellner MB, Nagorny P. Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues. Chemistry. 2015 Dec 21;21(52):19159-67. doi: 10.1002/chem.201503527. PMID 26577990


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Contributors: Prab R. Tumpati, MD