Lactimidomycin

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Lactimidomycin
File:Lactimidomycin.svg
INN
Drug class
Routes of administration
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CAS Number 134869-15-1
PubChem 11669726
DrugBank
ChemSpider 9844457
KEGG


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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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 Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  9. ↑ Nagasawa T, Kuwahara S. Formal total synthesis of lactimidomycin. Org Lett. 2013 Jun 21;15(12):3002-5. doi: 10.1021/ol401214f. Lua error in package.lua at line 80: module 'Module:No globals' not found.
  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. Lua error in package.lua at line 80: module 'Module:No globals' not found.


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