A series of ceramide analogs modified at the 1-position with potent activity against the intracellular growth of Chlamydia trachomatis

References

• 1 WHO. Global Incidence and Prevalence of Selected Curable Sexually Transmitted Infections. WHO, Geneva, Switzerland (2008).
  Google Scholar
• 2 Heinzen RA, Hackstadt T. The Chlamydia trachomatis parasitophorous vacuolar membrane is not passively permeable to low-molecular-weight compounds. Infect. Immun. 65(3), 1088–1094 (1997).
  Medline CASGoogle Scholar
• 3 van Ooij C, Kalman L, van I et al. Host cell-derived sphingolipids are required for the intracellular growth of Chlamydia trachomatis. Cell. Microbiol. 2(6), 627–637 (2000).
  Medline CASGoogle Scholar
• 4 Heuer D, Rejman Lipinski A, Machuy N et al. Chlamydia causes fragmentation of the Golgi compartment to ensure reproduction. Nature 457(7230), 731–735 (2009).
  Medline CASGoogle Scholar
• 5 Boncompain G, Muller C, Meas-Yedid V, Schmitt-Kopplin P, Lazarow PB, Subtil A. The intracellular bacteria Chlamydia hijack peroxisomes and utilize their enzymatic capacity to produce bacteria-specific phospholipids. PLoS ONE 9(1), e86196 (2014).
  MedlineGoogle Scholar
• 6 Subtil A. Rerouting of host lipids by bacteria: are you CERTain you need a vesicle? PLoS Pathog. 7(9), e1002208 (2011).
  Medline CASGoogle Scholar
• 7 Hackstadt T, Scidmore MA, Rockey DD. Lipid metabolism in Chlamydia trachomatis-infected cells: directed trafficking of Golgi-derived sphingolipids to the chlamydial inclusion. Proc. Natl Acad. Sci. USA 92(11), 4877–4881 (1995).
  Medline CASGoogle Scholar
• 8 Hackstadt T, Rockey DD, Heinzen RA, Scidmore MA. Chlamydia trachomatis interrupts an exocytic pathway to acquire endogenously synthesized sphingomyelin in transit from the Golgi apparatus to the plasma membrane. EMBO J. 15(5), 964–977 (1996).
  Medline CASGoogle Scholar
• 9 Robertson DK, Gu L, Rowe RK, Beatty WL. Inclusion biogenesis and reactivation of persistent Chlamydia trachomatis requires host cell sphingolipid biosynthesis. PLoS Pathog. 5(11), e1000664 (2009).
  MedlineGoogle Scholar
• 10 Elwell CA, Jiang S, Kim JH et al. Chlamydia trachomatis co-opts GBF1 and CERT to acquire host sphingomyelin for distinct roles during intracellular development. PLoS Pathog. 7(9), e1002198 (2011).
  Medline CASGoogle Scholar
• 11 Derre I, Swiss R, Agaisse H. The lipid transfer protein CERT interacts with the Chlamydia inclusion protein IncD and participates to ER-Chlamydia inclusion membrane contact sites. PLoS Pathog. 7(6), e1002092 (2011).
  Medline CASGoogle Scholar
• 12 Banhart S, Saied EM, Martini A et al. Improved plaque assay identifies a novel anti-Chlamydia ceramide derivative with altered intracellular localization. Antimicrob. Agents Chemother. 58(9), 5537–5546 (2014).
  MedlineGoogle Scholar
• 13 Lipsky NG, Pagano RE. A vital stain for the Golgi apparatus. Science 228(4700), 745–747 (1985).
  Medline CASGoogle Scholar
• 14 Putz U, Schwarzmann G. Golgi staining by two fluorescent ceramide analogues in cultured fibroblasts requires metabolism. Eur. J. Cell Biol. 68(2), 113–121 (1995).
  Medline CASGoogle Scholar
• 15 Makiyama T, Nakamura H, Nagasaka N et al. Trafficking of acetyl-C16-ceramide-NBD with long-term stability and no cytotoxicity into the Golgi complex. Traffic 16(5), 476–492 (2015).
  Medline CASGoogle Scholar
• 16 Yamamoto T, Hasegawa H, Hakogi T, Katsumura S. Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis. Org. Lett. 8(24), 5569–5572 (2006).
  Medline CASGoogle Scholar
• 17 Yamamoto T, Hasegawa H, Hakogi T, Katsumura S. Syntheses of fluorescence-labeled sphingosine 1-phosphate methylene and sulfur analogues as possible visible ligands to the receptor. Chem. Lett. 37(2), 188–189 (2008).
  CASGoogle Scholar
• 18 Bhabak KP, Hauser A, Redmer S, Banhart S, Heuer D, Arenz C. Development of a novel FRET probe for the real-time determination of ceramidase activity. ChemBioChem 14(9), 1049–1052 (2013).
  Medline CASGoogle Scholar
• 19 Bhabak KP, Proksch D, Redmer S, Arenz C. Novel fluorescent ceramide derivatives for probing ceramidase substrate specificity. Bioorg. Med. Chem. 20(20), 6154–6161 (2012).
  Medline CASGoogle Scholar
• 20 Chattopadhyay A, London E. Spectroscopic and ionization properties of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled lipids in model membranes. Biochim. Biophys. Acta 938(1), 24–34 (1988).
  Medline CASGoogle Scholar
• 21 Saied EM, Diederich S, Arenz C. Facile synthesis of the CERT inhibitor HPA-12 and some novel derivatives. Chem. Asian J. 9(8), 2092–2094 (2014).
  Medline CASGoogle Scholar
• 22 Ouellette SP, Carabeo RA. A functional slow recycling pathway of transferrin is required for growth of Chlamydia. Front. Microbiol. 1, 112 (2010).
  Medline CASGoogle Scholar
• 23 Sandoz KM, Eriksen SG, Jeffrey BM et al. Resistance to a novel antichlamydial compound is mediated through mutations in Chlamydia trachomatis secY. Antimicrob. Agents Chemother. 56(8), 4296–4302 (2012).
  Medline CASGoogle Scholar
• 24 Ben-David O, Futerman AH. The role of the ceramide acyl chain length in neurodegeneration: involvement of ceramide synthases. Neuromolecular Med. 12(4), 341–350 (2010).
  Medline CASGoogle Scholar
• 25 Nakamura Y, Matsubara R, Kitagawa H et al. Stereoselective synthesis and structure-activity relationship of novel ceramide trafficking inhibitors. (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and its analogues. J. Med. Chem. 46(17), 3688–3695 (2003).
  Medline CASGoogle Scholar
• 26 Golden MR, Whittington WL, Handsfield HH et al. Effect of expedited treatment of sex partners on recurrent or persistent gonorrhea or chlamydial infection. N. Engl. J. Med. 352, 676–685 (2005).
  Medline CASGoogle Scholar
• 27 Batteiger B, Tu W, Ofner S et al. Repeated Chlamydia trachomatis genital infections in adolescent women. J. Infect. Dis. 201, 42–51 (2010).
  MedlineGoogle Scholar