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Chemical Compound Review

CP-0     2-ethoxy-3-hexadecoxy-propan- 1-ol

Synonyms: CHEMBL28985, AC1L9QG2, 92758-87-7, 2-ethoxy-3-hexadecoxypropan-1-ol, 1-Propanol, 2-ethoxy-3-(hexadecyloxy)-, ...
 
 
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Disease relevance of AIDS-002137

 

High impact information on AIDS-002137

  • Local incorporation of a fluorescent lipid analog into the plasma membrane of fast-growing Xenopus neurites revealed an anterograde bulk membrane flow that correlated with neurite elongation [3].
  • The plasma membrane of human polymorphonuclear leukocytes was stained with a fluorescent lipid analog dihexadecanoyl indocarbocyanine [4].
  • The mean lateral diffusion coefficients (D) for the antibody-protein complex in interphase cells were in the range of 0.7-3.5 X 10(-10) cm2/s between 9 degrees and 37 degrees C, while that for the lipid analog probe, dihexadecylindocarbocyanine was about two orders of magnitude greater [5].
  • Biochemical studies demonstrated that at these time points, hydrolysis of the lipid analog was minimal ( approximately 7%) in both cell types [6].
  • Photobleaching-based assays were used to measure diffusion of three membrane proteins with differing topologies and putative lipid raft association, as well as the lipid analog dialkylindocarbocyanine (DiI C18, ), across the cleavage furrow [7].
 

Biological context of AIDS-002137

 

Anatomical context of AIDS-002137

  • By taking advantage of the monomer/excimer properties of the fluorescent lipid analog, we were also able to visualize LacCer segregation into distinct microdomains of high (red emission) and low (green emission) concentrations in the early endosomes of living cells [12].
  • The interaction of macrophages with red blood cells (RBC) displaying phosphatidylserine (PS) in their surface membranes was investigated after the transfer of an exogenously supplied fluorescent lipid analog to the RBC [13].
  • The fluorescent lipid analog DiIC16[3] was used to label either the external membranes (plasmalemma and transverse (T)-tubules) or the internal SR in living and fixed muscle [14].
  • Therewith we bleached circular areas on the surface of single living 3T3 cells labeled with the fluorescent lipid analog NBD-HPC [15].
  • We describe a technique to visualize substrate-attached materials (SAM) of polymorphonuclear leukocytes (PMN) using the fluorescent lipid analog 1,1'-dioctadecyl-3,3,3',3',-tetramethylindocarbocyanine-perchlorate (DiC18Icc) [16].
 

Associations of AIDS-002137 with other chemical compounds

  • A significant interaction of spin-labeled lysophosphatidylcholine with the hemagglutinin ectodomain of intact viruses was observed neither at neutral nor at low pH, whereas a strong interaction of the lipid analog with the viral lipid bilayer was evident [17].
  • The binding of the antimicrobial peptides temporins B and L to supported lipid bilayer (SLB) model membranes composed of phosphatidylcholine and phosphatidylglycerol (4:1, mol/mol) caused the formation of fibrillar protrusions, visible by fluorescent microscopy of both a fluorescent lipid analog and a labeled peptide [18].
  • A novel lipid analog with two long alkyl (C16) chains, an aspartate skeleton, a connecting alkyl (C8) chain, and 2-nitrophenol trigger group is synthesized by an efficient synthetic route, which can induce liposome fusion at physiological pH [19].
  • This asymmetry was maximal up to about 4 h following the addition of dimethylethanolamine to the culture medium and was of a transient nature as the lipid analog accumulated on both sides of the plasma membrane [20].
  • More specifically, collisional quenching of the fluorescence of a pyrene labeled fluorescent lipid analog 1-palmitoyl-2[10-(pyren-1-yl)]decanoyl-sn-glycero-3-phosphocholine (PPDPC) by CPZ was utilized, using 1-palmitoyl-2-oleyl-sn-glycero-3-phosphocholine and -serine (POPC and POPS) liposomes as model membranes [21].
 

Gene context of AIDS-002137

  • All lipases under investigation preferentially hydrolysed the sn-1 acyl ester bond, if the lipid analog was dispersed in albumin-containing Tris/HCl buffer in the absence of detergent or organic solvent [22].
  • With these modifications we were able to follow the interaction of the fluorescent lipid analog 1-acyl-2-(N-4-nitrobenzo-2-oxa-1,3-diazole)-aminododecanoyl phosphatidylcholine (I) with Naja-naja venom phospholipase A2 (PLA2) (E.C.3.1.1.4) [23].

References

  1. Enhanced molecular diffusibility in muscle membrane blebs: release of lateral constraints. Tank, D.W., Wu, E.S., Webb, W.W. J. Cell Biol. (1982) [Pubmed]
  2. Reduced lateral mobility of a fluorescent lipid analog in cell membranes of rat fibroblasts transformed by simian virus 40. Kawasaki, Y., Zundel, J.L., Miyakawa, T., Sakaguchi, K. FEBS Lett. (1989) [Pubmed]
  3. Forward plasma membrane flow in growing nerve processes. Popov, S., Brown, A., Poo, M.M. Science (1993) [Pubmed]
  4. The direction of membrane lipid flow in locomoting polymorphonuclear leukocytes. Lee, J., Gustafsson, M., Magnusson, K.E., Jacobson, K. Science (1990) [Pubmed]
  5. Lateral diffusion of an 80,000-dalton glycoprotein in the plasma membrane of murine fibroblasts: relationships to cell structure and function. Jacobson, K., O'Dell, D., August, J.T. J. Cell Biol. (1984) [Pubmed]
  6. Abnormal transport along the lysosomal pathway in mucolipidosis, type IV disease. Chen, C.S., Bach, G., Pagano, R.E. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  7. A barrier to lateral diffusion in the cleavage furrow of dividing mammalian cells. Schmidt, K., Nichols, B.J. Curr. Biol. (2004) [Pubmed]
  8. Changes in the spectral properties of a plasma membrane lipid analog during the first seconds of endocytosis in living cells. Chen, C.S., Martin, O.C., Pagano, R.E. Biophys. J. (1997) [Pubmed]
  9. Lateral motion of fluorescent molecules embedded into cell membranes of clonal myogenic cells, L6, changes upon cell maturation. Kawasaki, Y., Wakayama, N., Seto-Ohshima, A. FEBS Lett. (1988) [Pubmed]
  10. Identification of new inhibitors of E. coli cyclopropane fatty acid synthase using a colorimetric assay. Guianvarc'h, D., Drujon, T., Leang, T.E., Courtois, F., Ploux, O. Biochim. Biophys. Acta (2006) [Pubmed]
  11. Interaction of clathrin with large unilamellar phospholipid vesicles at neutral pH. Lipid dependence and protein penetration. Seppen, J., Ramalho-Santos, J., de Carvalho, A.P., ter Beest, M., Kok, J.W., de Lima, M.C., Hoekstra, D. Biochim. Biophys. Acta (1992) [Pubmed]
  12. Glycosphingolipids internalized via caveolar-related endocytosis rapidly merge with the clathrin pathway in early endosomes and form microdomains for recycling. Sharma, D.K., Choudhury, A., Singh, R.D., Wheatley, C.L., Marks, D.L., Pagano, R.E. J. Biol. Chem. (2003) [Pubmed]
  13. Insertion of fluorescent phosphatidylserine into the plasma membrane of red blood cells. Recognition by autologous macrophages. Tanaka, Y., Schroit, A.J. J. Biol. Chem. (1983) [Pubmed]
  14. Development of the excitation-contraction coupling apparatus in skeletal muscle: association of sarcoplasmic reticulum and transverse tubules with myofibrils. Flucher, B.E., Takekura, H., Franzini-Armstrong, C. Dev. Biol. (1993) [Pubmed]
  15. Lateral diffusion measurement at high spatial resolution by scanning microphotolysis in a confocal microscope. Kubitscheck, U., Wedekind, P., Peters, R. Biophys. J. (1994) [Pubmed]
  16. Fluorescence microscopy study of polymorphonuclear leukocyte substrate attached materials. Francis, J.W., Fabi, A.Y., Petty, H.R. Cell Motil. Cytoskeleton (1988) [Pubmed]
  17. Lysolipids do not inhibit influenza virus fusion by interaction with hemagglutinin. Baljinnyam, B., Schroth-Diez, B., Korte, T., Herrmann, A. J. Biol. Chem. (2002) [Pubmed]
  18. Antimicrobial peptides temporins B and L induce formation of tubular lipid protrusions from supported phospholipid bilayers. Domanov, Y.A., Kinnunen, P.K. Biophys. J. (2006) [Pubmed]
  19. Lipid analog with 2-nitrophenol trigger designed for liposome fusion at physiological pH. Shah, S.N., Tomohiro, T., Ogawa, Y., Kodaka, M., Okuno, H. Lipids (2000) [Pubmed]
  20. Translocation and turnover of phospholipid analogs in plasma membrane-derived vesicles from cell cultures. Yavin, E., Zutra, A. Biochim. Biophys. Acta (1979) [Pubmed]
  21. A versatile method for determining the molar ligand-membrane partition coefficient. Parry, M.J., Jutila, A., Kinnunen, P.K., Alakoskela, J.M. Journal of fluorescence (2007) [Pubmed]
  22. Inversion of lipase stereospecificity for fluorogenic alkyldiacyl glycerols. Effect of substrate solubilization. Zandonella, G., Haalck, L., Spener, F., Faber, K., Paltauf, F., Hermetter, A. Eur. J. Biochem. (1995) [Pubmed]
  23. Real-time fluorescence polarization measurements: interaction of phospholipase A2 with a fluorescent lecithin derivative. Monti, J.A., McBride, M.R., Barker, S.A., Linton, J.L., Christian, S.T. J. Biochem. Biophys. Methods (1985) [Pubmed]
 
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