Deuterium-labelled N-acyl-L-homoserine lactones (AHLs)-inter-kingdom signalling molecules-synthesis, structural studies, and interactions with model lipid membranes

Analytical and Bioanalytical Chemistry

Volumn 403, Issue 2, 2012, Pages 473-482

  Jakubczyk, Dorota ^a,b   Barth, Christoph ^b   Kubas, Adam ^b   Anastassacos, Frances ^b   Koelsch, Patrick ^b   Fink, Karin ^b   Schepers, Ute ^b   Brenner Weiß, Gerald ^b   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Deuterium labelled AHLs; DFT modelling; Geometry optimization; Inter kingdom signalling; Sum frequency generation (SFG) spectroscopy; Supported lipid bilayers (SLBs)

Indexed keywords

DEUTERIUM-LABELLED AHLS; DFT MODELLING; GEOMETRY OPTIMIZATION; SUM FREQUENCY GENERATION; SUPPORTED LIPID BILAYERS;

CELL MEMBRANES; CYTOLOGY; ISOMERS; LIPID BILAYERS; MASS SPECTROMETRY; RAMAN SPECTROSCOPY; SYNTHESIS (CHEMICAL);

DEUTERIUM;

DEUTERIUM; GAMMA BUTYROLACTONE DERIVATIVE; MEMBRANE LIPID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GRAM NEGATIVE BACTERIUM; METABOLISM; SIGNAL TRANSDUCTION; SYNTHESIS;

ACYL-BUTYROLACTONES; DEUTERIUM; GRAM-NEGATIVE BACTERIA; MEMBRANE LIPIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SIGNAL TRANSDUCTION;

BACTERIA (MICROORGANISMS); EUKARYOTA; NEGIBACTERIA;

EID: 84861234759     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-012-5839-4     Document Type: Article

References (66)

1. Schuster M, Greenberg EP (2006) Int J Med Microbiol 296:73
2. Amara N, Mashiach R, Amar D, Krief P, Spieser SAH, Bottomley MJ, Aharoni A, Meijler MM (2009) J Am Chem Soc 131:10610
3. Boyer M, Wisniewski-Dye F (2009) FEMS Microbiol Ecol 70:1
4. Ni N, Li M, Wang J, Wang B (2009) Med Res Rev 29:65
5. Chhabra SR, Harty C, Hooi DS, Daykin M, Williams P, Telford G, Pritchard DI, Bycroft BW (2003) J Med Chem 46:97
6. Olsen JA, Severinsen R, Rasmussen TB, Hentzer M, Givskov M, Nielsen J (2002) Bioorg Med Chem Lett 12:325
7. Costerton JW, Stewart PS, Greenberg EP (1999) Science 284:1318
8. Cooley M, Chhabra SR, Williams P (2008) Chem Biol 15:1141
9. Rumbaugh KP, Griswold JA, Hamood AN (2000) Microbes Infect 2:1721
10. Hughes DT, Sperandio V (2008) Nat Rev Microbiol 6:111
11. Telford G, Wheeler D, Williams P, Tomkins PT, Appleby P, Sewell H, Stewart GSAB, Bycroft BW, Pritchard DI (1998) Infect Immun 66:36
12. Ritchie AJ, Yam AO, Tanabe KM, Rice SA, Cooley MA (2003) Infect Immun 71:4421
13. Tateda K, Ishii Y, Horikawa M, Matsumoto T, Miyairi S, Pechere JC, Standiford TJ, Ishiguro M, Yamaguchi K (2003) Infect Immun 71:5785
14. Zimmermann S, Wagner C, Muller W, Brenner-Weiss G, Hug F, Prior B, Obst U, Hansch GM (2006) Infect Immun 74:5687
15. Heit B, Tavener S, Raharjo E, Kubes P (2002) J Cell Biol 159:91
16. Ritchie AJ, Whittall C, Lazenby JJ, Chhabra SR, Pritchard DI, Cooley MA (2007) Immunol Cell Biol 85:596
17. Davis BM, Jensen R, Williams P, O'Shea P (2010) PLoS ONE 5:e13522
18. Franken PA, Hill AE, Peters CW, Weinreich G (1961) Phys Rev Lett 7:118
19. Chen X, Chen Z (2006) Biochim Biophys Acta 1758:1257
20. Liu J, Conboy JC (2004) J Am Chem Soc 126:8894
21. Liu J, Conboy JC (2004) J Am Chem Soc 126:8376
22. Chen X, Wang J, Boughton AP, Kristalyn CB, Chen Z (2007) J Am Chem Soc 129:1420
23. Chen X, Wang J, Kristalyn CB, Chen Z (2007) Biophys J 93:866
24. Verreault D, Kurz V, Howell C, Koelsch P (2010) Rev Sci Instrum 81:063111
25. Chhabra SR, Stead P, Bainton NJ, Salmond GP, Stewart GS, Williams P, Bycroft BW (1993) J Antibiot (Tokyo) 46:441
26. Dekhane M, Douglas KT, Gilbert P (1996) Tetrahedron Lett 37:1883
27. Dubinsky L, Jarosz LM, Amara N, Krief P, Kravchenko VV, Krom BP, Meijler MM (2009) Chem Commun (Camb): 7378
28. Yajima A, van Brussel AAN, Schripsema J, Nukada T, Yabuta G (2008) Org Lett 10:2047
29. Thiel V, Kunze B, Verma P, Wagner-Dobler I, Schulz S (2009) ChemBioChem 10:1861
30. Bainton NJ, Stead P, Chhabra SR, Bycroft BW, Salmond GPC, Stewart GSAB, Williams P (1992) Biochem J 288(Pt 3):997
31. Kai K, Tani A, Hayashi H (2010) Bioorg Med Chem 18:3776
32. Gould TA, Herman J, Krank J, Murphy RC, Churchill MEA (2006) J Bacteriol 188:773
33. Wang Q, Liu L, Lin C, Sun H, Zhang WX, Xi Z (2009) Dalton Trans: 10433
34. Durazo A, Abu-Omar MM (2002) Chem Commun (Camb): 66
35. Merck E (1974) Dyeing reagents for thin layer and paper chromatography. Merck, Darmstadt
36. Lagutchev A, Hambir SA, Dlott DD (2007) Phys Chemistry Lett C 111:13645
37. Dirac PAM (1929) Proc Royal Soc A 123:714
38. Lee C, Yang W, Parr RG (1988) Phys Rev B Condens Matter 37:785
39. Becke AD (1993) J Chem Phys 98:5648
40. Hellweg A, Hattig C, Hofener S, Klopper W (2007) Theor Chem Acc 117:587
41. Weigend F, Kohn A, Hattig C (2002) J Chem Phys 116:3175
42. Turbomole V6.3 (2011) A development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH-, TURBOMOLE GmbH s (2011) Turbomole V6.3, www.turbomole.com
43. van Wullen C (2011) J Comput Chem 32:1195
44. Johnson RDI (2011) Computational chemistry comparison and benchmark database, NIST Standard Reference Database Number 101, Release 15b, http://cccbdb.nist.gov/
45. Schaftenaar G, Noordik JH (2000) J Comput Aided Mol Des 14:123
46. Cramer CJ (2006) Essentials of computational chemistry. Wiley, Chichester
47. Balabin RM (2008) J Chem Phys 129:164101
48. Balabin RM (2011) Mol Phys 109:943
49. Moller C, Plesset MS (1934) Phys Rev 46:618
50. Klopper W, Manby FR, Ten-no S, Valeev EF (2006) Int Rev Phys Chem 25:427
51. Grimme S (2003) J Chem Phys 118:9095
52. Hattig C, Klopper W, Kohn A, Tew DP (2012) Chem Rev 112:4
53. Bachorz RA, Bischoff FA, Glos A, Hattig C, Hofener S, Klopper W, Tew DP (2011) J Comput Chem 32:2492
54. Peterson KA, Adler TB, Werner HJ (2008) J Chem Phys 128:084102
55. Yousaf KE, Peterson KA (2008) J Chem Phys 129:184108
56. Hattig C (2005) Phys Chem Chem Phys 7:59
57. Weigend F, Haser M, Patzelt H, Ahlrichs R (1998) Chem Phys Lett 294:143
58. 20 20 values are in accordance with the literature: (a) Geske GD, Wezeman RJ, Siegel AP, Blackwell HE (2005) J Am Chem Soc 127:12762;
59. (b) Pomini AM, Marsaioli AJ (2008) J Nat Prod 71:1032
60. Raman spectra are in accordance with the literature: (a) Mayo DW, Miller FA, Hannah RW (2004) Course notes on the interpretation of infrared and raman spectra. John Wiley & Sons, Ltd, Chichester
61. (b) Silverstein RM, Webster FX, Kiemle DJ (2005) Spectrometric identification of organic compounds. Wiley, Chichester
62. Thomas GL, Bohner CM, Williams HE, Walsh CM, Ladlow M, Welch M, Bryant CE, Spring DR (2006) Mol Biosyst 2:132
63. Sundh M, Sofia S, Duncan SS (2010) Phys Chem Chem Phys 12:453
64. Maibaum J, Rich DH (1989) J Med Chem 32:1571
65. Vogiatzis KD, Mavrandonakis A, Klopper W, Froudakis GE (2009) ChemPhysChem 10:374
66. Grimme S (2006) Angew Chem Int Ed 118:4571