mycosubtilin; iturin; surfactin; lipopeptide; antifungal; surface; air-water interface; monolayer; molecular dynamics; GroMacs; modelisation; second harmonic generation; non linear optics; Martini
Résumé :
[en] Monolayers of the lipopeptide mycosubtilin are studied at the air/water interface. Their structure is investigated using molecular dynamics simulations. All-atom models suggest that the lipopeptide is flexible and aggregates at the interface. To achieve simulation times of several microseconds, a coarse-grained (CG) model based on the MARTINI force field was also used. These CG simulations describe the formation of half-micelles at the interface for surface densities up to 1 lipopeptide per nm2. In these aggregates, the tyrosine side chain orientation is found to be constrained: on average, its main axis, as defined along the C–OH bond, aligns along the interface normal and points towards the air side. The origin of the optical second harmonic generation (SHG) from mycosubtilin monolayers at the air/water interface is also investigated. The molecular hyperpolarizability of the lipopeptide is obtained from quantum chemistry calculations. The tyrosine side chain contribution to the hyperpolarizability is found to be dominant. The orientation distribution of tyrosine, associated with a dominant hyperpolarizability component along the C–OH bond of the tyrosine, yields a ratio of the susceptibility elements χ(2)ZZZ/χ(2)ZXX consistent with the experimental measurements recently reported by M. N. Nasir et al. [Phys. Chem. Chem. Phys., 2013, 15, 19919].
Disciplines :
Biochimie, biophysique & biologie moléculaire
Auteur, co-auteur :
Loison, Claire
Nasir, Mehmet Nail ; Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Benichou, Emmanuel
Besson, Françoise
Brevet, Pierre-François
Langue du document :
Anglais
Titre :
Multi-scale modeling of mycosubtilin lipopeptides at the air/water interface: structure and optical second harmonic generation
A. Makovitzki D. Avrahami Y. Shai Proc. Natl. Acad. Sci. U. S. A. 2006 103 15997 16002
A. Makovitzki J. Baram Y. Shai Biochemistry 2008 47 10630 10636
R. H. Baltz V. Miao S. K. Wrigley Nat. Prod. Rep. 2005 22 717 741
Y. Shai Biochim. Biophys. Acta, Biomembr. 1999 1462 55 70
J. N. Horn J. D. Sengillo D. Lin T. D. Romo A. Grossfield Biochim. Biophys. Acta, Biomembr. 2012 1818 212 218
S. K. Straus R. E. Hancock Biochim. Biophys. Acta, Biomembr. 2006 1758 1215 1223
S. Buchoux J. Lai-Kee-Him M. Garnier P. Tsan F. Besson A. Brisson E. J. Dufourc Biophys. J. 2008 95 3840 3849
L. Volpon F. Besson J. lancelin Eur. J. Biochem. 1999 264 200 210
R. Maget-Dana F. Peypoux Toxicology 1994 87 151 174
P. Jacques, Surfactin and Other Lipopeptides from Bacillus spp., Springer, Berlin Heidelberg, 2011, vol. 20, pp. 57-91
P. Fickers J. S. Guez C. Damblon V. Leclère M. Béchet P. Jacques B. Joris Appl. Environ. Microbiol. 2009 75 4636 4640
F. Besson F. Peypoux G. Michel FEBS Lett. 1978 90 36 40
F. Peypoux F. Besson G. Michel L. Delcambe J. Antibiot. 1979 32 136 140
F. Besson F. Peypoux G. Michel L. Delcambe J. Antibiot. 1979 32 828 833
F. Besson F. Peypoux M. Quentin G. Michel J. Antibiot. 1984 37 172 177
F. Besson M. Quentin G. Michel Microbios 1989 59 137 143
M. N. Nasir A. Thawani A. Kouzayha F. Besson Colloids Surf., B 2010 78 17 23
M. N. Nasir F. Besson Langmuir 2011 27 10785 10792
M. N. Nasir F. Besson Biochim. Biophys. Acta 2012 1818 1302 1308
M. N. Nasir E. Benichou C. Loison I. Russier-Antoine F. Besson P.-F. Brevet Phys. Chem. Chem. Phys. 2013 15 19919 19924
R. W. Boyd, Nonlinear Opt., Academic World Press, 2nd edn, 1984
Y. R. Shen Annu. Rev. Phys. Chem. 1989 40 327 350
K. B. Eisenthal Chem. Rev. 1996 96 1343 1360
J. S. Salafsky B. Cohen J. Phys. Chem. B 2008 112 15103 15107
S. G. Grubb M. W. Kim T. Rasing Y. R. Shen Langmuir 1988 4 452 454
G. Matar J. Duboisset E. Benichou G. Bachelier I. Russier-Antoine C. Jonin D. Ficheux P.-F. Brevet F. Besson Chem. Phys. Lett. 2010 500 161 166
A. A. Tamburello-Luca P. Hébert P. F. Brevet H. H. Girault Phys. Chem. Chem. Phys. 1996 92 3079 3085
P.-F. Brevet, Surface Second Harmonic Generation, PPUR Presses Polytechniques, 1997
F. Eisert O. Dannenberger M. Buck Phys. Rev. B: Condens. Matter Mater. Phys. 1998 58 10860 10870
S. A. Mitchell R. A. Mcaloney J. Phys. Chem. B 2004 108 1020 1029
F. Terenziani O. Mongin C. Katan B. K. G. Bhatthula M. Blanchard-Desce Chem.-Eur. J. 2006 12 3089 3102
S. A. Mitchell J. Phys. Chem. B 2009 113 10693 10707
J. Duboisset G. Matar I. Russier-Antoine E. Benichou G. Bachelier C. Jonin D. Ficheux F. Besson P. F. Brevet J. Phys. Chem. B 2010 114 13861 13865
J. Guthmuller D. Simon J. Phys. Chem. A 2006 110 9967 9973
C. Loison D. Simon J. Phys. Chem. A 2010 114 7769 7779
R. Mereau F. Castet E. Botek B. Champagne J. Phys. Chem. A 2009 113 6552 6554
N. A. Murugan J. Kongsted Z. Rinkevicius H. Ågren Proc. Natl. Acad. Sci. U. S. A. 2010 107 16453 16458
N. A. Murugan R. Apostolov Z. Rinkevicius J. Kongsted E. Lindahl H. Ågren J. Am. Chem. Soc. 2013 13590 13597
A. J. Rzepiela D. Sengupta N. Goga S. J. Marrink Faraday Discuss. 2009 144 431
P. J. Bond J. Holyoake A. Ivetac S. Khalid M. S. P. Sansom J. Struct. Biol. 2007 157 593 605
J. Bonmatin M. Genest H. Labbé M. Ptak Biopolymers 1994 34 975 986
M. Genest D. Marion M. Ptak J. Biomol. Struct. Dyn. 1985 2 849 857
D. Marion M. Genest A. Caille F. Peypoux G. Michel M. Ptak Biopolymers 1986 25 153 170
M. Genest D. Marion A. Caille M. Ptak Eur. J. Biochem. 1987 169 389 398
X. Gallet M. Deleu H. Razafindralambo P. Jacques P. Thonart M. Paquot R. Brasseur Langmuir 1999 15 2409 2413
J.-M. Bonmatin O. Laprevote F. Peypoux Comb. Chem. High Throughput Screening 2003 6 541 556
J. P. Nicolas Biophys. J. 2003 85 1377 1391
M. Deleu O. Bouffioux H. Razafindralambo M. Paquot C. Hbid P. Thonart P. Jacques R. Brasseur Langmuir 2003 19 3377 3385
P. Tsan L. Volpon F. Besson J.-M. Lancelin J. Am. Chem. Soc. 2007 129 1968 1977
H.-Z. Gang J.-F. Liu B.-Z. Mu J. Phys. Chem. B 2010 114 2728 2737
H.-Z. Gang J.-F. Liu B.-Z. Mu J. Phys. Chem. B 2011 115 12770 12777
S. J. Marrink H. J. Risselada S. Yefimov D. P. Tieleman A. H. de Vries J. Phys. Chem. B 2007 111 7812 7824
L. Monticelli S. K. Kandasamy X. Periole R. G. Larson D. P. Tieleman S.-J. Marrink J. Chem. Theory Comput. 2012 4 819 834
A. D. Mackerell D. Bashford M. Bellot R. L. Dunbrack J. D. Evanseck M. J. Field S. Fischer J. Gao H. Guo S. Ha D. Joseph-McCarthy L. Kuchnir K. Kuczera F. T. K. Lau C. Mattos S. Michnick T. Ngo D. T. Nguyen B. Prodhom W. E. Reiher B. Roux M. Schlenkrich J. C. Smith R. Stote J. Straub M. Watanabe J. Wiórkiewicz-Kuczera D. Yin M. Karplus J. Phys. Chem. B 1998 102 3586 3616
A. D. MacKerell M. Feig C. L. Brooks J. Am. Chem. Soc. 2004 126 698 699
S. E. Feller A. D. MacKerell J. Phys. Chem. B 2000 104 7510 7515
X. Zhu P. Koenig M. Hoffmann A. Yethiraj Q. Cui J. Comput. Chem. 2010 31 2063 2077
J. C. Phillips R. Braun W. Wang J. Gumbart E. Tajkhorshid E. Villa C. Chipot R. D. Skeel L. Kalé K. Schulten J. Comput. Chem. 2005 26 1781 1802
A. Patriksson D. van der Spoel Phys. Chem. Chem. Phys. 2008 10 2073 2077
Y. Sugita A. Kitao Y. Okamoto J. Chem. Phys. 2000 113 6042
D. E. Tanner K.-Y. Chan J. C. Phillips K. Schulten J. Chem. Theory Comput. 2011 7 3635 3642
X. Daura K. Gademann B. Jaun D. Seebach W. F. van Gunsteren A. E. Mark Angew. Chem., Int. Ed. 1999 38 236 240
B. Hess C. Kutzner D. van der Spoel E. Lindahl J. Chem. Theory Comput. 2008 4 435 447
M. Venturoli M. Maddalena Sperotto M. Kranenburg B. Smit Phys. Rep. 2006 437 1 54
F. Schmid, Lect. Notes Phys., Springer Verlag, Berlin, 2006, p. 211
G. Colombo P. Soto E. Gazit Trends Biotechnol. 2007 25 211 218
T. Bereau M. Deserno J. Chem. Phys. 2009 130 235106
S. Takada Curr. Opin. Struct. Biol. 2012 22 130 137
S. Riniker J. R. Allison W. F. van Gunsteren Phys. Chem. Chem. Phys. 2012 14 12423 12430
E. Brini E. A. Algaer P. Ganguly C. Li Soft Matter 2013 9 2108 2119
D. H. de Jong G. Singh W. F. D. Bennett C. Arnarez T. A. Wassenaar L. V. Schäfer X. Periole D. P. Tieleman S. J. Marrink J. Chem. Theory Comput. 2013 9 687 697
J. L. MacCallum W. F. D. Bennett D. P. Tieleman J. Gen. Physiol. 2007 129 371 377
X. Periole M. Cavalli S.-J. Marrink M. A. Ceruso J. Chem. Theory Comput. 2009 5 2531 2543
S. J. Marrink D. P. Tieleman Chem. Soc. Rev. 2013 42 6801 6822
W. Humphrey A. Dalke K. Schulten J. Mol. Graphics 1996 14 33 38
G. te Velde F. M. Bickelhaupt E. J. Baerends C. Fonseca Guerra S. J. A. van Gisbergen J. G. Snijders T. Ziegler J. Comput. Chem. 2001 22 931 967
C. Fonseca Guerra J. G. Snijders G. te Velde E. J. Baerends Theor. Chem. Acc. 1998 99 391 403
S. J. A. van Gisbergen J. G. Snijders E. J. Baerends J. Chem. Phys. 1998 109 10644 10656
P. R. T. Schipper O. V. Gritsenko S. J. A. van Gisbergen E. J. Baerends J. Chem. Phys. 2000 112 1344 1352
S. J. A. van Gisbergen V. P. Osinga O. V. Gritsenko R. van Leeuwen J. G. Snijders E. J. Baerends J. Chem. Phys. 1996 105 3142 3151
A. Willetts J. E. Rice D. M. Burland D. P. Shelton J. Chem. Phys. 1992 97 7590 7599
A. Alparone Comput. Theor. Chem. 2011 976 188 190
A. Alparone Phys. Chem. Chem. Phys. 2013 15 12958
F. Besson R. Buchet Spectrochim. Acta, Part A 1997 53 1913 1923
H.-H. Shen R. K. Thomas C.-Y. Chen R. C. Darton S. C. Baker J. Penfold Langmuir 2009 25 4211 4218
J. N. Israelachvili, Intermolecular and Surface Forces, 3rd edn, 2011
D. F. Evans and H. Wennerström, The Colloidal Domain: Where Physics, Chemistry, Biology, and Technology Meet, Wiley, 1999
A. Deniset-Besseau J. Duboisset E. Benichou F. Hache P.-F. Brevet M.-C. Schanne-Klein J. Phys. Chem. B 2009 113 13437 13445
G. Megariotis A. Avramopoulos M. G. Papadopoulos H. Reis J. Phys. Chem. C 2012 116 15449 15457
