Modelling of Congo red adsorption on the hydrophobic surface of cellulose using molecular dynamics

Cellulose

Volumn 19, Issue 5, 2012, Pages 1495-1506

  Mazeau, Karim ^a   Wyszomirski, Miroslaw ^b  

^a CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^b UNIVERSITY OF BIELSKO BIALA   (Poland)

Author keywords

Adsorption; Cellulose hydrophobic surface; Congo red; Molecular modelling

Indexed keywords

CELLULOSE CHAIN; CELLULOSE SURFACES; CONGO RED; CRYSTALLINE CELLULOSE; DIRECT DYES; DYE ADSORPTION; DYE MOLECULE; EXPLICIT WATER; GEOMETRIC FEATURE; HYDROPHOBIC SURFACES; IN-VACUUM; INITIAL POSITION; LONG AXIS; MICROFIBRIL; MOLECULAR DYNAMICS SIMULATIONS; RELATIVE POSITIONS; STABLE ADSORPTION;

ADSORPTION; AZO DYES; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR MODELING; MOLECULES; SURFACE CHEMISTRY; VACUUM;

CELLULOSE;

EID: 84865416363     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-012-9757-6     Document Type: Article

References (50)

1. Alves-Santos M, Davila LYA, Petrilli HM, Capaz RB, Caldas MJ (2006) Application of standard DFT theory for nonbonded interactions in soft matter: prototype study of poly-para-phenylene. J Comput Chem 27: 217-227.
2. Baker AA, Helbert W, Sugiyama J, Miles MJ (1997) High-resolution atomic force microscopy of native Valonia cellulose I microcrystals. J Struct Biol 119: 129-138.
3. Baker AA, Helbert W, Sugiyama J, Miles MJ (2000) New insight into cellulose structure by atomic force microscopy shows the Iα crystal phase at near-atomic resolution. Biophys J 79: 1139-1145.
4. Bird J, Brough N, Dixon S, Batchelor SN (2006) Understanding adsorption phenomena: investigation of the dye-cellulose interaction. J Phys Chem B 110: 19557-19561.
5. Burdett BC (1983) In: Whyn-Jones E, Gormally J (eds) Aggregation processes in solution. Elsevier, Amsterdam.
6. Da Silva Perez D, Ruggiero R, Morais LC, Machado AEH, Mazeau K (2004) Theoretical and experimental studies on the adsorption of aromatic compounds onto cellulose. Langmuir 20: 3151-3158.
7. Diaz MD, Fernadez-Alonso MC, Cuevas G, Canada FJ, Jimenez-Barbero J (2008) On the role of aromatic-sugar interactions in the molecular recognition of carbohydrates: a 3D view by using NMR. Pure Appl Chem 80: 1827-1835.
8. Dickerson RE (1989) Definitions and nomenclature of nucleic acid structure parameters. J Biomol Struc Dynamics 6: 627-634.
9. Fennell CJ, Kehoe CW, Dill KA (2011) Modeling aqueous solvation with semi-explicit assembly. Proc Natl Acad Sci USA 108: 3234-3239.
10. Fernandes NA, Thomas LH, Altaner CM, Callow P, Forsyth VT, Apperley DC, Kennedy CJ, Jarvis MC (2011) Nanostructure of cellulose microfibrils in spruce wood. Proc Natl Acad Sci USA 108: E1195-E1203.
11. Helbert W, Nishiyama Y, Okano T, Sugiyama J (1998) Molecular imaging of Halocynthia papillosa cellulose. J Struct Biol 124: 42-50.
12. Hillson PJ, McKay RB (1965) Aggregation of dye molecules in aqueous solution. A polarographic study. T Faraday Soc 61: 374-382.
13. Inglesby MK, Zeronian SH (2002) Direct dyes as molecular sensors to characterize cellulose substrates. Cellulose 9: 19-29.
14. Kalashnikova I, Bizot H, Cathala B, Capron I (2012) Modulation of cellulose nanocrystals amphiphilic properties to stabilize oil/water interface. Biomacromolecules 13: 267-275.
15. Kim N-H, Herth W, Vuong R, Chanzy H (1996) The cellulose system in the cell wall of Micrasterias. J Struct Biol 117: 195-203.
16. Lehtiö J, Sugiyama J, Gustavsson M, Fransson L, Linder M, Teeri TT (2003) The binding specificity and affinity determinants of family 1 and family 3 cellulose binding modules. PNAS 100: 484-489.
17. Linder M, Mattinen ML, Kontelli M, Lindberg G, Ståhlberg J, Drakenberg T, Reinikainen T, Pettersson G, Annila A (1995) Identification of functionally important amino acids in the cellulose-binding domain of Trichoderma reesei cellobiohydrolase I. Protein Sci 4: 1056-1064.
18. Lye J, Freeman HS, Cox RD (2000) Molecular modeling of Congo red analogues containing terphenyl and quarterphenyl moieties. Dyes Pigm 47: 53-64.
19. Mayo SL, Olafson BD, Goddard WA III (1990) DREIDING: a generic force field for molecular simulations. J Phys Chem 94: 8897-8909.
20. Mazeau K (2011) On the external morphology of native cellulose microfibrils. Carbohydr Polym 84: 524-532.
21. Mazeau K, Charlier L (2012) The molecular basis of the adsorption of xylans on cellulose surface. Cellulose 19: 337-349.
22. Mazeau K, Rivet A (2008) Wetting the (110) and (100) surfaces of Iβ cellulose studied by molecular dynamics. Biomacromolecules 9: 1352-1354.
23. Mazeau K, Vergelati C (2002) Atomistic modeling of the adsorption of benzophenone onto cellulosic surfaces. Langmuir 18: 1919-1927.
24. Medronho B, Romano A, Miguel MG, Stigsson L, Lindman B (2012) Rationalizing cellulose (in)solubility: reviewing basic physicochemical aspects and role of hydrophobic interactions. Cellulose 19: 581-587.
25. Mohamed MNA, Watts HD, Guo J, Catchmark JM, Kubicki JD (2010) MP2, density functional theory, and molecular mechanical calculations of C-H···π and hydrogen bond interactions in a cellulose-binding module-cellulose model system. Carbohydr Res 345: 1741-1751.
26. Morton TH (1946) The dichroic behavior of substantive dyes: molecular theory of the dyeing of cellulose. J Soc Dyers Colour 62: 272-280.
27. Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron x-ray and neutron fiber diffraction. J Am Chem Soc 124: 9074-9082.
28. Nose S (1984) A unified formulation of the constant temperature molecular dynamics methods. J Chem Phys 81: 511-519.
29. Ojala WH, Ojala CR, Gleason WB (1995) The x-ray crystal structure of the sulfonated azo dye Congo red, a non-peptidic inhibitor of HIV-1 protease which also binds to reverse transcriptase and amyloid proteins. Antiv Chem Chemoth 6: 25-33.
30. Pan JF, Chua SJ, Huang W (2000) Conformational analysis on biphenyls with theoretical calculations: modeling torsions in poly(para-phenylene)s with side chains. Thin Solid Films 363: 1-5.
31. Pielesz A (2007) Spectroscopic study of interactions between model direct dyes and cotton. J Appl Polym Sci 104: 758-766.
32. Quiocho FA (1989) Protein-carbohydrate interactions: basic molecular features. Pure Appl Chem 61: 1293-1306.
33. Rappé AK, Goddard WA III (1991) Charge equilibration for molecular dynamics simulations. J Phys Chem 95: 3358-3363.
34. Reinikainen T, Teleman O, Teeri TT (1995) Effects of pH and high ionic strength on the adsorption and activity of native and mutated cellobiohydrolase I from Trichoderma reesei. Proteins 22: 392-403.
35. Revol J-F (1982) On the cross-sectional shape of cellulose crystallites in Valonia ventricosa. Carbohydr Polym 2: 123-134.
36. Screen J, Stanca-Kaposta EC, Gamblin DP, Liu B, Macleod NA, Snoek LC, Davis BG, Simons JP (2007) IR-spectral signatures of aromatic-sugar complexes: probing carbohydrate-protein interactions. Angew Chem Int Ed 46: 3644-3648.
37. Shiiba H, Hayashi S, Yui T (2012) Molecular simulation study with complex models of the carbohydrate binding module of Cel6A and the cellulose Iα crystal. Cellulose 19: 635-645.
38. Sugiyama J, Harada H, Fujiyoshi Y, Uyeda N (1985) Lattice images from ultrathin sections of cellulose microfibrils in the cell wall of Valonia macrophysa Kütz. Planta 166: 161-168.
39. Sugiyama J, Vuong R, Chanzy H (1991) Electron diffraction study on the two crystalline phases occurring in native cellulose from an algal cell wall. Macromolecules 24: 4168-4175.
40. Takei Y, Yamaguchi T, Osamura Y, Fuke K, Kaya K (1988) Electronic spectra and molecular structure of biphenyl and para-substituted biphenyls in a supersonic jet. J Phys Chem 92: 577-581.
41. Tormo J, Lamed R, Chirino AJ, Morag E, Bayer EA, Shoham Y, Steltz TA (1996) Crystal structure of a bacterial family-III cellulose-binding domain: a general mechanism for attachment to cellulose. EMBO J 15: 5739-5751.
42. Verlet L (1967) Computer experiments on classical fluids. I. Thermodynamical properties of Lennard-Jones molecules. Phys Rev 159: 98-103.
43. Viegas A, Bras NF, Cerqueira NMFSA, Fernandes PA, Prates JAM, Fontes CMGA, Bruix M, Romano MJ, Carvalho AL, Ramos MJ, Macedo AL, Cabrita EJ (2008) Molecular determinants of ligand specificity in family 11 carbohydrate binding modules-an NMR, X-ray crystallography and computational chemistry approach. FEBS J 275: 2524-2535.
44. Wälchi O (1947) Die Einlagerung von Kongorot in Zellulose. Holzforschung 1: 20-32.
45. Weis WI, Drickamer K (1996) Structural basis of lectin-carbohydrate recognition. Annu Rev Biochem 65: 441-473.
46. Wood PJ (1980) The interaction of direct dyes with water soluble substituted celluloses and cereal β-glucans. Ind Eng Chem Prod Res Dev 19: 19-23.
47. Wood PJ (1982) Factors affecting precipitation and spectral changes associated with complex-formation between dyes and β-D-glucans. Carbohydr Res 102: 283-293.
48. Woodcock S, Henrissat B, Sugiyama J (1995) Docking of Congo red to the surface of crystalline cellulose using molecular mechanics. Biopolymers 36: 201-210.
49. Xu Q, Tucker MP, Arenkiel P, Ai X, Rumbles G, Sugiyama J, Himmel ME, Ding S-Y (2009) Labeling the planar face of crystalline cellulose using quantum dots directed by type-I carbohydrate-binding modules. Cellulose 16: 19-26.
50. Yamaki SB, Barros DS, Garcia CM, Socoloski P, Oliveira ON, Atvars TDZ (2005) Spectroscopic studies of the intermolecular interactions of Congo red and Tinopal CBS with modified cellulose fibers. Langmuir 21: 5414-5420.