Computational insights into octyl-D-xyloside isomers towards understanding the liquid crystalline structure: physico-chemical features

References

• Hautier G, Ong SP, Jain A, et al. Accuracy of density functional theory in predicting formation energies of ternary oxides from binary oxides and its implication on phase stability. Phys Rev B. 2012;85:155208. DOI:10.1103/PhysRevB.85.155208.
   Web of Science ®Google Scholar
• Bayach I, Sancho-García JC, Di Meo F, et al. π-Stacked polyphenolic dimers: a case study using dispersion-corrected methods. Chem Phys Lett. 2013;578:120–125. DOI:10.1016/j.cplett.2013.05.064.
   Web of Science ®Google Scholar
• Zoran S, Marković SVM. Electrochemical and density functional theory study on the reactivity of fisetin and its radicals: implications on in vitro antioxidant activity. J Phys Chem A. 2009;113:14170–14179. DOI:10.1021/jp907071v.
   PubMed Web of Science ®Google Scholar
• Anouar EH, Raweh S, Bayach I, et al. Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action. J Comput Aided Mol Des. 2013;27:951–964. DOI:10.1007/s10822-013-9692-0.
   PubMed Web of Science ®Google Scholar
• Sancho-García JC, Adamo C, Pérez-Jiménez AJ. Describing excited states of [n] cycloparaphenylenes by hybrid and double-hybrid density functionals: from isolated to weakly interacting molecules. Theor Chem Acc. 2016;135:1–12. DOI:10.1007/s00214-015-1778-4.
   Web of Science ®Google Scholar
• Vill V, Hashim R. Carbohydrate liquid crystals: structure - property relationship of thermotropic and lyotropic glycolipids. Curr Opin Colloid Interface Sci. 2002;7:395–409. DOI:10.1016/S1359-0294(02)00091-2.
   Web of Science ®Google Scholar
• Hoekstra FA, Golovina EA. The role of amphiphiles. Comp Biochem Physiol Mol Integr Physiol. 2002;131:527–533. DOI:10.1016/S1095-6433(01)00504-9.
   PubMed Web of Science ®Google Scholar
• Miethchen R, Faltin F. Aniphiphilic and mesogenic carbohydrates. 10. Change of the type of the mesophase by variation of the acyl chain of amphiphilic tetradecyl (N-acylamino)-2-deoxy-1-thio-β-D-glucopyranosides. J Prakt Chem Chem Ztg. 1998;340:544–550. DOI:10.1002/prac.19983400607.
   Google Scholar
• Hashim R, Mirzadeh SM, Heidelberg T, et al. A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies. Carbohydr Res. 2011;346:2948–2956. DOI:10.1016/j.carres.2011.10.032.
   PubMed Web of Science ®Google Scholar
• Deutschmann R, Dekker RFH. From plant biomass to bio-based chemicals: latest developments in xylan research. Biotechnol Adv. 2012;30:1627–1640. DOI:10.1016/j.biotechadv.2012.07.001.
   PubMed Web of Science ®Google Scholar
• Liew CY, Salim M, Zahid NI, et al. Biomass derived xylose Guerbet surfactants: thermotropic and lyotropic properties from small-angle X-ray scattering. RSC Adv. 2015;5:99125–99132. DOI:10.1039/C5RA17828B.
   Web of Science ®Google Scholar
• Papadopoulou E, Hatjiissaak A, Estrine B, et al. Novel use of biomass derived alkyl-xylosides in wetting agent for paper impregnation suitable for the wood-based industry. Eur J Wood Wood Prod. 2010;69:579–585. DOI:10.1007/s00107-010-0513-z.
   Web of Science ®Google Scholar
• Xu W, Osei-Prempeh G, Lema C, et al. Synthesis, thermal properties, and cytotoxicity evaluation of hydrocarbon and fluorocarbon alkyl β-D-xylopyranoside surfactants. Carbohydr Res. 2012;349:12–23. DOI:10.1016/j.carres.2011.11.020.
   PubMed Web of Science ®Google Scholar
• Kotena ZM, Behjatmanesh–Ardakani R, Hashim R. The interaction between sugar-based surfactant with zigzag single-walled carbon nanotubes: insight from a computational study. Liq Cryst. 2015;42:158–166. DOI:10.1080/02678292.2014.974082.
   Web of Science ®Google Scholar
• Faivre V, Rosilio V. Interest of glycolipids in drug delivery: from physicochemical properties to drug targeting. Expert Opin Drug Deliv. 2010;7:1031–1048. DOI:10.1517/17425247.2010.511172.
   PubMed Web of Science ®Google Scholar
• Garidel P, Kaconis Y, Heinbockel L, et al. Self-organisation, thermotropic and lyotropic properties of glycolipids related to their biological implications. Open Biochem J. 2015;9:49–72. DOI:10.2174/1874091X01509010049.
   PubMedGoogle Scholar
• Cortés-Sánchez AJ, Hernández-Sánchez H, Jaramillo-Flores ME. Biological activity of glycolipids produced by microorganisms: new trends and possible therapeutic alternatives. Microbiol Res. 2013;168:22–32. DOI:10.1016/j.micres.2012.07.002.
   PubMed Web of Science ®Google Scholar
• Lourith N, Kanlayavattanakul M. Natural surfactants used in cosmetics: glycolipids. Int J Cosmet Sci. 2009;31:255–261. DOI:10.1111/j.1468-2494.2009.00493.x.
   PubMedGoogle Scholar
• Kitamoto D, Isoda H, Nakahara T. Functions and potential applications of glycolipid biosurfactants - from energy-saving materials to gene delivery carriers. J Biosci Bioeng. 2002;94:187–201. DOI:10.1016/S1389-1723(02)80149-9.
   PubMed Web of Science ®Google Scholar
• Fukuoka T, Mortta T, Imura T, et al. Functional development of glycolipid biosurfactants. Kobunshi. 2011;60:753–754.
   Google Scholar
• Cox TM. Future perspectives for glycolipid research in medicine. Philos Trans R Soc B Biol Sci. 2003;358:967–973. DOI:10.1098/rstb.2003.1270.
   PubMed Web of Science ®Google Scholar
• Inès M, Dhouha G. Glycolipid biosurfactants: potential related biomedical and biotechnological applications. Carbohydr Res. 2015;416:59–69. DOI:10.1016/j.carres.2015.07.016.
   PubMed Web of Science ®Google Scholar
• Morita T, Fukuoka T, Imura T, et al. Production of mannosylerythritol lipids and their application in cosmetics. Appl Microbiol Biotechnol. 2013;97:4691–4700. DOI:10.1007/s00253-013-4858-1.
   PubMed Web of Science ®Google Scholar
• Abou Zied OK, Hashim RB, Timimi BA. Amphitropic liquid crystal phases from polyhydroxy sugar surfactants: fundamental studies. Proc SPIE 9338 Colloidal Nanoparticles Biomed Appl X. 2015;9338:933818–1.
   Google Scholar
• Salim M, Zahid NI, Liew CY, et al. Cubosome particles of a novel Guerbet branched chain glycolipid. Liq Cryst. 2016;43:168–174. DOI:10.1080/02678292.2015.1085104.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, revision A. 1. Wallingford, CT: Gaussian; 2009.
   Google Scholar
• Neese F. The ORCA program system. Wiley Interdiscip Rev Comput Mol Sci. 2012;2:73–78. DOI:10.1002/wcms.81.
   Web of Science ®Google Scholar
• Biegler-König F, Schönbohm J. Update of the AIM2000-program for atoms in molecules. J Comput Chem. 2002;23:1489–1494. DOI:10.1002/jcc.v23:15.
   PubMed Web of Science ®Google Scholar
• Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev. 1988;88:899–926. DOI:10.1021/cr00088a005.
   Web of Science ®Google Scholar
• Runge E, Gross EKU. Density-functional theory for time-dependent systems. Phys Rev Lett. 1984;52:997–1000. DOI:10.1103/PhysRevLett.52.997.
   Web of Science ®Google Scholar
• Sinnecker S, Rajendran A, Klamt A, et al. Calculation of solvent shifts on electronic g-tensors with the conductor-like screening model (COSMO) and its self-consistent generalization to real solvents (direct COSMO-RS). J Phys Chem A. 2006;110:2235–2245. DOI:10.1021/jp056016z.
   PubMed Web of Science ®Google Scholar
• Grimme S. Accurate description of van der Waals complexes by density functional theory including empirical corrections. J Comput Chem. 2004;25:1463–1473. DOI:10.1002/(ISSN)1096-987X.
   PubMed Web of Science ®Google Scholar
• Grimme S. Density functional theory with London dispersion corrections. Wiley Interdiscip Rev Comput Mol Sci. 2011 Mar;1:211–228. DOI:10.1002/wcms.30.
   Web of Science ®Google Scholar
• Dennington R, Keith T, Millam J. GaussView, version 5. Shawnee Mission, KS: Semichem Inc; 2009.
   Google Scholar
• Humphrey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J Mol Graph. 1996;14:33–38, 27–28. DOI:10.1016/0263-7855(96)00018-5.
   PubMedGoogle Scholar
• Nethercot J. Molecular dipole moments and electronegativity. Chem Phys Lett. 1978;59:346–350. DOI:10.1016/0009-2614(78)89109-X.
   Web of Science ®Google Scholar
• Reichardt C, Welton T. Solvents and solvent effects in organic chemistry. John Wiley & Sons; 2011.
   Google Scholar
• Silvestrelli PL, Parrinello M. Water molecule dipole in the gas and in the liquid phase. Phys Rev Lett. 1999;82:3308–3311. DOI:10.1103/PhysRevLett.82.3308.
   Web of Science ®Google Scholar
• Seddon JM. Lyotropic phase behaviour of biological amphiphiles. Berichte Bunsenges Für Phys Chem. 1996;100:380–393. DOI:10.1002/bbpc.19961000324.
   Web of Science ®Google Scholar
• Minamikawa H, Hato M. Reverse micellar cubic phase in a phytanyl-chained glucolipid/water system. Langmuir. 1998;14:4503–4509.
   Web of Science ®Google Scholar
• Seddon JM, Robins J, Gulik-Krzywicki T, et al. Inverse micellar phases of phospholipids and glycolipids. Invited Lecture Phys Chem Chem Phys. 2000;2:4485–4493. DOI:10.1039/b004916f.
   Web of Science ®Google Scholar
• Luzzati V, Vargas R, Gulik A, et al. Lipid polymorphism: a correction. The structure of the cubic phase of extinction symbol Fd– consists of two types of disjointed reverse micelles embedded in a three-dimensional hydrocarbon matrix. Biochemistry (Mosc.). 1992;31:279–285. DOI:10.1021/bi00116a038.
   Web of Science ®Google Scholar
• Yaghmur A, de Campo L, Salentinig S, et al. Oil-loaded monolinolein-based particles with confined inverse discontinuous cubic structure (Fd3m). Langmuir. 2006;22:517–521. DOI:10.1021/la052109w.
   PubMed Web of Science ®Google Scholar
• Corti M, Cantù L, Brocca P, et al. Self-assembly in glycolipids. Curr Opin Colloid Interface Sci. 2007;12:148–154. DOI:10.1016/j.cocis.2007.05.002.
   Web of Science ®Google Scholar
• Manna M, Róg T, Vattulainen I. The challenges of understanding glycolipid functions: an open outlook based on molecular simulations. Biochim Biophys Acta Mol Cell Biol Lipids. 2014;1841:1130–1145. DOI:10.1016/j.bbalip.2013.12.016.
   PubMed Web of Science ®Google Scholar
• Brooks NJ, Hamid HAA, Hashim R, et al. Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain β-D-glucosides. Liq Cryst. 2011;38:1725–1734. DOI:10.1080/02678292.2011.625689.
   Web of Science ®Google Scholar
• Zahid NI, Conn CE, Brooks NJ, et al. Investigation of the effect of sugar stereochemistry on biologically relevant lyotropic phases from branched-chain synthetic glycolipids by small-angle X-ray scattering. Langmuir. 2013;29:15794–15804. DOI:10.1021/la4040134.
   PubMed Web of Science ®Google Scholar
• Róg T, Vattulainen I, Bunker A, et al. Glycolipid membranes through atomistic simulations: effect of glucose and galactose head groups on lipid bilayer properties. J Phys Chem B. 2007;111:10146–10154. DOI:10.1021/jp0730895.
   PubMed Web of Science ®Google Scholar
• Achari VM, Nguan HS, Heidelberg T, et al. Molecular dynamics study of anhydrous lamellar structures of synthetic glycolipids: effects of chain branching and disaccharide headgroup. J Phys Chem B. 2012;116:11626–11634. DOI:10.1021/jp302292s.
   PubMed Web of Science ®Google Scholar
• Kotena ZM, Behjatmanesh–Ardakani R, Hashim R. AIM and NBO analyses on hydrogen bonds formation in sugar-based surfactants (α/β-d-mannose and n-octyl-α/β-d-mannopyranoside): a density functional theory study. Liq Cryst. 2014;41:784–792. DOI:10.1080/02678292.2014.886731.
   Web of Science ®Google Scholar
• Mosapour Kotena Z, Behjatmanesh-Ardakani R, Hashim R, et al. Hydrogen bonds in galactopyranoside and glucopyranoside: a density functional theory study. J Mol Model. 2013;19:589–599. DOI:10.1007/s00894-012-1576-z.
   PubMed Web of Science ®Google Scholar
• Gillespie RJ, Johnson SA. Study of bond angles and bond lengths in disiloxane and related molecules in terms of the topology of the electron density and its laplacian. Inorg Chem. 1997;36:3031–3039. DOI:10.1021/ic961381d.
   PubMed Web of Science ®Google Scholar
• Bader RFW, Essén H. The characterization of atomic interactions. J Chem Phys. 1984;80:1943–1960. DOI:10.1063/1.446956.
   Web of Science ®Google Scholar
• Gatti C. Modern charge-density analysis. Springer Science & Business Media; 2012.
   Google Scholar
• Nazari F, Doroodi Z. The substitution effect on heavy versions of cyclobutadiene. Int J Quantum Chem. 2010;110:1514–1528.
   Web of Science ®Google Scholar
• Bader RFW. A quantum theory of molecular structure and its applications. Chem Rev. 1991;91:893–928. DOI:10.1021/cr00005a013.
   Web of Science ®Google Scholar
• Manolopoulos DE, May JC, Down SE. Theoretical studies of the fullerenes: C34 to C70. Chem Phys Lett. 1991;181:105–111. DOI:10.1016/0009-2614(91)90340-F.
   Web of Science ®Google Scholar
• Pearson RG. The electronic chemical potential and chemical hardness. J Mol Struct THEOCHEM. 1992;255:261–270. DOI:10.1016/0166-1280(92)85014-C.
   Google Scholar
• Parr RG, Szentpály LV, Liu S. Electrophilicity index. J Am Chem Soc. 1999;121:1922–1924. DOI:10.1021/ja983494x.
   Web of Science ®Google Scholar
• Moro S, Bacilieri M, Ferrari C, et al. Autocorrelation of molecular electrostatic potential surface properties combined with partial least squares analysis as alternative attractive tool to generate ligand-based 3D-QSARs. Curr Drug Discov Technol. 2005;2:13–21. DOI:10.2174/1570163053175439.
   PubMedGoogle Scholar
• Weiner PK, Langridge R, Blaney JM, et al. Electrostatic potential molecular surfaces. Proc Natl Acad Sci U S A. 1982;79:3754–3758. DOI:10.1073/pnas.79.12.3754.
   PubMed Web of Science ®Google Scholar
• Abou-Zied OK, Zahid NI, Khyasudeen MF, et al. Detecting local heterogeneity and ionization ability in the head group region of different lipidic phases using modified fluorescent probes. Sci Rep. 2015;5:8699. DOI:10.1038/srep08699.
   PubMed Web of Science ®Google Scholar
• Murray CB, Kagan CR, Bawendi MG. Self-organization of CdSe nanocrystallites into three-dimensional quantum dot superlattices. Science. 1995;270:1335–1338. DOI:10.1126/science.270.5240.1335.
   Web of Science ®Google Scholar