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Invited Article

Nature-like synthetic alkyl branched-chain glycolipids: a review on chemical structure and self-assembly properties

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Pages 1-17 | Received 19 May 2011, Accepted 09 Aug 2011, Published online: 13 Oct 2011

References

  • Dembitsky , V.M. 2004 . Lipids , 39 : 933 – 953 .
  • Ernst , B. , Hart , G.W. and Sinaÿ , P. 2000 . Carbohydrates in Chemistry and Biology , Wiley-VCH : Weinheim .
  • Baron , M. 2001 . IUPAC Recommendations Pure Appl. Chem , 73 : 845 – 895 .
  • Holmberg , K. 2001 . Curr. Opin. Colloid Interface Sci , 6 : 148 – 159 .
  • Vill , V. and Hashim , R. 2002 . Curr. Opin. Colloid Interface Sci , 7 : 395 – 409 .
  • Carriere , M. , Escriou , V. , Jollet , A. , Scherman , D. , Azoulay , M. and Monneret , C. 2004 . Drug Deliv , 11 : 351 – 363 .
  • Corti , M. , Cantù , L , Brocca , P. and Del Favero , E. 2007 . Curr. Opin. Colloid Interface Sci , 12 : 148 – 154 .
  • Lipowsky , R. 1991 . Nature , 349 : 475 – 481 .
  • Jeffrey , G.A. 1986 . Acc. Chem. Res , 19 : 168 – 173 .
  • Vill , V. , Fischer , F. and Thiem , J. 1988 . Z. Naturforsch , 43a : 1119 – 1125 .
  • Mach , P. , Pindak , R. , Levelut , A.M. , Barois , P. , Nguyen , H.T. , Baltes , H. , Hird , M. , Toyne , K. , Seed , A. , Goodby , J.W. , Huang , C.C. and Furenlid , L. 1999 . Phys. Rev. E , 60 : 6793 – 6802 .
  • Stepniewski , M. , Bunker , A. , Pasenkiewicz-Gierula , M. , Karttunen , M. and Rog , T. 2010 . J. Phys. Chem. B , 114 : 11784 – 11792 .
  • Abeygunaratne , S. , Hashim , R. and Vill , V. 2006 . Phys. Rev. E Stat. Nonlin. Soft Matter Phys , 73 ( 1–6 ) : 011916
  • Liao , G. , Zewe , S.K. , Hagerty , J. , Hashim , R. , Abeygunaratne , S. , Vill , V. and Jákli , A. 2006 . Liq. Cryst , 33 : 361 – 366 .
  • Athenstaedt , H. 1961 . Naturwissenschaften , 48 : 465 – 472 .
  • Lee , S.-W. , Wood , B.M. and Belcher , A.M. 2002 . Langmuir , 19 : 1592 – 1598 .
  • Moore , L.E. , Holt , J.P. Jr. and Lindley , B.D. 1972 . Biophys. J , 12 : 157 – 174 .
  • Tasaki , I. and Iwasa , K. 1982 . Jpn. J. Physiol , 32 : 505 – 518 .
  • Miyajima , D. , Araoka , F. , Takezoe , H. , Kim , J. , Kato , K. , Takata , M. and Aida , T. 2010 . J. Am. Chem. Soc , 132 : 8530 – 8531 .
  • Takezoe , H. 2010 . Polar order in columnar phase of glycolipids. Personal communication
  • Stoller , P. , Reiser , K.M. , Celliers , P.M. and Rubenchik , A.M. 2002 . Biophys. J , 82 : 3330 – 3342 .
  • Vill, V. LiqCryst 4.2. In Database of Thermotropic Liquid Crystals; Fukuoka: Fujitsu FQS, 2002, also available from http://liqcryst.chemie.uni-hamburg.de (http://liqcryst.chemie.uni-hamburg.de)
  • Cook , A.G. , Wardell , J.L. and Imrie , C.T. 2011 . Chem. Phys. Lipids , 164 : 118 – 124 .
  • Vill , V. , von Minden , H.M. , Koch , M.H. , Seydel , U. and Brandenburg , K. 2000 . Chem. Phys. Lipids , 104 : 75 – 91 .
  • von Minden , H.M. , Brandenburg , K. , Seydel , U. , Koch , M.H. , Garamus , V. , Willumeit , R. and Vill , V. 2000 . Chem. Phys. Lipids , 106 : 157 – 179 .
  • Shearman , G.C. , Khoo , B.J. , Motherwell , M.-L. , Brakke , K.A. , Ces , O. , Seddon , J.M. and Templer , R.H. 2007 . Langmuir , 23 : 7276 – 7285 .
  • Mannock , D.A. , Collins , M.D. , Kreichbaum , M. , Harper , P.E. , Gruner , S.M. and McElhaney , R.N. 2007 . Chem. Phys. Lipids , 148 : 26 – 50 .
  • Tschierske , C. 2002 . Curr. Opin. Colloid Interface Sci , 7 : 355 – 370 .
  • Mannock , D.A. , Akiyama , M. , Lewis , R.N. and McElhaney , R.N. 2000 . Biochim. Biophys. Acta , 1509 : 203 – 215 .
  • Mannock , D.A. , Harper , P.E. , Gruner , S.M. and McElhaney , R.N. 2001 . Chem. Phys. Lipids , 111 : 139 – 161 .
  • Mannock , D.A. , Lewis , R.N. and McElhaney , R.N. 1990 . Biochemistry , 29 : 7790 – 7799 .
  • Koynova , R. and Caffrey , M. 1994 . Chem. Phys. Lipids , 69 : 181 – 207 .
  • Hato , M. 2001 . Curr. Opin. Colloid Interface Sci , 6 : 268 – 276 .
  • Mannock , D.A. and McElhaney , R.N. 2004 . Curr. Opin. Colloid Interface Sci , 8 : 426 – 447 .
  • Mannock , D.A. , Akiyama , M. , Lewis , R.N.A.H. and McElhaney , R.N. 2000 . Biochim. Biophys. Acta Biomembr , 1509 : 203 – 215 .
  • Hato , M. and Minamikawa , H. 1996 . Langmuir , 12 : 1658 – 1665 .
  • Hato , M. , Minamikawa , H. , Tamada , K. , Baba , T. and Tanabe , Y. 1999 . Adv. Colloid Interface Sci , 80 : 233 – 270 .
  • Minamikawa , H. and Hato , M. 1997 . Langmuir , 13 : 2564 – 2571 .
  • Milkereit , G. , Gerber , S. , Brandenburg , K. , Morr , M. and Vill , V. 2005 . Chem. Phys. Lipids , 135 : 1 – 14 .
  • Nilsson , F. , Söderman , O. and Johansson , I. 1997 . Langmuir , 13 : 3349 – 3354 .
  • Hashim , R. , Hashim , H.H.A. , Rodzi , N.Z.M. , Hussen , R.S.D. and Heidelberg , T. 2006 . Thin Solid Films , 509 : 27 – 35 .
  • Heidelberg , T. , Chuan , R. , Chie , N.C. , Anwar , S.A. and Hashim , R. 2009 . Malays. J. Sci , 28 : 105 – 114 .
  • Mannock , D.A. , Lewis , R.N. , McElhaney , R.N. , Akiyama , M. , Yamada , H. , Turner , D.C. and Gruner , S.M. 1992 . Biophys. J , 63 : 1355 – 1368 .
  • Bongat , A.F. and Demchenko , A.V. 2007 . Carbohydr. Res , 342 : 374 – 406 .
  • Demchenko , A.V. , ed. 2008 . “ Front matter ” . In Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance , Weinheim , , Germany : Wiley-VCH Verlag GmbH & Co. KGaA .
  • Carmona , A.T. , Fuentes , J. , Robina , I. , Garcia , E.R. , Demange , R. , Vogel , P. and Winters , A.L. 2003 . J. Org. Chem , 68 : 3874 – 3883 .
  • Carmona , A.T. , Moreno-Vargas , A.J. , Robina , I. and Robina , I. 2008 . Curr. Org. Synth , 5 : 33 – 60 . 81 – 116 .
  • Guerbet , M. 1909 . Comptes rendus de l'Académie des sciences , 149 : 129 – 132 .
  • Matsu-ura , T. , Sakaguchi , S. , Obora , Y. and Ishii , Y. 2006 . J. Org. Chem , 71 : 8306 – 8308 .
  • O'Lenick, A.J. A review of guerbet chemistry, 1987 http://www.zenitech.com/documents/guerbet_chemistry.pdf (http://www.zenitech.com/documents/guerbet_chemistry.pdf) (Accessed: 5 November 2010 ).
  • O'Lenick Jr , A.J. and Bilbo , R.E. 1987 . Soap Cosmetics Chem. Specialities , 63 : 52 – 65 .
  • Knothe , G. 2002 . Lipid Technol , 14 : 101 – 104 .
  • Knothe , G. 2002 . Chem. Phys. Lipids , 115 : 85 – 91 .
  • Nilsson , F. , Söderman , O. and Johansson , I. 1998 . J. Colloid Interface Sci , 203 : 131 – 139 .
  • Costantino , V. , Fattorusso , E. , Mangoni , A. , Di Rosa , M. and Ianaro , A. 1999 . Bioorg. Med. Chem. Lett , 9 : 271 – 276 .
  • Hashim , H.H.A. 2004 . Synthesis and liquid crystal phase behaviour of branched chain alkylglycosides, PhD Thesis , Department Of Chemistry, Faculty Of Science, University of Malaya, Kuala Lumpur, Malaysia .
  • Rodzi , N.B.M. 2006 . Branched chain galactosides and melibiosides: synthesis and mesomorphic properties, MSc Thesis , Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur .
  • Hussen , R.S.D. 2006 . Synthesis and liquid crystalline properties of secondary and branched chain of cellobiosides and lactosides, MSc Thesis , Department Of Chemistry, Faculty Of Science, University of Malaya, Kuala Lumpur .
  • Mannock , D.A. , McElhaney , R.N. , Harper , P.E. and Gruner , S.M. 1994 . Biophys. J , 66 : 734 – 740 .
  • Turner , D.C. , Wang , Z.G. , Gruner , S.M. , Mannock , D.A. and McElhaney , R.N. 1992 . J. Phys. II France , 2 : 2039 – 2063 .
  • Seddon , J.M. 1990 . Biochim. Biophys. Acta , 1031 : 1 – 69 .
  • Galema , S.A. and Hoeiland , H. 1991 . J. Phys. Chem , 95 : 5321 – 5326 .
  • Israelachvili , J.N. , Mitchell , D.J. and Ninham , B.W. 1976 . J. Chem. Soc. Faraday Trans. II , 72 : 1525 – 1568 .
  • Nguan , H.S. , Heidelberg , T. , Hashim , R. and Tiddy , G.J.T. 2010 . Liq. Cryst , 37 : 1205 – 1213 .
  • Kozlov , M. , Leikin , S. and Rand , R.P. 1994 . Biophys. J , 66 : A299 – A299 .
  • Turner , D.C. , Wang , Z. , Gruner , S.M. , Mannock , D.A. and McElhaney , R.N. 1992 . J. Phys. II France , 2 : 2039 – 2063 .
  • Gawrisch , K. , Parsegian , V.A. , Hajduk , D.A. , Tate , M.W. , Graner , S.M. , Fuller , N.L. and Rand , R.P. 1992 . Biochemistry , 31 : 2856 – 2864 .
  • Chong , T.T. , Heidelberg , T. , Hashim , R. and Gary , S. 2007 . Liq. Cryst , 34 : 251 – 265 .
  • Hashim , R. , Hamid , H.A.A. , Seddon , J.M. , Brooks , N.J. , Heidelberg , T. , Zahid , N.M. and Mirzadeh , S.M. September 2010 . Mesophase Structure Investigation of Branched Chain Glycosides , September , 1 – 3 . Osaka , , Japan : Proceedings of the 3rd International Symposium on the Manipulation of Advanced Smart Material .
  • Peric-Hassler , L. , Hansen , H.S. , Baron , R. and Hunenberger , P.H. 2010 . Carbohydr. Res , 345 : 1781 – 1801 .
  • Quinn , P.J. and Williams , W.P. 1983 . Biochim. Biophys. Acta , 737 : 223 – 226 .
  • Sen , A. , Mannock , D.A. , Collins , D.J. , Quinn , P.J. and Williams , W.P. 1983 . Proc. R. Soc. London Ser. A , 388 : 247 – 247 .
  • Sanderson , P.W. and Williams , W.P. 1992 . Biochim. Biophys. Acta , 1107 : 77 – 85 .
  • Vill , V. 2006 . Liq. Cryst , 33 : 1351 – 1352 .
  • Auvray , X. , Petipas , C. , Dupuy , C. , Louvet , S. , Anthore , R. , Rico-Lattes , I. and Lattes , A. 2001 . Eur. Phys. J. E , 4 : 489 – 504 .
  • Boyd , B.J. , Drummond , C.J. , Krodkiewska , I. and Grieser , F. 2000 . Langmuir , 16 : 7359 – 7367 .
  • Hato , M. , Minamikawa , H. and Kato , T. 2008 . Sugar-Based Surfactants with Isoprenoid-Type of Hydrophobic Chains: Physicochemical and Boiphysical Aspects , Boca Raton , FL : CRC Press .
  • Hato , M. , Yamashita , I. , Kato , T. and Abe , Y. 2004 . Langmuir , 20 : 11366 – 11373 .
  • Seddon , J.M. 1990 . Biochemistry , 29 : 7997 – 8002 .
  • Seddon , J.M. 1990 . Journal of Physics: Condensed Matter , 2 : SA285
  • Qiu , H. and Caffrey , M. 2000 . Biomaterials , 21 : 223 – 234 .
  • Minamikawa , H. and Hato , M. 2005 . Chem. Phys. Lipids , 134 : 151 – 160 .
  • Minamikawa , H. and Hato , M. 1998 . Langmuir , 14 : 4503 – 4509 .
  • Seddon , J.M. , Zeb , N. , Templer , R.H. , McElhaney , R.N. and Mannock , D.A. 1996 . Langmuir , 12 : 5250 – 5253 .
  • Shinoyama , H. , Gama , Y. , Nakahara , H. , Ishigami , Y. and Yasui , T. 1991 . Bull. Chem. Soc. Jpn , 64 : 291 – 292 .
  • Seddon , J.M. , Robins , J. , Gulik-Krzywicki , T. and Delacroix , H. 2000 . Phys. Chem. Chem. Phys , 2 : 4485 – 4493 .
  • Tamada , K. , Minamikawa , H. , Hato , M. and Miyano , K. 1996 . Langmuir , 12 : 1666 – 1674 .
  • Kates , M. 1990 . “ Glycolipids, Phosphoglycolipids, and Sulfoglycolipids ” . In Handbook of Lipid Research , Vol. 3 , New York : Plenum Press .
  • Smith , O.F. 1998 . Microbial Lipids , Vol. 1 , New York : Academic press .
  • Langworthy , T.A. and Pond , J.L. 1986 . “ Membranes and lipids of thermophiles ” . In Thermophiles: General, Molecular and Applied Microbiology , Edited by: Brock , T.D. 107 – 135 . New York : John Wiley and Sons .
  • Baba , T. , Minamikawa , H. , Hato , M. and Handa , T. 2001 . Biophys. J , 81 : 3377 – 3386 .
  • Baba , T. , Toshima , Y. , Minamikawa , H. , Hato , M. , Suzuki , K. and Kamo , N. 1999 . Biochim. Biophys. Acta , 1421 : 91 – 102 .
  • Baba , T. , Minamikawa , H. , Hato , M. , Motoki , A. , Hirano , M. , Zhou , D. and Kawasaki , K. 1999 . Biochem. Biophys. Res. Commun , 265 : 734 – 738 .
  • Tanford , C. 1980 . The Hydrophobic Effect , 2nd , New York : Wiley .
  • Milkereit , G. , Garamus , V.M. , Yamashita , J. , Hato , M. , Morr , M. and Vill , V. 2005 . J. Phys. Chem. B , 109 : 1599 – 1608 .
  • Marsh , D. 2010 . Chem. Phys. Lipids , 163 : 667 – 677 .
  • Hussen , R.S.D. 2010 . Preparation and Evaluation of Vesicles Based on Non-Ionic Branched Chain Glycolipids, PhD Thesis , Kuala Lumpur : Department of Chemistry, Faculty of Science, University of Malaya .
  • Ahmad , N. , Ramsch , R. , Solans , C. , Esquena , J. , Tajuddin , H.A. and Hashim , R. 2011 . Physico-Chemical Characterization of Natural-Like Branched-Chain Glycosides towards Formation of Hexosomes and Vesicles (manuscript in preparation)
  • Wai Ling , K. , Wee Chen , G. , Wan Haliza Abd , M. , Rauzah , H. and Thorsten , H. 2010 . Thin Solid Films , 518 : 4412 – 4416 .
  • Templer , R.H. , Seddon , J.M. , Duesing , P.M. , Winter , R. and Erbes , J. 1998 . J. Phys. Chem. B , 102 : 7262 – 7271 .
  • Seddon , J.M. , Squires , A.M. , Conn , C.E. , Ces , O. , Heron , A.J. , Mulet , X. , Shearman , G.C. and Templer , R.H. 2006 . Philos. Transact. A Math. Phys. Eng. Sci , 364 : 2635 – 2655 .
  • Kim , Y.H. , Choi , J.S. , Hong , J. , Yoo , J.S. and Kim , M.S. 1999 . Lipids , 34 : 847 – 853 .
  • Nainggolan , I. , Radiman , S. , Hamzah , A.S. and Hashim , R. 2009 . Colloids Surf. B , 73 : 84 – 91 .

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