A versatile method for functionalization and grafting of 2-hydroxyethyl cellulose (HEC) via Click chemistry

Carbohydrate Polymers

Volumn 90, Issue 2, 2012, Pages 859-869

  Eissa, Ahmed M ^a,b   Khosravi, Ezat ^a   Cimecioglu, A Levent ^c  

^a DURHAM UNIVERSITY   (United Kingdom)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c Expert Capability Group Process Technology   (United States)

Author keywords

2 Hydroxyethyl cellulose; Click chemistry; Hydrophilic modification; Hydrophobic modification; Poly(ethylene glycol); Poly(lactic acid); Polydimethylsiloxane

Indexed keywords

AFM; AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; CLICK REACTION; CYCLOADDITION REACTION; FTIR SPECTROSCOPY; FUNCTIONALIZATIONS; HYDROPHILIC MODIFICATION; HYDROPHOBIC AND HYDROPHILIC; HYDROPHOBIC MODIFICATION; POLY LACTIC ACID; POLYDIMETHYLSILOXANE PDMS; POLYLACTIC ACIDS; PROPARGYL; SIDE-CHAINS; SYNTHETIC APPROACH; VERSATILE METHODS;

ACETYLENE; CYCLOADDITION; ESTERIFICATION; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAFTING (CHEMICAL); HYDROPHILICITY; HYDROPHOBICITY; LACTIC ACID; POLYDIMETHYLSILOXANE; POLYETHYLENE OXIDES; SILICONES; SYNTHESIS (CHEMICAL);

POLYETHYLENE GLYCOLS;

AZIDE; CELLULOSE; DRUG DERIVATIVE; HYDROXYETHYLCELLULOSE; LACTIC ACID; MACROGOL DERIVATIVE; POLYLACTIC ACID; POLYMER;

ARTICLE; ATOMIC FORCE MICROSCOPY; BIOLOGICAL MODEL; CATALYSIS; CHEMISTRY; CLICK CHEMISTRY; INFRARED SPECTROSCOPY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AZIDES; CATALYSIS; CELLULOSE; CLICK CHEMISTRY; LACTIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ATOMIC FORCE; MODELS, BIOLOGICAL; POLYETHYLENE GLYCOLS; POLYMERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84864489008     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.06.012     Document Type: Article

References (42)

1. T. Akimoto, K. Kawahara, Y. Nagase, and T. Aoyagi Preparation of oligodimethylsiloxanes with sugar moiety at a terminal group as a transdermal penetration enhancer Macromolecular Chemistry and Physics 201 18 2000 2729 2734 [doi:10.1002/1521-3935(20001201)201:18<2729::aid-macp2729>3.0.co;2-u]
2. A.C. Albertsson, and M. Gruvegard Degradable high-molecular-weight random copolymers, based on epsilon-caprolactone and 1,5-dioxepan-2-one, with non-crystallizable units inserted in the crystalline-structure Polymer 36 5 1995 1009 1016 10.1016/0032-3861(95)93601-h
3. Bombeli, T. Retrieved from < http://www.makingcosmetics.com/articles/ 20-polysaccharides-sugars-gums-in-cosmetics.pdf >
4. G.L. Brode, R.L. Kreeger, E.M. Partain, and J.L. Pavlichko Polysaccharides for personal care applications Journal of the Society of Cosmetic Chemists 39 1 1988 78
5. H.J. Buschmann, and E. Schollmeyer Applications of cyclodextrins in cosmetic products: A review [Review] Journal of Cosmetic Science 53 3 2002 185 191
6. F.V. Carrillo, M. Costello, S.F.A. Creutz, L. Deklippel, B. Henault, and E.J. Joffre WO2006127882. Dow Corning Corp and Genencor Int. 2006
7. A.L. Cimecioglu, D.H. Ball, S.H. Huang, and D.L. Kaplan A direct regioselective route to 6-azido-6-deoxy polysaccharides under mild and homogeneous conditions Macromolecules 30 1 1997 155 156 (Pubitemid 127550561)
8. A.L. Cimecioglu, D.H. Ball, D.L. Kaplan, and S.H. Huang Preparation of amylose derivatives selectively modified at c-6-6-amino-6-deoxyamylose Macromolecules 27 11 1994 2917 2922 10.1021/ma00089a004
9. D.D. Diaz, S. Punna, P. Holzer, A.K. McPherson, K.B. Sharpless, and V.V. Fokin Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition Journal of Polymer Science Part A: Polymer Chemistry 42 17 2004 4392 4403 10.1002/pola.20330
10. D.K. Gilding, and A.M. Reed Biodegradable polymers for use in surgery - polyglycolic-poly(lactic acid) homopolymers and copolymers. 1 Polymer 20 12 1979 1459 1464 10.1016/0032-3861(79)90009-0 (Pubitemid 10435422)
11. K.L. Goa, and P. Benfield Hyaluronic-acid - a review of its pharmacology and use as a surgical aid in ophthalmology, and its therapeutic potential in joint disease and wound-healing Drugs 47 3 1994 536 566
12. E.D. Goddard, and J.V. Gruber Principles of Polymer Science and Technology Cosmetics and Personal Care 1999 Dekker New York
13. J. Hafren, W.B. Zou, and A. Cordova Heterogeneous 'organoclick' derivatization of polysaccharides Macromolecular Rapid Communications 27 16 2006 1362 1366 10.1002/marc.200600328 (Pubitemid 44369370)
14. S. Halila, M. Manguian, S. Fort, S. Cottaz, T. Hamaide, and E. Fleury Syntheses of well-defined glyco-polyorganosiloxanes by click chemistry and their surfactant properties Macromolecular Chemistry and Physics 209 12 2008 1282 1290 10.1002/macp.200700629
15. B. Helms, J.L. Mynar, C.J. Hawker, and J.M.J. Frechet Dendronized linear polymers via click chemistry Journal of the American Chemical Society 126 46 2004 15020 15021 10.1021/ja044744e (Pubitemid 39557249)
16. D. Henkensmeier, B.C. Abele, A. Candussio, and J. Thiem Synthesis and characterisation of terminal carbohydrate modified poly(dimethyl siloxane)s Macromolecular Chemistry and Physics 205 14 2004 1851 1857 10.1002/macp. 200400004
17. M. Jahn, D. Stoll, R.A.J. Warren, L. Szabo, P. Singh, and H.J. Gilbert Expansion of the glycosynthase repertoire to produce defined manno-oligosaccharides Chemical Communications 12 2003 1327 1329 10.1039/b302380j (Pubitemid 36734914)
18. E.J. Joffre, B.K. Johnson, B.J. Swanton, and M.S. Starch WO2006127883. Dow Corning Corp and Genencor Int. 2006
19. S. Kobayashi, H. Uyama, and S. Kimura Enzymatic polymerization Chemical Reviews 101 12 2001 3793 3818 10.1021/cr990121l (Pubitemid 35373048)
20. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: Diverse chemical function from a few good reactions Angewandte Chemie-International Edition 40 11 2001 [2004-+. doi: 10.1002/1521-3773(20010601)40:11<2004::aid- anie2004>3.0.co;2-5]
21. M. Krouit, J. Bras, and M.N. Belgacem Cellulose surface grafting with polycaprolactone by heterogeneous click-chemistry European Polymer Journal 44 12 2008 4074 4081 10.1016/j.eurpolymj.2008.09.016
22. T. Liebert, C. Hansch, and T. Heinze Click chemistry with polysaccharides Macromolecular Rapid Communications 27 3 2006 208 213 10.1002/marc.200500686 (Pubitemid 43220960)
23. J.F. Lutz, H.G. Borner, and K. Weichenhan Combining atom transfer radical polymerization and click chemistry: A versatile method for the preparation of end-functional polymers Macromolecular Rapid Communications 26 7 2005 514 518 10.1002/marc.200500002 (Pubitemid 40812047)
24. T.E. McAlindon, M.P. LaValley, and D.T. Felson Efficacy of glucosamine and chondroitin for treatment of osteoarthritis - Reply Journal of the American Medical Association 284 10 2000 1242
25. R.A.A. Muzzarelli, and C. Muzzarelli Chitosan chemistry: Relevance to the biomedical sciences Polysaccharides 1: Structure, Characterization and Use 186 2005 151 209 10.1007/b136820
26. A.J. Nijenhuis, D.W. Grijpma, and A.J. Pennings Lewis acid-catalyzed polymerization of l-lactide - Kinetics and mechanism of the bulk-polymerization Macromolecules 25 24 1992 6419 6424 10.1021/ma00050a006 (Pubitemid 23582377)
27. K.J. Quinn, and J.M. Courtney Silicones as biomaterials British Polymer Journal 20 1 1988 25 32 10.1002/pi.4980200106
28. C. Racles, and T. Hamaide Synthesis and characterization of water soluble saccharide functionalized polysiloxanes and their use as polymer surfactants for the stabilization of polycaprolactone nanoparticles Macromolecular Chemistry and Physics 206 17 2005 1757 1768 10.1002/macp.200500139 (Pubitemid 41312115)
29. C. Racles, T. Hamaide, and A. Ioanid Siloxane surfactants in polymer nanoparticles formulation Applied Organometallic Chemistry 20 4 2006 235 245 10.1002/aoc.1051
30. M. Rinaudo Role of substituents on the properties of some polysaccharides Biomacromolecules 5 4 2004 1155 1165 10.1021/bm030077q (Pubitemid 39089712)
31. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angewandte Chemie-International Edition 41 14 2002 2596-+
32. M. Rutnakornpituk, P. Ngamdee, and P. Phinyocheep Synthesis, characterization and properties of chitosan modified with poly(ethylene glycol)-polydimethylsiloxane amphiphilic block copolymers Polymer 46 23 2005 9742 9752 10.1016/j.polymer.2005.08.051 (Pubitemid 41455205)
33. J. Schulze Nahrup, Z.M. Gao, J.E. Mark, and A. Sakr Poly(dimethylsiloxane) coatings for controlled drug release - polymer modifications International Journal of Pharmaceutics 270 1-2 2004 199 208 10.1016/j.ijpharm.2003.10.007 (Pubitemid 38077100)
34. B.M. Shao, W. Xu, H. Dai, P.F. Tu, Z.J. Li, and X.M. Gao A study on the immune receptors for polysaccharides from the roots of Astragalus membranaceus, a Chinese medicinal herb Biochemical and Biophysical Research Communications 320 4 2004 1103 1111 10.1016/j.bbrc.2004.06.065 (Pubitemid 38916657)
35. J. Shey, K.M. Holtman, R.Y. Wong, K.S. Gregorski, A.P. Klamczynski, and W.J. Orts The azidation of starch Carbohydrate Polymers 65 4 2006 529 534 10.1016/j.carbpol.2006.02.009 (Pubitemid 44223713)
36. N.V. Tsarevsky, B.S. Sumerlin, and K. Matyjaszewski Step-growth click coupling of telechelic polymers prepared by atom transfer radical polymerization Macromolecules 38 9 2005 3558 3561 10.1021/ma050370d (Pubitemid 40672479)
37. R. Wagner, L. Richter, R. Wersig, G. Schmaucks, B. Weiland, and J. Weissmuller Silicon-modified carbohydrate surfactants. 1. Synthesis of siloxanyl moieties containing straight-chained glycosides and amides Applied Organometallic Chemistry 10 6 1996 421 435 [doi: 10.1002/(sici)1099-0739(199608) 10:6<421::aid-aoc495>3.0.co;2-c] (Pubitemid 126463618)
38. R. Wagner, L. Richter, Y. Wu, B. Weiland, J. Weissmuller, and J. Reiners Silicon-modified carbohydrate surfactants VI: Synthesis of carbosilane, silane, polysilane and non-permethylated siloxane derivatives; the wetting behaviour of epoxy-modified precursor liquids on non-polar surfaces Applied Organometallic Chemistry 12 1 1998 47 58 [doi: 10.1002/(sici)1099-0739(199801)12:1<47::aid- aoc670>3.3.co;2-1] (Pubitemid 128526157)
39. Z.J. Witczak, and K.A. Nieforth Carbohydrates in drug design 1997 Marcel Dekker Inc. New York
40. P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, and B. Voit Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes Angewandte Chemie-International Edition 43 30 2004 3928 3932 10.1002/anie.200454078 (Pubitemid 39257472)
41. Y. Xia, J.A. Kornfield, and R.H. Grubbs Efficient synthesis of narrowly dispersed brush polymers via living ring-opening metathesis polymerization of macromonomers Macromolecules 42 11 2009 3761 3766 10.1021/ma900280c
42. W.Y. Zhang, J.Y. Yang, J.P. Chen, Y.Y. Hou, and X.D. Han Immunomodulatory and antitumour effects of an exopolysaccharide fraction from cultivated Cordyceps sinensis (Chinese caterpillar fungus) on tumour-bearing mice Biotechnology and Applied Biochemistry 42 2005 9 15 10.1042/ba20040183 (Pubitemid 41117199)