470
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Per- and Poly-Substituted Trehalose Derivatives: Studies of Properties Relevant to Their Use as Excipients for Controlled Drug Release

&
Pages 198-221 | Received 19 Jul 2008, Accepted 11 Mar 2009, Published online: 19 May 2009

REFERENCES

  • Luo , Y. and Prestwich , G. D. 2001 . Novel biomaterials for drug delivery . Expert Opin Ther Patents , 11 : 1395 – 1410 .
  • Ghosh , S. 2004 . Recent research and development in synthetic polymer-based drug delivery systems . J. Chem. Res. , : 241 – 246 .
  • Hoare , T. R. and Kohane , D. S. 2008 . Hydrogels in drug delivery. Progress and challenges . Polymer , 49 : 1993 – 2007 .
  • Kulkarni , R. V. and Biswanath , S. 2007 . Electrically responsive smart hydrogels in drug delivery: a review . J. Appl. Biomat. Biomech. , 5 : 125 – 139 .
  • Oh , J. K. , Drumright , R. and Siegwart , D. J. 2008 . The development of microgels/nanogels for drug delivery applications . Prog. Polym. Sci. , 33 : 448 – 477 .
  • Haider , M. , Megeed , Z. and Ghandehari , H. 2004 . Genetically engineered polymers: status and prospects for controlled release . J. Controlled Release , 95 : 1 – 26 .
  • Tonnesen , H. H. and Karlsen , G. 2002 . Alginate in drug delivery systems . Drug. Dev. Ind. Pharm. , 28 : 621 – 630 .
  • Mulhbacher , J. , Ispas-Szabo , P. and Mateescu , M. A. 2004 . Cross-linked high amylose starch derivatives for drug release II. Swelling properties and mechanistic study . Int. J. Pharm. , 278 : 231 – 238 .
  • Kim , W. T. , Chung , H. and Shin , I. S. 2008 . Characterization of calcium alginate and chitosan-treated calcium alginate gel beads entrapping allyl isothiocyanate . Carb. Polym. , 71 : 566 – 573 .
  • Knowles , J. C. 2004 . Phosphate based glasses for biomedical applications. J. Mat Chem. 2003, 13, 2395–2003; Gao, H., Tan, T.; Wang, D. Effect of composition on the release kinetics of phosphate controlled release glasses in aqueous medium . J. Controlled Release , 96 : 21 – 28 .
  • Zhao , L. Z. , Yan , X. X. and Zhou , X. F. 2008 . Mesoporous bioactive glasses for controlled drug release . Microporous Mesophorous Mat. , 109 : 210 – 215 .
  • Uekama , K. 2004 . Design and evaluation of cyclodextrin-based drug formulation . Chem. Pharm. Bull. , 52 : 900 – 915 .
  • Pose-Vilarnovo , B. , Rodriquez-Tenreiro , C. , dos Santos , J. F. R. , Vazquez-Doval , J. , Concheiro , A. , Alvarez-Lorenzo , C. and Torres-Labandeira , J. J. 2004 . Modulating drug release with cyclodextrins in hydroxypropyl methylcellulose gels and tablets . J. Controlled Release , 94 : 351 – 363 .
  • Cal , K. and Centkowska , K. 2008 . Use of cyclodextrins in topical formulations: practical aspects . Eur. J. Pharm. Biopharm. , 68 : 467 – 478 .
  • Stella , V. J. and He , Q. 2008 . Cyclodextrins . Tox. Path. , 36 : 30 – 42 .
  • Giandalia , G. , de Caro , V. , Cordone , L. and Giannola , L. I. 2002 . Trehalose-hydroxyethylcellulose microspheres containing vancomycin for topical drug delivery . Eur. J. Pharm. BioPharm. , 52 : 83 – 89 .
  • Davidson , I. G. , Langner , E. J. , Plowman , S. V. and Blair , J. A. 2003 . Release mechanism of insulin encapsulated in trehalose ester derivative microparticles delivered via inhalation . Int. J. Pharm. , 254 : 211 – 222 .
  • Rochelle , C. and Lee , G. 2007 . Dextran or hydroxyethyl starch in spray-freeze-dried Trehalose/mannitol microparticles intended as ballistic particulate carriers for proteins . J. Pharm. Sci. , 96 : 2296 – 2309 .
  • Gribbon , E. M. , Hatley , R. H. M. , Gard , T. , Blair , J. A. , Kampinga , J. , Roser , B. , Karsa , D. R. and Stephenson , R. , eds. 1996 . Chemical Aspects of Drug Delivery Systems. , 138 – 145 . London : RSC .
  • Hatley , R. H. M. and Blair , J. A. 1999 . Stabilisation and delivery of labile materials by amorphous carbohydrates and their derivatives . J. Mol. Cat. B. Enzymatic , 7 : 11 – 19 .
  • Baddeley , T. C. , Davidson , I. G. , Glidewell , C. , Low , J. N. , Skakle , J. M. S. and Wardell , J. L. 2004 . Supramolecular structures of substituted α,α '-trehalose derivatives . Acta Crystallogra. Sect. B , B60 : 461 – 471 .
  • Liav , A. and Goren , M. B. 1980 . Concerning 2,3,4,2′,3′,4′-hexa-O-acetyl-6,6′-diamino-6,6′-dideoxy-α,α '-trehalose . Carbohydr. Res. , 87 : 287 – 293 .
  • Desai , M. C. and Stramiello , L. M. S. 1993 . Polymer-bound EDC (P-EDC) – a convenient reagent for formation of an amide bond . Tetrahedron Lett. , 34 : 7685 – 7768 .
  • Garcia , J. , Urpi , F. and Vilarrasa , J. 1984 . New synthetic tricks- triophenylphosphine-mediated amide formation from carboxylic acids andazides . Tetrahedron Lett. , 25 : 4841 – 4844 .
  • Wilt , J. W. and Tufano , M. D. 1985 . 8-Methylene-exo-3,3-diphenyltricyclo[3.2.1.02,4]octane. Probe for addition-reaction mechanism . J. Org. Chem. , 50 : 2601 – 2603 .
  • Kurita , K. , Masuda , N. , Aibe , S. , Murakami , K. , Ishii , S. and Nishimura , S. 1994 . Synthetic carbohydrate polymers containing trehalose residues in the main chain – preparation and characteristic properties . Macromolecules , 27 : 7544 – 7549 .
  • Albert , R. , Dax , K. , Stutz , A. E. and Weidmann , H. 1983 . Acetyl migration in partially acetylated D-glucopyranosidesand acylamidohexopyranosides . J. Carbohydr. Chem. , 2 : 279 – 292 .
  • Lam , S. N. and Gervay-Hague , J. 2002 . Solution-and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study . Carbohydr. Res. , 337 : 1953 – 1965 .
  • Fry , E. M. J. 1955 . Tri-O-acetyl-β-D-glucopyranurono-6,1-lactone . Am. Chem. Soc. , 77 : 3915 – 3916 .
  • Gilbertson , S. R. and Chang , C-W. T. 1995 . Synthesis of new disugar phosphine ligands and their use in asymmetric hydrogenation . J. Org. Chem. , 60 : 6226 – 6228 .
  • Baddeley , T. C. 2003 . Ph.D. Thesis University of Aberdeen .
  • Donovan , S. F. and Pescatore , M. C. 2002 . Method for measuring the logarithm of the octanol-water partition coefficient by using short octadecyl-poly(vinyl alcohol) high-performance liquid chromatography columns . J. Chromatogra. A , 952 : 47 – 61 .
  • Lee , C. K. 1976 . Chemical modification of trehalose.18. Synthesis of α -D-glucopyranosyl α -D-galactopyranoside . Carbohydr Res. , 50 : 152 – 157 .
  • Baer , H. H. and Radatus , B. 1984 . Preparation of some partially protected, α,α -trehalose-type disaccharides having the D-altro configuration . Carbohydr. Res. , 128 : 165 – 174 .
  • Bar-Guilloux , E. , Defaye , J. , Driguez , H. and Robic , D. 1975 . Asymmetric analogs of trehalose. 3. Synthesis, conformation and trehalase affinity of α -D-glucopyranosyl-α -D-xylopyranoside, α -D-glucopyranosyl-α -D-mannopyranoside and α -D-allopyranosyl-α -D-glucopyranoside . Carbohydr. Res. , 45 : 217 – 236 .
  • Bredereck , H. 1930 . Zur konstitution der trehalose . Ber. , 63 : 959 – 964 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.