660
Views
47
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Laminarin Fragments and Evaluation of a β-(1,3) Glucan Hexasaccaride-CRM197 Conjugate as Vaccine Candidate against Candida albicans

, , , , , , , & show all
Pages 249-280 | Received 09 May 2011, Accepted 07 Jul 2011, Published online: 09 Nov 2011

REFERENCES

  • Pfaller , M. A. and Diekema , D. J. 2007 . Epidemiology of invasive candidiasis: a persistent public health problem . Clin. Microbiol. Rev. , 20 : 133 – 163 .
  • Wisplinghoff , H. , Bishoff , T. , Tallent , S. M. , Seifert , H. , Wenzel , R. P. and Edmond , M. B. 2004 . Nosocomial bloodstream infections in US hospitals: analysis of 24,179 cases from a prospective nationwide surveillance study . Clin. Infect. Dis. , 39 : 309 – 317 .
  • Lass-Flörl , C . 2009 . The changing face of epidemiology of invasive fungal disease in Europe . Mycoses , 52 ( 3 ) : 197 – 205 .
  • Cassone , A. and Torosantucci , A. 2006 . Opportunistic fungi and fungal infections: the challenge of a single, general antifungal vaccine . Expert Rev Vaccines , 5 : 859 – 867 .
  • Cutler , J. E. , Deepe , G. S. Jr and Klein , B. S. 2007 . Advances in combating fungal diseases: vaccines on the threshold . Nature Microbiol. , 1 : 13 – 28 .
  • Bowman , S. M. and Free , S. J. 2006 . The structure and synthesis of the fungal cell wall . BioEssays , 28 : 799 – 808 .
  • Bromuro , C. , Torosantucci , A. , Chiani , P. , Conti , S. , Polonelli , L. and Cassone , A. 2002 . Interplay between protective and inhibitory antibodies dictates the outcome of experimentally disseminated candidiasis in recipients of a Candida albicans vaccine . Infect. Immun. , 70 : 5462 – 5470 .
  • Ada , G. and Isaacs , D. 2003 . Carbohydrate-protein conjugate vaccines . Clin. Microbiol. Infect. , 9 ( 2 ) : 79 – 85 .
  • Giannini , G. , Rappuoli , R. and Ratti , G. 1984 . The amino-acid sequence of the non toxic mutants of diphtheria toxins: CRM45 and CRM197 . Nucleic Acids Res. , 25 ( 12 ) : 4063 – 4069 .
  • Torosantucci , A. , Bromuro , C. , Chiani , P. , De Bernardis , F. , Berti , F. , Galli , C. , Norelli , F. , Bellucci , C. , Polonelli , L. , Costantino , P. , Rappuoli , R. and Cassone , A. 2005 . A novel glyco-conjugate vaccine against fungal pathogens . J. Exp. Med. , 202 ( 5 ) : 597 – 606 .
  • Han , Y. , Ulrich , M. A. and Cutler , J. E. 1999 . Candida albicans mannan extract-protein conjugates induce a protective immune response against experimental candidiasis . J. Infect. Dis. , 179 ( 6 ) : 1477 – 1484 .
  • Xin , H. , Dziadek , S. , Bundle , D. R. and Cutler , J. E. 2008 . Synthetic glycopeptide vaccines combining β-mannan and peptide epitopes induce protection against candidiasis . Proc. Natl. Acad. Sci. U S A , 105 ( 36 ) : 13526 – 13531 .
  • Paulovicova , L. , Bystricky , S. , Paulovicova , E. , Karelin , A. A. , Tsvetkov , Y. E. and Nifantiev , N. E. 2010 . Model α-mannoside conjugates: immunogenicity and induction of candidacidal activity . FEMS Immunol. Med. Microbiol. , 58 ( 3 ) : 307 – 313 .
  • Bromuro , C. , Romano , M. R. , Chiani , P. , Berti , F. , Tontini , M. , Proietti , D. , Mori , E. , Torosantucci , A. , Costantino , P. , Rappuoli , R. and Cassone , A. 2010 . Beta-glucan-CRM197 conjugates as candidates antifungal vaccines . Vaccine , 28 : 2615 – 2623 .
  • Torosantucci , A. , Chiani , P. , Bromuro , C. , De Bernardis , F. , Palma , A. S. , Liu , Y. , Mignogna , G. , Maras , B. , Colone , M. , Stringaro , A. , Zamboni , S. , Feizi , T. and Cassone , A. 2009 . Protection by anti-β-Glucan antibodies is associated with restricted β-1,3 glucan binding specificity and inhibition of fungal growth and adherence . PloS One , 4 ( 4 ) : e5392
  • Takeo , K. , Maki , K. , Wada , Y. and Kitamura , S. 1993 . Synthesis of the Laminara-oligosaccharide methyl P-glycosides of dp 3–8 . Carbohydr. Res. , 245 : 81 – 96 .
  • Yamada , H. , Harada , T. and Takahashi , T. 1994 . Synthesis of an elicitor-active hexaglucoside analogue by a one-pot, two-step glycosidation procedure . J. Am. Chem. Soc. , 116 : 7919 – 7920 .
  • Nicolaou , K. C. , Winssinger , N. , Pastor , J. and De Roose , F . 1997 . General and highly efficient solid phase synthesis of oligosaccharides. Total synthesis of a heptasaccharide phytoalexin elicitor (HPE) . J. Am. Chem. Soc. , 119 : 449 – 450 .
  • Geurtsen , R. , Coitć , F. , Hahn , M. G. and Boons , G.-J. 1999 . Chemoselective glycosylation strategy for the convergent assembly of phytoalexin-elicitor active oligosaccharides and their photoreactive derivatives . J. Org. Chem. , 64 : 7828 – 7835 .
  • Du , Y. , Zhang , M. and Kong , F . 2000 . Highly efficient and practical synthesis of 3,6-branched oligosaccharides . Org. Lett. , 2 ( 24 ) : 3797 – 3800 .
  • Yamada , H. , Takimoto , H. , Ikeda , T. , Tsukamoto , H. , Harada , T. and Takahashi , T . 2001 . Mixed branched-linear type one-pot glycosylation: synthesis of hepta-D-glucoside . Synlett , 11 : 1751 – 1753 .
  • Chénedé , A. , Perrin , E. , Rekaï , E. D. and Sinaÿ , P. 1994 . Synthesis of C-disaccharides by samarium diiodide induced intramolecular coupling reaction of tethered sugars . Synlett , : 420 – 422 .
  • Collins , P. M. , Gardiner , D. , Kumar , S. and Overend , W. G. 1972 . Arylazo-glycenosides. Part 1. Synthesis and reactions of some 2- and 3-arylazo-derivatives of methyl 4,6-O-benzylidene-2,3-dideoxy-D-hex-2-enopyranosides . J. Chem. Soc. Perkin Trans. 1 , : 1596 – 1610 .
  • Ning , J. , Yi , Y. and Kong , F. 2002 . A general strategy for the synthesis of 3,6-branched gluco-oligosaccharides: facile synthesis of the phytoalexine elicitor oligosaccharides . Tetrahedron Lett. , 43 : 5545 – 5549 .
  • Adamo , R. and Kováč , P. 2007 . Glycosylation under thermodynamic control: synthesis of the di- and the hexasaccharide fragments of the O-SP of Vibrio cholerae O:1 serotype Ogawa from fully functionalized building blocks . Eur. J. Org. Chem. , : 988 – 1000 .
  • van Boom , J. H. and Burgers , P. M.J. 1976 . Use of levulinic acid in the protection of oligonucleotides via the modified phosphotriester method: synthesis of decaribonucleotide . Tetrahedron Lett. , 17 : 4875 – 4878 .
  • Watt , G. M. and Boons , G.-J. 2004 . A convergent strategy for the preparation of N-glycan core di-, tri-, and pentasaccharide thioaldoses for the site-specific glycosylation of peptides and proteins bearing free cysteines . Carbohydr. Res. , 339 : 181 – 193 .
  • Sun , J. , Han , X. and Yu , B . 2005 . First total synthesis of Caminoside A, an antimicrobial glycolipid from sponge . Synlett , : 437 – 440 .
  • Ono , M. and Itoh , I . 1988 . A new deprotection method for levulinyl protecting group under neutral conditions . Chem. Lett. , 4 : 585 – 588 .
  • van Boeckel , C. A.A. , Hermans , J. P.G. , Westerduin , P. , Oltvoort , J. J. , van der Marel , G. A. and van Boom , J. H. 1982 . Chemical synthesis of diphosphorilated Lipid A derivatives . Tetrahedron Lett. , 23 ( 18 ) : 1951 – 1954 .
  • Lefeber , D. J. and Kamerling , J. P. 2000 . Vliegenthart J.F.G. The use of Diazabicyclo[2.2.2]octane as a novel highly selective dechloroacetylation reagent . Org. Lett. , 2 ( 5 ) : 701 – 713 .
  • Mo , K.-F. , Li , H. , Mague , J. T. and Ensley , H. E. 2009 . Synthesis of the β-1,3-glucan, laminarahexaose: NMR and conformational studies . Ensely Carbohydr. Res. , 344 : 439 – 447 .
  • Jamois , F. , Ferrières , V. , Guégan , J.-P. , Yvin , J.-C. , Plusquellec , D. and Vetvicka , V. 2005 . Glucan-like synthetic oligosaccharides: iterative synthesis of linear oligo-β-(1,3)-glucans and immunostimulatory effects . Glycobiology , 15 : 393 – 407 .
  • Nishimura , T. , Bignon , C. , Allouch , J. , Czjzek , M. , Darbon , H. , Watanabe , T. and Henrissat , B. 2001 . Streptomyces matensis laminaripentaose hydrolase is an ‘inverting’ β-1,3-glucanase . FEBS Lett. , 499 : 187 – 190 .
  • Petersen , B. O. , Krah , M. , Duus , J. Ø. and Thomsen , K. K. 2000 . A transglycosylating 1,3(4)-β-glucanase from Rhodothermus marinus . Eur. J. Biochem. , 267 : 361 – 369 .
  • Huang , G.-L. , Mei , X.-Y. and Liu , M.-X . 2005 . Synthesis of (R)-2,3-epoxypropyl(1–3)-β-D-pentaglucoside . Carbohydr. Res. , 340 : 603 – 608 .
  • Carvalho de Souza , A. , Halkes , K. M. , Meeldijk , J. D. , Verkleij , A. J. , Vliegenthart , J. F.G. and Kamerling , J. P. 2004 . Gold glyconanoparticles as probes to explore the carbohydrate-mediated self-recognition of marine sponge cells . Eur. J. Org. Chem. , : 4323 – 4339 .
  • Lee , R. T. and Lee , R. C. 1974 . Synthesis of 2-(3-Aminoethylthiopropyl) glucosides . Carbohydr. Res. , 37 : 193 – 201 .
  • Lefeber , D. J. , Kamerling , J. P. and Vliegenthart , J. F.G. 2001 . Synthesis of Streptococcus pneumoniae type 3 neoglycoproteins varying in oligosaccharide chain length, loading and carrier protein . Chem. Eur. J. , 7 ( 20 ) : 4411 – 4421 .
  • Galli , G. , Medini , D. , Borgogni , E. , Zedda , L. , Bardelli , M. , Malzone , C. , Nuti , S. , Tavarini , S. , Sammicheli , C. , Hilbert , A. K. , Brauer , V. , Banzhoff , A. , Rappuoli , R. , Del Giudice , G. and Castellino , F. 2009 . Adjuvamted H5N1 vaccine induced early CD4+ response that predicts long persistence of protective antibody levels . Proc. Natl. Acad. Sci. U S A , 106 : 3877 – 3882 .
  • Anderson , P. W. , Pichichero , M. E. , Stein , E. C. , Porcelli , S. , Betts , R. F. , Connuck , D. M. , Korones , D. , Insel , R. A. , Zaharadnik , J. M. and Eby , R. 1989 . Effect of oligosaccharide chain length, exposed terminal group, and hapten loading on the antibody response of human adults and infants to vaccines consisting of Haemophilus influenzae type b capsular antigen unterminally coupled to the diphtheria protein CRM197 . J. Immunol. , 142 ( 7 ) : 2464 – 2468 .
  • Pozsgay , V. , Chu , C. , Pannell , L. , Wolfe , J. , Robbins , J. B. and Schneerson , R. 1999 . Protein conjugates of synthetic saccharides elicit higher levels of serum IgG lipopolysaccharide antibodies in mice than do those of the O-specific polysaccharide from Shigella dysenteriae type 1 . Proc. Natl. Acad. Sci. U S A , 96 ( 9 ) : 5194 – 5197 .
  • Rachini , A. , Pietrella , D. , Lupo , P. , Torosantucci , A. , Chiani , P. , Bromuro , C. , Proietti , C. , Bistoni , F. , Cassone , A. and Vecchiarelli , A. 2007 . An antibeta-glucan monoclonal antibody inhibits growth and capsule formation of Cryptococcus neoformans in vitro and exerts therapeutic, anticryptococcal activity in vivo . Infect. Immun. , 75 ( 11 ) : 5085 – 5094 .
  • Liu , Y. , Feizi , T. , Campanero-Rhodes , M. A. , Childs , R. A. , Zhang , Y. , Mulloy , B. , Evans , P. G. , Osborn , H. M.I. , Otto , D. , Crocker , P. R. and Chai , W. 2007 . Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions . Chem. Biol. , 14 : 847 – 859 .
  • Takeo , K. 1979 . The Koenigs-Knorr reaction of methyl-4,6-O-benzylidene-β-D-glucopyranoside with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide . Carbohydr. Res. , 77 : 131 – 140 .

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.