Easy functionalization of amphiphilic poly(ethylene oxide)-b-poly(ε-caprolactone) copolymer micelles with unprotected sugar: synthesis and recognition by lectins
[en] This paper aims at reporting the end-functionalization of a PEO block of an amphiphilic α-acetal-PEO-b-PCL copolymer. The acetal end-group, which is the fragment of the initiator used in the EO polymerization, was first hydrolyzed into an aldehyde that was then reacted with an amine by reductive amination reaction in water. This two-step derivatization was carried out in one pot. In a preliminary study a model amine, i.e. fluorescein amine, was used and the impact of the composition, thus of the Hydrophilic–Lipophilic Balance (HLB) of the amphiphilic copolymer, was studied. The experimental conditions were extended to the coupling of an aminated mannose to the diblock copolymer. The frozen micelles formed by the mannosylated copolymer proved to form complexes with various lectins as shown by Surface Plasmon Resonance (SPR) and Isothermal Titration Calorimetry (ITC).
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Freichels, Hélène; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Auzély-Velty, Rachel; Université Joseph Fourier, Grenoble, France > Institut de Chimie Moléculaire de Grenoble > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Lecomte, Philippe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Easy functionalization of amphiphilic poly(ethylene oxide)-b-poly(ε-caprolactone) copolymer micelles with unprotected sugar: synthesis and recognition by lectins
Publication date :
June 2012
Journal title :
Polymer Chemistry
ISSN :
1759-9954
eISSN :
1759-9962
Publisher :
Royal Society Chemistry, Cambridge, United Kingdom
VACCINOR project The "CGRI-FNRS-CNRS" program in the framework of bilateral cooperation
Funders :
BELSPO - Service Public Fédéral de Programmation Politique scientifique [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] Walloon region [BE] Télévie [BE]
A. Mahmud X.-B. Xiong M. Aliabadi Hamidreza A. Lavasanifar Polymeric micelles for drug targeting J. Drug Targeting 2007 15 9 553 584 (Pubitemid 350031081)
C. Allen D. Maysinger A. Eisenberg Nano-engineering block copolymer aggregates for drug delivery Colloids Surf., B 1999 16 1-4 3 27
X. Wei C. Gong M. Gou S. Fu Q. Guo S. Shi F. Luo G. Guo L. Qiu Z. Qian Biodegradable poly(ε-caprolactone)-poly(ethylene glycol) copolymers as drug delivery system Int. J. Pharm. 2009 381 1 1 18
G. S. Kwon K. Kataoka Block copolymer micelles as long-circulating drug vehicles Adv. Drug Delivery Rev. 1996 16 295 309
K. Andrieux D. Desmaele J. D'Angelo P. Couvreur Nanotechnologies and new drugs Actual. Chim. 2003 11-12 135 139 (Pubitemid 38175595)
R. K. Jain Delivery of molecular and cellular medicine to solid tumors Adv. Drug Delivery Rev. 1997 26 2,3 71 90 (Pubitemid 27289526)
H. Maeda L. W. Seymour Y. Miyamoto Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo Bioconjugate Chem. 1992 3 5 351 362
A. K. Iyer G. Khaled J. Fang H. Maeda Exploiting the enhanced permeability and retention effect for tumor targeting Drug Discovery Today 2006 11 17-18 812 818 (Pubitemid 44280021)
G. Gaucher M.-H. Dufresne V. P. Sant N. Kang D. Maysinger J.-C. Leroux Block copolymer micelles: preparation, characterization and application in drug delivery J. Controlled Release 2005 109 169 188 (Pubitemid 41742123)
D. Sutton N. Nasongkla E. Blanco J. Gao Functionalized micellar systems for cancer targeted drug delivery Pharm. Res. 2007 24 6 1029 1046 (Pubitemid 46798882)
K. Van Butsele R. Jérôme C. Jérôme Functional amphiphilic and biodegradable copolymers for intravenous vectorisation Polymer 2007 48 26 7431 7443 (Pubitemid 350192500)
W. I. Weis M. E. Taylor K. Drickamer The C-type lectin superfamily in the immune system Immunol. Rev. 1998 163 19 34 (Pubitemid 28327859)
A. Gupta R. K. Gupta G. S. Gupta Targeting cells for drug and gene delivery: emerging applications of mannans and mannan binding lectins J. Sci. Ind. Res. 2009 68 6 465 483
H. H. Salman C. Gamazo M. A. Campanero J. M. Irache Bioadhesive mannosylated nanoparticles for oral drug delivery J. Nanosci. Nanotechnol. 2006 6 9-10 3203 3209 (Pubitemid 44580001)
V. Fievez L. Plapied A. des Rieux V. Pourcelle H. Freichels V. Wascotte M. L. Vanderhaeghen C. Jerome A. Vanderplasschen J. Marchand-Brynaert Y. J. Schneider V. Preat Targeting nanoparticles to M cells with non-peptidic ligands for oral vaccination Eur. J. Pharm. Biopharm. 2009 73 1 16 24
J. J. Lundquist E. J. Toone The cluster glycoside effect Chem. Rev. 2002 102 2 555 578 (Pubitemid 35377623)
Y. C. Lee R. T. Lee Carbohydrate-protein interactions - basis of glycobiology Acc. Chem. Res. 1995 28 8 321 327
M. Reynolds S. Pérez Thermodynamics and chemical characterization of protein-carbohydrate interactions: the multivalency issue C. R. Chim. 2010 14 1 74
H. Freichels R. Jérôme C. Jérôme Sugar-labeled and PEGylated (bio)degradable polymers intended for targeted drug delivery systems Carbohydr. Polym. 2011 86 3 1093 1106
J. Rieger F. Stoffelbach D. Cui A. Imberty E. Lameignere J. L. Putaux R. Jerome C. Jerome R. Auzely-Velty Mannosylated poly(ethylene oxide)-b- poly(ε-caprolactone) diblock copolymers: synthesis, characterization, and interaction with a bacterial lectin Biomacromolecules 2007 8 9 2717 2725 (Pubitemid 47516921)
K. L. Wang M. X. You Y. Chen D. Han Z. Zhu J. Huang K. Williams C. J. Yang W. H. Tan Self-assembly of a Bifunctional DNA carrier for drug delivery Angew. Chem., Int. Ed. 2011 50 27 6098 6101
Y. Nagasaki K. Yasugi Y. Yamamoto A. Harada K. Kataoka Sugar-installed block copolymer micelles: their preparation and specific interaction with lectin molecules Biomacromolecules 2001 2 4 1067 1070 (Pubitemid 34026879)
V. Pourcelle H. Freichels F. Stoffelbach R. Auzely-Velty C. Jerome J. Marchand-Brynaert Light induced functionalization of PCL-PEG block copolymers for the covalent immobilization of biomolecules Biomacromolecules 2009 10 4 966 974
E. Lameignere L. Malinovska M. Slavikova E. Duchaud E. P. Mitchell A. Varrot O. Sedo A. Imberty M. Wimmerova Structural basis for mannose recognition by a lectin from opportunistic bacteria Burkholderia cenocepacia Biochem. J. 2008 411 307 318 (Pubitemid 351580183)
Y. Tang R. Mernaugh X. Zeng Nonregeneration protocol for surface plasmon resonance: study of high-affinity interaction with high-density biosensors Anal. Chem. 2006 78 6 1841 1848
R. Karlsson P. S. Katsamba H. Nordin E. Pol D. G. Myszka Analyzing a kinetic titration series using affinity biosensors Anal. Biochem. 2006 349 1 136 147 (Pubitemid 43129567)
H. H. Trutnau New multi-step kinetics using common affinity biosensors saves time and sample at full access to kinetics and concentration J. Biotechnol. 2006 124 1 191 195
Z. Dische New color reactions for determination of sugars in polysaccharides Methods Biochem. Anal. 1955 2 313 358
M. Dubois K. A. Gilles J. K. Hamilton P. A. Rebers F. Smith Colorimetric method for determination of sugars and related substances Anal. Chem. 1956 28 3 350 356
Y. Nagasaki T. Kutsuna M. Iijima M. Kato K. Kataoka Formyl-ended heterobifunctional poly(ethylene oxide): synthesis of poly(ethylene oxide) with a formyl group at one end and a hydroxyl group at the other end Bioconjugate Chem. 1995 6 231 233
M. A. R. Meier S. N. H. Aerts B. B. P. Staal M. Rasa U. S. Schubert PEO-b-PCL block copolymers: synthesis, detailed characterization, and selected micellar drug encapsulation behavior Macromol. Rapid Commun. 2005 26 1918 1924 (Pubitemid 43051767)
J. Rieger, Synthesis, characterization and biomedical interest of amphiphilic biocompatible and bioeliminable (glyco)copolymers of various architectures, PhD Thesis, University of Liège, Belgium, 2006
P. Becher M. J. Schick Macroemulsions Surfactant Sci. Ser. 1987 23 435 491
T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., 3rd edn, 1999, p. 349
D. Wakebayashi N. Nishiyama Y. Yamasaki K. Itaka N. Kanayama A. Harada Y. Nagasaki K. Kataoka Lactose-conjugated polyion complex micelles incorporating plasmid DNA as a targetable gene vector system: their preparation and gene transfecting efficiency against cultured HepG2 cells J. Controlled Release 2004 95 3 653 664 (Pubitemid 38340512)
E. Jule Y. Nagasaki K. Kataoka Surface plasmon resonance study on the interaction between lactose-installed poly(ethylene glycol)-poly(d,l-lactide) block copolymer micelles and lectins immobilized on gold surface Langmuir 2002 18 10334 10339
M. Dubois K. A. Gilles J. K. Hamilton P. A. Rebers F. Smith A colorimetric method for the determination of sugars Nature 1951 168 167
M. J. Joralemon S. Murthy E. E. Remsen M. L. Becker K. L. Wooley Synthesis, characterization and bioavailability of mannosylated shell cross-linked nanoparticles Biomacromolecules 2004 5 903 913 (Pubitemid 38702264)
L.-C. You F.-Z. Lu Z.-C. Li W. Zhang F.-M. Li Glucose-sensitive aggregates formed by poly(ethylene oxide)-block-poly(2-glucosyl-oxyethyl acrylate) with concanavalin A in dilute aqueous medium Macromolecules 2002 36 1 1 4
L. L. Kiessling J. E. Gestwicki L. E. Strong Synthetic multivalent ligands as probes of signal transduction Angew. Chem., Int. Ed. 2006 45 15 2348 2368 (Pubitemid 44105109)
G. De Crescenzo C. Boucher Y. Durocher M. Jolicoeur Kinetic characterization by surface plasmon resonance-based biosensors: principle and emerging trends Cell. Mol. Bioeng. 2008 1 4 204 215
M. Rheinnecker C. Hardt L. L. Ilag P. Kufer R. Gruber A. Hoess A. Lupas C. Rottenberger A. Pluckthun P. Pack Multivalent antibody fragments with high functional affinity for a tumor-associated carbohydrate antigen J. Immunol. 1996 157 7 2989 2997 (Pubitemid 126450057)
S. R. S. Ting G. Chen M. H. Stenzel Synthesis of glycopolymers and their multivalent recognitions with lectins Polym. Chem. 2010 1 1392 1412
T. K. Dam C. F. Brewer Thermodynamic studies of lectin-carbohydrate interactions by isothermal titration calorimetry Chem. Rev. 2002 102 2 387 429 (Pubitemid 35381635)
J. Rieger H. Freichels A. Imberty J.-L. Putaux T. Delair C. Jerome R. Auzely-Velty Polyester nanoparticles presenting mannose residues: toward the development of new vaccine delivery systems combining biodegradability and targeting properties Biomacromolecules 2009 10 3 651 657
M. Pokorna G. Cioci S. Perret E. Rebuffet N. Kostlanova J. Adam N. Gilboa-Garber E. P. Mitchell A. Imberty M. Wimmerova Unusual entropy-driven affinity of Chromobacterium violaceum lectin CV-IIL toward fucose and mannose Biochemistry 2006 45 24 7501 7510 (Pubitemid 43894944)
