Label-free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

Journal of Molecular Recognition

Volumn 24, Issue 6, 2011, Pages 953-959

  Schumacher, Soeren ^a   Katterle, Martin ^a   Hettrich, Cornelia ^a   Paulke, Bernd Reiner ^b   Hall, Dennis G ^c   Scheller, Frieder W ^a   Gajovic Eichelmann, Nenad ^a  

^a FRAUNHOFER INSTITUTE FOR BIOMEDICAL ENGINEERING   (Germany)

^b FRAUNHOFER INSTITUTE FOR APPLIED POLYMER RESEARCH   (Germany)

^c UNIVERSITY OF ALBERTA   (Canada)

Author keywords

boroxole; isothermal titration calorimetry; monosaccharide detection; nanoparticle

Indexed keywords

3 AMINOBENZENEBORONIC ACID; 3-AMINOBENZENEBORONIC ACID; BENZENEBORONIC ACID; BORON DERIVATIVE; BORONIC ACID DERIVATIVE; CELL SURFACE RECEPTOR; FRUCTOSE; LATEX; LIGAND; NANOPARTICLE; SACCHARIDE BINDING PROTEINS; SACCHARIDE-BINDING PROTEINS; STYRENE DERIVATIVE;

ARTICLE; CALORIMETRY; CHEMISTRY; ENTROPY; METHODOLOGY; PH; PROTEIN BINDING; THERMODYNAMICS;

BORON COMPOUNDS; BORONIC ACIDS; CALORIMETRY; ENTROPY; FRUCTOSE; HYDROGEN-ION CONCENTRATION; LATEX; LIGANDS; NANOPARTICLES; PROTEIN BINDING; RECEPTORS, CELL SURFACE; STYRENES; THERMODYNAMICS;

EID: 80155178883     PISSN: 09523499     EISSN: 10991352     Source Type: Journal    
DOI: 10.1002/jmr.1142     Document Type: Article

References (25)

1. Bekiroglu S, Kenne L, Sandstrom C,. 2004. NMR study on the hydroxy protons of the Lewis X and Lewis Y oligosaccharides. Carbohydr. Res. 339 (14): 2465-2468. (Pubitemid 39248516)
2. Beres L, Sturtevant JM,. 1971. Calorimetric studies of activation of chymotrypsinogen-A. Biochemistry 10 (11): 2120-2126.
3. Berube M, Dowlut M, Hall DG,. 2008. Benzoboroxoles as efficient glycopyranoside-binding agents in physiological conditions: structure and selectivity of complex formation. J. Org. Chem. 73 (17): 6471-6479.
4. Bhat KL, Howard NJ, Rostami H, Lai JH, Bock CW,. 2005. Intramolecular dative bonds involving boron with oxygen and nitrogen in boronic acids and esters: a computational study. J. Mol. Struct. THEOCHEM 723 (1-3): 147-157. (Pubitemid 40630949)
5. Chiad K, Stelzig SH, Gropeanu R, Weil T, Klapper M, Mullen K,. 2009. Isothermal titration calorimetry: a powerful technique to quantify interactions in polymer hybrid systems. Macromolecules 42 (19): 7545-7552.
6. Dowlut M, Hall DG,. 2006. Development of an improved class of sugar-binding boronic acids for the design of receptors and sensors for glycopyranosides and glycoconjugates in water. J. Am. Chem. Soc. 128: 4226-4227.
7. James TD, Phillips MD, Shinkai S,. 2006. Boronic Acids in Saccharide Recognition. The Royal Society of Chemistry: Cambridge.
8. Jay JI, Lai BE, Myszka DG, Mahalingam A, Langheinrich K, Katz DF, Kiser PF,. 2010. Multivalent benzoboroxole functionalized polymers as gp120 glycan targeted microbicide entry inhibitors. Mol. Pharm. 7 (1): 116-129.
9. Jelinek R, Kolusheva S,. 2004. Carbohydrate biosensors. Chem. Rev. 104 (12): 5987-6016.
10. Jin S, Cheng YF, Reid S, Li MY, Wang BH,. 2010. Carbohydrate recognition by boronolectins, small molecules, and lectins. Med. Res. Rev. 30 (2): 171-257.
11. Kirchner R, Seidel J, Wolf G, Wulff G,. 2002. Calorimetric investigation of chiral recognition processes in a molecularly imprinted polymer. J. Incl. Phenom. Macrocycl. Chem. 43 (3-4): 279-283. (Pubitemid 38075760)
12. Kuivila HG, Keough AH, Soboczenski EJ,. 1954. Areneboronates from diols and polyols. J. Org. Chem. 19 (5): 780-783.
13. Nieba L, Krebber A, Pluckthun A,. 1996. Competition BIAcore for measuring true affinities: Large differences from values determined from binding kinetics. Anal. Biochem. 234 (2): 155-165. (Pubitemid 26063796)
14. CC coupling constants. J. Chem. Soc., Perkin Trans. 2 (12): 2583-2588. (Pubitemid 126436972)
15. Pal A, Berube M, Hall DG,. 2010. Design, synthesis, and screening of a library of peptidyl bis(boroxoles) as oligosaccharide receptors in water: identification of a receptor for the tumor marker TF-antigen disaccharide. Angew. Chem. Int. Ed. 49 (8): 1492-1495.
16. Paulke BR, Hartig W, Bruckner G,. 1992. Synthesis of nanoparticles for brain cell labelling in vivo. Acta Polym. 43 (5): 288-291.
17. Pierce MM, Raman CS, Nall BT,. 1999. Isothermal titration calorimetry of protein-protein interactions. Methods 19 (2): 213-221. (Pubitemid 29515856)
18. Schmidtchen FP,. 2007. Isothermal titration calorimetry in supramolecular chemistry, Schalley CA, (ed). Analytical Methods in Supramolecular Chemistry, 1st edn., Wiley-VCH: Weinheim. 55-78.
19. Schumacher S, Grüneberger F, Katterle M, Hettrich C, Hall DG, Scheller FW, Gajovic-Eichelmann N,. 2011. Molecular imprinting of fructose using a polymerizable benzoboroxole: effective complexation at pH 7.4. Polymer. 52 (7): 2485-2491.
20. Schumacher S, Katterle M, Hettrich C, Paulke B-R, Pal A, Hall DG, Scheller FW, Gajovic-Eichelmann N,. 2011. Chem. Sensor. 1 (1): 1-7.
21. Springsteen G, Wang BH,. 2002. A detailed examination of boronic acid-diol complexation. Tetrahedron 58 (26): 5291-5300. (Pubitemid 34663811)
22. Torun O, Dudak FC, Bas D, Tamer U, Boyaci IH,. 2009. Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor. Sens. Actuators, B 140 (2): 597-602.
23. Walker DB, Joshi G, Davis AP,. 2009. Progress in biomimetic carbohydrate recognition. Cell. Mol. Life Sci. 66 (19): 3177-3191.
24. Wulff G,. 1982. Selective binding to polymers via covalent bonds-the construction of chiral cavities as specific receptor-sites. Pure Appl. Chem. 54 (11): 2093-2102. (Pubitemid 14543090)
25. Yan J, Springsteen G, Deeter S, Wang BH,. 2004. The relationship among pK(a),pH, and binding constants in the interactions between boronic acids and diols-it is not as simple as it appears. Tetrahedron 60 (49): 11205-11209. (Pubitemid 39425240)