Fluorescent boronic acid polymer grafted on silica particles for affinity separation of saccharides

ACS Applied Materials and Interfaces

Volumn 6, Issue 3, 2014, Pages 1406-1414

  Xu, Zhifeng ^a,b,c   Uddin, Khan Mohammad Ahsan ^a   Kamra, Tripta ^a   Schnadt, Joachim ^a   Ye, Lei ^a  

^a LUND UNIVERSITY   (Sweden)

^b HENGYANG NORMAL UNIVERSITY   (China)

^c College of Hunan Province   (China)

Author keywords

affinity separation; atom transfer radical polymerization; boronic acid; click chemistry; molecular recognition

Indexed keywords

BORONIC ACID DERIVATIVE; CARBOHYDRATE; FRUCTOSE; HORSERADISH PEROXIDASE; POLYMER; SILICON DIOXIDE;

AFFINITY CHROMATOGRAPHY; CHEMISTRY; FLUORESCENCE MICROSCOPY; INFRARED SPECTROSCOPY; ISOLATION AND PURIFICATION; METABOLISM; PH; POLYMERIZATION; PROCEDURES; SCANNING ELECTRON MICROSCOPY; SPECTROFLUOROMETRY; SYNTHESIS; THERMOGRAVIMETRY; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY PHOTOELECTRON SPECTROSCOPY;

BORONIC ACIDS; CARBOHYDRATES; CHROMATOGRAPHY, AFFINITY; FRUCTOSE; HORSERADISH PEROXIDASE; HYDROGEN-ION CONCENTRATION; MICROSCOPY, ELECTRON, SCANNING; MICROSCOPY, FLUORESCENCE; PHOTOELECTRON SPECTROSCOPY; POLYMERIZATION; POLYMERS; SILICON DIOXIDE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY;

EID: 84894145335     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am405531n     Document Type: Article

References (57)

1. Bull, S. D.; Davidson, M. G.; van den Elsen, J. M. H.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao, J.; James, T. D. Exploiting the Reversible Covalent Bonding of Boronic Acids: Recognition, Sensing, and Assembly Acc. Chem. Res. 2013, 46, 312-326
2. Kim, K. T.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; van Hest, J. C. M. Polymeric Monosaccharide Receptors Responsive at Neutral pH J. Am. Chem. Soc. 2009, 131, 13908-13909
3. Tuma, P.; Malkova, K.; Samcova, E.; Stulik, K. Rapid Monitoring of Mono- and Disaccharides in Drinks, Foodstuffs and Foodstuff Additives by Capillary Electrophoresis with Contactless Conductivity Detection Anal. Chim. Acta 2011, 698, 1-5
4. Okutucu, B.; Önal, S.; Telefoncu, A. Noncovalent Galactose Imprinted Polymer for the Recognition of Different Saccharides Talanta 2009, 78, 1190-1193
5. Lee, J.-D.; Greene, N. T.; Rushton, G. T.; Shimizu, K. D.; Hong, J.-I. Carbohydrate Recognition by Porphyrin-Based Molecularly Imprinted Polymers Org. Lett. 2005, 7, 963-966
6. Yang, Y.; Yi, C.; Luo, J.; Liu, R.; Liu, J.; Jiang, J.; Liu, X. Glucose Sensors Based on Electrodeposition of Molecularly Imprinted Polymeric Micelles: A Novel Strategy for MIP Sensors Biosens. Bioelectron. 2011, 26, 2607-2612
7. a Changes of Poly(aniline boronic acid) J. Am. Chem. Soc. 2002, 124, 12486-12493
8. Gao, S.; Wang, W.; Wang, B. Building Fluorescent Sensors for Carbohydrates Using Template-Directed Polymerizations Bioorg. Chem. 2001, 29, 308-320
9. Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S. Boronic Acid Building Blocks: Tools for Sensing and Separation Chem. Commun. 2012, 47, 1106-1123
10. Schumacher, S.; Grüneberger, F.; Katterle, M.; Hettrich, C.; Hall, D. G.; Scheller, F. W.; Gajovic-Eichelmann, N. Molecular Imprinting of Fructose Using a Polymerizable Benzoboroxole: Effective Complexation at pH 7.4 Polymer 2011, 52, 2485-2491
11. Tan, J.; Wang, H.-F.; Yan, X.-P. Discrimination of Saccharides with a Fluorescent Molecular Imprinting Sensor Array Based on Phenylboronic Acid Functionalized Mesoporous Silica Anal. Chem. 2009, 81, 5273-5280
12. Manju, S.; Hari, P. R.; Sreenivasan, K. Fluorescent Molecularly Imprinted Polymer Film Binds Glucose with a Concomitant Changes in Fluorescence Biosens. Bioelectron. 2010, 26, 894-897
13. Cao, H.; McGill, T.; Heagy, M. D. Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N -Phenyl-1,8-naphthalenedicarboximides J. Org. Chem. 2004, 69, 2959-2966
14. Edwards, N. Y.; Sager, T. W.; McDevitt, J. T.; Anslyn, E. V. Boronic Acid Based Peptidic Receptors for Pattern-Based Saccharide Sensing in Neutral Aqueous Media, an Application in Real-Life Samples J. Am. Chem. Soc. 2007, 129, 13575-13583
15. Deng, G.; James, T. D.; Shinkai, S. Allosteric Interaction of Metal Ions with Saccharides in a Crowned Diboronic Acid J. Am. Chem. Soc. 1994, 116, 4567-4512
16. Zhu, W.; Wu, F. Monosaccharide Recognition Based on Fluorescent Receptor Containing Boronic Acid Prog. Chem. 2009, 21, 1241-1253
17. Ishi-i, T.; Iguchi, R.; Shinkai, S. DL Selective Re-binding of Saccharide-Imprinted [60]Fullerene-Bisadducts Based on a Saccharide-Boronic Acid Interaction: Development of a Molecular Imprinting Technique Useful in a Homogeneous System Tetrahedron 1999, 55, 3883-3892
18. Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-i, T.; Yoshihara, K.; Shinkai, S. Chiroselective Re-binding of Saccharides to the Fibrous Aggregates Prepared from Organic Gels of Cholesterylboronic Acid Tetrahedron Lett. 1998, 39, 2981-2984
19. Roy, D.; Sumerlin, B. S. Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH ACS Macro Lett. 2012, 1, 529-532
20. Suksrichavalit, T.; Yoshimatsu, K.; Prachayasittikul, V.; Bülow, L.; Ye, L. Clickable" Affinity Ligands for Effective Separation of Glycoproteins J. Chromatogr., A 2010, 1217, 3635-3641
21. Uddin, K. M. A.; Ye, L. Fluorogenic Affinity Gels Constructed from Clickable Boronic Acids J. Appl. Polym. Sci. 2013, 128, 1527-1533
22. Xu, Z.; Uddin, K. M. A.; Ye, L. Boronic Acid Terminated Thermo-Responsive and Fluorogenic Polymer: Controlling Polymer Architecture for Chemical Sensing and Affinity Separation Macromolecules 2012, 45, 6464-6470
23. De, P.; Gondi, S. R.; Roy, D.; Sumerlin, B. S. Boronic Acid-Terminated Polymers: Synthesis by RAFT and Subsequent Supramolecular and Dynamic Covalent Self-Assembly Macromolecules 2009, 42, 5614-5621
24. Bench, B. J.; Johnson, R.; Hamilton, C.; Gooch, J.; Wright, J. R. Avidin Self-Associates with Boronic Acid Gel Suspensions: An Affinity Boron Carrier that Might Be Developed for Boron Neutron-Capture Therapy J. Colloid Interface Sci. 2004, 270, 315-320
25. Roy, D.; Cambre, J. N.; Sumerlin, B. S. Sugar-Responsive Block Copolymers by Direct RAFT Polymerization of Unprotected Boronic Acid Monomers Chem. Commun. 2008, 2477-2479
26. Cambre, J. N.; Sumerlin, B. S. Biomedical Applications of Boronic Acid Polymers Polymer 2011, 52, 4631-4643
27. Cambre, J. N.; Roy, D.; Gondi, S. R.; Sumerlin, B. S. Facile Strategy to Well-Defined Water-Soluble Boronic Acid (Co)polymers J. Am. Chem. Soc. 2007, 129, 10348-10349
28. Wang, B.; Ma, R.; Liu, G.; Li, Y.; Liu, X.; An, Y.; Shi, L. Glucose-Responsive Micelles from Self-Assembly of Poly(ethylene glycol)- b -Poly(acrylic acid- co -acrylamidophenylboronic acid) and the Controlled Release of Insulin Langmuir 2009, 25, 12522-12528
29. Qin, Y.; Sukul, V.; Pagakos, D.; Cui, C.; Jäkle, F. Preparation of Organoboron Block Copolymers via ATRP of Silicon and Boron-Functionalized Monomers Macromolecules 2005, 38, 8987-8990
30. Niu, W.; O'Sullivan, C.; Rambo, B. M.; Smith, M. D.; Lavigne, J. J. Self-reparing Polymers: Poly(dioxaborolane)s Containing Trigonal Planar Boron Chem. Commun. 2005, 4342-4344
31. Niu, W.; Smith, M. D.; Lavigne, J. J. Self-Assembling Poly(dioxaborole)s as Blue-Emissive Materials J. Am. Chem. Soc. 2006, 128, 16466-16467
32. Tilford, R. W.; Gemmill, W. R.; Loye, H.-C. Z.; Lavigne, J. J. Facile Synthesis of a Highly Crystalline, Covalently Linked Porous Boronate Network Chem. Mater. 2006, 18, 5296-5301
33. Jäkle, F. Advances in the Synthesis of Organoborane Polymers for Optical, Electronic, and Sensory Applications Chem. Rev. 2010, 110, 3985-4022
34. Jay, J. I.; Shukair, S.; Langheinrich, K.; Hanson, M. C.; Cianci, G. C.; Johnson, T. J.; Clark, M. R.; Hope, T. J.; Kiser, P. F. Modulation of Viscoelasticity and HIV Transport as a Function of pH in a Reversibly Crosslinked Hydrogel Adv. Funct. Mater. 2009, 19, 2969-2977
35. Preinerstorfer, B.; Lämmerhofer, M.; Linder, W. Synthesis and Application of Novel Phenylboronate Affinity Materials Based on Organic Polymer Particles for Selective Trapping of Glycoproteins J. Sep. Sci. 2009, 32, 1673-1685
36. Foettinger, A.; Leitner, A.; Linder, W. Solid-Phase Capture and Release of Arginine Peptides by Selective Tagging and Boronate Affinity Chromatography J. Chromatogr. A 2005, 1079, 187-196
37. Pereira Morais, M. P.; Mackay, J. D.; Bhamra, S. K.; Buchanan, J. G.; James, T. D.; Fossey, J. S.; van den Elsen, J. M. H. Analysis of Protein Glycation Using Phenylboronate Acrylamide Gel Electrophoresis Proteomics 2010, 10, 48-58
38. Jackson, T. R.; Springall, J. S.; Rogalle, D.; Masumoto, N.; Ching Li, H.; D'Hooge, F.; Perera, S. P.; Jenkins, T. A.; James, T. D.; Fossey, J. S.; van den Elsen, J. M. H. Boronate Affinity Saccharide Electrophoresis: A Novel Carbohydrate Analysis Tool Electrophoresis 2008, 29, 4185-4191
39. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
40. Ivanov, A. E.; Eccles, J.; Panahi, H. A.; Kumar, A.; Kuzimenkova, M. V.; Nilsson, L.; BergenstaÌŠhl, B.; Long, N.; Philips, G. J.; Mikhalovsky, S. V.; Galaev, I.; Mattiasson, B. Boronate-Containing Polymer Brushes: Characterization, Interaction with Saccharides and Mammalian Cells J. Biomed. Mater. Res. 2009, 88A, 213-225
41. Liu, H.; Li, Y.; Sun, K.; Fan, J.; Zhang, P.; Meng, J.; Wang, S.; Jiang, L. Dual-Responsive Surfaces Modified with Phenylboronic Acid-Containing Polymer Brush To Reversibly Capture and Release Cancer Cells J. Am. Chem. Soc. 2013, 135, 7603-7609
42. Coessens, V.; Pintauer, T.; Matyjaszewski, K. Functional Polymers by Atom Transfer Radical Polymerization Prog. Polym. Sci. 2001, 26, 337-77
43. Pyun, J.; Matyjaszewski, K. Synthesis of Nanocomposite Organic/Inorganic Hybrid Materials Using Controlled/"Living" Radical Polymerization Chem. Mater. 2001, 13, 3436-48
44. Siegwart, D. J.; Oh, J. K.; Matyjaszewski, K. ATRP in the Design of Functional Materials for Biomedical Applications Prog. Polym. Sci. 2012, 37, 18-37
45. Couet, J.; Biesalski, M. Surface-Initiated ATRP of N -Isopropylacrylamide from Initiator-Modified Self-Assembled Peptide Nanotubes Macromolecules 2006, 39, 7258-7268
46. Matyjaszewski, K.; Xia, J. Atom Transfer Radical Polymerization Chem. Rev. 2001, 101, 2921-2990
47. Kamigaito, M.; Ando, T.; Sawamoto, M. Metal-Catalyzed Living Radical Polymerization Chem. Rev. 2001, 101, 3689-3745
48. Jiang, J.; Zhang, Y.; Guo, X.; Zhang, H. Narrow or Monodisperse, Highly Cross-Linked, and "Living" Polymer Microspheres by Atom Transfer Radical Precipitation Polymerization Macromolecules 2011, 44, 5893-5904
49. Hajizadeh, S.; Kirsebom, H.; Leistner, A.; Mattiasson, B. Composite Cryogel with Immobilized Concanavalin A for Affinity Chromatography of Glycoproteins J. Sep. Sci. 2012, 35, 2978-2985
50. Reynolds, G. A.; Drexhage, K. H. New Coumarin Dyes with Rigidized Structure for Flashlamp-Pumped Dye Lasers Opt. Commun. 1975, 13, 222-225
51. Sezgin, A.; Akbey, Ü.; Hansen, M. R.; Graf, R.; Bozkurt, A.; Baykal, A. Synthesis and NMR Studies of the Polymer Membranes Based on Poly(4-vinylbenzylboronic acid) and Phosphoric Acid Polymer 2008, 49, 3859-3864
52. De'Nève, B.; Delamar, M.; Nguyen, T. T.; Shanahan, M. E. R. Failure Mode and Aging of Steel/Epoxy Joints Appl. Surf. Sci. 1998, 134, 202-212
53. 3, and BN: An ESCA, Auger, SIMS, and SXS Study J. Chem. Phys. 1980, 72, 1095-1108
54. Vandencasteele, N.; Reniers, F. Plasma-Modified Polymer Surfaces: Characterization Using XPS J. Electron Spectrosc. Relat. Phenom. 2010, 178-179, 394-408
55. Springsteen, G.; Wang, B. Alizarin Red S. as a General Optical Reporter for Studying the Binding of Boronic Acids with Carbohydrates Chem. Commun. 2001, 1608-1609
56. Larkin, J. D.; Fossey, J. S.; James, T. D.; Brooks, B. R.; Bock, C. W. A Computational Investigation of the Nitrogen-Boron Interaction in o -(N, N -Dialkylaminomethyl)arylboronate Systems J. Phys. Chem. 2010, 114, 12531-12539
57. Collins, B. E.; Sorey, S.; Hargrove, A. E.; Shabbir, S. H.; Lynch, V. M.; Anslyn, E. V. Probing Intramolecular B-N Interactions in Ortho -Aminomethyl Arylboronic Acids J. Org. Chem. 2009, 74, 4055-4060