Temperature-controlled release of catechol dye in thermosensitive phenylboronate-containing copolymers: A quantitative study

European Polymer Journal

Volumn 46, Issue 6, 2010, Pages 1367-1373

  De Lusançay, Gaëlle Carré ^a   Norvez, Sophie ^a   Iliopoulos, Ilias ^a  

^a CNRS   (France)

Author keywords

Alizarin Red S (ARS); Binding constant; Dialysis; NIPAM; Phenylboronic acid; Thermosensitive copolymer

Indexed keywords

ACRYLIC MONOMERS; ALIZARIN; DIALYSIS; ORGANIC ACIDS; PHENOLS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

ALIZARIN RED; BINDING CONSTANT; NIPAM; PHENYLBORONIC ACIDS; THERMOSENSITIVE COPOLYMERS;

BINS;

EID: 79955867274     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2010.03.020     Document Type: Article

References (23)

1. Gil ES, Hudson SA. Stimuli-responsive polymers and their bioconjugates. Prog Polym Sci 2004;29:1173-222.
2. Hoffman AS. Bioconjugates of intelligent polymers and recognition proteins for use in diagnostics and affinity separations. Clin Chem 2000;46:1478-86.
3. Van de Heyden K, Babooram K, Ahmed M, Narain R. Protein encapsulation and release from degradable sugar based hydrogels. Eur Polym J 2009;45:1689-97.
4. Ivanov AE, Galaev IY, Mattiasson B. Binding of adenosine to pendant phenyl-boronate groups of thermoresponsive copolymer: a quantitative study. Macromol Biosci 2005;5:795-800. (Pubitemid 41232831)
5. Ivanov AE, Shiomori K, Kawano Y, Galaev IY, Mattiasson B. Effects of polyols, saccharides, and glycoproteins on thermoprecipitation of phenylboronate-containing copolymers. Biomacromolecules 2006;7:1017-24. (Pubitemid 43670786)
6. Kataoka K, Miyazaki H, Bunya M, Okano T, Sakurai Y. Totally synthetic polymer gels responding to external glucose concentration: their preparation and application to on-off regulation of insulin release. J Am Chem Soc 1998;120:12694-965.
7. Kikuchi A, Okano T. Pulsatile drug release control using hydrogels. Adv Drug Deliver Rev 2002;54:53-77. (Pubitemid 34075314)
8. Lorand JP, Edwards JO. Polyol complexes and structure of the benzeneboronate ion. J Org Chem 1959;24:769-74.
9. Fujita N, Shinkai S, James TD. Boronic acids in molecular selfassembly. Chem Asian J 2008;3:1076-91.
10. Kitano S, Kataoka K, Koyama K, Okano T, Sakurai Y. Glucoseresponsive complex formation between PVA and PVP with pendent phenylboronic acid moieties. Makromol Chem, Rapid Commun 1991;12:227-33.
11. Shiomori K, Ivanov AE, Galaev IY, Kawano Y, Mattiasson B. Thermoresponsive properties of sugar sensitive copolymer of Nisopropylacrylamide and 3-(acrylamido)phenylboronic acid. Macromol Chem Phys 2004;205:27-34.
12. Springsteen G, Wang BH. Alizarin Red S as a general optical reporter for studying the binding of boronic acids with carbohydrates. Chem Commun 2001:1608-9. (Pubitemid 32808017)
13. Springsteen G, Wang BH. A detailed examination of boronic acid-diol complexation. Tetrahedron 2002;58:5291-300. (Pubitemid 34663811)
14. Arimori S, Ward CJ, James TD. A D-glucose selective fluorescent assay. Tetrahedron Lett 2002;43:303-5. (Pubitemid 34024884)
15. Ma WMJ, Pereira Morais MP, D'Hooge F, van den Elsen JMH, Cox JPL, James TD, et al. Dye displacement assay for saccharide detection with boronate hydrogels. Chem Commun 2009:532-4.
16. Cannizzo C, Amigoni-Gerbier S, Larpent C. Boronic-acidfunctionalized nanoparticles: synthesis by microemulsion polymerization and application as a re-usable optical nanosensor for carbohydrates. Polymer 2005;46:1269-76. (Pubitemid 40143306)
17. Elmas B, Senel S, Tuncel A. A new thermosensitive fluorescent probe for diol sensing: poly(N-isopropylacrylamide-co-vinylphenylboronic acid)-Alizarin Red S complex. React Funct Polym 2007;67:87-96. (Pubitemid 46108641)
18. Hajizadeh S, Ivanov AE, Jahanshahi M, Sanati MH, Zhuravleva NV, Mikhalovska LI, et al. Glucose sensors with increased sensitivity based on composite gels containing immobilized boronic acid. React Funct Polym 2008;68:1625-35.
19. Ge H, Ding Y, Ma C, Zhang G. Temperature controlled release of diols from N-isopropylacrylamide-co-acrylamidophenylboronic acid microgels. J Phys Chem B 2006;110:20635-9. (Pubitemid 44797495)
20. Boudet C, Iliopoulos I, Poncelet O, Cloitre M. Control of the chemical cross-linking of gelatin by a thermosensitive polymer: example of switchable reactivity. Biomacromolecules 2005;6:3073-8. (Pubitemid 41764064)
21. Feil H, Bae YH, Feijen J, Kim SW. Effect of comonomer hydrophilicity and ionization on the lower critical solution temperature of Nisopropylacrylamide copolymers. Macromolecules 1993;26:2496.
22. Bokias G, Vasilevskaya VV, Iliopoulos I, Hourdet D, Khokhlov AR. Influence of migrating ionic groups on the solubility of polyelectrolytes: phase behavior of ionic poly(N-isopropylacrylamide) copolymers in water. Macromolecules 2000;33:9757-63. (Pubitemid 32091692)
23. Palit DK, Pal H, Mukherjee T, Mittal JP. Photodynamics of the S1 state of some hydroxy- and amino-substituted naphtoquinones and anthraquinones. J Chem Soc Faraday Trans 1990;86:3861-9.