Smart heparin-based bioconjugates synthesized by a combination of ATRP and click chemistry

Polymer Chemistry

Volumn 4, Issue 9, 2013, Pages 2800-2814

  Reyes Ortega, Felisa ^a,b   Parra Ruiz, Francisco J ^a,b   Averick, Saadyah E ^c   Rodríguez, Gema ^a,b   Aguilar, María Rosa ^a,b   Matyjaszewski, Krzysztof ^c   San Román, Julio ^a,b  

^a INSTITUTO DE CIENCIA Y TECNOLOGÍA DE POLÍMEROS   (Spain)

^b BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^c Carnegie Mellon University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER RADICAL POLYMERIZATION; CHLORINE COMPOUNDS; CYCLOADDITION; HYDROCARBONS; POLYSACCHARIDES; THERMOGRAVIMETRIC ANALYSIS;

'CLICK' CHEMISTRIES; BIOCONJUGATES; CLICK CHEMISTRY; DIPOLAR CYCLOADDITIONS; ELECTRON TRANSFER; FUNCTIONALIZED; LOW-MOLECULAR WEIGHT HEPARINS; STIMULI-RESPONSIVE;

BIOMOLECULES;

EID: 84875818141     PISSN: 17599954     EISSN: 17599962     Source Type: Journal    
DOI: 10.1039/c3py00055a     Document Type: Article

References (74)

1. X.-Q. Zhang X. Xu N. Bertrand E. Pridgen A. Swami O. C. Farokhzad Interactions of nanomaterials and biological systems: implications to personalized nanomedicine Adv. Drug Delivery Rev. 2012 64 13 1363 1384
2. T. D. Palmer W. J. Ashby J. D. Lewis A. Zijlstra Targeting tumor cell motility to prevent metastasis Adv. Drug Delivery Rev. 2011 63 8 568 581
3. M. Dash F. Chiellini R. M. Ottenbrite E. Chiellini Chitosan-A versatile semi-synthetic polymer in biomedical applications Prog. Polym. Sci. 2011 36 8 981 1014
4. Y. E. Shapiro Structure and dynamics of hydrogels and organogels: an NMR spectroscopy approach Prog. Polym. Sci. 2011 36 9 1184 1253
5. F. J. Xu W. T. Yang Polymer vectors via controlled/living radical polymerization for gene delivery Prog. Polym. Sci. 2011 36 9 1099 1131
6. S. Gomes I. B. Leonor J. F. Mano R. L. Reis D. L. Kaplan Natural and genetically engineered proteins for tissue engineering Prog. Polym. Sci. 2012 37 1 1 17
7. H. Tian Z. Tang X. Zhuang X. Chen X. Jing Biodegradable synthetic polymers: preparation, functionalization and biomedical application Prog. Polym. Sci. 2012 37 2 237 280
8. J. Zhang X. Li X. Li Stimuli-triggered structural engineering of synthetic and biological polymeric assemblies Prog. Polym. Sci. 2012 37 8 1130 1176
9. D. J. Siegwart J. K. Oh K. Matyjaszewski ATRP in the design of functional materials for biomedical applications Prog. Polym. Sci. 2012 37 1 18 37
10. K. Matyjaszewski Atom transfer radical polymerization: from mechanisms to applications Isr. J. Chem. 2012 52 3-4 206 220
11. K. Matyjaszewski Atom transfer radical polymerization (ATRP): current status and future perspectives Macromolecules 2012 45 10 4015 4039
12. N. V. Tsarevsky K. Matyjaszewski "Green" atom transfer radical polymerization: from process design to preparation of well-defined environmentally friendly polymeric materials Chem. Rev. 2007 107 6 2270 2299
13. K. Matyjaszewski J. Xia Atom transfer radical polymerization Chem. Rev. 2001 101 9 2921 2990
14. F. di Lena K. Matyjaszewski Transition metal catalysts for controlled radical polymerization Prog. Polym. Sci. 2010 35 8 959 1021
15. W. A. Braunecker K. Matyjaszewski Controlled/living radical polymerization: features, developments, and perspectives Prog. Polym. Sci. 2007 32 1 93 146
16. T. Pintauer K. Matyjaszewski Atom transfer radical addition and polymerization reactions catalyzed by ppm amounts of copper complexes Chem. Soc. Rev. 2008 37 6 1087 1097
17. S. Averick A. Simakova S. Park D. Konkolewicz A. J. D. Magenau R. A. Mehl K. Matyjaszewski ATRP under biologically relevant conditions: grafting from a protein ACS Macro Lett. 2012 1 1 6 10
18. D. Konkolewicz A. J. D. Magenau S. E. Averick A. Simakova H. He K. Matyjaszewski ICAR ATRP with ppm Cu catalyst in water Macromolecules 2012 45 11 4461 4468
19. A. Simakova S. E. Averick D. Konkolewicz K. Matyjaszewski Aqueous ARGET ATRP Macromolecules 2012 45 16 6371 6379
20. S. Averick E. Paredes W. Li K. Matyjaszewski R. Das Subha Direct DNA conjugation to star polymers for controlled reversible assemblies Bioconjugate Chem. 2011 22 10 2030 2037
21. P. L. Golas K. Matyjaszewski Click chemistry and ATRP: a beneficial union for the preparation of functional materials QSAR Comb. Sci. 2007 26 11-12 1116 1134
22. P. L. Golas N. V. Tsarevsky K. Matyjaszewski Structure-reactivity correlation in "click" chemistry: substituent effect on azide reactivity Macromol. Rapid Commun. 2008 29 12-13 1167 1171
23. P. L. Golas K. Matyjaszewski Marrying click chemistry with polymerization: expanding the scope of polymeric materials Chem. Soc. Rev. 2010 39 4 1338 1354
24. A. Qin J. W. Y. Lam B. Z. Tang Click polymerization: progresses, challenges, and opportunities Macromolecules 2010 43 21 8693 8702
25. N. V. Tsarevsky S. A. Bencherif K. Matyjaszewski Graft copolymers by a combination of ATRP and two different consecutive click reactions Macromolecules 2007 40 13 4439 4445
26. N. V. Tsarevsky B. S. Sumerlin K. Matyjaszewski Step-growth "click" coupling of telechelic polymers prepared by atom transfer radical polymerization Macromolecules 2005 38 9 3558 3561
27. N. V. Tsarevsky K. V. Bernaerts B. Dufour F. E. Du Prez K. Matyjaszewski Well-defined (co)polymers with 5-vinyltetrazole units via combination of atom transfer radical (co)polymerization of acrylonitrile and "click chemistry"-type postpolymerization modification Macromolecules 2004 37 25 9308 9313
28. T. Hasegawa M. Umeda M. Numata C. Li A.-H. Bae T. Fujisawa S. Haraguchi K. Sakurai S. Shinkai 'Click chemistry' on polysaccharides: a convenient, general, and monitorable approach to develop (1-3)-β-d-glucans with various functional appendages Carbohydr. Res. 2006 341 1 35 40
29. P.-H. Elchinger P.-A. Faugeras B. Boëns F. Brouillette D. Montplaisir R. Zerrouki R. Lucas Polysaccharides: the "click" chemistry impact Polymer 2011 3 4 1607 1651
30. W. H. Binder R. Sachsenhofer 'Click' chemistry in polymer and material science: an update Macromol. Rapid Commun. 2008 29 12-13 952 981
31. V. Vázquez-Dorbatt Z. P. Tolstyka H. D. Maynard Synthesis of aminooxy end-functionalized pNIPAAm by RAFT polymerization for protein and polysaccharide conjugation Macromolecules 2009 42 20 7650 7656
32. I. Capila R. J. Linhardt Heparin-protein interactions Angew. Chem., Int. Ed. 2002 41 3 390 412
33. J. Whitelock J. Melrose Heparan sulfate proteoglycans in healthy and diseased systems Wiley Interdiscip. Rev.: Syst. Biol. Med. 2011 3 6 739 751
34. D. B. Pike S. Cai K. R. Pomraning M. A. Firpo R. J. Fisher X. Z. Shu G. D. Prestwich R. A. Peattie Heparin-regulated release of growth factors in vitro and angiogenic response in vivo to implanted hyaluronan hydrogels containing VEGF and bFGF Biomaterials 2006 27 30 5242 5251
35. N. Yamaguchi L. Zhang B.-S. Chae C. S. Palla E. M. Furst K. L. Kiick Growth factor mediated assembly of cell receptor-responsive hydrogels J. Am. Chem. Soc. 2007 129 11 3040 3041
36. T. H. Tran B.-c. Bae Y.-k. Lee K. Na K. M. Huh Heparin-folate-retinoic acid bioconjugates for targeted delivery of hydrophobic photosensitizers Carbohydr. Polym. 2013 92 2 1615 1624
37. A. Greinacher S. Alban M. A. Omer-Adam W. Weitschies T. E. Warkentin Heparin-induced thrombocytopenia: a stoichiometry-based model to explain the differing immunogenicities of unfractionated heparin, low-molecular-weight heparin, and fondaparinux in different clinical settings Thromb. Res. 2008 122 2 211 220
38. K. Norrby Low-molecular-weight heparins and angiogenesis APMIS 2006 114 2 79 102
39. A. D. Baldwin K. G. Robinson J. L. Militar C. D. Derby K. L. Kiick R. E. Akins In situ crosslinkable heparin-containing poly(ethylene glycol) hydrogels for sustained anticoagulant release J. Biomed. Mater. Res., Part A 2012 100 8 2106 2118
40. J. Martínez-González L. Vila C. Rodríguez Bemiparin: second-generation, low-molecular-weight heparin for treatment and prophylaxis of venous thromboembolism Expert Rev. Cardiovasc. Ther. 2008 6 6 793 802
41. K. Wei L. Su G. Chen M. Jiang Does PNIPAM block really retard the micelle-to-vesicle transition of its copolymer? Polymer 2011 52 16 3647 3654
42. K. Hongliang, G. Xia, L. Ruigang and H. Yong, Synthesis and Properties of Cellulose Graft Copolymers with Well-Defined Architecture, in Functional Materials from Renewable Sources, American Chemical Society, 2012, vol. 1107, pp. 109-131
43. J.-F. Lutz Polymerization of oligo(ethylene glycol) (meth)acrylates: toward new generations of smart biocompatible materials J. Polym. Sci., Part A: Polym. Chem. 2008 46 11 3459 3470
44. S.-I. Yamamoto J. Pietrasik K. Matyjaszewski The effect of structure on the thermoresponsive nature of well-defined poly(oligo(ethylene oxide) methacrylates) synthesized by ATRP J. Polym. Sci., Part A: Polym. Chem. 2008 46 1 194 202
45. 2MA-co- OEOMA) copolymers via AGET ATRP in miniemulsion Macromolecules 2010 43 10 4623 4628
46. S. H. Cho M. S. Jhon S. Hong Yuk Temperature-sensitive swelling behavior of polymer gel composed of poly (N,N-dimethylaminoethyl methacrylate) and its copolymers Eur. Polym. J. 1999 35 10 1841 1845
47. A. Emileh E. Vasheghani-Farahani M. Imani Swelling behavior, mechanical properties and network parameters of pH- and temperature-sensitive hydrogels of poly((2-dimethyl amino)ethyl methacrylate-co-butyl methacrylate) Eur. Polym. J. 2007 43 5 1986 1995
48. L. Mespouille O. Coulembier D. Paneva P. Degée I. Rashkov P. Dubois Synthesis of adaptative and amphiphilic polymer model conetworks by versatile combination of ATRP, ROP, and "Click chemistry" J. Polym. Sci., Part A: Polym. Chem. 2008 46 15 4997 5013
49. W. Agut D. Taton S. Lecommandoux A versatile synthetic approach to polypeptide based rod-coil block copolymers by click chemistry Macromolecules 2007 40 16 5653 5661
50. S.-i. Yamamoto J. Pietrasik K. Matyjaszewski ATRP synthesis of thermally responsive molecular brushes from oligo(ethylene oxide)methacrylates Macromolecules 2007 40 26 9348 9353
51. S.-i. Yamamoto J. Pietrasik K. Matyjaszewski Temperature- and pH-responsive dense copolymer brushes prepared by ATRP Macromolecules 2008 41 19 7013 7020
52. L. Gu Z. Shen S. Zhang G. Lu X. Zhang X. Huang Novel amphiphilic centipede-like copolymer bearing polyacrylate backbone and poly(ethylene glycol) and polystyrene side chains Macromolecules 2007 40 13 4486 4493
53. H. Bao L. Li L. H. Gan Y. Ping J. Li P. Ravi Thermo- and pH-responsive association behavior of dual hydrophilic graft chitosan terpolymer synthesized via ATRP and click chemistry Macromolecules 2010 43 13 5679 5687
54. A. El-Faham F. Albericio Novel proton acceptor immonium-type coupling reagents: application in solution and solid-phase peptide synthesis Org. Lett. 2007 9 22 4475 4477
55. I. Ponedel'kina V. Odinokov E. Lukina T. Tyumkina L. Khalilov U. Dzhemilev Chemical modification of heparin Russ. J. Bioorg. Chem. 2006 32 5 472 477
56. J. M. Pelet D. Putnam An in-depth analysis of polymer-analogous conjugation using DMTMM Bioconjugate Chem. 2011 22 3 329 337
57. B. Le Droumaguet J. Nicolas Recent advances in the design of bioconjugates from controlled/living radical polymerization Polym. Chem. 2010 1 5 563 598
58. K. L. Heredia H. D. Maynard Synthesis of protein-polymer conjugates Org. Biomol. Chem. 2007 5 1 45 53
59. L. A. Canalle D. W. P. M. Lowik J. C. M. van Hest Polypeptide-polymer bioconjugates Chem. Soc. Rev. 2010 39 1 329 353
60. B. S. Sumerlin Proteins as initiators of controlled radical polymerization: grafting-from via ATRP and RAFT ACS Macro Lett. 2011 1 1 141 145
61. J. Nicolas G. Mantovani D. M. Haddleton Living radical polymerization as a tool for the synthesis of polymer-protein/peptide bioconjugates Macromol. Rapid Commun. 2007 28 10 1083 1111
62. S. E. Averick E. Paredes D. Grahacharya B. F. Woodman S. J. Miyake-Stoner R. A. Mehl K. Matyjaszewski S. R. Das A protein-polymer hybrid mediated by DNA Langmuir 2012 28 4 1954 1958
63. C. E. Schanté G. Zuber C. Herlin T. F. Vandamme Chemical modifications of hyaluronic acid for the synthesis of derivatives for a broad range of biomedical applications Carbohydr. Polym. 2011 85 3 469 489
64. A.-F. Li J.-H. Wang F. Wang Y.-B. Jiang Anion complexation and sensing using modified urea and thiourea-based receptors Chem. Soc. Rev. 2010 39 10 3729 3745
65. K. T. Goodall C. C. Chooi A. S. Gallus Heparin stability: effects of diluent, heparin activity, container, and pH J. Clin. Pathol. 1980 33 12 1206 1211
66. M. Kunishima C. Kawachi K. Hioki K. Terao S. Tani ChemInform abstract: formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM ChemInform 2001 32 27 1551 1558
67. M. Kunishima C. Kawachi J. Monta K. Terao F. Iwasaki S. Tani 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formation of amides and esters Tetrahedron 1999 55 46 13159 13170
68. S. Flor V. Tripodi M. Contin C. Dobrecky S. Lucangioli Spectroscopic approach of the association of heparin and its contaminant and related polysaccharides with polymers used in electrokinetic chromatography J. Chem. Pharm. Res. 2012 4 2 972 979
69. G. David F. L. William B. W. Frank Infrared spectroscopy of heparin-cation complexes Biochem. J. 1987 244 143 149
70. X. Jiang M. C. Lok W. E. Hennink Degradable-brushed pHEMA-pDMAEMA synthesized via ATRP and click chemistry for gene delivery Bioconjugate Chem. 2007 18 6 2077 2084
71. M. Bertoldo G. Zampano F. L. Terra V. Villari V. Castelvetro Amphiphilic amylose-g-poly(meth)acrylate copolymers through "click" onto grafting method Biomacromolecules 2010 12 2 388 398
72. 13C nuclear magnetic resonance spectroscopy for characterization of heparin preparations Semin. Thromb. Hemostasis 2001 27 05 473 482
73. X. Zhang K. Matyjaszewski Synthesis of well-defined amphiphilic block copolymers with 2-(dimethylamino)ethyl methacrylate by controlled radical polymerization Macromolecules 1999 32 6 1763 1766
74. X. Zhang J. Xia K. Matyjaszewski Controlled-living radical polymerization of 2-(dimethylamino)ethyl methacrylate Macromolecules 1998 31 15 5167 5169