Multifunctional dendritic sialopolymersomes as potential antiviral agents: Their lectin binding and drug release properties

Langmuir

Volumn 29, Issue 21, 2013, Pages 6420-6428

  Nazemi, Ali ^a   Haeryfar, S M Mansour ^a   Gillies, Elizabeth R ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILIC CO-POLYMERS; BINDING AFFINITIES; BIOACTIVE MOLECULES; BIOMEDICAL APPLICATIONS; DRUG RELEASE PROPERTIES; N-ACETYLNEURAMINIC ACID; NEURAMINIDASE INHIBITORS; SELF-ORGANIZED MATERIAL;

ANTIVIRAL AGENTS; BINDING ENERGY; CARBOXYLIC ACIDS; DENDRIMERS; DRUG PRODUCTS; ENZYME INHIBITION; LOADING; MEDICAL APPLICATIONS; MOLECULES; POLYETHYLENE OXIDES; SURFACES; VIRUSES;

FUNCTIONAL POLYMERS;

ANTIVIRUS AGENT; DENDRIMER; LECTIN; MACROGOL DERIVATIVE; N ACETYLNEURAMINIC ACID; POLYCAPROLACTONE; POLYESTER;

BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; ORTHOMYXOVIRUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIVIRAL AGENTS; BINDING SITES; DENDRIMERS; LECTINS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; N-ACETYLNEURAMINIC ACID; ORTHOMYXOVIRIDAE; POLYESTERS; POLYETHYLENE GLYCOLS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84878343866     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la400890f     Document Type: Article

References (62)

1. Zhang, L. F.; Eisenberg, A. Multiple Morphologies of Crew-Cut Aggregates of Polystyrene- b -poly(acrylic acid) Block-Copolymers Science 1995, 268, 1728-1731
2. Cornelissen, J.; Fischer, M.; Sommerdijk, N.; Nolte, R. J. M. Helical Superstructures from Charged Poly(styrene)-poly(isocyanodipeptide) Block Copolymers Science 1998, 280, 1427-1430
3. Pochan, D. J.; Chen, Z. Y.; Cui, H. G.; Hales, K.; Qi, K.; Wooley, K. L. Toroidal Triblock Copolymer Assemblies Science 2004, 306, 94-97
4. Discher, D. E.; Eisenberg, A. Polymer Vesicles Science 2002, 297, 967-973
5. Yan, D. Y.; Zhou, Y. F.; Hou, J. Supramolecular Self-Assembly of Macroscopic Tubes Science 2004, 303, 65-67
6. Cui, H. G.; Chen, Z. Y.; Zhong, S.; Wooley, K. L.; Pochan, D. J. Block Copolymer Assembly via Kinetic Control Science 2007, 317, 647-650
7. Brinkhuis, R. P.; Rutjes, F.; van Hest, J. C. M. Polymeric Vesicles in Biomedical Applications Polym. Chem. 2011, 2, 1449-1462
8. LoPresti, C.; Lomas, H.; Massignani, M.; Smart, T.; Battaglia, G. Polymersomes: Nature Inspired Nanometer Sized Compartments J. Mater. Chem. 2009, 19, 3576-3590
9. Meng, F. H.; Zhong, Z. Y.; Feijen, J. Stimuli-Responsive Polymersomes for Programmed Drug Delivery Biomacromolecules 2009, 10, 197-209
10. Zhang, S. Y.; Zhao, Y. Rapid Release of Entrapped Contents from Multi-Functionalizable, Surface Cross-Linked Micelles upon Different Stimulation J. Am. Chem. Soc. 2010, 132, 10642-10644
11. Ranquin, A.; Versees, W.; Meier, W.; Steyaert, J.; Van Gelder, P. Therapeutic Nanoreactors: Combining Chemistry and Biology in a Novel Triblock Copolymer Drug Delivery System Nano Lett. 2005, 5, 2220-2224
12. Arifin, D. R.; Palmer, A. F. Polymersome Encapsulated Hemoglobin: A Novel Type of Oxygen Carrier Biomacromolecules 2005, 6, 2172-2181
13. Ahmed, F.; Pakunlu, R. I.; Srinivas, G.; Brannan, A.; Bates, F.; Klein, M. L.; Minko, T.; Discher, D. E. Shrinkage of a Rapidly Growing Tumor by Drug-Loaded Polymersomes: pH-Triggered Release through Copolymer Degradation Mol. Pharm. 2006, 3, 340-350
14. Brown, M. D.; Schatzlein, A.; Brownlie, A.; Jack, V.; Wang, W.; Tetley, L.; Gray, A. I.; Uchegbu, I. F. Preliminary Characterization of Novel Amino Acid Based Polymeric Vesicles as Gene and Drug Delivery Agents Bioconjugate Chem. 2000, 11, 880-891
15. Ghoroghchian, P. P.; Frail, P. R.; Susumu, K.; Blessington, D.; Brannan, A. K.; Bates, F. S.; Chance, B.; Hammer, D. A.; Therien, M. J. Near-Infrared-Emissive Polymersomes: Self-Assembled Soft Matter for in Vivo Optical Imaging Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 2922-2927
16. Webster, R. G.; Bean, W. J.; Gorman, O. T.; Chambers, T. M.; Kawaoka, Y. Evolution and Ecology of Influenza-A Viruses Microbiol. Rev. 1992, 56, 152-179
17. Lees, W. J.; Spaltenstein, A.; Kingery-Wood, J. E.; Whitesides, G. M. Polyacrylamides Bearing Pendant α-Sialoside Groups Strongly Inhibit Agglutination of Erythrocytes by Influenza A Virus: Multivalency and Steric Stabilization of Particulate Biological Systems J. Med. Chem. 1994, 37, 3419-3433
18. Mammen, M.; Choi, S. K.; Whitesides, G. M. Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors Angew. Chem., Int. Ed. 1998, 37, 2755-2794
19. Carlescu, I.; Scutaru, D.; Popa, M.; Uglea, C. V. Synthetic Sialic-Acid-Containing Polyvalent Antiviral Inhibitors Med. Chem. Res. 2009, 18, 477-494
20. Gubareva, L. V.; Kaiser, L.; Hayden, F. G. Influenza Virus Neuraminidase Inhibitors Lancet 2000, 355, 827-835
21. Reuter, J. D.; Myc, A.; Hayes, M. M.; Gan, Z. H.; Roy, R.; Qin, D. J.; Yin, R.; Piehler, L. T.; Esfand, R.; Tomalia, D. A.; Baker, J. R. Inhibition of Viral Adhesion and Infection by Sialic-Acid-Conjugated Dendritic Polymers Bioconjugate Chem 1999, 10, 271-278
22. Spaltenstein, A.; Whitesides, G. M. Polyacrylamides Bearing Pendant α-Sialoside Groups Strongly Inhibit Agglutination of Erythrocytes by Influenza-Virus J. Am. Chem. Soc. 1991, 113, 686-687
23. Mammen, M.; Dahmann, G.; Whitesides, G. M. Effective Inhibitors of Hemagglutination by Influenza-Virus Synthesized from Polymers Having Active Ester Groups. Insight into Mechanism of Inhibition J. Med. Chem. 1995, 38, 4179-4190
24. Tuzikov, A. B.; Chinarev, A. A.; Gambaryan, A. S.; Oleinikov, V. A.; Klinov, D. V.; Matsko, N. B.; Kadykov, V. A.; Ermishov, M. A.; Demin, I. y. V.; Demin, V. V.; Rye, P. D.; Bovin, N. V. Polyglycine II Nanosheets: Supramolecular Antivirals? ChemBioChem 2003, 4, 147-154
25. Roy, R.; Zanini, D.; Meunier, S. J.; Romanowska, A. Solid-Phase Synthesis of Dendritic Sialoside Inhibitors of Influenza-A Virus Hemagglutinin J. Chem. Soc., Chem. Commun. 1993, 1869-1872
26. Zanini, D.; Roy, R. Novel Dendritic α-Sialosides: Synthesis of Glycodendrimers Based on a 3,3′-Iminobis(propylamine) Core J. Org. Chem. 1996, 61, 7348-7354
27. Llinares, M.; Roy, R. Multivalent Neoglycoconjugates: Solid-Phase Synthesis of N-Linked α-Sialodendrimers Chem. Commun. 1997, 2119-2120
28. Zanini, D.; Roy, R. Synthesis of New α-Thiosialodendrimers and Their Binding Properties to the Sialic Acid Specific Lectin from Limax Flavus J. Am. Chem. Soc. 1997, 119, 2088-2095
29. Zanini, D.; Roy, R. Practical Synthesis of Starburst PAMAM α-Thiosialodendrimers for Probing Multivalent Carbohydrate-Lectin Binding Properties J. Org. Chem. 1998, 63, 3486-3491
30. Sashiwa, H.; Shigemasa, Y.; Roy, R. Chemical Modification of Chitosan. 3. Hyperbranched Chitosan-Sialic Acid Dendrimer Hybrid with Tetraethylene Glycol Spacer Macromolecules 2000, 33, 6913-6915
31. Kingerywood, J. E.; Williams, K. W.; Sigal, G. B.; Whitesides, G. M. The Agglutination of Erythrocytes by Influenza-Virus Is Strongly Inhibited by Liposomes Incorporating an Analog of Sialyl Gangliosides J. Am. Chem. Soc. 1992, 114, 7303-7305
32. Spevak, W.; Nagy, J. O.; Charych, D. H.; Schaefer, M. E.; Gilbert, J. H.; Bednarski, M. D. Polymerized Liposomes Containing C-Glycosides of Sialic-Acid: Potent Inhibitors of Influenza-Virus in Vitro Infectivity J. Am. Chem. Soc. 1993, 115, 1146-1147
33. Reichert, A.; Nagy, J. O.; Spevak, W.; Charych, D. Polydiacetylene Liposomes Functionalized with Sialic Acid Bind and Colorimetrically Detect Influenza Virus J. Am. Chem. Soc. 1995, 117, 829-830
34. Zhang, L.; Wei, G. H.; Do, Y. G. Synthesis of Neu5Ac-Gal-Functionalized Gold Glyconanoparticles Carbohydr. Res. 2009, 344, 2083-2087
35. Papp, I.; Sieben, C.; Ludwig, K.; Roskamp, M.; Bottcher, C.; Schlecht, S.; Herrmann, A.; Haag, R. Inhibition of Influenza Virus Infection by Multivalent Sialic-Acid-Functionalized Gold Nanoparticles Small 2010, 6, 2900-2906
36. Papp, I.; Sieben, C.; Sisson, A. L.; Kostka, J.; Bottcher, C.; Ludwig, K.; Herrmann, A.; Haag, R. Inhibition of Influenza Virus Activity by Multivalent Glycoarchitectures with Matched Sizes ChemBioChem 2011, 12, 887-895
37. Bondioli, L.; Costantino, L.; Ballestrazzi, A.; Lucchesi, D.; Boraschi, D.; Pellati, F.; Benvenuti, S.; Tosi, G.; Vandelli, M. A. PLGA Nanoparticles Surface Decorated with the Sialic Acid, N -Acetylneuraminic Acid Biomaterials 2010, 31, 3395-3403
38. Kim, B. S.; Hong, D. J.; Bae, J.; Lee, M. Controlled Self-Assembly of Carbohydrate Conjugate Rod-Coil Amphiphiles for Supramolecular Multivalent Ligands J. Am. Chem. Soc. 2005, 127, 16333-16337
39. Kim, B. S.; Yang, W. Y.; Ryu, J. H.; Yoo, Y. S.; Lee, M. Carbohydrate-Coated Nanocapsules from Amphiphilic Rod-Coil Molecule: Binding to Bacterial Type 1 Pili Chem. Commun. 2005, 2035-2037
40. Dai, X.-H.; Dong, C.-M. Synthesis, Self-Assembly and Recognition Properties of Biomimetic Star-Shaped Poly(ε-caprolactone)- b -glycopolymer Block Copolymers J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 817-829
41. Pasparakis, G.; Alexander, C. Sweet Talking Double Hydrophilic Block Copolymer Vesicles Angew. Chem., Int. Ed. 2008, 47, 4847-4850
42. Martin, A. L.; Li, B.; Gillies, E. R. Surface Functionalization of Nanomaterials with Dendritic Groups: Toward Enhanced Binding to Biological Targets J. Am. Chem. Soc. 2009, 131, 734-741
43. Huang, J.; Bonduelle, C.; Thevenot, J.; Lecommandoux, S.; Heise, A. Biologically Active Polymersomes from Amphiphilic Glycopeptides J. Am. Chem. Soc. 2012, 134, 119-122
44. Zhou, W.; Dai, X.-H.; Dong, C.-M. Biodegradable and Biomimetic Poly(ε-caprolactone)/Poly(lactobionarnidoethyl methacrylate) Biohybrids: Synthesis, Lactose-Installed Nanoparticles and Recognition Properties Macromol. Biosci. 2008, 8, 268-278
45. Quer, C. B.; Marsden, H. R.; Romeijn, S.; Zope, H.; Kros, A.; Jiskoot, W. Polymersomes Enhance the Immunogenicity of Influenza Subunit Vaccine Polym. Chem. 2011, 2, 1482-1485
46. Li, B.; Martin, A. L.; Gillies, E. R. Multivalent Polymer Vesicles via Surface Functionalization Chem. Commun. 2007, 5217-5219
47. Nazemi, A.; Amos, R. C.; Bonduelle, C. V.; Gillies, E. R. Dendritic Surface Functionalization of Biodegradable Polymer Assemblies J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2546-2559
48. Amos, R. C.; Nazemi, A.; Bonduelle, C. V.; Gillies, E. R. Tuning Polymersome Surfaces: Functionalization with Dendritic Groups Soft Matter 2012, 8, 5947-5958
49. De Jesus, O. L. P.; Ihre, H. R.; Gagne, L.; Frechet, J. M. J.; Szoka, F. C. Polyester Dendritic Systems for Drug Delivery Applications: In Vitro and in Vivo Evaluation Bioconjugate Chem. 2002, 13, 453-461
50. Rothermel, J.; Faillard, H. Phase-Transfer-Catalyzed Synthesis of N-Acetylneuraminic Acid α-Thioketosides and Inhibitor Studies with Clostridium perfringens Sialidase Biol. Chem. Hoppe-Seyler 1989, 370, 1077-1084
51. Martin, A. L.; Bernas, L. M.; Rutt, B. K.; Foster, P. J.; Gillies, E. R. Enhanced Cell Uptake of Superparamagnetic Iron Oxide Nanoparticles Functionalized with Dendritic Guanidines Bioconjugate Chem. 2008, 19, 2375-2384
52. Miller, R. L.; Collawn, J. F.; Fish, W. W. Purification and Macromolecular Properties of a Sialic Acid-Specific Lectin from the Slug Limax flavus J. Biol. Chem. 1982, 257, 7574-7580
53. Page, D.; Roy, R. Synthesis and Biological Properties of Mannosylated Starburst Poly(amidoamine) Dendrimers Bioconjugate Chem. 1997, 8, 714-723
54. Andre, S.; Ortega, P. J. C.; Perez, M. A.; Roy, R.; Gabius, H. J. Lactose-Containing Starburst Dendrimers: Influence of Dendrimer Generation and Binding-Site Orientation of Receptors (Plant/Animal Lectins and Immunoglobulins) on Binding Properties Glycobiology 1999, 9, 1253-1261
55. Roy, R.; Laferriere, C. A.; Gamian, A.; Jennings, H. J. N-Acetylneuraminic Acid: Neoglycoproteins and Pseudopolysaccharides J. Carbohydr. Chem. 1987, 6, 161-165
56. Roy, R.; Laferriere, C. A. Synthesis of Antigenic Copolymers of N -Acetylneuraminic Acid Binding to Wheat Germ Agglutinin and Antibodies Carbohydr. Res. 1988, 177, c1-c4
57. Byramova, N. E.; Mochalova, L. V.; Belyanchikov, I. M.; Matrosovich, M. N.; Bovin, N. V. Synthesis of Sialic-Acid Pseudopolysaccharides by Coupling of Spacer-Connected Neu5Ac with Activated Polymer J. Carbohydr. Chem. 1991, 10, 691-700
58. Gamian, A.; Chomik, M.; Laferriere, C. A.; Roy, R. Inhibition of Influenza-A Virus Hemagglutinin and Induction of Interferon by Synthetic Sialylated Glycoconjugates Can. J. Microbiol. 1991, 37, 233-237
59. Roy, R.; Andersson, F. O.; Harms, G.; Kelm, S.; Schauer, R. Synthesis of Esterase-Resistant 9-O-Acetylated Polysialoside as Inhibitor of Influenza-C Virus Hemagglutinin Angew. Chem., Int. Ed. 1992, 31, 1478-1481
60. Sigal, G. B.; Mammen, M.; Dahmann, G.; Whitesides, G. M. Polyacrylamides Bearing Pendant α-Sialoside Groups Strongly Inhibit Agglutination of Erythrocytes by Influenza Virus: The Strong Inhibition Reflects Enhanced Binding through Cooperative Polyvalent Interactions J. Am. Chem. Soc. 1996, 118, 3789-3800
61. Haldar, J.; de Cienfuegos, L. A.; Tumpey, T. M.; Gubareva, L. V.; Chen, J. Z.; Klibanov, A. M. Bifunctional Polymeric Inhibitors of Human Influenza A Viruses Pharm. Res. 2010, 27, 259-263
62. Nazemi, A.; Martinez, F.; Scholl, T. J.; Gillies, E. R. Biodegradable Dendritic Polymersomes as Modular, High-Relaxivity MRI Contrast Agents RSC Adv. 2012, 2, 7971-7973