Novel poly(ethylene oxide)-b-poly(propylene oxide) copolymer-glucose conjugate by the microwave-assisted ring opening of a sugar lactone

Macromolecular Bioscience

Volumn 14, Issue 11, 2014, Pages 1639-1651

  Glisoni, Romina J ^a,b   Sosnik, Alejandro ^c  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b Facultad de Ciencias Naturales e Instituto M Lillo   (Argentina)

^c TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

darunavir free base; gluconolactone; Glucosylated poly(ethylene oxide) b poly(propylene oxide) block copolymers; microwave assisted ring opening conjugation; polymeric micelles

Indexed keywords

ANTIGEN-ANTIBODY REACTIONS; BLOCK COPOLYMERS; COPOLYMERS; DYES; ENZYME INHIBITION; ETHYLENE; GLUCOSE; MICELLES; POLYETHYLENE OXIDES; POLYMERS; SOLUBILITY;

AQUEOUS SOLUBILITY; CRITICAL MICELLAR CONCENTRATIONS; FREE BASE; GLUCONOLACTONE; MICROWAVE ASSISTED; POLYMERIC MICELLE; RING OPENING; RING OPENING REACTION;

PROPYLENE;

COPOLYMER; DARUNAVIR; GLUCONOLACTONE; GLUCOSE; HYDROXYL GROUP; LACTONE; LECTIN; MACROGOL; NANOCARRIER; POLY(ETHYLENE OXIDE) POLY(PROPYLENE OXIDE); POLYPROPYLENE; RITONAVIR; UNCLASSIFIED DRUG; BETA-GLUCONO-1,5-LACTONE; CONCANAVALIN A; GLUCONIC ACID; GLUCURONIC ACID; MACROGOL DERIVATIVE; MICELLE; POLYETHYLENE DERIVATIVE; POLYMER; POLYPROPYLENE GLYCOL; PROPANEDIOL DERIVATIVE; PROPYLENE GLYCOL; SULFONAMIDE; UCON 50-HB-5100; WATER;

ANTIGEN ANTIBODY REACTION; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATION; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DRUG SOLUBILITY; ENCAPSULATION; GLYCOSYLATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICELLE; MICROWAVE RADIATION; PARTICLE SIZE; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SOLUBILIZATION; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROSCOPY; LIGHT; MASS SPECTROMETRY; MOLECULAR WEIGHT; RADIATION SCATTERING; SOLUBILITY; STATIC ELECTRICITY; TRANSMISSION ELECTRON MICROSCOPY;

AGGLUTINATION; CALORIMETRY, DIFFERENTIAL SCANNING; CONCANAVALIN A; GLUCONATES; GLUCOSE; GLUCURONATES; GLYCOSYLATION; LACTONES; LIGHT; MICELLES; MICROSCOPY, ELECTRON, TRANSMISSION; MICROWAVES; MOLECULAR WEIGHT; PARTICLE SIZE; POLYETHYLENE GLYCOLS; POLYETHYLENES; POLYMERS; POLYPROPYLENES; PROPYLENE GLYCOL; PROPYLENE GLYCOLS; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SCATTERING, RADIATION; SOLUBILITY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STATIC ELECTRICITY; SULFONAMIDES; WATER;

EID: 84927649753     PISSN: 16165187     EISSN: 16165195     Source Type: Journal    
DOI: 10.1002/mabi.201400235     Document Type: Article

References (75)

1. C. F. Nathan, J. Clin. Invest. 1987, 79, 319.
2. Y. R. Mahida, Inflamm. Bowel. Dis. 2000, 6, 21.
3. J. L. Flynn, J. Chan, Infect. Immun. 2001, 69, 4195.
4. S. Koening, H. E. Gendelman, J. M. Orenstein, M. C. Dal Canto, G. H. Pezeshkpour, M. Yungbluth, F. Janotta, A. Aksamit, M. A. Martin, A. S. Fauci, Science 1986, 233, 1089.
5. F. Chappuis, S. Sundar, A. Hailu, H. Ghalib, S. Rijal, R. W. Peeling, J. Alvar, M. Boelaert, Nat. Rev. Microbiol. 2007, S7-S16.
6. A. N. Zelensky, J. E. Gready, FEBS J. 2005, 272, 6179.
7. R. T. Lee, T. L. Hsu, S. K. Huang, S. L. Hsieh, C. H. Wong, Y. C. Lee, Glycobiology 2011, 21, 512.
8. S.-H. Kim, M. Goto, T. Akaike, J. Biol. Chem. 2001, 276, 35312.
9. K. C. Carvalho, I. W. Cunha, R. M. Rocha, F. R. Ayala, M. M. Cajaíba, M. D. Begnami, R. S. Vilela, G. R. Paiva, R. G. Andrade, F. A. Soares, Clinics 2011, 66, 965.
10. A. M. Kerrigan, G. D. Brown, Immunobiology 2009, 214, 562.
11. H. Sheikh, H. Yarwood, A. Ashworth, C. M. Isacke, J. Cell. Sci. 2000, 113, 1021.
12. S. Burgdorf, V. Lukacs-Kornek, C. Kurts, J. Immunol. 2006, 176, 6770.
13. C. A. Janeway, P. Travers, M. Walport, M. J. Shlomchik, In " Immunobiology: The Immune System in Health and Disease ", 5th edition, Garland Science, New York 2001.
14. Y. Han, L. Zhao, Z. Yu, J. Feng, Q. Yu, Int. Immunopharmacol. 2005, 5, 1533.
15. H.-L. Jiang, M.-L. Kang, J.-S. Quan, S.-G. Kang, T. Akaike, H. S. Yoo, Biomaterials 2008, 29, 1931.
16. J. M. Irache, H. H. Salman, C. Gamazo, S. Espuelas, Expert Opin. Drug Deliv. 2008, 5, 703.
17. R. Duncan, Nat. Rev. Cancer 2006, 6, 688.
18. M. A. Moretton, D. A. Chiappetta, F. Andrade, J. das Neves, D. Ferreira, B. Sarmento, A. Sosnik, J. Biomed. Nanotechnol. 2013, 9, 1076.
19. K. N. Jain, V. Mishra, N. K. Mehra, Expert Opin. Drug Del. 2013, 10, 353.
20. K. Kataoka, A. Harada, Y. Nagasaki, Adv. Drug Del. Rev. 2001, 47, 113.
21. A. Sosnik, In Smart Materials for Drug Delivery., C. Alvarez-Lorenzo, A. Concheiro, Eds., " Royal Society of Chemistry ", London 2013, Chapter 5 pp. 115.
22. C. Alvarez-Lorenzo, A. Sosnik, A. Concheiro, Curr. Drug Targets 2011, 12, 1112.
23. L. Bromberg, J. Control. Release 2008, 128, 99.
24. X.-B. Xiong, Z. Binkhathlan, O. Molavi, A. Lavasanifar, Acta Biomater. 2012, 8, 2017.
25. G. Gaucher, P. Satturwar, M.-C. Jones, A. Furtos, J.-C. Leroux, Eur. J. Pharm. Biopharm. 2010, 76, 147.
26. A. Sosnik, A. Carcaboso, D. A. Chiappetta, Recent Pat. Biomed. Eng. 2008, 1, 43.
27. D. A. Chiappetta, A. Sosnik, Eur. J. Pharm. Biopharm. 2007, 66, 303.
28. E. V. Batrakova, A. V. Kabanov, J. Control. Release 2008, 130, 98 Pluronic Block Copolymers.
29. J. Gonzalez-Lopez, C. Alvarez-Lorenzo, P. Taboada, A. Sosnik, I. Sandez-Macho, A. Concheiro, Langmuir 2008, 24, 10688.
30. D. A. Chiappetta, J. Degrossi, S. Teves, M. D'Aquino, C. Bregni, A. Sosnik, Eur. J. Pharm. Biopharm. 2008, 69, 535.
31. R. N. Peroni, S. S. Di Gennaro, C. Hocht, D. A. Chiappetta, M. C. Rubio, A. Sosnik, G. F. Bramuglia, Biochem. Pharmacol. 2011, 82, 1227.
32. D. A. Chiappetta, C. Hocht, C. Taira, A. Sosnik, Nanomedicine (Lond.) 2010, 5, 11.
33. D. A. Chiappetta, C. Alvarez-Lorenzo, A. Rey-Rico, P. Taboada, A. Concheiro, A. Sosnik, Eur. J. Pharm. Biopharm. 2010, 76, 24.
34. D. A. Chiappetta, C. Hocht, C. Taira, A. Sosnik, Biomaterials 2011, 32, 2379.
35. D. A. Chiappetta, G. Facorro, E. Rubin de Celis, A. Sosnik, Nanomed.: Nanotechnol. Biol. Med. 2011, 7, 624.
36. A. Ribeiro, A. Sosnik, D. A. Chiappetta, F. Veiga, A. Concheiro, C. Alvarez-Lorenzo, J. R. Soc. Interface 2012, 9, 2059.
37. C. Garcia Vior, J. Marino, L. P. Roguin, A. Sosnik, J. Awruch, Photochem. Photobiol. 2013, 89, 492.
38. D. A. Chiappetta, C. Hocht, J. A. W. Opezzo, A. Sosnik, Nanomedicine (Lond.) 2013, 8, 223.
39. C. Alvarez-Lorenzo, A. Rey-Rico, J. Brea, M. I. Loza, A. Concheiro, A. Sosnik, Nanomedicine (Lond.) 2010, 5, 1371.
40. M. L. Cuestas, A. Sosnik, V. L. Mathet, Mol. Pharmaceutics 2011, 8, 1152.
41. M. L. Cuestas, A. Castillo, A. Sosnik, V. L. Mathet, Bioorg. Med. Chem. Lett. 2012, 22, 6577.
42. A. Sosnik, Adv. Drug Deliv. Rev. 2013, 65, 1828.
43. C. R. Becer, Macromol. Rapid Commun. 2012, 33, 742.
44. M. L. Cuestas, R. J. Glisoni, V. L. Mathet, A. Sosnik, J. Nanopart. Res. 2013, 15, 1389.
45. R. Glisoni, A. Sosnik, J. Nanosci. Nanotechnol. 2014, 14, 4670.
46. M. L. Cuestas, V. Mathet, J. R. Oubiña, A. Sosnik, Pharm. Res. 2010, 27, 1184.
47. X. Li, Y. Huang, X. Chen, Y. Zhou, Y. Zhang, P. Li, Y. Liu, Y. Sun, J. Zhao, F. Wang, J. Drug Target. 2009, 17, 739.
48. A. Sosnik, G. Gotelli, G. A. Abraham, Prog. Polym. Sci. 2011, 36, 1050.
49. M. A. Moretton, R. J. Glisoni, D. A. Chiappetta, A. Sosnik, Colloids Surf. B: Biointerfaces 2010, 79, 467.
50. G. Gotelli, P. Bonelli, G. Abraham, A. Sosnik, J. Appl. Polym. Sci. 2011, 121, 1321.
51. R. J. Glisoni, D. A. Chiappetta, A. G. Moglioni, A. Sosnik, Pharm. Res. 2012, 79, 739.
52. P. Hole, K. Sillence, C. Hannell, C. M. Maguire, M. Roesslein, G. Suarez, S. Capracotta, Z. Magdolenova, L. Horev-Azaria, A. Dybowska, L. Cooke, A. Haase, S. Contal, S. Manø, A. Vennemann, J.-J. Sauvain, K. C. Staunton, S. Anguissola, A. Luch, M. Dusinska, R. Korenstein, A. C. Gutleb, M. Wiemann, A. Prina-Mello, M. Riediker, P. Wick, J. Nanopart. Res. 2013, 15, 2101.
53. V. Filipe, A. Hawe, W. Jiskoot, Pharm. Res. 2010, 27, 796.
54. X. Wang, O. Ramström, M. Yan, J. Mater. Chem. 2009, 19, 8944.
55. J. H. Ahire, I. Chambrier, A. Mueller, Y. Bao, Y. Chao, ACS Appl. Mater. Interface 2013, 5, 7384.
56. C. Lu, X. Chen, Z. Xie, T. Lu, X. Wang, J. Ma, X. Ji, Biomacromolecules 2006, 7, 1806.
57. M. Tang, A. J. P. White, M. M. Stevens, C. K. Williams, Chem. Commun. 2009, 941.
58. A. Sosnik, D. Cohn, J. San Román, G. A. Abraham, J. Biomater. Sci. Pol. Ed. 2003, 14, 227.
59. V. Bordegé, A. Muñoz-Bonilla, O. Leõn, R. Cuervo-Rodríguez, M. Sánchez-Chaves, M. Fernandez-García, J. Pol. Sci. Part A: Pol. Chem. 2011, 49, 526.
60. M. Bierenstiel, M. Schla, Eur. J. Org. Chem. 2004, 7, 1474.
61. C. Zhang, Q. Ping, Y. Ding, J. Appl. Pol. Sci. 2005, 97, 2161.
62. H. Fan, C. Wang, Y. Li, Y. Wei, J. Memb. Sci. 2012, 415-416, 161.
63. Z. Takáts, K. Vékey, L. HegedGreek small letter upsilon with dialytikas, Rap. Commun. Mass Spectrom. 2001, 15, 805.
64. K. Raith, C. E. H. Schmelzer, R. H. H. Neubert, Int. J. Pharm. 2006, 319, 1.
65. D. Cohn, A. Sosnik, J. Mater. Sci. Mater. Med. 2003, 14, 175.
66. D. Cohn, A. Sosnik, A. Levy, Biomaterials 2003, 24, 3707.
67. D. Cohn, G. Lando, A. Sosnik, S. Garty, A. Levi, Biomaterials 2006, 27, 1718.
68. I. J. Goldstein, C. E. Hollerman, E. E. Smith, Biochemistry 1965, 4, 876.
69. W. I. Weis, K. Drickamer, Annu. Rev. Biochem. 1996, 65, 441.
70. H. Meng-Xin, X. Zhi-Kang, Colloids Surf. B: Biointerfaces 2011, 85, 19.
71. T. N. Kakuda, V. Sekar, L. Lavreys, E. De Paepe, T. Stevens, M. Vanstockem, T. Vangeneugden, R. M. Hoetelmans, Clin. Pharmacol. Drug Dev. 2014, DOI: 10.1002/cpdd.88.
72. Consolidated guidelines on the use of antiretroviral drugs for treating and preventing HIV infection: Summary of new recommendations. Geneva: OMS, 2013. http://www.who.int/hiv/pub/guidelines/arv2013/art/arv2013-chapter07-low.pdf.
73. A. Sosnik, D. A. Chiappetta, A. Carcaboso, J. Control. Release 2009, 138, 2.
74. A. Sosnik, Nanomedicine (Lond.) 2010, 5, 833.
75. A. Sosnik, A. Carcaboso, Adv. Drug Deliv. Rev. 2014, 73, 140.