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Synthesis and application of new photocrosslinkers for poly(ethylene glycol)

Bibliographic reference Mehenni, Hakim ; Pourcelle, Vincent ; Gohy, Jean-François ; Marchand-Brynaert, Jacqueline. Synthesis and application of new photocrosslinkers for poly(ethylene glycol). In: Australian Journal of Chemistry, Vol. 65, no. 2, p. 193-201 (2012)
Permanent URL http://hdl.handle.net/2078.1/124524
  1. Pasut, Prog. Polym. Sci., 32, 933 (2007)
  2. Allen, Science, 303, 1818 (2004)
  3. Duncan, Endocr.-Relat. Cancer, 12, 189 (2005)
  4. Bhadra, Pharmazie, 57, 5 (2002)
  5. Monfardini, Bioconjugate Chem., 9, 418 (1998)
  6. Abuchowski, J. Biol. Chem., 252, 3578 (1977)
  7. Abuchowski, J. Biol. Chem., 252, 3582 (1977)
  8. Veronese, Adv. Drug Delivery Rev., 54, 167 (2002)
  9. Veronese, Adv. Drug Delivery Rev., 55, 1259 (2003)
  10. Gref, Science, 263, 1600 (1994)
  11. Kreuter, Int. J. Pharm., 331, 1 (2007)
  12. Gregoriadis, N. Engl. J. Med., 295, 704 (1976)
  13. Gregoriadis, N. Engl. J. Med., 295, 765 (1976)
  14. Klibanov, FEBS Lett., 268, 235 (1990)
  15. Blume, Biochim. Biophys. Acta Biomembr., 1029, 91 (1990)
  16. Woodle, Proc. Int. Symp. Controlled Release Bioact. Mater., 17, 77 (1990)
  17. Woodle, Adv. Drug Delivery Rev., 16, 249 (1995)
  18. Lasic, Chem. Rev., 95, 2601 (1995)
  19. Torchilin, Nat. Rev. Drug Discovery, 4, 145 (2005)
  20. Kabanov, FEBS Lett., 258, 343 (1989)
  21. Kwon, Adv. Drug Delivery Rev., 16, 295 (1995)
  22. Svenson, Adv. Drug Delivery Rev., 57, 2106 (2005)
  23. Oupicky, Mol. Ther., 5, 463 (2002)
  24. Ogris, Gene Ther., 6, 595 (1999)
  25. Nguyen, Gene Ther., 7, 126 (2000)
  26. Aigner, Gene Ther., 9, 1700 (2002)
  27. Parveen, Clin. Pharmacokinet., 45, 965 (2006)
  28. Maeda, J. Controlled Release, 65, 271 (2000)
  29. Greish, J. Drug Targeting, 15, 457 (2007)
  30. Haag, Angew. Chem., 118, 1218 (2006)
  31. Angew. Chem. Int. Ed., 45, 1198 (2006)
  32. Schmaljohann, Adv. Drug Delivery Rev., 58, 1655 (2006)
  33. Kost, Adv. Drug Delivery Rev., 46, 125 (2001)
  34. de Las Heras Alarcon, Chem. Soc. Rev., 34, 276 (2005)
  35. York, Adv. Drug Delivery Rev., 60, 1018 (2008)
  36. Torchilin, Adv. Drug Delivery Rev., 16, 141 (1995)
  37. Grayson, J. Drug Targeting, 16, 329 (2008)
  38. Luxenhofer, Macromol. Rapid Commun., 29, 1509 (2008)
  39. Veronese, Drug Discovery Today, 10, 1451 (2005)
  40. Passirani, Biomaterials for Delivery and Targeting of Proteins and Nucleic Acids (2005)
  41. Torchilin, J. Microencapsulation, 15, 1 (1998)
  42. Petersen, Macromolecules, 35, 6867 (2002)
  43. http://www.inchem.org/documents/jecfa/jecmono/v14je19.htm
  44. Biondi, Mutagenesis, 17, 261 (2002)
  45. Mosbah, Transplant. Proc., 38, 1229 (2006)
  46. Balakrishnana, Biomaterials, 26, 3495 (2005)
  47. Rahman, Prog. Polym. Sci., 29, 1223 (2004)
  48. Lakshmi, Artif. Organs, 22, 222 (1998)
  49. Suggs, Biomaterials, 20, 683 (1999)
  50. Encyclopedia of Polymer Science and Technology (2007)
  51. Asatekin, J. Membr. Sci., 298, 136 (2007)
  52. Cheng, Lancet, 354, 179 (1999)
  53. Kwon, J. Ind. Eng. Chem., 9, 138 (2003)
  54. Johnson, Int. J. Toxicol., 20, 13 (2001)
  55. le Coz Christophe-J., Lepoittevin Jean-Pierre, Clothing dermatitis from Naphthol AS, 10.1034/j.1600-0536.2001.044006366.x
  56. Chanan-Khan, Ann. Oncol., 14, 1430 (2003)
  57. Szebeni, Toxicology, 216, 106 (2005)
  58. Janatova, ASAIO J., 53 (2000)
  59. Szebeni, J. Liposome Res., 12, 165 (2002)
  60. Szebeni, J. Natl. Cancer Inst., 90, 300 (1998)
  61. 2006
  62. Brouwers, J. Drug Targeting, 8, 225 (2000)
  63. Parr, J. Pharmacol. Exp. Ther., 280, 1319 (1997)
  64. Calvo, Rev. Esp. Cardiol., 59, 399 (2006)
  65. de Groot, Ned. Tijdschr. Geneeskd., 148, 1887 (2004)
  66. Dijkmans, Eur. J. Echocardiogr., 6, 363 (2005)
  67. Dewachter, Allergy, 60, 705 (2005)
  68. Richter, Int. Arch. Allergy Appl. Immunol., 70, 124 (1983)
  69. Richter, Int. Arch. Allergy Appl. Immunol., 74, 36 (1984)
  70. Armstrong, Cancer, 110, 103 (2007)
  71. Ganson, Arthritis Res. Ther., 8, 12 (2005)
  72. Assal, Gastrointest. Endocrinol., 64, 294 (2006)
  73. Schuman, Gastrointest. Endocrinol., 37, 411 (1991)
  74. Brullet, Gastrointest. Endocrinol., 38, 400 (1992)
  75. Stollman, Gastrointest. Endocrinol., 44, 209 (1996)
  76. Ito, Contact Dermatitis, 54, 225 (2006)
  77. Kwee, J. Allergy Clin. Immunol., 69, 138 (1982)
  78. Fisher, Contact Dermatitis, 414, 135 (1978)
  79. Quartier, Contact Dermatitis, 55, 257 (2006)
  80. Dams, J. Pharmacol. Exp. Ther., 292, 1071 (2000)
  81. Ishida, J. Controlled Release, 88, 35 (2003)
  82. Koide, Int. J. Pharm., 362, 197 (2008)
  83. Ishida, J. Controlled Release, 105, 305 (2005)
  84. Ishida, Int. J. Pharm., 354, 56 (2008)
  85. Ishida, Int. J. Pharm., 255, 167 (2003)
  86. Ishida Tatsuhiro, Kashima Syuntaro, Kiwada Hiroshi, The contribution of phagocytic activity of liver macrophages to the accelerated blood clearance (ABC) phenomenon of PEGylated liposomes in rats, 10.1016/j.jconrel.2007.11.009
  87. Laverman, J. Pharmacol. Exp. Ther., 293, 996 (2000)
  88. Herold, Biochem. Pharmacol., 38, 73 (1989)
  89. Hinds, Biomaterials for Delivery and Targeting of Proteins and Nucleic Acids (2005)
  90. Torchilin, Adv. Drug Delivery Rev., 58, 1532 (2006)
  91. Takakura, Pharm. Res., 4, 293 (1987)
  92. Moghimi, Pharmacol. Rev., 52, 283 (2001)
  93. Boyd Shaffer C., Critchfield H., Nair John H., The Absorption and Excretion of a Liquid Polyethylene Glycol*, 10.1002/jps.3030390613
  94. Carpenter, Toxicol. Appl. Pharmacol., 18, 35 (1971)
  95. Smyth, J. Am. Pharm. Assoc. Sci. Ed., 39, 349 (1950)
  96. Moghimi, Prog. Lipid Res., 42, 463 (2003)
  97. Romberg, Int. J. Pharm., 331, 186 (2007)
  98. Porteer, Polym. Eng. Sci., 25, 129 (1985)
  99. Zhang, Macromolecules, 35, 4017 (2002)
  100. Papaioannou, Int. J. Cardiol., 113, 12 (2006)
  101. D’Almeida, Polym. Degrad. Stab., 56, 331 (1997)
  102. White, Chem. Eng. Sci., 25, 1255 (1970)
  103. Minoura, J. Polym. Sci. Part A, 5, 125 (1967)
  104. Aarthi, Ind. Eng. Chem. Res., 46, 6204 (2007)
  105. Nakano, J. Appl. Polym. Sci., 15, 927 (1971)
  106. Han, Polymer, 38, 317 (1997)
  107. Scheirs, Polymer, 32, 2014 (1991)
  108. Morlat, Polymer, 42, 6071 (2001)
  109. Afih-Effat, Eur. Polym. J., 8, 289 (1972)
  110. Lee, J. Controlled Release, 117, 204 (2007)
  111. Larsen, Adv. Drug Delivery Rev., 3, 103 (1989)
  112. Sugahara, J. Controlled Release, 117, 40 (2007)
  113. Janes, Adv. Drug Delivery Rev., 47, 83 (2001)
  114. Li, Adv. Drug Delivery Rev., 60, 886 (2008)
  115. Pytela, J. Controlled Release, 10, 17 (1989)
  116. Romberg, Biochim. Biophys. Acta Biomembr., 1768, 737 (2007)
  117. Romberg, Int. J. Pharm., 355, 108 (2008)
  118. Metselaar, Bioconjugate Chem., 14, 1156 (2003)
  119. Middleton, Biomaterials, 21, 2335 (2000)
  120. De Winne, J. Bioact. Compat. Polym., 19, 439 (2004)
  121. Yang, J. Controlled Release, 114, 60 (2006)
  122. Pitarresi, Biomacromolecules, 7, 1302 (2006)
  123. Obst, Biomacromolecules, 5, 1166 (2004)
  124. O’Brien, J. Thorac. Oncol., 3, 728 (2008)
  125. Li, Clin. Cancer Res., 5, 891 (1999)
  126. Li, Cancer Res., 58, 2404 (1998)
  127. http://www.emea.europa.eu/humandocs/PDFs/EPAR/opaxio/601200 09en.pdf
  128. Fernandes, J. Mater. Sci. Mater. Med., 17, 105 (2006)
  129. Maruyama, Int. J. Pharm., 111, 103 (1994)
  130. Stiriba, J. Am. Chem. Soc., 124, 9698 (2002)
  131. Oudshoorn, Biomaterials, 27, 5471 (2006)
  132. Kainthan, Biomaterials, 28, 4779 (2007)
  133. Siegers, Chem. Eur. J., 10, 2831 (2004)
  134. Yeh, Langmuir, 24, 4907 (2008)
  135. Kainthan, Biomacromolecules, 7, 703 (2006)
  136. Kainthan, Biomaterials, 28, 4581 (2007)
  137. Turk, Bioconjugate Chem., 15, 162 (2004)
  138. Michael, Toxicol. Appl. Pharmacol., 20, 334 (1971)
  139. Frey, Rev. Mol. Biotechnol., 90, 257 (2002)
  140. Haag, Macromolecules, 33, 8158 (2000)
  141. O’Brien, Fats and Oils-Formulating and Processing for Applications (2004)
  142. Kainthan, Bioconjugate Chem., 19, 2231 (2008)
  143. Tomalia, J. Polym. Sci. Part A, 4, 2253 (1966)
  144. Seeliger, Angew. Chem., 78, 913 (1966)
  145. Angew. Chem. Int. Ed. Engl., 5, 875 (1966)
  146. Kagiya, J. Polym. Sci. Part B, 4, 441 (1966)
  147. Bassiri, J. Polym. Sci. Part B, 5, 871 (1967)
  148. Kobayashi, Prog. Polym. Sci., 15, 751 (1990)
  149. Wiesbrock, Macromolecules, 38, 5025 (2005)
  150. Adams, Adv. Drug Delivery Rev., 59, 1504 (2007)
  151. Hoogenboom, Angew. Chem., 121, 8122 (2009)
  152. Angew. Chem. Int. Ed., 48, 7978 (2009)
  153. Wang, J. Controlled Release, 108, 140 (2005)
  154. Lee, J. Controlled Release, 89, 437 (2003)
  155. Mero, J. Controlled Release, 125, 87 (2008)
  156. Konradi, Langmuir, 24, 613 (2008)
  157. Pidhatika, Chimia, 62, 264 (2008)
  158. 36th Ann. Meeting & Exposition CRS 2009
  159. Woodle, Bioconjugate Chem., 5, 493 (1994)
  160. Zalpinsky, J. Pharm. Sci., 85, 133 (1996)
  161. Gaertner, J. Controlled Release, 119, 291 (2007)
  162. Weber, Macromolecules, 42, 2965 (2009)
  163. Wang, Biomaterials, 26, 2803 (2005)
  164. Jeong, J. Controlled Release, 73, 391 (2001)
  165. Fischer, Pharm. Res., 16, 1273 (1999)
  166. Torchilin, Biochim. Biophys. Acta Biomembr., 1195, 181 (1994)
  167. Sairam, Int. J. Pharm., 320, 131 (2006)
  168. Gao, Angew. Chem., 119, 2274 (2007)
  169. Angew. Chem. Int. Ed., 46, 2224 (2007)
  170. Patton, Langmuir, 22, 2212 (2006)
  171. Hynd, J. Biomater. Sci. Polym. Ed., 18, 1223 (2007)
  172. Saraydin, Nucl. Instrum. Methods Phys. Res. Sect. B, 217, 281 (2004)
  173. You, J. Ind. Eng. Chem., 13, 219 (2007)
  174. Fernandez-Cossio, Plast. Reconstr. Surg., 117, 1789 (2006)
  175. Christensen, Plast. Reconstr. Surg., 111, 1883 (2003)
  176. Gin H., Dupuy B., Bonnemaison-Bourignon D., Bordenave L., Bareille R., Latapie M. J., Baquey Ch., Bezian J. H., Ducassou D., Biocompatibility of Polyacrylamide Microcapsules Implanted in Peritoneal Cavity or Spleen of the Rat. Effect on Various Inflammatory Reactions in Vitro, 10.3109/10731199009117287
  177. Xi, J. Biomed. Mater. Res. Part A, 78, 283 (2006)
  178. Stach, Macromolecules, 41, 5174 (2008)
  179. Gulsen, J. Membr. Sci., 269, 35 (2006)
  180. Payne, J. Biomed. Mater. Res., 21, 843 (1987)
  181. Torchilin, J. Pharm. Sci., 84, 1049 (1995)
  182. Caliceti, J. Bioact. Compat. Polym., 10, 103 (1995)
  183. Caliceti, Bioconjugate Chem., 12, 515 (2001)
  184. Le Garrec, J. Drug Targeting, 10, 429 (2002)
  185. Benahmed, Pharm. Res., 18, 323 (2001)
  186. Luo, Macromolecules, 37, 4008 (2004)
  187. Moneghini, Pharm. Dev. Technol., 5, 347 (2000)
  188. Lopes, Biomaterials, 24, 1279 (2003)
  189. Mumper, Pharm. Res., 13, 701 (1996)
  190. Chin, Eur. J. Pharm. Biopharm., 69, 1083 (2008)
  191. Nicolaou, Polymeric gene delivery (2005)
  192. Shibaev, J. Macromol. Sci. Phys., 47, 276 (2008)
  193. Hartauer, Pharm. Dev. Technol., 5, 303 (2000)
  194. Dunn, Am. J. Hematol., 57, 68 (1998)
  195. Yusa, Macromolecules, 40, 5907 (2007)
  196. Ray, Macromolecules, 39, 5259 (2006)
  197. Wan, Macromolecules, 38, 10397 (2005)
  198. Ranucci, Macromol. Biosci., 6, 216 (2006)
  199. Duncan, Nat. Rev. Cancer, 6, 688 (2006)
  200. Soo, Nanotechnology in Drug Delivery (2009)
  201. Zheng, Bioconjugate Chem., 16, 598 (2005)
  202. Kasuya, J. Controlled Release, 74, 203 (2001)
  203. Borgman, Pharm. Res., 26, 1407 (2009)
  204. Kamei, Pharm. Res., 12, 663 (1995)
  205. Sure, J. Bioact. Compat. Polym., 17, 105 (2002)
  206. Wang, Biomacromolecules, 1, 313 (2000)
  207. Lu, J. Controlled Release, 78, 165 (2002)
  208. Oupicky, Bioconjugate Chem., 11, 492 (2000)
  209. Paasonen, Bioconjugate Chem., 18, 2131 (2007)
  210. Whiteman, J. Liposome Res., 11, 153 (2001)
  211. Woerly, Biomacromolecules, 9, 2329 (2008)
  212. Stastny, J. Controlled Release, 81, 101 (2002)
  213. Save, Macromolecules, 35, 1152 (2002)
  214. Scales, Biomacromolecules, 6, 1846 (2005)
  215. Hong, Macromolecules, 39, 3517 (2006)
  216. York, Biomacromolecules, 8, 2337 (2007)
  217. Demirelli, Polym. Degrad. Stab., 78, 333 (2002)
  218. Sprincl, J. Biomed. Mater. Res., 10, 953 (1976)
  219. Seymour, J. Biomed. Mater. Res., 21, 1341 (1987)
  220. Seymour, Eur. J. Cancer Part A, 31, 766 (1995)
  221. Shiah, Eur. J. Cancer, 37, 131 (2001)
  222. Duncan, Adv. Drug Delivery Rev., 61, 1131 (2009)
  223. Nowotnika, Adv. Drug Delivery Rev., 61, 1214 (2009)