Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses

Journal of Fluorine Chemistry

Volumn 130, Issue 3, 2009, Pages 308-316

  Kaplánek, Robert ^a   Paleta, Oldřich ^a   Ferjentsiková, Ivana ^a   Kodíček, Milan ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

1 O Fluoroalkyl d xylitol; Hemocompatibility; Microemulsion stability; Perfluoroalkylated oligo(oxyethylene) ethers; Perfluoroalkylated oxiranes; Radical addition; Reduction of C I bond

Indexed keywords

EID: 60649092886     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.12.001     Document Type: Article

References (63)

1. Reed T.M. In: Simons J.H. (Ed). Fluorine Chemistry vol. 2 (1954), Academic Press, New York (Chapter 2)
2. Battino R., and Clever H.I. Chem. Rev. 66 (1966) 395-463
3. Riess J.G., and LeBlanc M. Angew. Chem. Int. Ed. Engl. 17 (1978) 621-634
4. Mathis G., Leempoel P., Ravey J.-C., Selve C., and Delpuech J.-J. J. Am. Chem. Soc. 106 (1984) 6162-6171
5. Krafft M.P. Biomaterials 19 (1998) 1529-1539
6. Riess J.G., Vierling P., Santaella C., and Greiner J. J. Fluorine Chem. 107 (2001) 337-354
7. Riess J.G. Tetrahedron 58 (2002) 4113-4131
8. Riess J.G., and Krafft M.P. Biomaterials 19 (1998) 1529-1539
9. Riess J.G., and Greiner J. Carbohydr. Res. 327 (2000) 147-168
10. Lowe K.C. J. Fluorine Chem. 109 (2001) 59-65
11. Krafft M.P. Adv. Drug Deliv. Rev. 47 (2001) 209-228
12. Riess J.G. J. Fluorine Chem. 114 (2002) 119-126
13. Riess J.G. J. Fluorine Chem. 118 (2002) 19-26
14. Selve C., Castro B., Leempoel P., Mathis G., Gartiser T., and Delpuech J.-J. Tetrahedron 39 (1983) 1313-1316
15. Zarif L., Manfredi A., Varescon C., Le Blanc M., and Riess J.G. J. Am. Oil Chem. Soc. 66 (1989) 1515-1523
16. Riess J.G., Pace S., and Zarif L. Adv. Mater. 3 (1991) 249-251
17. Greiner J., Riess J.G., and Vierling P. In: Filler R., Kobayashi Y., and Yagupolskii L.M. (Eds). Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (1993), Elsevier, Amsterdam 339-380
18. In: Kissa E. (Ed). Fluorinated Surfactants, Synthesis, Properties, Applications (1994), M. Dekker, New York 469
19. Krafft M.P., and Riess J.G. Biochimie 80 (1998) 489-514
20. Barthelemy P., Maurizis J.C., Lacombe J.M., and Pucci B. Bioorg. Med. Chem. Lett. 8 (1998) 1559-1562
21. Barthelemy P., Cuvillier N., Chaudier Y., Benattar J.J., and Pucci B. J. Fluorine Chem. 105 (2000) 95-102
22. Paleta O., Dlouhá I., Kaplánek R., Kefurt K., and Kodíček M. Carbohydr. Res. 337 (2002) 2411-2418
23. Církva V., Kaplánek R., Paleta O., and Kodíček M. Collect. Czech Chem. Commun. 67 (2002) 1436-1448
24. Selve C., and Achilefu S. J. Chem. Soc. Chem. Commun. 13 (1990) 911-912
25. Szönyi F., and Cambon A. J. Fluorine Chem. 36 (1987) 195-209
26. Afzal J., Fung B.M., and O'Rear E.A. J. Fluorine Chem. 34 (1987) 385-394
27. Meinert H., and Geister U. J. Fluorine Chem. 68 (1994) 221-226
28. Achilefu S., Mansuy L., Selve C., and Thiebaut S. J. Fluorine Chem. 70 (1995) 19-26
29. Jaoued N.G., Oueslati R., and Hedhli A. Synth. Commun. 35 (2005) 543-556
30. Dieng S., Bertaina B., and Cambon A. J. Fluorine Chem. 28 (1985) 425-440
31. Kaplánek R., and Paleta O. J. Fluorine Chem. 128 (2007) 789-796
32. Vierling P., Santaella C., and Greiner J. J. Fluorine Chem. 107 (2001) 337-354
33. Gaysinski M., Le Forestier J.P., Cambon A., Devoiselle J.M., Maillols H., and Chang P. J. Fluorine Chem. 83 (1997) 175-182
34. Meinert H., Reuter P., Mader J., Haidmann L., and Northoff H. Biomater. Artif. Cells Immobilization Biotechnol. 20 (1992) 115-124
35. Gentilini C., Boccalon M., and Pasquato L. Eur. J. Org. Chem. (2008) 3308-3313
36. Církva V., Ameduri B., Boutevin B., and Paleta O. J. Fluorine Chem. 84 (1997) 53-62
37. Církva V., Polák R., Paleta O., Kefurt K., Moravcová J., Kodíček M., and Forman S. Carbohydr. Res. 339 (2004) 2177-2186
38. Kaplánek R., Paleta O., Michálek J., and Přádný M. J. Fluorine Chem. 126 (2005) 595-600
39. Oka K., Fujiue N., Nakanishi S., Takata T., West R., and Dohmaru T. J. Organomet. Chem. 611 (2000) 45-51
40. Zhang Z., Sherlock D., West R., West R., Amine K., and Lyons L.J. Macromolecules 36 (2003) 9176-9180
41. Brace N.O. J. Fluorine Chem. 93 (1999) 1-25
42. Kaplánek R., Bříza T., Havlík M., Martásek P., and Král V. J. Fluorine Chem. 128 (2007) 179-183
43. Huang W.Y. J. Fluorine Chem. 58 (1992) 1-8
44. Wang Z.F., and Xu J.C. Tetrahedron 54 (1998) 12597-12608
45. Hein M., and Miethchen R. Tetrahedron Lett. 39 (1998) 6679-6682
46. Hein M., Miethchen R., and Schwaebisch D.J. J. Fluorine Chem. 98 (1999) 55-60
47. Metzger J.O., and Linker U. Liebigs Ann. Chem. 3 (1992) 209-216
48. Naud C., Calas P., Blancou H., and Commeyras A. J. Fluorine Chem. 104 (2000) 173-184
49. Arehart S.V., and Pugh C. J. Am. Chem. Soc. 119 (1997) 3027-3037
50. Hartmann P., Collet A., and Viguier M. J. Fluorine Chem. 95 (1999) 145-152
51. Amato C., and Calas P. J. Fluorine Chem. 124 (2003) 169-176
52. Brace N.O. J. Org. Chem. 27 (1962) 4491-4498
53. Greiner J., Milius A., and Riess J.G. J. Fluorine Chem. 56 (1992) 285-293
54. Nostro P.L., and Chen S.H. J. Phys. Chem. 97 (1993) 6535-6540
55. Brace N.O., and Van Elswyk J.E. J. Org. Chem. 41 (1976) 766-771
56. Graupe M., Koini T., Wang V.Y., Nassif G.M., Colorado R., Villazana R.J., Dong H., Miura Y.F., Shmakova O.E., and Lee T.R. J. Fluorine Chem. 93 (1999) 107-116
57. Davis C.J., Burton D., and Yang Z.-Y. J. Fluorine Chem. 70 (1995) 135-140
58. Takai K., Takagi T., Baba T., and Kanamori T. J. Fluorine Chem. 125 (2004) 1959-1964
59. Kotora M., Hajek M., Ameduri B., and Boutevin B. J. Fluorine Chem. 68 (1994) 49-56
60. Bonafoux D., Hua Z., Wang B., and Ojima I. J. Fluorine Chem. 112 (2001) 101-108
61. Cheng X.H.D., Malay K., Diele S., and Tschierske C. Angew. Chem. Int. Ed. Engl. 41 (2002) 4031-4035
62. Církva V., Ameduri B., Boutevin B., and Paleta O. J. Fluorine Chem. 83 (1997) 151-158
63. Holý A. Collect. Czech. Chem. Commun. 47 (1982) 2786-2805