Fluorinated materials for in vivo oxygen transport (blood substitutes), diagnosis and drug delivery

Biomaterials

Volumn 19, Issue 16, 1998, Pages 1529-1539

  Riess, Jean G ^a   Krafft, Marie Pierre ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b INSTITUT CHARLES SADRON   (France)

Author keywords

Bilayers; Drug delivery; Fluorinated amphiphiles; Fluorocarbon emulsions; Fluorocarbons; Gels; Liposomes; Oxygen delivery; Perfluorochemicals; Tubules; Vesicles

Indexed keywords

BIOMEDICAL ENGINEERING; BLOOD SUBSTITUTES; DIAGNOSIS; FLUOROCARBONS; GELS; PHARMACOKINETICS;

LIPOSOMES; OXYGEN TRANSPORT;

BIOMATERIALS;

BLOOD SUBSTITUTE; FLUOROCARBON;

BLOOD SUBSTITUTION; CONFERENCE PAPER; DRUG DELIVERY SYSTEM; HYDROPHOBICITY; HYPOXEMIA; ISCHEMIA; MOLECULAR INTERACTION; OXYGEN TRANSPORT; PRIORITY JOURNAL;

BLOOD SUBSTITUTES; CHEMISTRY, PHYSICAL; CLINICAL TRIALS; DRUG DELIVERY SYSTEMS; FLUOROCARBONS; HUMANS; OXYGEN; SURFACE-ACTIVE AGENTS;

EID: 0032143835     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0142-9612(98)00071-4     Document Type: Conference Paper

References (103)

1. Proc Vth Int Symp Blood Substitutes, San Diego, USA 1993.
2. (a) Vol. I, Blood Substitutes: General. In: Chang TMS, Riess JG, Winslow RM, editors. Art cells, blood subst, immob biotech 1994: 22(2);
3. (b) Vol. II, Blood Substitutes: Hemoglobin. In: Winslow RM, editor. Art cells, blood subst, immob biotech 1994:22(3);
4. (c) Vol. III, Blood Substitutes and Related Products: The Fluorocarbon Approach. In: Riess JG, editor. Art cells, blood subst, immob biotech 1994:22(4).
5. [2] (a) Faithfull NS. The role of perfluorochemicals in surgery and the ITU. In: Vincent JL, editor. Yearbook of intensive Care and Emergency Medicine. Berlin: Springer, 1994:237-51;
6. (b) Keipert PE, Faithfull NS, Roth DJ et al. Supporting tissue oxygenation during acute surgical bleeding using a perfluorochemical-based oxygen carrier. In: Ince C, Kesecioglu J, Telci L, Akpir K, editors. Oxygen Transport to Tissue XVII. New York: Plenum Press, 1996:603-9;
7. (c) Zuck TF, Riess JG. Current status of injectable oxygen carriers. Crit Rev Clin Lab Sci 1994;31:295-324.
8. [3] (a) Riess JG. Highly fluorinated systems for oxygen transport, diagnosis and drug delivery. Colloids Surf A 1994;84:33-48;
9. (b) Riess JG. Du fluor dans nos artères. New J Chem 1995; 19:891-909;
10. (c) Riess JG, Krafft MP. Advanced fluorocar bon-based systems for oxygen and drug delivery, and diagnosis. Art cells, blood subst, immob biotech 1997;25:43-52;
11. (d) Krafft MP, Riess JG. Highly fluorinated amphiphiles and colloidal systems. Biochimie 1998;80:in press.
12. [4] Riess JG, Le Blanc M. Perfluorocompounds as blood substitutes. Angew Chem Int Ed Engl 1978;17:621-34;
13. (b) Riess JG. Fluorocarbon-based in vivo oxygen transport and delivery systems. Vox Sang 1991;61:225-39;
14. (c) Weers JG. A physicochemical evaluation of perfluorochemicals for oxygen transport applications. J Fluorine Chem 1992;64:73-93;
15. (d) Riess JG. Fluorocarbon-based oxygen delivery: basic principles and product development. In: Chang TMS, editor. Blood Substitutes: Principles, Methods, Products and Clinical Trials. Georgetown, Karger Landes, 1998:101-26;
16. (e) Krafft MP, Riess JG, Weers JG. The design and engineering of oxygen-delivering fluorocarbon emulsions. In: Benita S, editor. Submicron Emulsions in Drug Targeting and Delivery. Amsterdam: Harwood, 1998:xxx.
17. [5] (a) Shaffer TH, Wolfson MR, Greenspan JS, Rubenstein SD, Stern RG. Perfluorochemical liquid as a respiratory medium, in Ref 2(a), 1994:315-26;
18. (b) Overbeck MC, Pranikoff T, Yadao CM, Hirschl RB. Efficacy of perfluorocarbon partial liquid ventilation in a large animal model of acute respiratory failure. Crit Care Med 1996;24:1208-14;
19. (c) Leach CL, Greenspan JS, Rubenstein SD et al. Partial liquid ventilation with perflubron in premature infants with severe respiratory distress syndrome. New Engl J Med 1996;335:761-7;
20. (d) Faithfull NS, Weers JG, US Pat Applic 92/19232 (1992);
21. (e) Fuhrman BP, US Pat 5,437,272 (1995).
22. [6] Chang S, Reppucci V, Zimmerman NJ, Heinemann MH, Coleman DJ. Perfluorocarbon liquids in the management of traumatic retinal detachment. Ophthalmol 1989;96:785-92;
23. (b) Blinder KJ, Peyman GA, Paris CL et al. Vitreon. a new perfluorocarbon. Brit J Ophthalmol 1991;75:240-4.
24. [7] (a) Mattrey RF, Wrigley R, Steinbach GC, Schutt EG, Evitts DP. Invest Radiol 1994;29:S139-S141;
25. (b) Schutt EG, Pelura TJ, Hopkins RM. Osmotically stabilized microbubbles sonographic contrast agents. Acad Radiol 1996;35:188-190;
26. (c) Quay S. PCT Applic WO 93/05819;
27. (d) Schutt EG, Evitts DP, Kinner R, Anderson, Weers JG, US Pat 5,639,443 (1997).
28. [8] Mattrey RF. The potential role of perfluorochemicals (PFCs) in diagnostic imaging, in Ref. 2(a) 1994;295-313;
29. (b) Bruneton JN, Falewee MN, François E, Cambon P, Philip C, Riess JG, Balu-Maestro C, Rogopoulos A. Preliminary clinical results using perfluorooctylbromide (PFOB) for CT imaging of the liver, spleen and vessels. Radiology 1989;170:179-84.
30. [9] (a) Krafft MP, Riess JG. Stable highly concentrated fluorocarbon gels. Angew Chem Int Ed Engl 1994;33:1100-1;
31. (b) Riess JG, Krafft MP, Fr. Pat 2710,840 (1995), U.S. Pat 5,573,757 (1996);
32. (b) Riess JG, Krafft MP, Fr. Pat 2710,840 (1995), U.S. Pat 5,573,757 (1996);
33. (c) Krafft MP, Riess JG, Fr Pat Applic 2,737,135 (1995);
34. (d) Ravey JC, Stébé MJ. Structure of inverse micelles and emulsion gels with fluorinated noionic surfactants. A small angle neutron scattering study. Progr Colloid Polym Sci 1990;82:218-28;
35. (e) Krafft MP. Fluorocarbon gels. In: Magdassi S, Tovitor E, editors. Novel Cosmetic Delivery Systems. New York: Marcel Dekker, 1988.
36. [10] (a) Riess JG, Krafft MP, Fr Pat Applic 94/07068 (1994);
37. (b) Sadtler V, Krafft MP, Riess JG. Achieving stable reverse water-in-fluorocarbon emulsions. Angew Chem Intl Ed Engl 1996; 35:1976-8.
38. [11] Johnson KA. US Pat 5,126,123 (1992).
39. [12] (a) Riess JG. Fluorinated vesicles. J Drug Targeting 1994;2: 455-68;
40. (b) Riess JG. Introducing a new element-fluorine-into the liposomal membrane. J Liposome Res 1995;5:413-30.
41. [13] Riess JG, Krafft MP. Fluorinated phosphocholine-based amphiphiles as components of fluorocarbon emulsions and fluorinated vesicles. Chem Phys Lipids 1995;75:1-14.
42. [14] Riess JG, Frézard F. Greiner J. Krafft MP, Santaella C, Vierling P, Zarif L. Membranes, vesicles, and other supramolecular systems made from fluorinated amphiphiles. In Barenholz, Y, Lasic, DD, editors. Handbook of Nonmedical Applications of Liposomes, vol III. Chap. 8, Boca Raton: CRC Press, 1996:98-141.
43. [15] (a) Riess JG, Arlen C, Greiner J. et al. Design, synthesis and evaluation of fluorocarbons and surfactants for in vivo applications: new perfluoroalkylated polyhydroxylated surfactants. In: Chang TMS, Geyer RP, editors. Blood Substitutes. New York: Marcel Dekker, 1989:421-30;
44. (b) Riess JG, Greiner J. Perfluoroalkylated sugar derivatives as potent surfactants for biomedical uses. In: Descotes G, editor. Carbohydrates as Organic Raw Materials. Weinheim: VCH Verlagsgesellschaft, 1993:209-59;
45. (c) Greiner J, Riess JG, Vierling P. Fluorinated surfactants intended for biomedical uses. In: Filler R, Kobayashi Y, Yagupolskii LM, editors. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Amsterdam: Elsevier, 1993:339-80.
46. [16] Charpiot B, Greiner J, Le Blanc M, Manfredi A, Riess JG, Zarif L. Europ Pat 0 255 443 A1 (1992); US Pat 4,985,550 (1991).
47. [16] Charpiot B, Greiner J, Le Blanc M, Manfredi A, Riess JG, Zarif L. Europ Pat 0 255 443 A1 (1992); US Pat 4,985,550 (1991).
48. [17] (a) Pavia AA, Pucci B, Riess JG, Zarif L, Fr Pat 2,665,705 (1993); U.S. Pat 5,527,962 (1996);
49. [17] (a) Pavia AA, Pucci B, Riess JG, Zarif L, Fr Pat 2,665,705 (1993); U.S. Pat 5,527,962 (1996);
50. (b) Pavia AA, Pucci B, Riess JG, Zarif L, Guedj C, Fr Pat 2, 694,559 (1994); U.S. Pat 5,446,023 (1995); U.S. Pat 5,637,564 (1997); U.S. Pat 5,650,393 (1997);
51. (b) Pavia AA, Pucci B, Riess JG, Zarif L, Guedj C, Fr Pat 2, 694,559 (1994); U.S. Pat 5,446,023 (1995); U.S. Pat 5,637,564 (1997); U.S. Pat 5,650,393 (1997);
52. (b) Pavia AA, Pucci B, Riess JG, Zarif L, Guedj C, Fr Pat 2, 694,559 (1994); U.S. Pat 5,446,023 (1995); U.S. Pat 5,637,564 (1997); U.S. Pat 5,650,393 (1997);
53. (b) Pavia AA, Pucci B, Riess JG, Zarif L, Guedj C, Fr Pat 2, 694,559 (1994); U.S. Pat 5,446,023 (1995); U.S. Pat 5,637,564 (1997); U.S. Pat 5,650,393 (1997);
54. (c) Polidori A, Pucci B, Maurizis JC, Pavia AA. Synthesis of nonionic glycosidic surfactants derived from tris(hydroxymethyl)aminomethane. Preliminary assessment. New J Chem 1994;18:839-848.
55. [18] (a) Riess JG, Blaignon C, Le Blanc M. Fr Pat 2,620,445 (1990);
56. (b) Nivet JB, Bernelin R, Le Blanc M, Riess JG. Synthesis and bioacceptability of fluorinated surfactants derived from F-al-kylated tertiary amines. Eur J Med Chem 1992;27:891-8;
57. (c) Price A. US Pat 3,828,085 (1974).
58. [19] Riess JG, Jeanneaux F, Krafft MP, Santaella C, Vierling P. Europ Pat 0,478,686 (1993); US Pat 5,344,930 (1994).
59. [19] Riess JG, Jeanneaux F, Krafft MP, Santaella C, Vierling P. Europ Pat 0,478,686 (1993); US Pat 5,344,930 (1994).
60. [20] Riess JG, Greiner J, Milius A, Vierling P, Guillot F, Gaentzler S. Fr Pat 2,677,360 (1995); US Pat 5,679,459 (1997).
61. [20] Riess JG, Greiner J, Milius A, Vierling P, Guillot F, Gaentzler S. Fr Pat 2,677,360 (1995); US Pat 5,679,459 (1997).
62. [21] Kissa E. Fluorinated Surfactants, Synthesis, Properties, Applications. New York: Marcel Dekker, 1993.
63. [22] Jones MN. Carbohydrate-mediated liposomal targeting and drug delivery. Adv Drug Delivery Rev 1994;13:215-50.
64. [23] (a) Pavia AA, Pucci B, Zarif L, Riess JG. Hydrocarbon and/or fluorocarbon telomers: an alternative approach to drug carrying and delivery. Proc Int Symp Control Rel Bioact Mater 1994;21:87-8;
65. (b) Maurizis JC, Azim M, Rapp M et al. Disposition in rat of a new fluorinated biocompatible, non-ionic telomeric carrier. Xenobiotica 1994;24:535-41.
66. [24] (a) Riess JG, Vierling P, Garelli N. US Pat 5,399,634 (1995);
67. (b) Garelli N, Vierling P, Fischel JL, Milano G. Cytotoxic activity of new amphiphilic perfluoroalkylated bipyridine platinum and palladium complexes incorporated into liposomes. Eur J Med Chem 1993;28:235-42.
68. [25] Riess JG, Pace S, Zarif L. Highly effective surfactants with low hemolytic activity. Adv Mat 1991;3:249-51.
69. [26] (a) Riess JG, Sole-Violan L, Postel M. A new concept in the stabilization of injectable fluorocarbon emulsions: the use of mixed fluorocarbon-hydrocarbon dowels. J Disp Sci Technol 1992;13:349-55;
70. (b) Riess JG, Cornélus C, Krafft MP, Mahé AM, Postel M, Zarif L. Novel flurocarbon-based injectable oxygen-carrying formulations with long-term room-temperature storage stability. Adv Exp Med Biol 345:227-35;
71. (c) Riess JG, Solé-Violan L, Postel M, French Pat 2,679,150 (1994); US Pat Applic 07/916216 (1992).
72. (c) Riess JG, Solé-Violan L, Postel M, French Pat 2,679,150 (1994); US Pat Applic 07/916216 (1992).
73. [27] Trevino L, Frézard F, Rolland JP, Postel M, Riess JG. Novel liposome systems based on the incorporation of (perfluoroalkyl)alkenes into the bilayer of phospholipid liposomes. Colloids Surf 1994;88:223-33.
74. 2 is slowed down when (perfluoroalkyl)alkanes are incorporated into the liposomal membrane. Biochim Biophys Acta 1995;1254:1-6.
75. [29] (a) Elbert R, Folda T, Ringsdorf H. Saturated and polymerizable amphiphiles with fluorocarbon chains. Investigation in monolayers and liposomes. J Am Chem Soc 1984;106:7687-92.
76. (b) Kunitake T. Synthetic bilayer membranes: molecular design, self-organization, and application. Angew Chem Int Ed Engl 1992;31:709-26.
77. [30] (a) Krafft MP, Giulieri F, Riess JG. Can single-chain perfluoroalkylated amphiphiles alone form vesicles and other organized supramolecular systems. Angew Chem Int Ed Engl 1993; 32:741-43;
78. (b) Krafft MP, Giulieri F, Riess JG. Supramolecular assemblies from single-chain perfluoroalkylated phosphorylated amphiphiles. Colloids Surf 1994;84:113-9.
79. + permeability, active doxorubicin encapsulation and stability in human serum. Biochim Biophys Acta 1994;1194:61-8.
80. [32] Santaella C, Frézard F, Vierling P, Riess JG. Extended in vivo blood circulation time of fluorinated liposome. FEBS Lett 1993;336:481-4.
81. [33] (a) Fuhrhop JH, Helfrich W. Fluid and solid fibers made from lipid molecular bilayers. Chem Rev 1993;93:1565-82;
82. (b) Imae T., Takahashi Y, Muramatu H. Formation of fibrous molecular assemblies by amino acids surfactants in water. J Am Chem Soc 1992;114:3414-19;
83. (c) Schnur JM. Fluid and solid fibers made from lipid molecular bilayers. Science 1993;262:1669-76.
84. [34] (a) Giulieri F, Krafft MP, Riess JG. Stable fluorinated fibers and rigid tubules from single-chain perfluoroalkylated amphiphiles. Angew Chem Int Ed Engl 1994;33:1514-5;
85. (b) Riess JG, Giulieri F, Krafft MP, Zarif L. US Pat Applic 08/214,411 (1994).
86. [35] (a) Yokoyama K, Yamanouchi K, Suyama T. Recent advances in a perfluorochemical blood substitute and its biomedical application. Life Chem Reports 1983;2:35-93;
87. (b) Jaffe C, Wohlgelernter D, Cabin H. Preservation of left ventricular ejection fraction during percutaneous transluminal coronary angioplasty by distal transcatheter coronary perfusion of oxygenated Fluosol DA 20%. Am Heart J 1988;115:1156-64.
88. [36] (a) Long DC, Long DM, Riess JG, Follana R, Burgan A, Mattrey RF. Preparation and application of highly concentrated perfluorooctyl bromide fluorocarbon emulsions. In: Chang TMS, Geyer RP, editors. Blood Substitutes. New York: Marcel Dekker, 1989:441-3;
89. (b) Riess JG, Dalfors JL, Hanna GK, Klein DH, Krafft MP, Pelura TJ, Schutt EG. Development of highly fluid, concentrated and stable fluorocarbon emulsions for diagnosis and therapy. Biomat Art cells, immob biotech 1992;20:839-42;
90. (c) Riess JG, Flaim SF, Klein DH, Weers JG. The relative physicochemical and biological attributes of perflubron emulsions. In: Vorobyev SI, Ivanitsky GR, editors. Proc Int Symp Blood Substitutes, Pushchino 1994. Russian Academy of Sciences, (Pushchino, Russia): 1996;
91. (d) Long DM, US Pat 4,987,154 (1991).
92. [37] (a) Wahr JA, Trouwborst A, Spence RK et al. A pilot study of the effects of a Perflubron emulsion, AF0104, on mixed venous oxygen tension in anesthetized surgical patients. Anesth Analg 1996;82:103-10;
93. (b) Riess JG, Keipert PE. Update on perfluorocarbon-based oxygen delivery systems. In: Tsuchida E, editor. Blood Substitutes. Amsterdam: Elsevier, 1998.
94. [38] Weers JG, Liu J, Resch P, Cavin J, Arlauskas RA. Room temperature stable perfluorocarbon emulsions with acceptable half-lives in the reticuloendothelial system. Art cells, blood subst, immob biotech 1994;22:1175-82.
95. [39] Krafft MP, Dellamare L, Tarara T, Riess JG, Trevino L. PCT WO 97/21425. Colloidal systems made from fluorinated amphiphiles. 15th Intl. Symp. Fluorine Chem., August 1997.
96. [40] (a) Rosano HL, Gerbacia WE, US Patent, 3,778,381 (1973);
97. (b) Mathis G, Leempoel P, Ravey JC, Selve C, Delpuech JJ. A novel class of nonionic microemulsions: fluorocarbons in aqueous solutions of fluorinated poly(oxyethylene) surfactants. J Am Chem Soc 1984;106:6162-71;
98. (c) Lattes A, Rico-Lattes I. Microemulsions of perfluorinated and semi-fluorinated compounds, in Ref. 2c, 1994:1007-18;
99. (d) Schubert KV, Kaler EW. Microemulsifying fluorinated oils with mixtures of fluorinated and hydrogenated surfactants. Colloids Surf A 1994; 84:97-106.
100. [41] (a) Lehn JM. Perspectives in supramolecular chemistry - From molecular recognition towards molecular information processing and self-organization. Angew Chem Int Ed Engl 1990;29: 1304-19;
101. (b) Lehn JM. Supramolecular chemistry - Molecular information and the design of supramolecular materials. Makromol Chem Macromol Symp 1993;69:1-17.
102. [42] (a) Ceve G, editor. Phospholipids Handbook. New York: Marcel Dekker, 1993;
103. (b) Gregoriadis G, editor. Liposome Technology. Boca Raton: CRC Press, 1993.