Highly fluorinated amphiphilic molecules and self-assemblies with biomedical potential

Current Opinion in Colloid and Interface Science

Volumn 14, Issue 5, 2009, Pages 294-304

  Riess, Jean G ^a  

^a Harangoutte les Roses ^*  (France)

Author keywords

Amphiphiles; Biomimetics; Emulsions; Environmental issues; Fluorinated proteins; Fluorinated surfactants; Fluorocarbon hydrocarbon diblocks; Micelles; Microbubbles; PFOA; PFOS; Self assembly; Semi fluorinated alkanes; Soft matter; Toxicity; Vesicles

Indexed keywords

ENVIRONMENTAL ISSUES; FLUORINATED PROTEINS; FLUORINATED SURFACTANTS; FLUOROCARBON/HYDROCARBON DIBLOCKS; MICROBUBBLES; PFOA; PFOS; SEMI-FLUORINATED ALKANES; SOFT-MATTER; VESICLES;

BIOMIMETICS; ENVIRONMENTAL PROTECTION; MICELLES; PARAFFINS; PROTEINS; SELF ASSEMBLY; TOXICITY;

AMPHIPHILES;

AMINO ACID; AMPHOPHILE; FLUORIDE; FLUOROCARBON; HYDROCARBON; INSULIN; NANOPARTICLE; PERFLUOROOCTANESULFONIC ACID; PERFLUOROOCTANOIC ACID; SELF ASSEMBLED MONOLAYER; SURFACTANT;

AMINO ACID SUBSTITUTION; BIOMIMETICS; CYTOTOXICITY; DRUG DELIVERY SYSTEM; EMULSION; FLUORINATION; HEMOLYSIS; HUMAN; LIVER CARCINOGENESIS; LIVER TOXICITY; MEDICAL TECHNOLOGY; NONHUMAN; REVIEW;

EID: 68949181727     PISSN: 13590294     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cocis.2009.05.008     Document Type: Review

References (190)

1. Krafft M.P., and Riess J.G. Chemistry, physical chemistry and uses of molecular fluorocarbon-hydrocarbon diblocks, triblocks and related compounds - unique apolar components for self-assembled colloid and interface engineering. Chem. Rev. 109 (2009) 1714-1792 A comprehensive critical review of all aspects of (F-alkyl)alkane diblock chemistry and applications. It also provides an updated digest of the specific characteristics and behavior of perfluorocarbons and perfluoroalkyl chains
2. Riess J.G. Fluorous materials for biomedical uses. In: Gladysz J.A., Curran D.P., and Horváth I. (Eds). Handbook of fluorous chemistry (2004), Wiley-VCH 521-573
3. Krafft M.P., and Riess J.G. Perfluorochemical-based oxygen therapeutics, contrast agents, and beyond. In: Tressaud A., and Haufe G. (Eds). Advances in fluorine science - fluorine and health. Molecular imaging, biomedical materials and pharmaceuticals (2008), Elsevier 447-486 Chapter 11
4. Riess J.G. Understanding the fundamentals of perfluorocarbons and perfluorocarbon emulsions relevant to in vivo oxygen delivery. Artif. Cells, Blood Subst., Immob. Biotech. 33 (2005) 47-63
5. Riess J.G., and Krafft M.P. Fluorocarbon emulsions as in vivo oxygen delivery systems: background and chemistry. In: Winslow R.M. (Ed). Blood substitutes (2006), Elsevier 259-275 Chap. 24
6. Schutt E.S., Klein D.H., Mattrey R.M., and Riess J.G. Injectable microbubbles as contrast agents for diagnostic ultrasound imaging: the key role of perfluorochemicals. Angew. Chem. Int. Ed. 42 (2003) 3218-3235
7. Lehmler H.-J. Perfluorocarbon compounds as vehicles for pulmonary drug delivery. Expert Opin. Drug Deliv. 4 (2007) 247-262
8. Rico-Lattes I., Quintyn J.C., Pagot-Mathis V., Benouaich X., and Mathis A. Fluorinated molecules in eye surgery: experimental and clinical benefit of a heavy silicone oil Oxane Hd (mixture of silicone oil and RMN3 fluorine olefin) in the treatment of retinal detachment. In: Tressaud A., and Haufe G. (Eds). Advances in fluorine science - fluorine and health. Molecular Imaging, Biomedical Materials and Pharmaceuticals (2008), Elsevier 407-420 Chap. 9
9. Jäckel C., and Koksch B. Fluorine in peptide design and protein engineering. Eur. J. Org. Chem. (2005) 4483-4503 An overview of progress in peptide and protein modification involving fluorinated amino acid residues
10. Wang L., and Schultz P.G. Expanding the genetic code. Angew. Chem. Int. Ed. 44 (2005) 34-66
11. Budisa N. Engineering the genetic code (2006), Wiley-VCH, Weinheim
12. Connor R.E., and Tirrell D.A. Non-canonical amino acids in protein polymer design. Polym. Rev. 47 (2007) 9-28 How to engineer proteins with non-natural amino acids in vitro and in vivo
13. Riess J.G., and Greiner J. Carbohydrate- and related polyol-derived fluorosurfactants - an update. Carbohydr. Res. 327 (2000) 147-168
14. Kissa E. Fluorinated surfactants and repellents. Surfactant science series vol. 97 (2001), Marcel Dekker, New York
15. Riess J.G. Fluorous micro- and nanophases with a biomedical perspective. Tetrahedron 58 (2002) 4113-4131
16. Krafft M.P., and Goldmann M. Monolayers made from fluorinated amphiphiles. Curr. Opin. Colloid Interf. Sci. 8 (2003) 243-250
17. Krafft M.P., and Riess J.G. Perfluorocarbons, life sciences and biomedical uses (highlight). J. Polym. Sci. Part A: Polymer Chem. 45 (2007) 1185-1198
18. Blazejewski J.-C., Wilmshurst M.P., Popkin M.D., Wakselman C., Laurent G., Nonclercq D., et al. Synthesis, characterization and biological evaluation of 7α-perfluoroalkylestradiol derivatives. Bioorg. Med. Chem. 11 (2003) 335-345
19. Courrier H.M., Krafft M.P., Butz N., Porté C., Frossard N., Rémy-Kristensen A., et al. Evaluation of cytotoxicity of new semi-fluorinated amphiphiles derived from dimorpholinophosphate. Biomaterials 24 (2003) 689-696
20. Courrier H.M., Vandamme T.F., and Krafft M.P. Reverse water-in-fluorocarbon emulsions and microemulsions obtained with a fluorinated surfactant. Colloids Surf. A: Physicochem. Eng. Aspects 244 (2004) 141-148
21. Massi L., Guittard F., Levy R., and Géribaldi S. Enhanced activity of fluorinated quaternary ammonium surfactants against Pseudomonas aeruginosa. Eur.J. Med. Chem. 44 (2009) 1615-1622
22. Caillier L., Taffin de Givenchy E., Levy R., Vandenberghe Y., Géribaldi S., and Guittard F. Polymerizable semi-fluorinated gemini surfactants designed for antimicrobial materials. J. Colloid Interf. Sci. 332 (2009) 201-207
23. Thebault P., Taffin de Givenchy E., Guittard F., Guimon C., and Géribaldi S. Self-assembled monolayers of semi-fluorinated thiols and disulfides with a potentially antibacterial terminal fragment on gold surfaces. Thin Solid Films 516 (2008) 1765-1772
24. Vyas S.M., Turánek J., Knötigová P., Kašná A., Kvardová V., Koganti V., et al. Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides. New J. Chem. 30 (2006) 944-951
25. Panza J.L., Russell A.J., and Beckman E.J. Synthesis of fluorinated NAD as a soluble coenzyme for enzymatic chemistry in fluorous solvents and carbon dioxide. Tetrahedron 58 (2002) 4091-4104
26. Lehmler H.-J., Xu L., Vyas S.M., Ojogun V.A., Knutson B.L., and Ludewig G. Synthesis, physicochemical properties and in vitro cytotoxicity of nicotinic acid ester prodrugs intended for pulmonary delivery using perfluorooctyl bromide as vehicle. Int. J. Pharm. 353 (2008) 35-44
27. Li X., Turánek J., Knötigová P., Kudlácková H., Mašek J., Pennington D.B., et al. Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants. New J. Chem. 32 (2008) 2169-2179
28. Kaplánek R., Paleta O., Ferjensiková I., and Kodícek M. Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses. J. Fluorine Chem. 130 (2009) 308-316
29. Církva V., Duchek J., Kaplánek R., Paleta O., Michálek J., Prádny M., et al. New perfluoroalkylated amphiphilic methacrylates bearing sulfinyl group as monomers for biomedical applications: water content and oxygen permeability of their copolymers with DEGMA. Eur. J. Med. Chem. 41 (2006) 1320-1326
30. Hiranita T., Nakamura S., Kawachi M., Courrier H.M., Vandamme T.F., Krafft M.P., et al. Miscibility behavior of dipalmitoylphosphatidylcholine with a single-chain partially fluorinated amphiphile in Langmuir monolayers. J. Colloid Interf. Sci. 265 (2003) 83-92
31. Courrier H.M., Vandamme T.F., Krafft M.P., Nakamura S., and Shibata O. Mixed monolayers made from dipalmitoyl phosphatidylcholine and a fluorinated amphiphile. Colloids Surf. A. Physicochem. Engineer. Aspects 215 (2003) 33-41
32. Nakamura S., Nakahara H., Krafft M.P., and Shibata O. Two-component Langmuir monolayers of single chain partially fluorinated amphiphiles with dipalmitoylphosphatidylcholine (DPPC). Langmuir 23 (2007) 12634-12644
33. Lehmler H.J., and Bummer P.M. Mixing behavior of 10-(perfluorohexyl)-decanol and DPPC. Colloids Surf. B 44 (2005) 74-81
34. Lehmler H.-J., and Bummer P.M. Interaction of a partially fluorinated long-chain nicotinate with dipalmitoylphosphatidylcholine. J. Lipid Res. 46 (2005) 2415-2422
35. Yoder N.C., Kalsani V., Schuy S., Vogel R., Janshoff A., and Kumar K. Nanoscale patterning in mixed fluorocarbon-hydrocarbon phospholipid bilayers. J. Am. Chem. Soc. 129 (2007) 9037-9043
36. In: Gladysz J.A., Curran D.P., and Horváth I. (Eds). Handbook of fluorous chemistry (2004), Wiley-VCH, Weinheim
37. Montanari V., and Kumar K. Just add water: a new fluorous capping reagent for facile purification of peptide synthesized on the solid phase. J. Am. Chem. Soc. 126 (2004) 9528-9529
38. 18F]fluoride ion: nucleophilic fluorination as the detagging process. Angew. Chem. Int. Ed. 48 (2009) 586-589 Fluorous chemistry facilitates preparation of radiotracers for positron emission tomography
39. Polidori A., Presset M., Lebaupain F., Ameduri B., Popot J.-L., Breyton C., et al. Fluorinated and hemifluorinated surfactants derived from maltose: synthesis and application to handling membrane proteins in aqueous solution. Bioorg. Med. Chem. Lett. 16 (2006) 5827-5831
40. Park K.-H., Berrier C., Lebaupain F., Pucci B., Popot J.-L., Ghazi A., et al. Fluorinated and hemifluorinated surfactants as alternatives to detergents for membrane protein cell-free synthesis. Biochem. J. 403 (2007) 183-187
41. Petkova V., Benattar J.-J., Zoonens M., Zito F., Popot J.-L., Polidori A., et al. Free-standing films of fluorinated surfactants as 2D matrices for organizing detergent-solubilized membrane proteins. Langmuir 23 (2007) 4303-4309 A new method for 2D confinement of membrane proteins
42. Kasuya M.C.Z., Cusi R., Ishihara O., Miyagawa A., Hashimoto K., Sato T., et al. Fluorous-tagged compound: a viable scaffold to prime oligosaccharide synthesis by cellular enzymes. Biochem. Biophys. Res. Commun. 316 (2004) 599-604 A fluorous strategy for intracellular enzymatic biosynthesis and isolation of oligosaccharides
43. Giulieri F., and Krafft M.P. Tubular microstructures made from non-chiral single-chain fluorinated amphiphiles: impact of the structure of the hydrophobic chain on the rolling-up of bilayer membranes. J. Colloid Interf. Sci. 258 (2003) 335-344
44. Krafft M.P. Basic principles and recent advances in fluorinated self-assemblies and colloidal systems. In: Gladysz J.A., Curran D.P., and Horvàth I.T. (Eds). Handbook of fluorous chemistry (2004), Wiley-VCH 478-490 Chapter 12.1
45. Krafft M.P. Highly fluorinated compounds induce phase separation in, and nanostructuration of liquid media. possible impact on, and use in chemical reactivity control (Highlight). J. Polym. Sci. Part A: Polymer Chem. 44 (2006) 4251-4258
46. Sato S., Iida J., Suzuki K., Kawano M., Ozeki T., and Fujita M. Fluorous nanodroplets structurally confined in an organopalladium sphere. Science 313 (2006) 1273-1276
47. Kubowicz S., Baussard J.-F., Lutz J.-F., Thünemann A.F., von Berlepsch H., and Laschewsky A. Multicompartment micelles formed by self-assembly of linear ABC triblock copolymers in aqueous medium. Angew. Chem. Int. Ed. 44 (2005) 5262-5265
48. Li Z., Kesselman E., Talmon Y., Hillmyer M.A., and Lodge T.P. Multicompartment micelles from ABC miktoarm stars in water. Science 306 (2004) 98-101
49. Saito N., Liu C., Lodge T.P., and Hillmyer M.A. Multicompartment micelles from polyester-containing ABC miktoarm star terpolymers. Macromolecules 41 (2008) 8815-8822
50. Kubowicz S., Thünemann A.T., Weberskirch R., and Möhwald H. Cylindrical micelles of α-fluorocarbon-ω-hydrocarbon end-capped poly(N-acylethylene imine)s. Langmuir 21 (2005) 7214-7219
51. Thünemann A.F., Kubowicz S., von Berlepsch H., and Möhwald H. Two-compartment micellar assemblies obtained via aqueous self-organization of synthetic polymer building blocks. Langmuir 22 (2006) 2506-2510
52. Laschewsky A., Mertoglu M., Kubowicz S., and Thünemann A.F. Lamellar structured nanoparticles formed by complexes of a cationic block copolymer and perfluorodecanoic acid. Macromolecules 39 (2006) 9337-9345
53. Sanchez-Dominguez M., Benoit N., and Krafft M.P. Synthesis of triphilic, Y-shaped molecular surfactants. Tetrahedron 64 (2008) 522-528
54. Fontaine P., Goldmann M., Muller P., Fauré M.-C., Konovalov O., and Krafft M.P. Direct evidence for highly organized networks of circular surface micelles of surfactant at the air/water interface. J. Am. Chem. Soc. 127 (2005) 512-513 Highly ordered hexagonal arrays of surface micelles of inert semifluorinated alkanes form spontaneously on water, with potential for the elaboration of biosensors
55. Takai K., Takagi T., Baba T., and Kanamori T. Highly fluorinated C18 fatty acids: synthesis and interfacial properties. J. Fluorine Chem. 125 (2004) 1959-1964
56. Maaloum M., Muller P., and Krafft M.P. Lateral and vertical nanophase separation in Langmuir-Blodgett films of phospholipids and semifluorinated alkanes. Langmuir 20 (2004) 2261-2264
57. Tareste D., Pincet F., Lebeau L., and Perez E. Hydrophobic forces and hydrogen bonds in the adhesion between retinoid-coated surfaces. Langmuir 23 (2007) 3225-3229
58. Klein E., Kerth P., and Lebeau L. Enhanced selective immobilization of biomolecules onto solid supports coated with semifluorinate self-assembled monolayers. Biomaterials 29 (2008) 204-214
59. Gonzàlez-Pérez A., Schmutz M., Waton G., Romero M.J., and Krafft M.P. Isolated fluid polyhedral vesicles. J. Am. Chem. Soc. 129 (2007) 756-757
60. Courrier H.M., Pons F., Lessinger J.M., Frossard N., Krafft M.P., and Vandamme T.F. In vivo evaluation of a reverse water-in-fluorocarbon emulsion stabilized with a semifluorinated amphiphile as a drug delivery system through the pulmonary route. Int. J. Pharmaceutics 282 (2004) 131-140
61. Butz N., Porté C., Courrier H., Krafft M.P., and Vandamme T.F. Reverse water-in-fluorocarbon emulsions for use in pressurized metered-dose inhalers containing hydrofluoroalkane propellants. Int. J. Pharm. 238 (2002) 257-269
62. Brubach J.-B., Mermet A., Filabozzi A., Gerschel A., Lairez D., Krafft M.P., et al. Dependence of water dynamics upon confinement size. J. Phys. Chem. B 105 (2001) 430-435
63. Maruyama T., Kotani T., Yamamura H., Kamiya N., and Goto M. Poly(ethylene glycol)-lipase complexes catalytically active in fluorous solvents. Org. Biomol. Chem. 2 (2004) 524-527
64. Roach L.S., Song H., and Ismagilov R.F. Controlling nonspecific protein adsorption in a plug based microfluidic system by controlling interfacial chemistry using fluorous-phase surfactants. Anal. Chem. 77 (2005) 785-796 Provides evidence for interactions between fluorinated amphiphiles and proteins in a microfluidic plug
65. Holtze C., Rowat A.C., Agresti J.J., Hutchinson J.B., Angilè F.E., Schmitz C.H.J., Köster S., Duan H., Humphry K.J., Scanga R.A., et al. Biocompatible surfactants for water-in-fluorocarbon emulsions. Lab. Chip 8 (2008) 1632-1639 F-surfactant-stabilized water-in-FC emulsions for nanocompartmentation in microfluidics systems
66. Köster S., Angilè F.E., Duan H., Agresti J.J., Wintner A., Schmitz C., Rowat A.C., Merten C.A., Pisignano D., Griffiths A.D., et al. Drop-based microfluidic devices for encapsulation of single cells. Lab. Chip 8 (2008) 1110-1115
67. Chen D.L., and Ismagilov R.F. Microfluidic cartridges preloaded with nanoliter plugs of reagents: an alternative to 96-well plates for screening. Curr. Opin. Chem. Biol. 10 (2006) 226-231
68. Whitesides G.M. The origins and the future of microfluidics. Nature 442 (2006) 368-373
69. Song H., Chen D.L., and Ismagilov R.F. Reactions in droplets in microfluidic channels. Angew. Chem. Int. Ed. 45 (2006) 7336-7356
70. Gerber F., Krafft M.P., Waton G., and Vandamme T.F. Microbubbles with exceptionally long life - synergy between shell and internal phase components. New J. Chem. 30 (2006) 524-527
71. Gerber F., Waton G., Krafft M.P., and Vandamme T.F. Long-lived microbubbles for oxygen delivery. Artif. Cells Blood Subst. Immob. Biotechnol. 35 (2007) 119-124
72. Pasc-Banu A., Stan R., Blanzat M., Perez E., Rico-Lattes I., Lattes A., et al. Microstructures in aqueous solutions of hybrid fluorocarbon/hydrocarbon catanionic surfactants. Colloid Surf. A: Physicochem. Eng. Aspects 242 (2004) 195-201
73. Matsuoka K., Yoshimura T., Bong M., Honda C., and Endo K. Nanocage aggregates composed of bilayer sheets. Langmuir 24 (2008) 5676-5678
74. Garcia-Bernabé A., Krämer M., Olàh B., and Haag R. Syntheses and phase-transfer properties of dendritic nanocarriers that contain perfluorinated shell structures. Chem. Eur. J. 10 (2004) 2822-2830
75. Caminade A.-M., Turrin C.-O., Sutra P., and Majoral J.-P. Fluorinated dendrimers. Curr. Opin. Colloid Interf. Sci. 8 (2003) 282-295
76. Bertino-Ghera B., Perret F., Fenet B., and Parrot-Lopez H. Control of the regioselectivity for new fluorinated amphiphilic cyclodextrines: synthesis of di- and tetra(6-deoxy-6-alkylthio)- and 6-(perfluoroalkylpropanethio)-α-cyclodextrin derivatives. J. Org. Chem. 73 (2008) 7317-7326
77. Leroy J., and Bondon A. β-Fluorinated porphyrins and related compounds: an overview. Eur. J. Org. Chem. (2008) 417-433
78. Maaloum M., Muller P., and Krafft M.P. Monodisperse surface micelles of nonpolar amphiphiles in Langmuir monolayers. Angew. Chem. Int. Ed. 41 (2002) 4331-4334
79. Zhang G.-F., Marie P., Maaloum M., Muller P., Benoit N., and Krafft M.P. Occurrence, shape and dimensions of large surface hemimicelles made of semifluorinated alkanes. Elongated vs. circular hemimicelles. Pit- and tip-centered hemimicelles. J. Am. Chem. Soc. 127 (2005) 10412-10419
80. Mourran A., Tartsch B., Gallyamov M.O., Magonov S., Lambreva D., Ostrovskii B.I., et al. Self-assembly of the perfluoroalkyl-alkane F14H20 in ultrathin films. Langmuir 21 (2005) 2308-2316
81. Gonzàlez-Pérez A., Contal C., and Krafft M.P. Experimental evidence for a surface concentration-dependent mechanism of formation of hemimicelles in Langmuir monolayers of semi-fluorinated alkanes. Soft Matter 3 (2007) 191-193
82. Semenov A.N., Gonzàlez-Pérez A., Krafft M.P., and Legrand J.-F. Theory of surface micelles of semifluorinated alkanes. Langmuir 22 (2006) 8703-8717
83. Wang S., Lunn R., Krafft M.P., and Leblanc R.M. One and a half layers? Mixed Langmuir monolayer of 10,12-pentacosadiynoic acid and a semifluorinated tetracosane. Langmuir 16 (2000) 2882-2886
84. Schmutz M., Michels B., Marie P., and Krafft M.P. Fluorinated vesicles made from combinations of phospholipids and semi-fluorinated alkanes. Direct evidence of the location of the semifluorinated alkane in the bilayer. Langmuir 19 (2003) 4889-4894
85. Menz D.-H., and Dresp J.H. Biocompatibility of highly fluorinated liquids used in ophthalmologic surgery. In: Tressaud A., and Haufe G. (Eds). Advances in fluorine science: fluorine and health (2008), Elsevier 421-445 Chap. 10
86. Gerber F., Krafft M.P., Vandamme T.F., Goldmann M., and Fontaine P. Preventing crystallization of phospholipids in monolayers: a new approach to lung surfactant therapy. Angew. Chem. Int. Ed. 44 (2005) 2749-2752
87. Gerber F., Krafft M.P., Vandamme T.F., Goldmann M., and Fontaine P. Fluidization of a dipalmitoyl phosphatidylcholine monolayer by fluorocarbon gases: potential use in lung surfactant therapy. Biophys. J. 90 (2006) 3184-3192 A new approach to therapy of lung surfactant-related diseases
88. Gerber F., Vandamme T.F., and Krafft M.P. Impact of perfluorooctylethane on the formation of a semi-crystalline liquid condensed phase in a phospholipid monolayer and of perfluorooctyl bromide on the adsorption of albumin on such a monolayer. C. R. Acad. Sci. (Chimie) 12 (2009) 180-187
89. Gerber F., Krafft M.P., and Vandamme T.F. The detrimental effect of serum albumin on the re-spreading of a dipalmitoyl phosphatidylcholine Langmuir monolayer is counteracted by a fluorocarbon gas. Biochim. Biophys. Acta - Biomembranes 1768 (2007) 490-494
90. Murphy G.J., Reeves B.C., Rogers C.A., Rizvi S.I.A., Culliford L., and Angelini G.D. Increased mortality, postoperative morbidity, and cost after red blood cell transfusion in patients having cardiac surgery. Circulation 116 (2007) 2544-2552
91. Bateman S.T., Lacroix J., Boven K., Forbes P., Barton R., Thomas N.J., Jacobs B., Markovitz B., Goldstein B., Hanson J.H., et al. Anemia, blood loss, and blood transfusions in North American children in the intensive care unit. Am. J. Resp. Crit. Care Med. 178 (2008) 26-33
92. Marik P.E., and Corwin H.L. Efficacy of red blood cell transfusion in the critically ill: a systematic review of the literature. Crit. Care Med. 36 (2008) 2667-2674
93. Salim A., Hadjizacharia P., DuBose J., Brown C., Inaba K., Chan L., et al. Role of anemia in traumatic brain surgery. J. Am. Coll. Surg. 207 (2008) 398-406
94. Riess J.G. Injectable oxygen carriers (blood substitutes) - Raison d'être, chemistry, and some physiology. Chem. Rev. 101 (2001) 2797-2920
95. Riess J.G. Perfluorocarbon-based oxygen delivery. Artif. Cells, Blood Subst., Immob. Biotech. 34 (2006) 567-580
96. Sanchez-Dominguez M., Krafft M.P., Maillard E., Siegrist S., and Belcourt A. Prevention of adhesion and promotion of pseudoislets formation from a β-cell line by fluorocarbon emulsions. ChemBioChem 7 (2006) 1160-1163
97. Marie Bertilla S., Thomas J.-L., Marie P., and Krafft M.P. Co-surfactant effect of a semifluorinated alkane at a fluorocarbon/water interface. Impact on the stabilization of fluorocarbon-in-water emulsions. Langmuir 20 (2004) 3920-3924
98. Deschamps J., Gomes M.F.C., and Padua A.A.H. Solubility of oxygen, carbon dioxide and water in semifluorinated alkanes and in perfluorooctylbromide by molecular simulation. J. Fluorine Chem. 125 (2004) 409-413
99. Audonnet-Blaise S., Krafft M.P., Smani Y., Mertes P.-M., Marie P.-Y., Labrude P., et al. Resuscitation of severe but brief haemorrhagic shock with PFC in rabbits restores skeletal muscle oxygen delivery and does not alter skeletal muscle metabolism. Resuscitation 70 (2006) 124-132
100. Haiss F., Jolivet R., Wyss M.T., Reichold J., Scheffold F., Krafft M.P., et al. In vivo two-photon imaging after blood replacement by perfluorocarbon transfusion. J. Physiol. (2009) 10.1113/jphysiol.2009.169474
101. Broniatowski M., Suarez M.N., Vila Romeu N., and Dynarowicz-Latka P. Gramicidin a channel in a matrix from a semifluorinated surfactant monolayer. J. Phys. Chem. B 110 (2006) 19450-19455
102. Rossi S., Watton G., and Krafft M.P. Small phospholipid-coated gas bubbles can last longer than larger ones. ChemPhysChem 9 (2008) 1982-1985 A remarkable, dogma-breaking demonstration
103. Budisa N. Prolegoma to future experimental efforts on genetic code engineering by expanding its amino acid repertoire. Angew. Chem. Int. Ed. (2004) 43
104. Hendrickson T.L., de Crécy-Lagard V., and Schimmel P. Incorporation of nonnatural amino acids into proteins. Annu. Rev. Biochem. 73 (2004) 147-176
105. Zanda M. Trifluoromethyl group: an effective xenobiotic function for peptide backbone modification. New J. Chem. 28 (2004) 1401-1411
106. Hakelberg M., and Koksch B. Fluorine in peptides: coiled coil model systems as tools to evaluate the influence of fluorinated amino acids on structure and stability of peptides. Chimica Oggi 25 (2007) 48-53
107. Bilgiçer B., Fichera A., and Kumar K. A coiled coil with a fluorous core. J. Am. Chem. Soc. 123 (2001) 4393-4399
108. Thust S., and Koksch B. Discovery of carboxypeptidase Y as a catalyst for the incorporation of sterically demanding α-fluoroalkyl amino acids into peptides. Tet. Lett. 45 (2004) 1163-1165
109. Wang P., Tang Y., and Tirrell D.A. Incorporation of trifluoroisoleucine into proteins in vivo. J. Am. Chem. Soc. 125 (2003) 6900-6906
110. Bilgiçer B., and Kumar K. De novo design of defined helical bundles in membrane environments. Proceed. Nat. Acad. Sci. U. S. A. 101 (2004) 15324-15329
111. Jäckel C., Salwiczek M., and Koksch B. Fluorine in a native protein environment - how the spatial demand and polarity of fluoroalkyl groups affect protein folding. Angew. Chem. Int. Ed. 45 (2006) 4198-4203
112. Panchenko T., Zhu W.W., and Montclare J.K. Influence of global fluorination on chloramphenicol acetyltransferase activity and stability. Biotechnol. Bioeng. 94 (2006) 921-930
113. Montclare J.K., and Tirrell D.A. Evolving proteins of novel composition. Angew. Chem. Int. Ed. 45 (2006) 4518-4521
114. Voloshchuk N., Lee M.X., Zhu W.W., Tanrikulu I.C., and Montclare J.K. Fluorinate chloramphenicol acetyltransferase thermostability and activity: improved thermostability by a single-isoleucine mutant. Bioorg. Med. Chem. Lett. 17 (2007) 5907-5911
115. Koksch B., Dahl C., Radics G., Vocks A., Arnold K., Arnhold J., et al. Fluoro-modified chemotactic peptides: fMLF analogues. J. Peptide Sci. 10 (2004) 67-81
116. Tang Y., Ghirlanda G., Vaidehi N., Kua J., Mainz D.T., Goddard III W.A., et al. Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine. Biochemistry 40 (2001) 2790-2796
117. 5-phenylalanine mutations on the folding of a small protein. J. Am. Chem. Soc. 128 (2006) 15932-15933
118. 3 groups (6 hexafluoroleucines) on the structure, stability and dynamics of a 27 amino acid peptide
119. Son S., Tanrikulu I.C., and Tirrell D.A. Stabilization of bzip peptides through incorporation of fluorinated aliphatic residues. ChemBioChem 7 (2006) 1251-1257
120. Chiu H.-P., Suzuki Y., Gullickson D., Ahmad R., Kokona B., Fairman R., et al. Helix propensity of highly fluorinated amino acids. J. Am. Chem. Soc. 128 (2006) 15556-15557
121. 6, a 4-α-helix bundle protein with a fluorocarbon core. Biochemistry 47 (2008) 4484-4490
122. Montclare J.K., Son S., Clark G.A., Kumar K., and Tirell D.A. Biosynthesis and stability of coiled-coil peptides containing (2S,4R)-5,5,5-trifluoroleucine and (2S,4S)-5,5,5-trifluoroleucine. ChemBioChem 10 (2009) 84-86
123. Meng H., and Kumar K. Antimicrobial activity and protease stability of peptides containing fluorinated amino acids. J. Am. Chem. Soc. 129 (2007) 15615-15622 Substitution of leucine by hexafluoroleucine residues can significantly increase the antimicrobial potency of peptides and increase their resistance to protease degradation
124. Yoo T.H., Link A.J., and Tirell D.A. Evolution of a fluorinated green fluorescent protein. Proc. Natl. Acad. Sci. U. S. A. 104 (2007) 13887-13890 A directed evolution strategy restores protein structure and function that have been impaired by global replacement of leucine residues by trifluoroleucines
125. Naarmann N., Bilgiçer B., Meng H., Kumar K., and Steinem C. Fluorinated interfaces drive self-association of transmembrane α helices in lipid bilayers. Angew. Chem. Int. Ed. 45 (2006) 2588-2591 Fluorinated interfaces were more efficient than the natural ones at directing the association of peptides in phospholipid membranes
126. Zheng H., Comeforo K., and Gao J. Expanding the fluorous arsenal: tetrafluorinated phenylalanines for protein design. J. Am. Chem. Soc. 131 (2009) 18-19
127. Lai J.S., and Kool E.T. Selective pairing of polyfluorinated DNA bases. J. Am. Chem. Soc. 126 (2004) 3040-3041
128. Lai J.S., and Kool E.T. Fluorous base-pairing effects in a DNA polymerase active site. Chem. Europ. J. 11 (2005) 2966-2971
129. Zahn A., Brotschi C., and Leumann C.J. Pentafluorophenyl-phenyl interactions in biphenyl-DNA. Chem. Eur. J. 11 (2005) 2125-2129
130. Krafft M.P., and Riess J.G. Highly fluorinated amphiphiles and colloidal systems, and their applications in the biomedical field - a contribution. Biochimie 80 (1998) 489-514
131. Lehmler H.-J. Synthesis of environmentally relevant fluorinated surfactants - a review. Chemosphere 58 (2005) 1471-1496 Indispensable for F-chemists intending to investigate the issues related to the environmentally persistent industrial F-surfactants
132. Houde M., Martin J.W., Letcher R.J., Solomon K.R., and Muir D.C.G. Biological monitoring of polyfluoroalkyl substances. Environ. Sci. Technol. 40 (2006) 3463-3473 Compares contamination profiles among species and locations, evaluates bioaccumulation/biomagnification in humans and wildlife, discusses possible sources, and identifies knowledge gaps
133. Prevedouros K., Cousins I.T., Buck R.C., and Korzeniowski S.H. Sources, fate and transport of perfluorocarboxylates. Environ. Sci. Technol. 40 (2006) 32-44 Provides a detailed accounting of the sources, direct and indirect, transport and fate of perfluorocarboxylates released in the environment
134. Lau C., Anitole K., Hodes C., Lai D., Pfahles-Hutchens A., and Seed J. Perfluoroalkyl acids: a review of monitoring and toxicological findings. Toxicol. Sci. 99 (2007) 366-394 An exhaustive review of the toxicology, including developmental toxicity, immunotoxicity and hepatotoxicity, and modes of action of some industrial fluorosurfactants
135. Dinglasan M.J.A., Ye Y., Edwards E.A., and Mabury S.A. Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids. Environ. Sci. Technol. 38 (2004) 2857-2864
136. Lehmler H.J., Rao R., Nauduri D., Vargo J.D., and Parkin S. Synthesis and structure of environmentally relevant perfluorinated sulfonamides. J. Fluorine Chem. 128 (2007) 595-607
137. Powley C.R., George S.W., Ryan T.W., and Buck R.C. Matrix effect-free analytical methods for determination of perfluorinated carboxylic acids in environmental matrixes. Anal. Chem. 77 (2005) 6353-6358
138. Yamashita N., Kannan K., Taniyazu S., Horii Y., Petrick G., and Gamo T. A global survey of perfluorinated acids in oceans. Mar. Pollut. Bull. 51 (2005) 658-668
139. Miyake Y., Yamashita N., Rostkowski P., So M.K., Taniyasu S., Lam P.K.S., et al. Determination of trace levels of total fluorine in water using combustion ion chromatography for fluorine: a mass balance approach to determine individual perfluorinated chemicals in water. J. Chromatogr. A 1143 (2007) 98-104
140. van Leeuwen S.P.J., Kärrman A., van Bavel B., de Boer J., and Lindström G. Struggle for quality in determination of perfluorinated contaminants in environmental and human samples. Environ. Sci. Technol. 40 (2006) 7854-7860
141. Kubwabo C., Stewart B., Zhu J., and Marro L. Occurrence of perfluorosulfonates and other perfluorochemicals in dust from selected homes in the city of Ottawa, Canada. J. Environ. Monit. 7 (2005) 1074-1078
142. Schoeib M., Harner T., Wilford B.H., Jones K.C., and Zhu J. Perfluorinated sulfonamides in indoor and outdoor air and indoor dust: occurrence, partitioning, and human exposure. Environ. Sci. Technol. 39 (2005) 6599-6606
143. Barber J.L., Berger U., Chaemfa C., Huber S., Jahnke A., Temme C., et al. Analysis of per- and polyfluorinated alkyl substances in air samples from Northwest Europe. J. Environ. Monit. 9 (2007) 530-541
144. Young C.J., Furdui V.I., Franklin J., Koerner R.M., Muir D.C.G., and Mabury S.A. Perfluorinated acids in arctic snow: new evidence for atmospheric formation. Environ. Sci. Technol. 41 (2007) 3455-3461
145. Boulanger B., Vargo J., Schnoor J.L., and Hornbuckle K.C. Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product. Environ. Sci. Technol. 39 (2005) 5524-5530
146. Loganathan B.G., Sajwan K.S., Sinclair E., Kumar K.S., and Kannan K. Perfluoroalkyl sulfonates and perfluorocarboxylates in two wastewater treatment facilities in Kentucky and Georgia. Water Res. 41 (2007) 4611-4620
147. Saito N., Harada K., Inoue K., Sasaki K., Yoshinaga T., and Koizumi A. Perfluorooctanoate and perfluorooctane sulfonate concentrations in surface water in Japan. J. Occup. Health 46 (2004) 49-59
148. Skutlarek D., Exner M., and Färber H. Perfluorinated surfactants in surface and drinking waters. Environ. Sci. Pollut. Res. 13 (2006) 299-307
149. Emmett E.A., Shofer F.S., Zhang H., Freeman D., Desai C., and Shaw L.M. Community exposure to perfluorooctanoate: relationships between serum concentrations and exposure sources. J. Occup. Environ. Med. 48 (2006) 759-770
150. Tao L., Kannan K., Kajiwara N., Costa M.M., Fillmann G., Takahashi S., et al. Perfluorooctanesulfonate and related fluorochemicals in albatrosses, elephant seals, penguins, and polar skuas from the Southern Ocean. Environ. Sci. Technol. 40 (2006) 7642-7648
151. Sanderson H., Boudreau T.M., Mabury S.A., and Solomon K.R. Effects of perfluorooctane sulfonate and perfluorooctanoic acid on the zooplanktonic community. Ecotoxicol. Environ. Saf. 58 (2004) 68-76
152. Hanson M.L., Small J., Sibley P.K., Boudreau T.M., Brain R.A., Mabury S.A., et al. Microcosm evaluation of the fate, toxicity, and risk to aquatic macrophytes from perfluorooctanoic acid (PFOA). Arch. Environ. Contam. Toxicol. 49 (2005) 307-316
153. Falandysz J., Taniyasu S., Gulkowska A., Yamashita N., and Schulte-Oehlmann U. Is fish a major source of fluorinated surfactants and repellents in humans living on the Baltic coast? Environ. Sci. Technol. 40 (2006) 748-751
154. Sinclair E., Mayack D.T., Roblee K., Yamashita N., and Kannan K. Occurrence of perfluoroalkyl surfactants in water, fish, and birds from New York State. Arch. Environ. Contam. Toxicol. 50 (2006) 398-410
155. Furdui V.I., Stock N.L., Ellis D.A., Butt C.M., Whittle D.M., Crozier P.W., et al. Spatial distribution of perfluoroalkyl contaminants in lake trout from the Great Lakes. Environ. Sci. Technol. 41 (2007) 1554-1559
156. Calafat A.M., Needham L.L., Kuklenyik Z., Reidy J.A., Tully J.S., Aguilar-Villalobos M., et al. Perfluorinated chemicals in selected residents of the American continent. Chemosphere 63 (2006) 490-496
157. Fromme H., Midasch O., Twardella D., Angerer J., Boehmer S., and Liebl B. Occurrence of perfluorinated substances in an adult German population in southern Bavaria. Int. Arch. Occup. Environ. Health 80 (2007) 313-319
158. Ehresman D.J., Froehlich J.W., Olsen G.W., Chang S.-C., and Butenhoff J.L. Comparison of human whole blood, plasma, and serum matrices for the determination of perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA), and other fluorochemicals. Environ. Res. 103 (2007) 176-184
159. Calafat A.M., Wong L.-Y., Kuklenyik S., Reidy J.A., and Needham L.L. Polyfluoroalkyl chemicals in the U.S. population: data from the National Health and Nutrition Examination Survey (NHANES) 2003-2004 and comparisons with NHANES 1999-2000. Environ. Health Perspect. 115 (2007) 1596-1602 A study from the National Center for Environmental Health providing evidence for a reduction in serum concentration levels for PFOA and PFOS in the general US population between surveys performed in 1999-2000 and in 2003-2004
160. Olsen G.W., Mair D.C., Church T.C., Ellefson M.E., Reagen W.K., Boyd T.M., Herron R.M., Medhdizadehkashi Z., Nobiletti J.B., Rios J.A., et al. Decline in perfluorooctanesulfonate and other polyfluoroalkyl chemicals in American Red Cross adult blood donors, 2000-2006. Environ. Sci. Technol. 42 (2008) 4989-4995
161. So M.K., Namashita N., Taniyasu S., Jiang Q., Giesy J.P., Chen K., et al. Health risk in infants associated with exposure to perfluorinated compounds in human breast milk from Zhoushan, China. Environ. Sci. Technol. 40 (2006) 2924-2929
162. Kärrman A., Ericson I., van Bavel B., Darnerud P.O., Aune M., Glynn A., et al. Exposure of perfluorinated chemicals through lactation: levels of matched human milk and serum and a temporal trend, 1996-2004 in Sweden. Environ. Health Perspect. 115 (2007) 226-230
163. Washburn S.T., Bingman T.S., Braithwaite S.K., Buck R.C., Buxton L.W., Clewell H.J., et al. Exposure assessment and risk characterization for perfluorooctanoate in selected consumer articles. Environ. Sci. Technol. 39 (2005) 3904-3910
164. Tittlemier S.A., Pepper K., Seymour C., Moisey J., Bronson R., Cao X.-L., et al. Dietary exposure of Canadians to perfluorinated carboxylates and perfluorooctane sulfonate via consumption of meat, fish, fast foods, and food items prepared in their packaging. J. Agric. Food Chem. 55 (2007) 3203-3210
165. Ericson I., Marti-Cid R., Nadal M., Van Bavel B., Lindström G., and Domingo J.L. Human exposure to perfluorinated chemicals through the diet: intake of perfluorinated compounds in foods from the Catalan (Spain) market. J. Agric. Food Chem. 56 (2008) 1787-1794
166. Trudel D., Horowitz L., Wormuth M., Scheringer M., Cousins I.T., and Hungerbühler K. Estimating consumer exposure to PFOS and PFOA. Risk Anal. 28 (2008) 251-269
167. Davis K.L., Aucoin M.D., Larsen B.S., Kaiser M.A., and Hartten A.S. Transport of ammonium perfluorooctanoate in environmental media near a fluoropolymer manufacturing facility. Chemosphere 67 (2007) 2011-2019
168. 2OH: kinetics and mechanism of reaction with OH. Environ. Sci. Technol. 40 (2006) 1862-1868
169. Begley T.H., White K., Honigfort P., Twaroski M.L., Neches R.N., and Walker R.A. Perfluorochemicals: potential sources of and migration from food packaging. Food Add. Contam. A 22 (2005) 1023-1031
170. Olsen G.W., Burris J.M., Ehresman D.J., Froehlich J.W., Seacat A.M., Butenhoff J.L., et al. Half-life of serum elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers. Environ. Health Perspect. 115 (2007) 1298-1305
171. Kannan K., Tao L., Sinclair E., Pastva S.D., Jude D.J., and Giesy J.P. Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain. Arch. Environ. Contam. Toxicol. 48 (2005) 559-566
172. Houde M., Bujas T.A.D., Small J., Wells R.S., Fair P.A., Bossart G.D., et al. Biomagnification of perfluoroalkyl compounds in the bottlenose dolphin (Tursiops truncatus) food web. Environ. Sci. Technol. 40 (2006) 4138-4144
173. Morikawa A., Kamei N., Harada K., Inoue K., Yoshinaga T., Saito N., et al. The bioconcentration factor of perfluorooctane sulfonate is significantly larger than that of perfluorooctanoate in wild turtles (Trachemys scripta elegans and Chinemys reevesii): an Ai river ecological study in Japan. Ecotoxicol. Environ. Saf. 65 (2006) 14-21
174. Conder J.M., Hoke R.A., de Wolf W., Russell M.H., and Buck R.C. Are PFCAs bioaccumulative? A critical review and comparison with regulatory criteria and persistent lipophilic compounds. Environ. Sci. Technol. 42 (2008) 995-1003
175. Chang S.-C., Thibodeaux J.R., Eastvold M.L., Ehresman D.J., Bjork J.A., Froehlich J.W., et al. Thyroid hormone status and pituitary function in adult rats given oral doses of perfluorooctanesulfonate (PFOS). Toxicology 243 (2008) 330-339
176. Mulkiewicz E., Jastorff B., Skladanoski A.C., Kleszczynski K., and Stepnowski P. Evaluation of the acute toxicity of perfluorinated carboxylic acids using eukariotic cell lines, bacteria and enzymatic assays. Environ. Toxicol. Pharmacol. 23 (2007) 279-285
177. Han X., Kemper R.A., and Jepson G.W. Subcellular distribution and protein binding of perfluorooctanoic acid in rat liver and kidney. Drug Chem. Toxicol. 28 (2005) 197-209
178. Hundley S.G., Sarrif A.M., and Kennedy G.L. Absorption, distribution, and excretion of ammonium perfluorooctanoate (APFO) after oral administration to various species. Drug Chem. Toxicol. 29 (2006) 137-145
179. Apelberg B.L., Goldman L.R., Calafat A.M., Herbstman J.B., Kuklenyik Z., Heidler J., et al. Determinants of fetal exposure to polyfluoroalkyl compounds in Baltimore, Maryland. Environ. Sci. Technol. 41 (2007) 3891-3897
180. Midasch O., Drexler H., Hart N., and Beckmann M.W. Transplacental exposure of neonates to perfluorooctane sulfonate and perfluorooctanoate: a pilot study. Arch. Occup. Environ. Health 80 (2007) 643-648
181. Vanden Heuvel J.P., Thompson J.T., Frame S.R., and Gillies P.J. Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-α, -β, and -γ, liver X receptor-β, and retinoid X receptor-α. Toxicol. Sci. 92 (2006) 476-489
182. Martin M.T., Brennan R.J., Hu W., Ayanuglu E., Lau C., Ren H., et al. Toxicogenomic study of triazole fungicides and perfluoroalkyl acids in rat livers predicts toxicity and categorizes chemicals based on mechanisms of toxicity. Toxicol. Sci. 97 (2007) 595-613
183. Takacs M.L., and Abbott B.D. Activation of mouse and human peroxisome proliferator-activated receptors (α, β/δ, γ) by perfluorooctanoic acid and perfluorooctane sulfonate. Toxicol. Sci. 95 (2007) 108-117
184. DeWitt J.C., Shnyra A., Badr M.Z., Loveless S.E., Hoban D., Frame S.R., Cunard R., Anderson S.E., Meade B.J., Peden-Adams M.M., et al. Immunotoxicity of perfluorooctanoic acid and perfluorooctane sulfonate and the role of peroxisome proliferator-activated receptor alpha. Crit. Rev. Toxicol. 39 (2009) 76-94 A multiauthored review of research on immunomodulation by PFOS and PFOA
185. Xie W., Kania-Korwel I., Bummer P.M., and Lehmler H.-J. Effect of potassium perfluorooctanesulfonate, perfluorooctanoate and octanesulfonate on the phase transition of dipalmitoylphosphatidylcholine (DPPC) bilayers. Biochim. Biophys. Acta 1768 (2007) 1299-1308
186. Jensen A.A., and Leffers H. Emerging endocrine disrupters: perfluoroalkylated substances. Int. J. Andrology 31 (2008) 161-169
187. Lau C., Butenhoff J.L., and Rogers J.M. The developmental toxicity of perfluoroalkyl acids and their derivatives. Toxicol. Appl. Pharmacol. 198 (2004) 231-241
188. Bjork J.A., Lau C., Chang S.C., Butenhoff J.L., and Wallace K.B. Perfluorooctane sulfonate-induced changes in fetal rat liver gene expression. Toxicology 251 (2008) 8-20
189. Emmett E.A., Zhang H., Shofer F.S., Freeman D., Rodway N.V., Desai C., et al. Community exposure to perfluorooctanoate: relationships between serum concentrations and certain health parameters. J. Occup. Environ. Med. 48 (2006) 771-779
190. Lampert D.J., Frisch M.A., and Speitel G.E. Removal of perfluorooctanoic acid and perfluorooctane sulfonate from wastewater by ion exchange. Pract. Periodical Haz. Toxic Radioact. Waste Mgmt. 11 (2007) 60-68