메뉴 건너뛰기




Volumn 73, Issue 1, 2009, Pages 65-74

Hydrophobic tail length, degree of fluorination and headgroup stereochemistry are determinants of the biocompatibility of (fluorinated) carbohydrate surfactants

Author keywords

Cytotoxicity; DPPC; Fluorescence anisotropy; Haemolytic activity; Surfactant lipid interactions

Indexed keywords

BIOMEDICAL APPLICATIONS; CUT-OFF; DPPC; FLUORESCENCE ANISOTROPY; GALACTOPYRANOSIDE; GLUCOPYRANOSIDE; HAEMOLYTIC ACTIVITY; HEAD GROUPS; HYDROPHOBIC TAILS; MODEL MEMBRANES; OH GROUP; PARTITION COEFFICIENT; PHASE BEHAVIOUR; STEADY-STATE FLUORESCENCE; STRUCTURAL DETERMINANTS; SURFACTANT-LIPID INTERACTIONS; TAIL LENGTH;

EID: 67650397831     PISSN: 09277765     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2009.04.023     Document Type: Article
Times cited : (47)

References (35)
  • 1
    • 0037452442 scopus 로고    scopus 로고
    • The usefulness of sugar surfactants as solubilizing agents in parenteral formulations
    • Söderlind E., Wollbratt M., and von Corswant C. The usefulness of sugar surfactants as solubilizing agents in parenteral formulations. Int. J. Pharm. 252 (2003) 61-71
    • (2003) Int. J. Pharm. , vol.252 , pp. 61-71
    • Söderlind, E.1    Wollbratt, M.2    von Corswant, C.3
  • 2
    • 33644822618 scopus 로고    scopus 로고
    • Haemolytic activity of maltopyranoside surfactants
    • Söderlind E., and Karlsson L. Haemolytic activity of maltopyranoside surfactants. Eur. J. Pharm. Biopharm. 62 (2006) 254-259
    • (2006) Eur. J. Pharm. Biopharm. , vol.62 , pp. 254-259
    • Söderlind, E.1    Karlsson, L.2
  • 3
    • 0032658367 scopus 로고    scopus 로고
    • Fluorocarbons and fluorosurfactants for in vivo oxygen transport (blood substitutes), imaging, and drug delivery
    • Riess J.G., and Krafft M.P. Fluorocarbons and fluorosurfactants for in vivo oxygen transport (blood substitutes), imaging, and drug delivery. MRS Bull. 24 (1999) 42-48
    • (1999) MRS Bull. , vol.24 , pp. 42-48
    • Riess, J.G.1    Krafft, M.P.2
  • 4
    • 34248634294 scopus 로고    scopus 로고
    • Perfluorocarbon compounds as vehicles for pulmonary drug delivery
    • Lehmler H.-J. Perfluorocarbon compounds as vehicles for pulmonary drug delivery. Expert Opin. Drug Deliv. 4 (2007) 247-262
    • (2007) Expert Opin. Drug Deliv. , vol.4 , pp. 247-262
    • Lehmler, H.-J.1
  • 5
    • 0002560983 scopus 로고    scopus 로고
    • Liquid ventilation-a new way to deliver drugs to diseased lungs?
    • Lehmler H.-J., Bummer P.M., and Jay M. Liquid ventilation-a new way to deliver drugs to diseased lungs?. Chemtech 29 (1999) 7-12
    • (1999) Chemtech , vol.29 , pp. 7-12
    • Lehmler, H.-J.1    Bummer, P.M.2    Jay, M.3
  • 7
    • 0842265481 scopus 로고    scopus 로고
    • Liquid ventilation: an adjunct for respiratory management
    • Wolfson M.R., and Shaffer T.H. Liquid ventilation: an adjunct for respiratory management. Paediatr. Anaesth. 14 (2004) 15-23
    • (2004) Paediatr. Anaesth. , vol.14 , pp. 15-23
    • Wolfson, M.R.1    Shaffer, T.H.2
  • 8
    • 0022922539 scopus 로고
    • Permeability alterations and antihemolysis induced by amphiphiles in human erythrocytes
    • Isomaa B., Haegerstrand H., Paatero G., and Engblom A.C. Permeability alterations and antihemolysis induced by amphiphiles in human erythrocytes. Biochim. Biophys. Acta 860 (1986) 510-524
    • (1986) Biochim. Biophys. Acta , vol.860 , pp. 510-524
    • Isomaa, B.1    Haegerstrand, H.2    Paatero, G.3    Engblom, A.C.4
  • 9
    • 0023277777 scopus 로고
    • Shape transformations induced by amphiphiles in erythrocytes
    • Isomaa B., Haegerstrand H., and Paatero G. Shape transformations induced by amphiphiles in erythrocytes. Biochim. Biophys. Acta 899 (1987) 93-103
    • (1987) Biochim. Biophys. Acta , vol.899 , pp. 93-103
    • Isomaa, B.1    Haegerstrand, H.2    Paatero, G.3
  • 10
    • 0000075260 scopus 로고
    • Synthesis of f-alkylated glycosides as surfactants for in vivo uses. Effects of the length of the hydrocarbonated spacer in the aglycone on königs-knorr reaction, surface activity and biological properties
    • Milius A., Greiner J., and Riess J.G. Synthesis of f-alkylated glycosides as surfactants for in vivo uses. Effects of the length of the hydrocarbonated spacer in the aglycone on königs-knorr reaction, surface activity and biological properties. New J. Chem. 15 (1991) 337-344
    • (1991) New J. Chem. , vol.15 , pp. 337-344
    • Milius, A.1    Greiner, J.2    Riess, J.G.3
  • 11
    • 0343782059 scopus 로고
    • Perfluoroalkylated monoesters of 1,4-d-sorbitan, isosorbide, and isomannide: new surfactants for biomedical applications
    • Zarif L., Greiner J., and Riess J.G. Perfluoroalkylated monoesters of 1,4-d-sorbitan, isosorbide, and isomannide: new surfactants for biomedical applications. J. Fluorine Chem. 44 (1989) 73-85
    • (1989) J. Fluorine Chem. , vol.44 , pp. 73-85
    • Zarif, L.1    Greiner, J.2    Riess, J.G.3
  • 12
    • 0025232483 scopus 로고
    • Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses
    • Zarif L., Greiner J., Pace S., and Riess J.G. Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses. J. Med. Chem. 33 (1990) 1262-1269
    • (1990) J. Med. Chem. , vol.33 , pp. 1262-1269
    • Zarif, L.1    Greiner, J.2    Pace, S.3    Riess, J.G.4
  • 14
    • 23944441707 scopus 로고    scopus 로고
    • Cellular uptake and saccharide chain elongation of "fluoro-amphiphilic" glycosides
    • Kasuya M.C.Z., Ito A., Cusi R., Sato T., and Hatanaka K. Cellular uptake and saccharide chain elongation of "fluoro-amphiphilic" glycosides. Chem. Lett. 34 (2005) 856-857
    • (2005) Chem. Lett. , vol.34 , pp. 856-857
    • Kasuya, M.C.Z.1    Ito, A.2    Cusi, R.3    Sato, T.4    Hatanaka, K.5
  • 16
    • 33845738351 scopus 로고    scopus 로고
    • Effects of nonionic sugar surfactants on the phase transition of dppc membranes
    • Rozycka-Roszak B., Jurczak B., and Wilk K.A. Effects of nonionic sugar surfactants on the phase transition of dppc membranes. Thermochim. Acta 453 (2007) 27-30
    • (2007) Thermochim. Acta , vol.453 , pp. 27-30
    • Rozycka-Roszak, B.1    Jurczak, B.2    Wilk, K.A.3
  • 17
    • 0030581202 scopus 로고    scopus 로고
    • Cut-off effects in biological activities of surfactants
    • Balgavy P., and Devinsky F. Cut-off effects in biological activities of surfactants. Adv. Colloid Interf. Sci. 66 (1996) 23-63
    • (1996) Adv. Colloid Interf. Sci. , vol.66 , pp. 23-63
    • Balgavy, P.1    Devinsky, F.2
  • 18
    • 2942522715 scopus 로고    scopus 로고
    • New platinum(iv) complex with adamantylamine ligand as a promising anti-cancer drug: comparison of in vitro cytotoxic potential towards a2780/cisr cisplatin-resistant cell line within homologous series of platinum(iv) complexes
    • Turanek J., Kasna A., Zaluska D., Neca J., Kvardova V., Knotigova P., Horvath V., Sindlerova L., Kozubik A., Sova P., Kroutil A., Zak F., and Mistr A. New platinum(iv) complex with adamantylamine ligand as a promising anti-cancer drug: comparison of in vitro cytotoxic potential towards a2780/cisr cisplatin-resistant cell line within homologous series of platinum(iv) complexes. Anti-Cancer Drugs 15 (2004) 537-543
    • (2004) Anti-Cancer Drugs , vol.15 , pp. 537-543
    • Turanek, J.1    Kasna, A.2    Zaluska, D.3    Neca, J.4    Kvardova, V.5    Knotigova, P.6    Horvath, V.7    Sindlerova, L.8    Kozubik, A.9    Sova, P.10    Kroutil, A.11    Zak, F.12    Mistr, A.13
  • 20
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays
    • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 21
    • 17944393947 scopus 로고
    • Measurement of cellular activity by means of the mtt color test. Optimization of the method
    • Bank U., Reinhold D., and Ansorge S. Measurement of cellular activity by means of the mtt color test. Optimization of the method. Allerg. Immunol. 37 (1991) 119-123
    • (1991) Allerg. Immunol. , vol.37 , pp. 119-123
    • Bank, U.1    Reinhold, D.2    Ansorge, S.3
  • 22
    • 34047249045 scopus 로고    scopus 로고
    • Effect of potassium perfluorooctanesulfonate, perfluorooctanoate and octanesulfonate on the phase transition of dipalmitoylphosphatidylcholine (dppc) bilayers
    • 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
    • (2007) Biochim. Biophys. Acta , vol.1768 , pp. 1299-1308
    • Xie, W.1    Kania-Korwel, I.2    Bummer, P.M.3    Lehmler, H.-J.4
  • 23
    • 0023709975 scopus 로고
    • Effect of sodium octanoate and sodium perfluorooctanoate on gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine vesicle membrane
    • Inoue T., Iwanaga T., Fukushima K., and Shimozawa R. Effect of sodium octanoate and sodium perfluorooctanoate on gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine vesicle membrane. Chem. Phys. Lipids 46 (1988) 25-30
    • (1988) Chem. Phys. Lipids , vol.46 , pp. 25-30
    • Inoue, T.1    Iwanaga, T.2    Fukushima, K.3    Shimozawa, R.4
  • 24
    • 0027375156 scopus 로고
    • The use of differential scanning calorimetry as a tool to characterize liposome preparations
    • Biltonen R.L., and Lichtenberg D. The use of differential scanning calorimetry as a tool to characterize liposome preparations. Chem. Phys. Lipids 64 (1993) 129-142
    • (1993) Chem. Phys. Lipids , vol.64 , pp. 129-142
    • Biltonen, R.L.1    Lichtenberg, D.2
  • 26
    • 33646020106 scopus 로고    scopus 로고
    • Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization
    • Ladmiral V., Mantovani G., Clarkson G.J., Cauet S., Irwin J.L., and Haddleton D.M. Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization. J. Am. Chem. Soc. 128 (2006) 4823-4830
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4823-4830
    • Ladmiral, V.1    Mantovani, G.2    Clarkson, G.J.3    Cauet, S.4    Irwin, J.L.5    Haddleton, D.M.6
  • 27
    • 0347683375 scopus 로고    scopus 로고
    • Thermotropic and lyotropic properties of long chain alkyl glycopyranosides part iii: Ph-sensitive headgroups
    • Milkereit G., Morr M., Thiem J., and Vill V. Thermotropic and lyotropic properties of long chain alkyl glycopyranosides part iii: Ph-sensitive headgroups. Chem. Phys. Lipids 127 (2004) 47-63
    • (2004) Chem. Phys. Lipids , vol.127 , pp. 47-63
    • Milkereit, G.1    Morr, M.2    Thiem, J.3    Vill, V.4
  • 28
    • 0033991513 scopus 로고    scopus 로고
    • Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part I: monosaccharide headgroups
    • Vill V., von Minden H.M., Koch M.H.J., Seydel U., and Brandenburg K. Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part I: monosaccharide headgroups. Chem. Phys. Lipids 104 (2000) 75-91
    • (2000) Chem. Phys. Lipids , vol.104 , pp. 75-91
    • Vill, V.1    von Minden, H.M.2    Koch, M.H.J.3    Seydel, U.4    Brandenburg, K.5
  • 30
    • 33747881291 scopus 로고    scopus 로고
    • How fatty acids of different chain length enter and leave cells by free diffusion, Prostaglandins Leukot
    • Kamp F., and Hamilton J.A. How fatty acids of different chain length enter and leave cells by free diffusion, Prostaglandins Leukot. Essent. Fatty Acids 75 (2006) 149-159
    • (2006) Essent. Fatty Acids , vol.75 , pp. 149-159
    • Kamp, F.1    Hamilton, J.A.2
  • 31
    • 33745254719 scopus 로고    scopus 로고
    • Fas/cd95 death receptor and lipid rafts: new targets for apoptosis-directed cancer therapy
    • Mollinedo F., and Gajate C. Fas/cd95 death receptor and lipid rafts: new targets for apoptosis-directed cancer therapy. Drug Resistance Updates 9 (2006) 51-73
    • (2006) Drug Resistance Updates , vol.9 , pp. 51-73
    • Mollinedo, F.1    Gajate, C.2
  • 32
    • 0026670315 scopus 로고
    • Morphological characterization of exovesicles and endovesicles released from human erythrocytes following treatment with amphiphiles
    • Haegerstrand H., and Isomaa B. Morphological characterization of exovesicles and endovesicles released from human erythrocytes following treatment with amphiphiles. Biochim. Biophys. Acta 1109 (1992) 117-126
    • (1992) Biochim. Biophys. Acta , vol.1109 , pp. 117-126
    • Haegerstrand, H.1    Isomaa, B.2
  • 33
    • 33644822618 scopus 로고    scopus 로고
    • Haemolytic activity of maltopyranoside surfactants
    • Soederlind E., and Karlsson L. Haemolytic activity of maltopyranoside surfactants. Eur. J. Pharm. Biopharm. 62 (2006) 254-259
    • (2006) Eur. J. Pharm. Biopharm. , vol.62 , pp. 254-259
    • Soederlind, E.1    Karlsson, L.2
  • 34
    • 0343346352 scopus 로고
    • Perfluoroalkylated fatty acid monoesters of trehalose and sucrose for biomedical applications: remarkable emulsifying properties of 6-0-[3'-(perfluorooctyl)propanoyl]trehalose
    • Abouhilale S., Greiner J., and Riess J.G. Perfluoroalkylated fatty acid monoesters of trehalose and sucrose for biomedical applications: remarkable emulsifying properties of 6-0-[3'-(perfluorooctyl)propanoyl]trehalose. J. Am. Oil Chem. Soc. 69 (1992) 1-8
    • (1992) J. Am. Oil Chem. Soc. , vol.69 , pp. 1-8
    • Abouhilale, S.1    Greiner, J.2    Riess, J.G.3
  • 35
    • 0026084947 scopus 로고
    • Effects of small organic molecules on phospholipid phase transitions
    • Lohner K. Effects of small organic molecules on phospholipid phase transitions. Chem. Phys. Lipids 57 (1991) 341-362
    • (1991) Chem. Phys. Lipids , vol.57 , pp. 341-362
    • Lohner, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.