Squalamine is not a proton ionophore

Biochimica et Biophysica Acta - Biomembranes

Volumn 1464, Issue 1, 2000, Pages 135-141

  Selinsky, Barry S ^a   Smith, Rob ^a   Frangiosi, Andrea ^a   Vonbaur, Beth ^a   Pedersen, Larry ^b  

^a VILLANOVA UNIVERSITY   (United States)

^b University of New York   (United States)

Author keywords

Aminosterol; Antimicrobial agent; Proton ionophore; Squalamine

Indexed keywords

ANTIINFECTIVE AGENT; IONOPHORE; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLGLYCEROL; SQUALAMINE; STEROL DERIVATIVE;

ANTIMICROBIAL ACTIVITY; ARTICLE; PHOSPHOLIPID VESICLE; PRIORITY JOURNAL; PROTON TRANSPORT;

ANIMALS; ANTI-BACTERIAL AGENTS; CHOLESTANOLS; DOGFISH; FLUORESCEINS; FLUORESCENT DYES; HYDROGEN-ION CONCENTRATION; IONOPHORES; LIPOSOMES; PERMEABILITY; PROTONS;

CHONDRICHTHYES; SQUALIDAE; SQUALUS ACANTHIAS;

EID: 0033954397     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0005-2736(99)00256-4     Document Type: Article

References (15)

1. Moore K.S., Wehrli S., Roder H., Rogers M., Forrest J.N. Jr., McCrimmon D., Zasloff M. Squalamine: an aminosterol antibiotic from the shark. Proc. Natl. Acad. Sci. USA. 90:1993;1354-1358.
2. Wehrli S.L., Moore K.S., Roder H., Durell S., Zasloff M. Structure of the novel steroidal antibiotic squalamine determined by two-dimensional NMR spectroscopy. Steroids. 58:1993;370-377.
3. Moriarity R.M., Tuladhar S.M., Gao L., Wehrli S. Synthesis of squalamine, a steroidal antibiotic from the shark. Tetrahedron Lett. 35:1994;8103-8106.
4. Pechulis A.D., Bellevue III F.H., Cioffi C.L., Trapp S.G., Fotjik J.P., McKitty A.A., Kinney W.A., Frye L.L. Total synthesis of squalamine, an anti-infective steroidal polyamine. J. Org. Chem. 60:1995;5121-5126.
5. Sills A.K. Jr., Williams J.I., Tyler B.M., Epstein D.S., Sipos E.P., Davis J.D., McLane M.P., Pitchford S., Cheshire K., Gannon F.H., Kinney W.A., Chao T.L., Donowitz M., Laterra J., Zasloff M., Brem H. Squalamine inhibits angiogenesis and solid tumor growth in vivo and perturbs embryonic vasculature. Cancer Res. 58:1998;2784-2792.
6. Jones S.R., Kinney W.A., Zhang X., Jones L.M., Selinsky B.S. The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6β-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid. Steroids. 61:1996;565-571.
7. Jones S.R. The synthesis and characterization of antibiotic analogs of squalamine. Biophys. J. 68:1995;A99.
8. Sadownik A., Deng G., Janout V., Regen S.L., Bernard E.M., Kikuchi K., Armstrong D. Rapid construction of a squalamine mimic. J. Am. Chem. Soc. 117:1995;6138-6139.
9. Kikuchi K., Bernard E.M., Sadownik A., Regen S.L., Armstrong D. Antimicrobial activities of squalamine mimics. Antimicrob. Agents Chemother. 41:1997;1433-1438.
10. Selinsky B.S., Zhou Z., Fotjik K.G., Jones S.R., Dollahon N.R., Shinnar A.E. The aminosterol antibiotic squalamine permeabilizes large unilamellar vesicles. Biochim. Biophys. Acta. 1370:1998;218-234.
11. Deng G., Dewa T., Regen S.L. A synthetic ionophore that recognizes negatively charged phospholipid membranes. J. Am. Chem. Soc. 118:1996;8975-8976.
12. P.I. Lelkes, Methodological aspects dealing with stability measurements of liposomes in vitro using the carboxyfluorescein assay, in: G. Gregoriadis (Ed.), Liposome Technology, vol. III: Targeted Drug Delivery and Biological Interaction, CRC Press, Boca Raton, FL, 1984, pp. 225-246.
13. MacDonald R.C., MacDonald R.I., Menco B.Ph.M., Takeshita K., Subbarao N.K., Hu L.-R. Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim. Biophys. Acta. 1061:1991;297-303.
14. Daleke D.L., Hong K., Papahadjopoulos D. Endocytosis of liposomes by macrophages: binding, acidification and leakage of liposomes monitored by a new fluorescence assay. Biochim. Biophys. Acta. 1024:1990;352-366.
15. Komatsu H., Chong P.L.-G. Low permeability of liposomal membranes composed of bipolar tetraether lipids from thermoacidophilic archaebacterium Sulfolobus acidocaldarius. Biochemistry. 37:1998;107-115.