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The Aminosterol Antibiotic Squalamine Permeabilizes Large Unilamellar Phospholipid Vesicles.

B. Selinsky, Z. Zhou, K. G. Fojtik, S. Jones, N. Dollahon, A. Shinnar
Published 1998 · Chemistry, Medicine

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The ability of the shark antimicrobial aminosterol squalamine to induce the leakage of polar fluorescent dyes from large unilamellar phospholipid vesicles (LUVs) has been measured. Micromolar squalamine causes leakage of carboxyfluorescein (CF) from vesicles prepared from the anionic phospholipids phosphatidylglycerol (PG), phosphatidylserine (PS), and cardiolipin. Binding analyses based on the leakage data show that squalamine has its highest affinity to phosphatidylglycerol membranes, followed by phosphatidylserine and cardiolipin membranes. Squalamine will also induce the leakage of CF from phosphatidylcholine (PC) LUVs at low phospholipid concentrations. At high phospholipid concentrations, the leakage of CF from PC LUVs deviates from a simple dose-response relationship, and it appears that some of the squalamine can no longer cause leakage. Fluorescent dye leakage generated by squalamine is graded, suggesting the formation of a discrete membrane pore rather than a generalized disruption of vesicular membranes. By using fluorescently labeled dextrans of different molecular weight, material with molecular weight /=10,000 is retained. Negative stain electron microscopy of squalamine-treated LUVs shows that squalamine decreases the average vesicular size in a concentration-dependent manner. Squalamine decreases the size of vesicles containing anionic phospholipid at a lower squalamine/lipid molar ratio than pure PC LUVs. In a centrifugation assay, squalamine solubilizes phospholipid, but only at significantly higher squalamine/phospholipid ratios than required for either dye leakage or vesicle size reduction. Squalamine solubilizes PC at lower squalamine/phospholipid ratios than PG. We suggest that squalamine complexes with phospholipid to form a discrete structure within the bilayers of LUVs, resulting in the transient leakage of small encapsulated molecules. At higher squalamine/phospholipid ratios, these structures release from the bilayers and aggregate to form either new vesicles or squalamine/phospholipid mixed micelles.
This paper references
10.1016/0005-2736(91)90295-J
Small-volume extrusion apparatus for preparation of large, unilamellar vesicles.
R. Macdonald (1991)
10.1021/BI00019A033
Translocation of a channel-forming antimicrobial peptide, magainin 2, across lipid bilayers by forming a pore.
K. Matsuzaki (1995)
10.1016/0076-6879(79)56066-2
[63] Properties of detergents
A. Helenius (1979)
10.1016/S0006-3495(95)80066-4
Leakage of membrane vesicle contents: determination of mechanism using fluorescence requenching.
A. S. Ladokhin (1995)
10.1016/0092-8674(91)90154-Q
Antibacterial peptides: Key components needed in immunity
H. G. Boman (1991)
10.1016/0005-2736(89)90090-4
Magainin 1-induced leakage of entrapped calcein out of negatively-charged lipid vesicles.
K. Matsuzaki (1989)
10.1021/BI00262A010
Solubilization of phosphatidylcholine bilayers by octyl glucoside.
M. Jackson (1982)
10.1021/JA961269E
A SYNTHETIC IONOPHORE THAT RECOGNIZES NEGATIVELY CHARGED PHOSPHOLIPID MEMBRANES
G. Deng (1996)
10.1021/BI00366A042
Structural changes in membranes of large unilamellar vesicles after binding of sodium cholate.
R. Schubert (1986)
10.1016/0040-4039(94)88254-1
Synthesis of squalamine. A steroidal antibiotic from the shark
R. Moriarty (1994)
10.1016/s0021-9258(18)70226-3
Phosphorus assay in column chromatography.
G. R. Bartlett (1959)
10.1016/0005-2736(87)90383-X
The influence of membrane composition on the solubilizing effects of Triton X-100.
M. Urbaneja (1987)
10.1016/0005-2736(91)90366-G
Physicochemical determinants for the interactions of magainins 1 and 2 with acidic lipid bilayers.
K. Matsuzaki (1991)
10.1016/S0006-3495(97)78822-2
Sizing membrane pores in lipid vesicles by leakage of co-encapsulated markers: pore formation by melittin.
A. S. Ladokhin (1997)
10.1002/PRO.5560030902
Interactions between human defensins and lipid bilayers: Evidence for formation of multimeric pores
W. Wimley (1994)
10.1021/JA00055A047
Control over vesicle rupture and leakage by membrane packing and by the aggregation state of an attacking surfactant
Y. Liu (1993)
10.1016/0304-4157(83)90004-7
Solubilization of phospholipids by detergents. Structural and kinetic aspects.
D. Lichtenberg (1983)
10.1021/BI960016V
An antimicrobial peptide, magainin 2, induced rapid flip-flop of phospholipids coupled with pore formation and peptide translocation.
K. Matsuzaki (1996)
10.1016/0005-2736(90)90366-V
Interaction of calcium and cholesterol sulphate induces membrane destabilization and fusion: implications for the acrosome reaction.
J. Cheetham (1990)
10.1111/J.1432-1033.1986.TB10088.X
The interaction of phosphatidylcholine bilayers with Triton X-100.
F. Goñi (1986)
10.1021/BI00177A027
Orientational and aggregational states of magainin 2 in phospholipid bilayers.
K. Matsuzaki (1994)
10.1021/BI00156A008
Mechanism of magainin 2a induced permeabilization of phospholipid vesicles.
E. Grant (1992)
10.1016/0005-2736(88)90234-9
Surfactant-induced release of liposomal contents. A survey of methods and results.
J. Ruíz (1988)
10.1021/BI00408A006
Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (prepared by reverse-phase evaporation) by triton X-100, octyl glucoside, and sodium cholate.
M. Paternostre (1988)
10.1021/BI00357A048
Kinetic and structural aspects of reconstitution of phosphatidylcholine vesicles by dilution of phosphatidylcholine-sodium cholate mixed micelles.
S. Almog (1986)
10.1021/BI00071A011
Electric potentiation, cooperativity, and synergism of magainin peptides in protein-free liposomes.
A. Vaz Gomes (1993)
Micelles: Theoretical and Applied Aspects
Y. Moroi (1992)
10.1085/JGP.74.5.583
Influence of molecular configuration on the passage of macromolecules across the glomerular capillary wall
M. Bohrer (1979)
10.1016/0039-128X(94)90005-1
2′(3α-Benzyloxy-24-norcholan-23-yl)-2′,4′4′-trimethyl-4′,5′-dihydrooxazoline-N-oxyl as a potential spin probe for model membranes
Sharmila Banerjee (1994)
10.1016/0952-7915(92)90115-U
Antibiotic peptides as mediators of innate immunity.
M. Zasloff (1992)
10.1021/J100881A041
Solubilization of a Water-Insoluble Dye as a Method for Determining Micellar Molecular Weights
H. Schott (1966)
10.1016/0005-2736(92)90299-2
Kinetics of melittin induced pore formation in the membrane of lipid vesicles.
G. Schwarz (1992)



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10.1038/s41467-018-07699-5
Trodusquemine enhances Aβ42 aggregation but suppresses its toxicity by displacing oligomers from cell membranes
Ryan Limbocker (2019)
10.1016/S0960-894X(00)00196-7
Squalamine analogues as potential anti-trypanosomal and anti-leishmanial compounds.
S. Khabnadideh (2000)
10.1016/J.BBAMEM.2004.09.002
Membrane-permeabilizing activities of amphidinol 3, polyene-polyhydroxy antifungal from a marine dinoflagellate.
Toshihiro Houdai (2004)
10.1080/10837450802471180
Transdermal drug delivery enhanced by low voltage electropulsation (LVE)
S. Sammeta (2009)
10.1517/13543784.7.10.1629
Anti-angiogenic therapies in cancer clinical trials.
H. Zhang (1998)
10.1073/pnas.1620159114
Modulating membrane binding of α-synuclein as a therapeutic strategy
André Pineda (2017)
10.1201/B14723-13
Structural Characteristics of Bioactive Marine Natural Products
Snezana Agatonovic-Kustrin (2013)
10.1016/j.bmcl.2013.03.094
Structure-activity relationships in aminosterol antibiotics: the effect of stereochemistry at the 7-OH group.
Tsemre-Dingel Tessema (2013)
10.1016/j.chemphyslip.2009.10.006
Biophysical studies of the interaction of squalamine and other cationic amphiphilic molecules with bacterial and eukaryotic membranes: importance of the distribution coefficient in membrane selectivity.
E. Di Pasquale (2010)
10.1046/j.1365-2141.2000.01864.x
Current Status Of Antiangiogenic Factors
K. Talks (2000)
10.1271/bbb.64.985
Design of a Novel Membrane-Destabilizing Peptide Selectively Acting on Acidic Liposomes
S. Machida (2000)
10.1517/13543784.9.2.263
Cholic acid derivatives: novel antimicrobials
P. Savage (2000)
10.1194/jlr.M700294-JLR200
Identification of squalamine in the plasma membrane of white blood cells in the sea lamprey, Petromyzon marinus Published, JLR Papers in Press, August 28, 2007.
Sang-Seon Yun (2007)
STMULATION AND ENHANCEMENT OF REGENERATION OF TISSUES
(2017)
10.1016/S0039-128X(01)00161-1
The synthesis of spermine analogs of the shark aminosterol squalamine
Youheng Shu (2002)
10.1371/journal.pone.0002765
Squalamine: An Appropriate Strategy against the Emergence of Multidrug Resistant Gram-Negative Bacteria?
C. Salmi (2008)
10.15761/nfo.1000219
Squalamine and age-related macular degeneration. Did the Shark lose its teeth?
Ayseguel Tura (2018)
10.1016/j.bmc.2015.10.034
Helical peptide-polyamine and -polyether conjugates as synthetic ionophores.
M. Benincasa (2015)
10.1517/13543784.16.8.1143
Therapeutic potential of cationic steroid antibacterials
C. Salmi (2007)
10.1073/pnas.1108558108
Squalamine as a broad-spectrum systemic antiviral agent with therapeutic potential
M. Zasloff (2011)
10.1016/S0005-2736(99)00256-4
Squalamine is not a proton ionophore.
B. Selinsky (2000)
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