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Direct and Stereospecific Interaction of Amphidinol 3 with Sterol in Lipid Bilayers

https://doi.org/10.1021/bi5002932
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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1016/0040-4039(95)01259-kopenalex-snapshot
Isolation and chemical structure of amphidinol 2, a potent hemolytic compound from marine dinoflagellate Amphidinium klebsii
inferredcites →https://doi.org/10.1016/j.bbamem.2005.03.003openalex-snapshot
Detergent-like properties of magainin antibiotic peptides: A 31P solid-state NMR spectroscopy study
inferredcites →https://doi.org/10.1016/j.bbamem.2008.05.004openalex-snapshot
Comparative calorimetric and spectroscopic studies of the effects of cholesterol and epicholesterol on the thermotropic phase behaviour of dipalmitoylphosphatidylcholine bilayer membranes
inferredcites →https://doi.org/10.1016/j.bbamem.2008.08.022openalex-snapshot
Ordering effects of cholesterol and its analogues
inferredcites →https://doi.org/10.1016/j.bmc.2006.06.012openalex-snapshot
Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities
inferredcites →https://doi.org/10.1016/j.bmc.2007.12.029openalex-snapshot
Effects of lipid constituents on membrane-permeabilizing activity of amphidinols
inferredcites →https://doi.org/10.1016/j.bmcl.2010.02.025openalex-snapshot
Sterol effect on interaction between amphidinol 3 and liposomal membrane as evidenced by surface plasmon resonance
inferredcites →https://doi.org/10.1016/j.hal.2004.07.004openalex-snapshot
The structures of five new antifungal and hemolytic amphidinol analogs from Amphidinium carterae collected in New Zealand
inferredcites →https://doi.org/10.1016/j.tet.2005.01.069openalex-snapshot
Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities
inferredcites →https://doi.org/10.1016/j.tet.2005.07.004openalex-snapshot
Isolation and structure elucidation of a new amphidinol with a truncated polyhydroxyl chain from Amphidinium klebsii
inferredcites →https://doi.org/10.1016/j.tetlet.2004.05.067openalex-snapshot
Lingshuiols A and B, two new polyhydroxy compounds from the Chinese marine dinoflagellate Amphidinium sp.
inferredcites →https://doi.org/10.1016/j.tetlet.2006.02.045openalex-snapshot
Karatungiols A and B, two novel antimicrobial polyol compounds, from the symbiotic marine dinoflagellate Amphidinium sp.
inferredcites →https://doi.org/10.1016/s0006-3495(01)75729-3openalex-snapshot
Interactions of Cholesterol with Lipid Bilayers: The Preferred Configuration and Fluctuations
inferredcites →https://doi.org/10.1016/s0006-3495(03)74989-3openalex-snapshot
Effects of Epicholesterol on the Phosphatidylcholine Bilayer: A Molecular Simulation Study
inferredcites →https://doi.org/10.1021/bi00353a017openalex-snapshot
Sterol orientations in phosphatidylcholine liposomes as determined by deuterium NMR
inferredcites →https://doi.org/10.1021/bi3015086openalex-snapshot
The Lipid Dependence of Antimicrobial Peptide Activity Is an Unreliable Experimental Test for Different Pore Models
inferredcites →https://doi.org/10.1021/bi4000854openalex-snapshot
Interaction between the Marine Sponge Cyclic Peptide Theonellamide A and Sterols in Lipid Bilayers As Viewed by Surface Plasmon Resonance and Solid-State 2H Nuclear Magnetic Resonance
inferredcites →https://doi.org/10.1021/bi800334popenalex-snapshot
Complex Formation of Amphotericin B in Sterol-Containing Membranes As Evidenced by Surface Plasmon Resonance
inferredcites →https://doi.org/10.1021/cr3004778openalex-snapshot
Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea
inferredcites →https://doi.org/10.1021/ja00026a027openalex-snapshot
Amphidinol, a polyhydroxy-polyene antifungal agent with an unprecedented structure, from a marine dinoflagellate, Amphidinium klebsii
inferredcites →https://doi.org/10.1021/ja9033473openalex-snapshot
Direct Interaction between Amphotericin B and Ergosterol in Lipid Bilayers As Revealed by 2H NMR Spectroscopy
inferredcites →https://doi.org/10.1021/ja9091853openalex-snapshot
Structure and Absolute Configuration of Karlotoxin-2, an Ichthyotoxin from the Marine Dinoflagellate Karlodinium veneficum
inferredcites →https://doi.org/10.1021/ja983655xopenalex-snapshot
Absolute Configuration of Amphidinol 3, the First Complete Structure Determination from Amphidinol Homologues: Application of a New Configuration Analysis Based on Carbon−Hydrogen Spin-Coupling Constants
inferredcites →https://doi.org/10.1021/jo070414bopenalex-snapshot
Iriomoteolide-1a, a Potent Cytotoxic 20-Membered Macrolide from a Benthic Dinoflagellate Amphidinium Species
inferredcites →https://doi.org/10.1021/jo102585kopenalex-snapshot
Prorocentrol, a Polyoxy Linear Carbon Chain Compound Isolated from the Toxic Dinoflagellate Prorocentrum hoffmannianum
inferredcites →https://doi.org/10.1021/jo702440sopenalex-snapshot
Iriomoteolide-3a, a Cytotoxic 15-Membered Macrolide from a Marine Dinoflagellate Amphidinium Species
inferredcites →https://doi.org/10.1021/np100221kopenalex-snapshot
Symbiopolyol, a VCAM-1 Inhibitor from a Symbiotic Dinoflagellate of the Jellyfish Mastigias papua
inferredcites →https://doi.org/10.1021/np900616qopenalex-snapshot
Structure and Biosynthesis of Amphidinol 17, a Hemolytic Compound from Amphidinium carterae
inferredcites →https://doi.org/10.1021/ol401176aopenalex-snapshot
Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3
inferredcites →https://doi.org/10.1021/ol8016337openalex-snapshot
Structure of Membrane-Bound Amphidinol 3 in Isotropic Small Bicelles
inferredcites →https://doi.org/10.1038/ja.2008.39openalex-snapshot
Amphidinolides and Its Related Macrolides from Marine Dinoflagellates
inferredcites →https://doi.org/10.1039/dc9868100303openalex-snapshot
Liposome electroformation
inferredcites →https://doi.org/10.1529/biophysj.105.073890openalex-snapshot
Solid-State NMR Investigation of the Membrane-Disrupting Mechanism of Antimicrobial Peptides MSI-78 and MSI-594 Derived from Magainin 2 and Melittin
inferredcites →https://doi.org/10.3390/md304113openalex-snapshot
Luteophanol D, New Polyhydroxyl Metabolite from Marine Dinoflagellate Amphidinium sp.
inferredcites →https://doi.org/10.3987/com-06-s(k)49openalex-snapshot
Amphidinolactone A, a New 13-Membered Macrolide from Dinoflagellate Amphidinium sp.

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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inferred← citeshttps://doi.org/10.1002/ange.201507418openalex-snapshot
Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical‐Shift Analysis: Insights into their Mechanism of Action
inferred← citeshttps://doi.org/10.1002/ange.201712167openalex-snapshot
Synthesis and Stereochemical Revision of the C31–C67 Fragment of Amphidinol 3
inferred← citeshttps://doi.org/10.1002/anie.201507418openalex-snapshot
Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical‐Shift Analysis: Insights into their Mechanism of Action
inferred← citeshttps://doi.org/10.1002/anie.201712167openalex-snapshot
Synthesis and Stereochemical Revision of the C31–C67 Fragment of Amphidinol 3
inferred← citeshttps://doi.org/10.1002/asia.70353openalex-snapshot
Synthesis and Structure–Activity Relationship Studies of Truncated Artificial Analogues of Amphidinol 3
inferred← citeshttps://doi.org/10.1002/cbic.202000685openalex-snapshot
Genomic and Targeted Approaches Unveil the Cell Membrane as a Major Target of the Antifungal Cytotoxin Amantelide A
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Probing the Role of Chirality in Phospholipid Membranes
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NMR Studies on Natural Product—Stereochemical Determination and Conformational Analysis in Solution and in Membrane
inferred← citeshttps://doi.org/10.1016/bs.arnmr.2017.12.003openalex-snapshot
Recent Solid-State NMR Studies of Hydrated Lipid Membranes
inferred← citeshttps://doi.org/10.1016/j.algal.2018.01.010openalex-snapshot
A pilot-scale bioprocess to produce amphidinols from the marine microalga Amphidinium carterae: Isolation of a novel analogue
inferred← citeshttps://doi.org/10.1016/j.bbamem.2017.09.019openalex-snapshot
Sterol-recognition ability and membrane-disrupting activity of Ornithogalum saponin OSW-1 and usual 3-O-glycosyl saponins
inferred← citeshttps://doi.org/10.1016/j.bbamem.2018.07.010openalex-snapshot
Theonellamide A, a marine-sponge-derived bicyclic peptide, binds to cholesterol in aqueous DMSO: Solution NMR-based analysis of peptide-sterol interactions using hydroxylated sterol
inferred← citeshttps://doi.org/10.1016/j.bbamem.2020.183496openalex-snapshot
β-Glucosylation of cholesterol reduces sterol-sphingomyelin interactions
inferred← citeshttps://doi.org/10.1016/j.bbrep.2021.100941openalex-snapshot
Amphidinol 3 preferentially binds to cholesterol in disordered domains and disrupts membrane phase separation
inferred← citeshttps://doi.org/10.1016/j.bmc.2016.08.043openalex-snapshot
Sterol-dependent membrane association of the marine sponge-derived bicyclic peptide Theonellamide A as examined by 1H NMR
inferred← citeshttps://doi.org/10.1016/j.bmcl.2023.129594openalex-snapshot
Truncated Derivatives of Amphidinol 3 Reveal the Functional Role of Polyol Chain in Sterol-Recognition and Pore Formation
inferred← citeshttps://doi.org/10.1016/j.lwt.2025.118633openalex-snapshot
Algal amphidinols, an alternative to sulfites in the fight against Brettanomyces bruxellensis
inferred← citeshttps://doi.org/10.1021/acs.biochem.6b00193openalex-snapshot
The Structure of the Bimolecular Complex between Amphotericin B and Ergosterol in Membranes Is Stabilized by Face-to-Face van der Waals Interaction with Their Rigid Cyclic Cores
inferred← citeshttps://doi.org/10.1021/acs.jnatprod.7b00345openalex-snapshot
Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure–Activity Relationships
inferred← citeshttps://doi.org/10.1021/acs.langmuir.0c01344openalex-snapshot
Stereochemical Purity Can Induce a New Crystalline Mesophase in Phytantriol Lipids
inferred← citeshttps://doi.org/10.1021/bi5012942openalex-snapshot
Axial Hydrogen at C7 Position and Bumpy Tetracyclic Core Markedly Reduce Sterol’s Affinity to Amphotericin B in Membrane
inferred← citeshttps://doi.org/10.1021/jacs.9b11789openalex-snapshot
Total Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure–Activity Relationship Study
inferred← citeshttps://doi.org/10.1021/jo502322mopenalex-snapshot
Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3
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Marine natural products targeting the eukaryotic cell membrane
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Channel Formation and Membrane Deformation via Sterol-Aided Polymorphism of Amphidinol 3
inferred← citeshttps://doi.org/10.1038/s41598-024-68669-0openalex-snapshot
Sterolysin from a 1950s culture of Karlodinium veneficum (aka Gymnodinium veneficum Ballantine) forms lethal sterol dependent membrane pores
inferred← citeshttps://doi.org/10.1039/c5sc00814jopenalex-snapshot
A highly convergent synthesis of the C1–C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry
inferred← citeshttps://doi.org/10.1039/c9np00059copenalex-snapshot
Chemical diversity and mode of action of natural products targeting lipids in the eukaryotic cell membrane
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Formation of a Tight Complex between Amphidinol 3 and Sterols in Lipid Bilayers Revealed by Short-Range Energy Transfer
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Membrane permeabilizing action of amphidinol 3 and theonellamide A in raft-forming lipid mixtures
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Conformational dynamics and molecular interactions of natural products: unveiling functional structures in biological membranes
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Antibacterial Activity and Amphidinol Profiling of the Marine Dinoflagellate Amphidinium carterae (Subclade III)
inferred← citeshttps://doi.org/10.3390/md13095736openalex-snapshot
Development and Application of a Novel SPE-Method for Bioassay-Guided Fractionation of Marine Extracts
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Biotechnological and Pharmacological Applications of Biotoxins and Other Bioactive Molecules from Dinoflagellates
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A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate Amphidinium gibbosum: Absolute Configuration and Multi-Segment Modification
inferred← citeshttps://doi.org/10.3390/md19080432openalex-snapshot
Isolation and Structural Elucidation of New Amphidinol Analogues from Amphidinium carterae Cultivated in a Pilot-Scale Photobioreactor
inferred← citeshttps://doi.org/10.3390/md22040180openalex-snapshot
Marine-Derived Metabolites Act as Promising Antifungal Agents
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Discrimination of Stereoisomers by Their Enantioselective Interactions with Chiral Cholesterol-Containing Membranes
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Le plaste des diatomées : centre énergétique et cible des interactions allélopathiques
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