Alamethicin

SKU
A-1286
  • CAS:27061-78-5
  • Formula:C92H150N22O25
  • MW:1964.4 Da
  • Appearance:Off-white to beige powder
  • Purity:>99% by TLC

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Product Name Qty
Alamethicin
5 mg
$159.99
Alamethicin
10 mg
$299.99

Description

Alameticin is a linear peptide antibiotic isolated from the fungus Trichoderma viridae. It is linear and consists of 20 amino acid residues. Under proper conditions it can produce action potentials similar to that of nerve axons. Alamethicin is known to exhibit voltage dependent ion channel activity in membrane environments. Alamethicin has a high affinity for lipid bilayers, therefore, alamethicin binds to the surface of lipid bilayers and can be inserted into the membrane.

Alamethicin channels are formed by parallel bundles of the transmembrane helical monomers surrounding a central water-filled pore, and are composed of 3–12 alamethicin molecules. The ion channel activity of alamethicin makes it a suitable model to investigate voltage dependent ion channel proteins. Effective against gram positive bacteria and fungi.

Not for human therapeutic use or for medicinal purposes. For research applications only.

More Information
Alternate Name/Synonyms
Antibiotic U-22324
SKU
A-1286
CAS #
27061-78-5
Chemical Name
(4S)-4-[[2-[[2-[[(2S)-2-[[(2S)-1-[2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-5-
Chemical Formula
C92H150N22O25
Molecular Weight
1964.4 Da
Appearance
Off-white to beige powder
Purity
>99% by TLC
Solubility
DMSO: 10 mg/mL clear solution; CH3OH: 10 mg/mL clear solution
Melting Point
268-271°C
Preparation
Store Solutions at -20°C for up to 2 months.
Storage Temp
-20°C
THERAPEUTIC AREA
Infectious Diseases
USE
Alamethicin is an antibiotic that functions as a monovalent cation ionophore. It has been used to develop methods for the routine assessment of potential new drug candidates to elicit their pharmacokinetic drug interactions. Alamethicin forms voltage-dependent ion channels in the lipid bilayer, and this channel-forming activity has been exploited as a tool for introducing hydrophilic small molecules into mitochondria without disrupting the integrity of the membrane.
Merck Index
N/A
MDL NUMBER
MFCD00151517
CHEMACX
X1009632-9
INCHI
InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54+,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1
SMILES
C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NC(C)(C)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc2ccccc2)CO)NC(=O)C(C
Peptide sequence
AC-AIB-PRO-AIB-ALA-AIB-ALA-GLN-AIB-VAL-AIB-GLY-LEU-AIB-PRO-VAL-AIB-AIB-GLU-GLN-PHENYLALANINOL
RTECS
Not Applicable
UN #'S
UN 3288
PACKING GROUP
III
HAZARD CLASS
Not Applicable
Handling
WARNING: TOXIC! Use only in area provided with appropriate exhaust ventilation. Keep away from heat and source of ignition. Empty containers pose a fire risk, evaporate residue under fume hood. Ground all equipment containing material. Do not breathe dust.
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
GHS PICTOGRAMS
Handling WARNING: TOXIC! Use only in area provided with appropriate exhaust ventilation. Keep away from heat and source of ignition. Empty containers pose a fire risk, evaporate residue under fume hood. Ground all equipment containing material. Do not breathe dust.
UN #'S UN 3288
Packing Group III
Citations Memristive Ion Channel-Doped Biomembranes as Synaptic Mimics
The failing heart utilizes 3-hydroxybutyrate as a metabolic stress defense
Physical encapsulation of droplet interface bilayers for durable, portable biomolecular networks
Glucuronidation of estrone and 16α-hydroxyestrone by human UGT enzymes: The key roles of UGT1A10 and UGT2B7
UGT1A10 Is a High Activity and Important Extrahepatic Enzyme: Why Has Its Role in Intestinal Glucuronidation Been Frequently Underestimated?
Dog UDP-glucuronosyltransferase enzymes of subfamily 1A: cloning, expression, and activity
Hydrogel Microelectrodes for the Rapid, Reliable, and Repeatable Characterization of Lipid Membranes
Automated formation of black lipid membranes within a microfluidic device via confocal fluorescence feedback-controlled hydrostatic pressure manipulations
Multianalyte Microphysiometry of Macrophage Responses to Phorbol Myristate Acetate, Lipopolysaccharide, and Lipoarabinomannan
Application of multianalyte microphysiometry to characterize macrophage metabolic responses to oxidized LDL and effects of an apoA-1 mimetic
Identification and characterization of human UDP-glucuronosyltransferases responsible for xanthotoxol glucuronidation
In vitro metabolism of the anti-inflammatory clerodane diterpenoid polyandric acid A and its hydrolysis product by human liver microsomes and recombinant cytochrome P450 and UDP-glucuronosyltransferase enzymes
In Vitro Drug Metabolism Using Liver Microsomes
Physical encapsulation and controlled assembly of lipid bilayers within flexible substrates
Incorporation and characterization of biological molecules in droplet-interface bilayer networks for novel active systems
The Roles of Hsp90 and Calcineurin in Antifungal Drug Resistance
Synapse-Inspired Variable Conductance in Biomembranes: A Preliminary Study
Durable Biomolecular Assemblies for Protein-Powered Device Concepts
Formation and encapsulation of biomolecular arrays for developing arrays of membrane-based artificial hair cell sensors
High-Throughput Functional System for Encapsulated Networks of Model Cell Membranes
Improving Droplet Interface Bilayers as Models for Cell Membranes
Bilayer formation between lipid-encased hydrogels contained in solid substrates
Regulated attachment method for reconstituting lipid bilayers of prescribed size within flexible substrates
Electrophysiological interrogation of asymmetric droplet interface bilayers reveals surface-bound alamethicin induces lipid flip-flop
USING LIPID BILAYERS IN AN ARTIFICIAL AXON SYSTEM
Air-stable droplet interface bilayers on oil-infused surfaces
Hydrodynamic trapping for rapid assembly and in situ electrical characterization of droplet interface bilayer arrays
Droplet immobilization within a polymeric organogel improves lipid bilayer durability and portability
Heating-enabled formation of droplet interface bilayers using Escherichia coli total lipid extract
Microfluidic Generation, Encapsulation and Characterization of Asymmetric Droplet Interface Bilayers
A Microfluidic Assembly and Simultaneous Interrogation of Networks of Asymmetric Biomimetic Membranes
Interrogation of Bilayers in a Multi-Droplet Cluster for Membrane-Based Sensing
Encapsulating Networks of Droplet Interface Bilayers in a Thermoreversible Organogel
The use of virtual ground to control transmembrane voltages and measure bilayer currents in serial arrays of droplet interface bilayers
Design, fabrication, and validation of membrane-based sensors
Multianalyte microphysiometry reveals changes in cellular bioenergetics upon exposure to fluorescent dyes
Metabolic multianalyte microphysiometry reveals extracellular acidosis is an essential mediator of neuronal preconditioning
Prostaglandin E2 Regulation of Macrophage Innate Immunity
The effects of cholera toxin on cellular energy metabolism
Neuron specific metabolic adaptations following multi-day exposures to oxygen glucose deprivation
Development of multianalyte microphysiometry for the study of islets and biological toxins
Novel Electrochemical Techniques for Metabolic Profiling of Cellular Stress
Bilayer Network Modeling
Modeling the Conductance of the Peptide Alamethicin With and Without Ion Gradients
Bilayer membrane permeability of ionic liquid-filled block copolymer vesicles in aqueous solution
Model Neural Membrane Droplet Interface Bilayers from Brain Total Lipid Extract for Studying Membrane-Peptide Interactions with Amyloid-β
Tailored Current—Voltage Relationships of Droplet-Interface Bilayers Using Biomolecules and External Feedback Control
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