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Alamethicin (U-22324; U22324) is a natural product extracted from Trichoderma viride, acting as a membrane channel-forming peptide antibiotic and inducing voltage-gated conductance in model and cell membranes. Alamethicin is a monovalent cation ionophore that can mimic nerve action potential across artificial membranes. Alamethicin has also been used to study membrane interactions of antimicrobial peptides.
| Targets |
- Biological membranes (cell membranes/lipid bilayers) for ion channel formation [2]
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|---|---|
| ln Vitro |
- Alamethicin (U22324) acts as a membrane dipole potential modifier and induces ion channel formation in biological membranes. In artificial lipid bilayer membranes, it forms voltage-dependent cation channels at concentrations of 0.1–1 μM, increasing membrane permeability to monovalent cations (e.g., Na⁺, K⁺) [2]
- It modulates membrane dipole potential, thereby affecting the gating and function of intrinsic ion channels in cell membranes. At 0.5 μM, it shifts the dipole potential of lipid bilayers by ~50 mV, altering the open probability of ion channels [2] |
| Cell Assay |
- Lipid bilayer ion channel assay: Artificial lipid bilayers were prepared by depositing phospholipids on a porous support. Alamethicin (U22324) (0.1–1 μM) was added to the aqueous phase, and voltage was applied across the bilayer. Ion currents were recorded using patch-clamp techniques to detect channel formation and ion permeability [2]
- Membrane dipole potential measurement assay: Fluorescent probes sensitive to dipole potential were incorporated into lipid vesicles. Alamethicin (U22324) (0.2–0.8 μM) was incubated with the vesicles, and fluorescence intensity changes were measured at specific wavelengths to quantify dipole potential shifts [2] |
| References | |
| Additional Infomation |
A cyclic 19-peptide antibiotic, which can be used as an ion carrier, is produced by Trichoderma viride strains. (Excerpt from Dictionary of Microbiology and Molecular Biology, 2nd edition, by Singleton and Sainsbury) - Aramamycin (U22324) is a cyclic peptide antibiotic biosynthesized by Trichoderma viride [1] - Its core mechanism involves insertion into the biomembrane (lipid bilayer) and self-assembly to form ion channels, thereby disrupting membrane permeability and ion homeostasis [2] - It is widely used as a tool for studying ion channel formation, membrane dipole potential regulation, and membrane transport processes [2] - The biosynthesis of aramamycin (U22324) involves peptide chain assembly mediated by nonribosomal peptide synthases (NRPS) in Trichoderma viride [1]
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| Molecular Formula |
C92H150N22O25
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|---|---|
| Molecular Weight |
1964.30
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| Exact Mass |
1963.11
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| CAS # |
27061-78-5
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| PubChem CID |
16132042
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| Sequence |
Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH2)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH2)-phenylalaninol
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| Appearance |
White to yellow solid powder
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| Melting Point |
255-270ºC
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| LogP |
3.967
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| Hydrogen Bond Donor Count |
22
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| Hydrogen Bond Acceptor Count |
25
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| Rotatable Bond Count |
53
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| Heavy Atom Count |
139
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| Complexity |
4520
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| Defined Atom Stereocenter Count |
11
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| 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](CC2=CC=CC=C2)CO)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C
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| InChi Key |
LGHSQOCGTJHDIL-UTXLBGCNSA-N
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| InChi Code |
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
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| 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-amino-5-oxopentanoyl]amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-5-[[(2S)-5-amino-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-oxopentanoic acid
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| Synonyms |
U-22324 U-22324 U-22324
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~50.91 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.5091 mL | 2.5454 mL | 5.0909 mL | |
| 5 mM | 0.1018 mL | 0.5091 mL | 1.0182 mL | |
| 10 mM | 0.0509 mL | 0.2545 mL | 0.5091 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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