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Alamethicin

Catalog No.
C4395
antibiotic peptide
Grouped product items
SizePriceStock Qty
1mg
$65.00
Ship with 5-10 days
5mg
$240.00
Ship with 5-10 days
10mg
$450.00
Ship with 5-10 days
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

Alamethicin is an antibiotic peptide.

Plenty of peptide antibiotics have been identified in the past half-century, falling into two classes, non-ribosomally synthesized peptides, such as polymyxins, gramicidins, bacitracins, glycopeptides, and ribosomally synthesized (natural) peptides. The former are usually modified and produced by bacteria, while the latter are produced by all species as a major component of the host defense molecules.

In vitro: Alamethicin was identified as an antibiotic peptide belonging to membrane active peptides of fungal origin with an unusual amphiphilic amino acid, 2-aminoisobutyric acid, which can induce helical peptide structures strongly, leading to the formation of voltage-gated ion channels in the cell membrane bilayers. Alamethicin is also widely used as agent to induce various defense responses and physiological in eukaryotic cells [1]. In addition, alamethicin was quite often used to evaluate voltage gating, ion channel assembly, as well as peptide-membrane interactions [2, 3].

In vivo: Up to now, alamethicin is only for in-vitro usage and there is no animal in-vivo study reported.

Clinical trial: So far, no clinical study has been conducted.

References:
[1] Maischak, H. ,Zimmermann, M.R.,Felle, H.H., et al. Alamethicin-induced electrical long distance signaling in plants. Plant Signal.Behav. 5(8), 988-990 (2010).
[2] Jones, L. R.,Maddock, S.W. and Besch, H.R., Jr. Unmasking effect of alamethicin on the (Na+,K+)-ATPase, β-adrenergic receptor-coupled adenylate cyclase, and cAMP-dependent protein kinase activities of cardiac sarcolemmal vesicles. The Journal of Biological Chemisty 255(20), 9971-9980 (1980).
[3] Pan, J. ,Tristram-Nagle, S. and Nagle, J.F. Alamethicin aggregation in lipid membranes. Journal of Membrane Biology 231(1), 1-36 (2009).

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt1964.3
Cas No.27061-78-5
FormulaC92H150N22O25
SynonymsAntibiotic U-22324
Solubility≤10mg/ml in methanol;10mg/ml in DMSO
Chemical Name(3S,12R)-1-((S)-1-((6S,12S,15S,21S,30S)-1-((R)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl)-15-(3-amino-3-oxopropyl)-30-isobutyl-21-isopropyl-3,3,6,9,9,12,18,18,24,24,33,33-dodecamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaoxo-2,5,8,11,14,17,20,23,26,
SDFDownload SDF
Canonical SMILESCC(C[C@H](NC(CNC(C(C)(NC([C@@H](NC(C(C)(NC([C@@H](NC([C@@H](NC(C(C)(NC([C@@H](NC(C(C)(NC([C@H]1CCCN1C(C(C)(NC(C)=O)C)=O)=O)C)=O)C)=O)C)=O)C)=O)CCC(N)=O)=O)C)=O)C(C)C)=O)C)=O)=O)C(NC(C)(C(N2CCC[C@H]2C(N[C@H](C(NC(C)(C(NC(C)(C(N[C@@H](C(N[C@@H](C(N[C@H
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:

Cell lines

The dicotyledonous lima bean

Preparation method

The solubility of this compound in DMSO is ≤ 10mg/ml. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

5nM, 25nM

Applications

Upon a 5nM ALA stimulus a 40mV depolarization was induced and detected at a distance of 5 cm on the same leaf in lima bean. Systemic electric propagation was tested and demonstrated in barley. Application of 25 nM ALA on one leaf (S-leaf) resulted in a 45mV depolarization response at a distant of 25 cm on a different leaf (T-leaf), indi-cating that ALA induced a systemic elec-trical response that moved from one to the other leaf.

References:

[1]. Maischak H, Zimmermann MR, Felle HH, Boland W, Mithöfer A. Alamethicin-induced electrical long distance signaling in plants. Plant Signal Behav. 2010 Aug;5(8):988-90. doi: 10.1104/pp.108.133884. Epub 2010 Aug 1. PubMed PMID:20724839; PubMed Central PMCID: PMC3115176.

Quality Control

Quality Control & MSDS

View current batch:

Chemical structure

Alamethicin