Alamethicin (U-22324) A membrane channel-forming peptide

Alamethicin (U-22324) (CAS 27061-78-5)

Alamethicin (U-22324) | CAS 27061-78-5 is rated 5.0 out of 5 by 1.
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Synonym: U-22324
Application: A membrane channel-forming peptide
CAS Number: 27061-78-5
Molecular Weight: 1964.30
Molecular Formula: C92H150N22O25
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Alamethicin (U-22324) is a polypeptide natural product antibiotic supplied as a mixture of homologs: Alamethicin and Alamethicin I. These compounds form voltage-dependent ion channels in the lipid bilayer, through the spontaneous assembly of units into a multimeric barrel-stave structure spanning the membrane. This formation results in a hydrophilic pore which permits non-specific ion efflux through the membrane. The non-specific ion efflux obliterates the normal electrochemical gradient of the cell, producing the antibiotic property of Alamethicin. Substantiated by experiments with covalently tethered molecules of Alamethicin, It is suggested that different multimeric aggregation states create varying pore sizes with varying stabilities, correlating to differential specificity for ions. This channel-forming activity has been exploited as a tool for introducing hydrophilic small molecules into mitochondria without disrupting the integrity of the membrane.


References

1. Martin, D.R., et al. 1976. Biochem. J. 153: 181-190. PMID: 1275883
2. Brewer, D., et al. 1987. Can. J. Microbiol. 33: 619-625. PMID: 3664367
3. Kaduk, C., et al. 1997. Biophys. J. 72: 2151-2159. PMID: 9129817
4. Gostimskaya, I.S., et al. 2003. Anal. Biochem. 313: 46-52. PMID: 12576057
5. Kirschbaum, J., et al. 2003. J. Pept. Sci. 9: 799-809. PMID: 14658799
6. Stella, L., et al. 2007. Chem. Biodivers. 4: 1299-1312. PMID: 17589867
7. Woolley, G.A. 2007. Chem. Biodivers. 4: 1323-1337. PMID: 17589884
8. Vedovato, N., et al. 2007. Chem. Biodivers. 4: 1338-1346. PMID: 17589885
9. Qian, S., et al. 2008. Biophys. J. 94: 3512-3522. PMID: 18199659

Physical State :
Solid
Solubility :
Soluble in DMSO and ethanol
Storage :
Store at -20° C
Melting Point :
263-265° C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
16132042
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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Alamethicin (U-22324)  Product Citations

See how others have used Alamethicin (U-22324). Click on the entry to view the PubMed entry .

Citations 1 to 8 of 8 total

PMID: # 28097507  Van Peer, E. et al. 2017. Pharm. Res. 34: 750-764.

PMID: # 27671344  Kretschmer, SB. et al. 2017. Biochem. Pharmacol. 123: 52-62.

PMID: # 29198856  Isobe, T. et al. 2017. Food Chem. Toxicol. 111: 417-422.

PMID: # 27050398  Nilsson, L. et al. 2016. PLoS ONE. 11: e0153112.

PMID: # 27405656  Hanioka, N. et al. 2016. Arch. Toxicol.

PMID: # 27071666  Hanioka, N. et al. 2016. Arch. Toxicol.

PMID: # 22987451  Porceddu, M. et al. 2012. Toxicol. Sci. 129: 332-45.

PMID: # 18098064  Jeong, H. et al. 2008. Xenobiotica. 38: 62-75.

Citations 1 to 8 of 8 total

what is the purity of alamethicin (U-22324). Thank you.

Asked by: Xiaowei
Thank you for your question. The purity of our current lot in stock of Alamethicin (U-22324) : sc-200094 is 98 % (TLC). Please contact our Technical Support department for questions about any specific lots. You can reach us by phone at (800)-457-3801 option 2, or by email at scbt@scbt.com, or by live chat.
Answered by: Technical Support
Date published: 2016-09-26
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Rated 5 out of 5 by from Vedovato et al Vedovato et al. (PubMed ID 17589885) found that alamethicin (U-22324) reduced delay as well as activation of tau(a) and deactivation of tau(d) in photoreceptor rod outer segments from frog retina.
Date published: 2015-02-14
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