113-73-5
Chemical Structure
Gramicidin S
Synonym(s): Gramicidin soviet
- CAS No.: 113-73-5
- Formula:C60H92N12O10
- Molecular Weight:1141.45
InChIKey: IUAYMJGZBVDSGL-XNNAEKOYSA-N
SMILES: O=C1N2[C@](CCC2)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](C(N3[C@](CCC3)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H]1CC4=CC=CC=C4)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O)=O)CC5=CC=CC=C5)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O
Biological Activity: Gramicidin S (Gramicidin soviet) is a cationic cyclic peptide antibiotic that selectively targets bacterial cell membranes and has anticancer activity. Gramicidin S also exerts antibacterial activity by destroying membrane integrity and interfering with membrane protein function. Gramicidin S inserts into the phospholipid bilayer through hydrophobic amino acid residues, specifically binds to negatively charged membrane lipids and disrupts membrane structure, thereby inhibiting cell division and cell wall synthesis, and ultimately causing bacterial death. Gramicidin S also inhibits ion channels, with IC50s of 41 μM, 24 μM, and 3 μM for Na+/K+-ATPase, tobacco leaf plasma membrane Mg2+/K+-ATPase, and rat heart plasma membrane Ca2+-ATPase, respectively[1][2][3].
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Gramicidin S | 99.89% | Gramicidin S (Gramicidin soviet) is a cationic cyclic peptide antibiotic that selectively targets bacterial cell membranes and has anticancer activity. Gramicidin S also exerts antibacterial activity by destroying membrane integrity and interfering with membrane protein function. Gramicidin S inserts into the phospholipid bilayer through hydrophobic amino acid residues, specifically binds to negatively charged membrane lipids and disrupts membrane structure, thereby inhibiting cell division and cell wall synthesis, and ultimately causing bacterial death. Gramicidin S also inhibits ion channels, with IC50s of 41 μM, 24 μM, and 3 μM for Na+/K+-ATPase, tobacco leaf plasma membrane Mg2+/K+-ATPase, and rat heart plasma membrane Ca2+-ATPase, respectively. | ||||||||||||||||||||
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- [1]. Mogi T, et al. Gramicidin S and polymyxins: the revival of cationic cyclic peptide antibiotics. Cell Mol Life Sci. 2009 Dec;66(23):3821-6. [Content Brief]
- [2]. Wenzel M, et al. The Multifaceted Antibacterial Mechanisms of the Pioneering Peptide Antibiotics Tyrocidine and Gramicidin S. mBio. 2018 Oct 9;9(5):e00802-18. [Content Brief]
- [3]. Okamoto K, et al. Inhibitory effect of gramicidin S on the growth of murine tumor cells in vitro and in vivo. Oncology. 1984;41(1):43-8. [Content Brief]
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