| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg | |||
| Other Sizes |
| Targets |
Bacterial plasma membrane. Gramicidin assembles as transmembrane channels consisting of two molecules associated head-to-head, forming a β-helix structure with an internal pore that allows permeation of cations across the membrane, disrupting ionic balance. No specific IC₅₀ or Kᵢ values were reported in this study. [1]
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| ln Vitro |
Antimicrobial activity against bacteria: Gramicidin alone showed poor activity against Escherichia coli (Gram-negative) with a minimum bactericidal concentration (MBC) > 20 μM, but was effective against Staphylococcus aureus (Gram-positive) with an MBC of 4.0 μM. [1]
Cytotoxicity against eukaryotic cells: Gramicidin alone was highly toxic to Saccharomyces cerevisiae (a eukaryotic yeast model), with significant cell death observed at concentrations as low as 1 μM. [1] Mechanism of action: Gramicidin forms functional ion channels in dioctadecyldimethylammonium bromide (DODAB) lipid bilayers, as demonstrated by osmotic swelling assays. Addition of hyperosmotic KCl or glucose to DODAB large vesicles (LV) containing Gr caused vesicle swelling rather than shrinkage, indicating increased cation permeability. Leakage of phosphorylated compounds from bacteria treated with DODAB/Gr formulations confirmed bacterial cell lysis. [1] Spectroscopic characterization: The intrinsic fluorescence of Gr (due to tryptophan residues) and circular dichroism (CD) spectra were used to characterize Gr conformation in different environments. In DODAB LV, Gr exhibited a CD spectrum resembling that in 2,2,2-trifluoroethanol (TFE), indicating a β-helix conformation. In DODAB bilayer disks (BF), Gr displayed a CD spectrum more similar to that in ethanol, suggesting different localization (adsorbed at BF borders rather than inserted). [1] Gramicidin is an antimicrobial peptide that forms membrane channels and raises the permeability of those channels to cations. In contrast to its action on Staphylococcus aureus, gramicidin exhibits weak effectiveness against Escherichia coli and Saccharomyces cerevisiae, as evidenced by the survival rate (%) of bacteria within a specific dose range. Saccharomyces cerevisiae is not harmed by bactericidal activity, which is observed over a range of low gramicidin and DODAB concentrations [1]. |
| Cell Assay |
Microbial viability assay (CFU counting): E. coli, S. aureus, or S. cerevisiae cells were mixed with various concentrations of gramicidin (alone or incorporated into DODAB formulations) in 0.264 M D-glucose solution and incubated for 1 hour. Serial dilutions were plated on agar plates, incubated for 24–48 hours, and colony-forming units (CFU) were counted. Cell survival (%) was calculated relative to controls without antimicrobial agents. [1]
Bacterial cell lysis assay (inorganic phosphorus release): Bacteria were pelleted and resuspended in gramicidin dispersions in 1 mM NaCl. After 1 hour of interaction, the supernatant was collected and inorganic phosphorus concentration was determined. Bacterial lysis was expressed as percent leakage relative to control (bacteria lysed by sonication or other means). [1] Scanning electron microscopy (SEM): Bacteria treated with DODAB/Gr formulations above the MBC were fixed, dehydrated, and sputter-coated with gold before imaging. SEM revealed distorted cell morphology, including cell enlargement and surface alterations. [1] Osmotic swelling assay: DODAB large vesicles (LV) with or without incorporated gramicidin were prepared. Addition of hyperosmotic KCl or glucose solutions to the dispersion was followed by monitoring turbidity at 400 nm over time. Increased turbidity indicated vesicle shrinkage, while decreased turbidity indicated swelling. Gr-containing LV showed swelling upon hyperosmotic challenge, confirming functional channel formation. [1] Fluorescence spectroscopy: Gr intrinsic fluorescence was measured at λₑₓc = 280 nm. The emission spectra were recorded for Gr in TFE, ethanol, DODAB LV, and DODAB BF to assess the microenvironment of tryptophan residues. [1] Circular dichroism (CD) spectroscopy: CD spectra of Gr were acquired in the 200–280 nm range in different media (TFE, ethanol, DODAB LV, DODAB BF) to determine Gr secondary structure and conformation. [1] Dynamic light scattering (DLS) and zeta potential: Hydrodynamic diameter, polydispersity index, and zeta potential of DODAB/Gr dispersions were measured at 90° scattering angle to characterize particle size and surface charge. [1] |
| Toxicity/Toxicokinetics |
Cytotoxicity against eukaryotic cells: Gramicidin alone was highly toxic to S. cerevisiae, with cell viability significantly reduced at concentrations above 1 μM. However, when incorporated into DODAB formulations (DODAB BF/Gr or DODAB LV/Gr), the toxicity was substantially reduced, with yeast viability remaining high at bactericidal concentrations. [1]
Minimum bactericidal concentrations (MBC): The MBC of gramicidin alone against S. aureus was 4.0 μM. In combination with DODAB, the MBC for Gr decreased to 0.80 μM (with DODAB LV) and 0.32 μM (with DODAB BF), indicating improved delivery and reduced effective dose. [1] |
| References | |
| Additional Infomation |
There have been reports and data regarding the presence of gramicidin in Brevibacillus brevis. Gramicidin is a heterogeneous mixture of six antibiotic peptides extracted from the soil bacterium Bacillus brevis. Gramicidin is effective against most Gram-positive bacteria and some Gram-negative bacteria. It is administered topically. This is a group of peptide antibiotics derived from Bacillus brevis. Gramidin C or S is a cyclic ten-amino acid polypeptide, while Gramidin A, B, and D are linear. Gramicidin is one of the two main components of tyrosinin.
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| Molecular Formula |
C99H140N20O17
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|---|---|
| Molecular Weight |
1882.29472351074
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| Exact Mass |
1810.033419
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| CAS # |
1405-97-6
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| PubChem CID |
16130140
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| Sequence |
N-formyl-L-valyl-glycyl-D-leucyl-L-alanyl-D-valyl-L-valyl-D-valyl-L-tryptophyl-D-leucyl-L-tryptophyl-D-leucyl-L-tryptophyl-D-leucyl-L-tryptophyl-glycinol; For-Val-Gly-D-Leu-Ala-D-Val-Val-D-Val-Trp-D-Leu-Trp-D-Leu-Trp-D-Leu-Trp-Gly-ol
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| SequenceShortening |
VGLAVVVWLWLWLWG
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| Appearance |
White to off-white solid powder
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| Melting Point |
229-230℃
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| Vapour Pressure |
0mmHg at 25°C
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| LogP |
10.9
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| Hydrogen Bond Donor Count |
21
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| Hydrogen Bond Acceptor Count |
17
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| Rotatable Bond Count |
52
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| Heavy Atom Count |
136
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| Complexity |
3980
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| Defined Atom Stereocenter Count |
14
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| SMILES |
O=C([C@@H](CC(C)C)NC([C@H](CC1=CNC2C=CC=CC1=2)NC([C@H](C(C)C)NC([C@H](C(C)C)NC([C@@H](C(C)C)NC([C@H](C)NC([C@@H](CC(C)C)NC([C@H](C)NC(CNC([C@H](C(C)C)NC=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)N[C@H](C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@H](C(NCCO)=O)CC1=CNC2C=CC=CC1=2)=O)CC(C)C)=O)CC1=CNC2C=CC=CC1=2)=O)CC(C)C)=O)CC1=CNC2C=CC=CC1=2
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| InChi Key |
ZWCXYZRRTRDGQE-SORVKSEFSA-N
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| InChi Code |
InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83-,84+,85-/m0/s1
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| Chemical Name |
(2R)-2-[[(2S)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]propanoyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-(2-hydroxyethylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-4-methylpentanamide
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| Synonyms |
Gramicidine; Bacillus brevis gramicidin D; 1393-88-0; ...; 1405-97-6;
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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 (~53.13 mM)
H2O : ~1 mg/mL (~0.53 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 10 mg/mL (5.31 mM) = in 5% DMSO + 40% PEG300 + 5% Tween80 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 10 mg/mL (5.31 mM) in 5% DMSO + 95% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.= View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (1.33 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (1.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL corn oil and mix evenly. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.5313 mL | 2.6563 mL | 5.3126 mL | |
| 5 mM | 0.1063 mL | 0.5313 mL | 1.0625 mL | |
| 10 mM | 0.0531 mL | 0.2656 mL | 0.5313 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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