| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Cinnamycin targets phosphatidylethanolamine (PE), a phospholipid that is abundantly present in the inner leaflet of the plasma membrane and in bacterial membranes. By binding specifically to PE, cinnamycin sequesters this phospholipid and indirectly inhibits phospholipase A2 activity. The compound's binding to PE is highly specific, making it a valuable tool for studying PE biology and membrane dynamics. The antiviral activity of cinnamycin against HSV-1 is believed to be related to its PE-binding properties, which may disrupt viral entry or membrane fusion.
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|---|---|
| ln Vitro |
In the POPC membrane, the binding constant K0 of the Cinnamycin-PE complex is approximately 107-108 M-1, whereas in the octyl glucoside micelle, it is only roughly 10(6) M(-1)[1].
Cinnamycin demonstrates potent in vitro activity as a PE-binding peptide antibiotic. Its specific binding to PE has been characterized using various biophysical techniques. The compound exhibits antiviral activity against HSV-1 KOS strain infection in Vero cells. Its antibacterial activity is attributed to its ability to bind PE in bacterial membranes, disrupting membrane integrity and function. The compound's in vitro activity is assessed using PE-binding assays (e.g., SPR, fluorescence), antibacterial susceptibility testing, and antiviral plaque reduction assays. |
| ln Vivo |
Cinnamycin has demonstrated antiviral activity against HSV-1 in Vero cells, suggesting potential in vivo efficacy against viral infections. The compound's ability to bind PE may contribute to its antiviral mechanism by disrupting viral envelope function or entry. However, detailed in vivo efficacy data are limited, and cinnamycin is primarily used as a research tool for studying PE biology and membrane interactions. Its potential as a therapeutic agent is limited by its peptide nature, which may result in poor oral bioavailability and rapid clearance.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for cinnamycin involve measuring its binding affinity to phosphatidylethanolamine (PE). The assay typically uses liposomes containing PE or PE-coated surfaces in surface plasmon resonance (SPR) or fluorescence-based binding assays. The compound is incubated with PE-containing liposomes or immobilized PE, and binding is quantified by changes in SPR signal or fluorescence intensity. Binding specificity is confirmed by comparing binding to PE versus other phospholipids (e.g., phosphatidylcholine, phosphatidylserine). The compound's inhibition of phospholipase A2 activity is assessed by measuring the release of fatty acids from PE-containing substrates.
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| Cell Assay |
Cellular assays for cinnamycin are conducted to evaluate its antiviral and antibacterial activities. For antiviral assays, Vero cells are infected with HSV-1 and treated with varying concentrations of the compound. Viral replication is quantified by plaque reduction assays or by measuring viral titers. For antibacterial assays, bacteria are cultured in appropriate media and treated with the compound, with minimum inhibitory concentrations (MIC) determined by broth microdilution. The compound's effects on cell viability are assessed using MTT or similar assays. PE-binding in cells is confirmed by immunofluorescence or by using fluorescently labeled cinnamycin.
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| Animal Protocol |
In vivo animal studies with cinnamycin are limited, as the compound is primarily used as a research tool for studying PE biology and membrane interactions. For antiviral studies, animal models of HSV-1 infection may be used, though detailed protocols are not extensively reported. The compound's peptide nature limits its oral bioavailability, and it would likely require parenteral administration for in vivo studies. Its in vivo utility is further limited by potential immunogenicity and rapid clearance. The compound is not intended for therapeutic use in humans.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of cinnamycin are characteristic of peptide antibiotics. The compound has a molecular weight of approximately 2041.29 g/mol and a molecular formula of C₈₉H12₅N2₅O2₅S3. As a peptide, cinnamycin has poor oral bioavailability and is likely rapidly cleared by proteolytic degradation and renal excretion. Its large size and cyclic structure may provide some stability against proteolysis compared to linear peptides. The compound is typically stored at -20degC. Detailed PK parameters are not extensively reported in the available literature.
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| Toxicity/Toxicokinetics |
Toxicological data for cinnamycin are limited, as the compound is primarily used as a research tool rather than a therapeutic agent. The compound is not intended for human therapeutic use and is supplied for research purposes only. In cell-based assays, the compound is generally well-tolerated at concentrations used for PE-binding studies and antiviral assays. The compound's specificity for PE may limit its toxicity, as PE is abundant in cell membranes. However, high concentrations may cause membrane disruption and cytotoxicity. Standard safety precautions should be followed when handling this compound.
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| References | |
| Additional Infomation |
Cinnamomum is a type B lantigenin produced by Streptomyces cinnamon, and is a tetracyclic polypeptide composed of 19 amino acids. It is a heterocyclic peptide, macrocyclic compound, type B lantigenin, and L-cysteine thioether.
Cinnamycin is a tetracyclic peptide antibiotic that binds specifically to phosphatidylethanolamine (PE). It is produced by Streptomyces cinnamoneus and contains four unusual amino acids. The compound is a potent indirect inhibitor of phospholipase A2 by specifically sequestering PE. It has demonstrated antiviral activity against HSV-1 in Vero cells. Cinnamycin is not an FDA-approved drug and has no clinical indications. It is available in high purity (≥95%) and is typically stored at -20degC. |
| Molecular Formula |
C89H125N25O25S3
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|---|---|
| Molecular Weight |
2041.30
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| Exact Mass |
2067.838
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| CAS # |
110655-58-8
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| PubChem CID |
131801649
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.6±0.1 g/cm3
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| Index of Refraction |
1.724
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| LogP |
-10.74
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| Hydrogen Bond Donor Count |
27
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| Hydrogen Bond Acceptor Count |
31
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| Rotatable Bond Count |
20
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| Heavy Atom Count |
142
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| Complexity |
4510
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| Defined Atom Stereocenter Count |
20
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| SMILES |
NC(NCCC[C@@H]1NC(=O)[C@@H](N)CS[C@H](C)C2C(N[C@H](C(=O)O)CCCCNC[C@H]3C(N[C@H](C(NCC(N4CCC[C@H]4C(N[C@H](C(N[C@@H]4C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(NCC(N[C@H](C(N2)=O)CC(=O)N)=O)=O)[C@H](C(=O)O)O)=O)CSC[C@@H](C(N[C@@H](CSC4C)C(N3)=O)=O)NC(=O)[C@H](CCC(=O)N)NC1=O)=O)C(C)C)=O)CC1C=CC=CC=1)=O)=O)CC1C=CC=CC=1)=O)=O)=O)CC1C=CC=CC=1)=O)=O)=N
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| InChi Key |
QJDWKBINWOWJNZ-OURZNGJWSA-N
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| InChi Code |
InChI=1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/t44-,45-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59-,60-,61-,66-,67+,68+,69-,70+/m0/s1
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| Chemical Name |
(1S,4S,13S,16S,19S,22S,25S,28R,31S,37S,40S,41S,44R,47S,50S,53S,56R,65S,70S)-44-amino-37-(2-amino-2-oxoethyl)-50-(3-amino-3-oxopropyl)-4,16,22-tribenzyl-47-(3-carbamimidamidopropyl)-31-[(R)-carboxy(hydroxy)methyl]-41,70-dimethyl-2,5,8,14,17,20,23,26,29,32,35,38,45,48,51,54,57,67-octadecaoxo-25-propan-2-yl-42,69,72-trithia-3,6,9,15,18,21,24,27,30,33,36,39,46,49,52,55,58,60,66-nonadecazapentacyclo[38.18.9.319,56.328,53.09,13]triheptacontane-65-carboxylic acid
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 0.4899 mL | 2.4494 mL | 4.8988 mL | |
| 5 mM | 0.0980 mL | 0.4899 mL | 0.9798 mL | |
| 10 mM | 0.0490 mL | 0.2449 mL | 0.4899 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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