| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Phospho-N-acetylmuramyl-pentapeptide transferase (MraY) (IC50 = 0.35 μM)[1]
Lethal target: Tunicamycin V targets bacterial phospho-N-acetylmuramyl-pentapeptide transferase (MraY), a membrane-bound enzyme that catalyzes the transfer of phospho-MurNAc-pentapeptide from UDP-MurNAc-pentapeptide to the lipid carrier undecaprenyl phosphate (C55-P). This reaction is a key step in the biosynthesis of bacterial cell wall peptidoglycan, forming lipid I. By inhibiting MraY, Tunicamycin V blocks peptidoglycan synthesis, leading to bacterial cell lysis and death. The compound shows potent inhibition with an IC₅0 of 0.35 microM. Tunicamycin V is a nucleoside natural product with antibacterial activities. |
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| ln Vitro |
In 1971, Streptomyces lysosuperficus fermentation broths yielded nucleoside natural compounds known as tunitoxinamycins. These chemicals have a range of biological actions, including antibacterial, antiviral, antifungal, and anticancer effects. The enzyme polyprenol phosphate translocase, which is in charge of the initial N-acetylglucosamination of the N-linked glycopeptide in the endoplasmic reticulum (ER), is severely inhibited by tunitamycins when it comes to UDP-N-acetylglucosamine (GlcNAc)[2].
In vitro, Tunicamycin V inhibits bacterial phospho-N-acetylmuramyl-pentapeptide transferase (MraY) with an IC₅0 of 0.35 microM. The compound has antibacterial activities against various bacterial species. In cellular assays using bacterial cultures, Tunicamycin V inhibits cell growth and induces cell lysis by blocking peptidoglycan synthesis. The compound's mechanism of action involves inhibition of MraY, leading to the accumulation of UDP-MurNAc-pentapeptide and depletion of lipid I and subsequent peptidoglycan precursors. The compound is a valuable tool for studying bacterial cell wall biosynthesis and for identifying new antibacterial agents. |
| ln Vivo |
In vivo data for Tunicamycin V are limited as the compound is primarily used in in vitro antibacterial research. Tunicamycin antibiotics are known to have antibacterial activity, but their in vivo efficacy and pharmacokinetic properties have not been extensively characterized. The compound's poor bioavailability and potential toxicity may limit its in vivo utility. Tunicamycin V is intended for research use only and is not for human therapeutic applications. Researchers interested in in vivo applications should consult the primary literature for the most current information.
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| Enzyme Assay |
In vitro enzyme assays for Tunicamycin V involve measuring MraY activity using membrane preparations from bacterial cells or recombinant MraY enzyme. The assay is performed in buffer containing the substrate UDP-MurNAc-pentapeptide (radiolabeled with [14C] or [3H]) and the lipid acceptor undecaprenyl phosphate (C55-P). Varying concentrations of Tunicamycin V (0.001-10 microM) are incubated with the enzyme and substrates at 37degC for 30-60 minutes. The reaction products (lipid I) are extracted with organic solvents and quantified by TLC or scintillation counting. IC₅0 values for MraY inhibition are determined from dose-response curves.
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| Cell Assay |
Elucidating a structure-activity relationship study by evaluating a series of truncated analogues is a simple but important and effective tactic in medicinal chemistry based on natural products with a large and complex chemical structure. In this study, a series of truncated analogues of tunicamycin V were designed and synthesized and their MraY inhibitory activity was investigated in order to gain insight into the effect of these moieties on MraY inhibition[1].
Cellular assays for Tunicamycin V are performed using bacterial cultures to assess antibacterial activity. Bacterial strains (e.g., Staphylococcus aureus, Escherichia coli, Bacillus subtilis) are cultured in appropriate medium and seeded in 96-well plates. Serial dilutions of Tunicamycin V (0.001-100 microg/mL) are added, and plates are incubated at 37degC for 16-24 hours. Minimum inhibitory concentrations (MICs) are determined visually or by measuring optical density at 600 nm. Time-kill kinetics are assessed by plating aliquots at various time points and counting colony-forming units. The effect of the compound on bacterial cell morphology is assessed by electron microscopy. |
| Animal Protocol |
In vivo animal studies for Tunicamycin V are not typically performed, as the compound is used as a research tool for studying bacterial cell wall biosynthesis rather than as a therapeutic agent. For in vivo studies of MraY inhibitors, researchers typically use animal models of bacterial infection (e.g., murine sepsis, pneumonia models). However, specific protocols for Tunicamycin V have not been reported. The compound is intended for research use only and is not for human therapeutic applications.
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| ADME/Pharmacokinetics |
Lethal: Tunicamycin V (CAS#: 66054-36-2) has molecular formula C3₉H₆4N4O1₆ and molecular weight 844.94. The compound is also known as Tunicamycin A and is a nucleoside natural product produced by Streptomyces species. It inhibits bacterial phospho-N-acetylmuramyl-pentapeptide transferase (MraY) with an IC₅0 of 0.35 microM. The compound has antibacterial activities. Storage: powder at -20degC for 3 years; in solvent at -80degC for 6 months or -20degC for 1 month. The compound is a research chemical for laboratory use only.
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| References | |
| Additional Infomation |
Chlamycin B2 is a nucleoside and one of the homologues of chlamycin mixtures, characterized by a 13-methyltetradecano-2-enoyl fatty acyl substituent on the amino group of the chlamycin moiety. It has antibacterial activity.
Tunicamycin V (CAS#: 66054-36-2), also known as Tunicamycin A, is a nucleoside natural product that inhibits bacterial phospho-N-acetylmuramyl-pentapeptide transferase (MraY) with an IC₅0 of 0.35 microM. MraY is a membrane-bound enzyme that catalyzes a key step in bacterial cell wall peptidoglycan biosynthesis, making it an important target for antibacterial drug discovery. Tunicamycin V is a discrete, structurally-defined nucleoside antibiotic naturally produced by Streptomyces species. The compound has antibacterial activities and is used in research to study bacterial cell wall biosynthesis and glycosylation. As of the current date, Tunicamycin V is not approved for clinical use. |
| Molecular Formula |
C39H64N4O16
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|---|---|
| Molecular Weight |
844.94
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| Exact Mass |
830.416
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| Elemental Analysis |
C, 54.93; H, 7.52; N, 6.74; O, 30.81
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| CAS # |
66054-36-2
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| PubChem CID |
11104835
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| Appearance |
White to off-white solid powder
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| Source |
Streptomyces xinghaiensis
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| LogP |
0.2
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| Hydrogen Bond Donor Count |
11
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| Hydrogen Bond Acceptor Count |
16
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| Rotatable Bond Count |
20
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| Heavy Atom Count |
58
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| Complexity |
1420
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| Defined Atom Stereocenter Count |
15
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| SMILES |
O1[C@H]([C@@H]([C@H]([C@H]([C@H]1C[C@H]([C@@H]1[C@H]([C@H]([C@H](N2C=CC(NC2=O)=O)O1)O)O)O)O)O)NC(/C=C/CCCCCCCCCC(C)C)=O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)NC(C)=O
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| InChi Key |
MEYZYGMYMLNUHJ-DIRMKAHISA-N
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| InChi Code |
InChI=1S/C38H62N4O16/c1-19(2)13-11-9-7-5-4-6-8-10-12-14-24(46)40-27-31(51)28(48)22(55-37(27)58-36-26(39-20(3)44)30(50)29(49)23(18-43)56-36)17-21(45)34-32(52)33(53)35(57-34)42-16-15-25(47)41-38(42)54/h12,14-16,19,21-23,26-37,43,45,48-53H,4-11,13,17-18H2,1-3H3,(H,39,44)(H,40,46)(H,41,47,54)/b14-12+/t21-,22-,23-,26-,27-,28+,29-,30-,31-,32+,33-,34-,35-,36-,37+/m1/s1
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| Chemical Name |
(E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-13-methyltetradec-2-enamide
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| Synonyms |
tunicamycin V; tunicamycin A; Tunicamycin B2; (+)-Tunicamycin V; 66054-36-2; 17RV2Q5O9O; CHEMBL4534172; (2E)-N-[(2S,3R,4R,5R,6R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-{(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-2-hydroxyethyl}-4,5-dihydroxytetrahydro-2H-pyran-3-yl]-13-methyltetradec-2-enamide;
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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 | 1.1835 mL | 5.9176 mL | 11.8352 mL | |
| 5 mM | 0.2367 mL | 1.1835 mL | 2.3670 mL | |
| 10 mM | 0.1184 mL | 0.5918 mL | 1.1835 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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