| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Ascamycin is a nucleoside antibiotic that targets protein synthesis in bacteria, but its antibacterial activity is selective against Xanthomonas species due to the presence of a specific cell-surface enzyme, Xc aminopeptidase, which hydrolyzes the alanyl group from ascamycin to form dealanylascamycin. Dealanylascamycin shows broad antibacterial activity against various Gram-negative and Gram-positive bacteria by inhibiting protein synthesis. [2]
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| ln Vitro |
Since C-1' lacks chlorine, ascamycin employs C2-chloroadenine as its base [1]. Ascamycin exhibits Xanthomonas species-specific antibacterial action. Dealanylascamycin demonstrates extensive antibacterial activity against a range of Gram-positive and Gram-negative bacteria when Ascamycin is deaminated. A mechanism by which Xanthomonas citrus is susceptible to asmycin is the asmycin deaminase present on its surface [2].
Ascamycin exhibits selective antibacterial activity against Xanthomonas species, while its dealanylated form, dealanylascamycin, shows broad antibacterial activity against various Gram-negative and Gram-positive bacteria. Both compounds strongly inhibit protein synthesis in vitro. [2] |
| ln Vivo |
Dealanylascamycin is reported to be toxic to mice.
Dealanylascamycin also showed trypanocidal activity (e.g., against Trypanosoma equiperdum) and anti-amoebae activity (e.g., against Endamoeba histolytica), making it valuable for treating animal diseases caused by these microorganisms. [3] |
| Enzyme Assay |
The activity of Xc aminopeptidase (the ascamycin-hydrolyzing enzyme) was assayed by incubating 10 μl of enzyme solution with 20 μg of ascamycin in 20 mM Tris/HCl buffer (pH 7.8) at 37°C for 90 minutes. The reaction mixture was analyzed by silica-gel thin-layer chromatography (TLC) using a solvent system of propan-2-ol/1 M NH₃ (7:3, v/v). Dealanylation was detected by the change in Rf value from ascamycin (0.59) to dealanylascamycin (0.72) and the appearance of antibacterial activity against Escherichia coli BE1186. [2]
Enzyme activity was also measured spectrophotometrically using L-alanine β-naphthylamide as substrate. A mixture of 0.4 ml of 20 mM Tris/HCl buffer (pH 7.8) and 0.5 ml of 2 mM L-alanine β-naphthylamide was equilibrated at 37°C, then 0.1 ml of enzyme solution was added, and the change in absorbance at 340 nm was recorded. The hydrolysis rate was calculated using Δε = 1.78×10⁹ M⁻¹·cm⁻¹. [2] |
| Cell Assay |
The susceptibility of Xanthomonas citri to ascamycin was attributed to the presence of Xc aminopeptidase on the cell surface, which hydrolyzes ascamycin to dealanylascamycin. Other bacteria lacking this enzyme were not susceptible to ascamycin. The dealanylation activity was also detected in simian-virus-40-transformed Balb3T3 cells, which showed higher ascamycin-dealanylating activity compared to normal cells, as observed using immunofluorescence technique. [2]
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| Toxicity/Toxicokinetics |
The toxicity of ascamycin to mice is mentioned to be one-sixteenth that of dealanylascamycin. [1]
The LD50 for dealanylascamycin is reported as 0.2 mg/kg (mice, intraperitoneal injection). [1] |
| References |
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| Additional Infomation |
There have been reports that Streptomyces contains ascamycin, and relevant data is available for reference.
Ascamycin (also identified as AT-265) and dealanylascamycin are nucleoside antibiotics produced by Streptomyces sp. JCM9888. They feature an unusual 5'-O-sulfonamide moiety attached to an adenosine nucleoside. Ascamycin contains a C2-chloroadenine base and an N-alanylated sulfonamide group. Dealanylascamycin lacks the alanyl group. The biosynthetic gene cluster (acmA-acmW) spanning 30 kb was identified, including genes proposed to be involved in 5'-O-sulfonamide formation, chlorination, and N-alanylation. Gene disruption of acmE (encoding an esterase) resulted in a mutant that produced only dealanylascamycin but not ascamycin, indicating AcmE's key role in converting dealanylascamycin to ascamycin via a tRNA-dependent alanylation. The study also identified two flavin-dependent halogenase genes (acmX and acmY) remote from the main cluster, postulated to be responsible for chlorination at the C2 position of adenine. The biological activity difference is due to the requirement for an aminopeptidase to activate ascamycin by removing the alanyl group to form dealanylascamycin, which is the broad-spectrum active form. [3] |
| Exact Mass |
451.068
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|---|---|
| CAS # |
91432-48-3
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| PubChem CID |
13994715
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
0.159
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
712
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@@H](C(=O)NS(=O)(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)N)O)O)N
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| InChi Key |
LZMCAAGVMFMSKC-IZKXYQSCSA-N
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| InChi Code |
InChI=1S/C13H18ClN7O7S/c1-4(15)11(24)20-29(25,26)27-2-5-7(22)8(23)12(28-5)21-3-17-6-9(16)18-13(14)19-10(6)21/h3-5,7-8,12,22-23H,2,15H2,1H3,(H,20,24)(H2,16,18,19)/t4-,5+,7+,8+,12+/m0/s1
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| Chemical Name |
[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-[(2S)-2-aminopropanoyl]sulfamate
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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.) |
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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