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| 5mg |
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Purity: ≥98%
Sinefungin (Adenosyl-Ornithine, Antibiotic 32232RP, A-9145) is a 5′-aminoalkyl analog of SAH and a natural product from cultures of Streptomyces incamatus and S. griseolus, acting as a novel and potent inhibitor of histone G9a and DNA methyltransferase. It is a nucleoside structurally related to S-
| Targets |
DNA/RNA methyltransferase
|
|---|---|
| ln Vitro |
Sinefungin (0.5 or 1.0 μg/mL, 60 min) suppresses the elevation of histone H3K4 monomethylation in renal fibroblasts and renal epithelial cells and attenuates the increase in α-SMA caused by TGF-β1 [2].
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| ln Vivo |
For obstructive nephropathy, sinefungin (10 mg/kg daily) improves renal fibrosis right after UUO [2].
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| Enzyme Assay |
Sinefungin (A9145) and a related metabolite, A9145C, were found to be potent inhibitors of Newcastle disease virion and vaccinia virion mRNA(guanine-7-)-methyltransferase and vaccinia virion mRNA(nucleoside-2'-)-methyltransferase. Both Sinefungin and A9145C were competitive inhibitors of these S-adenosyl-L-methionine-dependent enzymes having inhibition constants substantially less than S-adenosyl-L-homocysteine. These compounds also inhibited plaque formation by vaccinia virus in mouse L-cells [1].
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| Cell Assay |
Western Blot Analysis[2]
Cell Types: Renal epithelial cells. Tested Concentrations: 0.5 or 1.0 μg/mL. Incubation Duration: 60 minutes pretreatment before TGF-β1 (10 ng/mL). Experimental Results: In NRK-52E and NRK-49F cells, TGF-β1-induced α-SMA protein expression was Dramatically diminished and H3K4me1 was inhibited in a dose-dependent manner. |
| Animal Protocol |
Animal/Disease Models: Male C57BL/6J mice (8 weeks old) [2].
Doses: 10 mg/kg Route of Administration: UUO (prepared as a suspension in distilled water and 0.9% NaCl solution) is administered intraperitoneally (ip) (ip) immediately. Experimental Results: Inhibition of α-SMA protein expression. These indicators (α-SMA, FSP-1, collagen 1, collagen 3) were improved on days 3 and 7 after UUO. |
| References |
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| Additional Infomation |
Sinefungin is an adenosine that is the the delta-(5'-adenosyl) derivative of ornithine. It has a role as an antifungal agent and an antimicrobial agent. It is a member of adenosines and a non-proteinogenic alpha-amino acid. It is functionally related to a L-ornithine.
Sinefungin is a solid. This compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar. The proteins that adenosyl-ornithine target include RdmB, modification methylase TaqI, rRNA (adenine-N6-)-methyltransferase, and modification methylase RsrI. Sinefungin has been reported in Streptomyces griseolus and Streptomyces halstedii with data available. Sinefungin is a natural nucleoside related to S-adenosylmethionine that has been isolated from Streptomyces species with antifungal, antiviral and antiparasitic activity. Sinefungin inhibits DNA methyltransferase which leads to an inhibition of DNA synthesis. |
| Molecular Formula |
C15H23N7O5
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|---|---|
| Molecular Weight |
381.38702
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| Exact Mass |
381.176
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| Elemental Analysis |
C, 47.24; H, 6.08; N, 25.71; O, 20.97
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| CAS # |
58944-73-3
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| PubChem CID |
65482
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| Appearance |
White to yellow solid
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| Density |
1.9±0.1 g/cm3
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| Boiling Point |
783.2±70.0 °C at 760 mmHg
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| Flash Point |
427.5±35.7 °C
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| Vapour Pressure |
0.0±2.8 mmHg at 25°C
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| Index of Refraction |
1.832
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| LogP |
-1.33
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
27
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| Complexity |
529
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C(C[C@@H](C(=O)O)N)[C@@H](C[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N)N=CN=C32)O1)O)O)N
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| InChi Key |
LMXOHSDXUQEUSF-YECHIGJVSA-N
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| InChi Code |
InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1
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| Chemical Name |
(2S,5S)-2,5-Diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
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| Synonyms |
A 9145; Antibiotic A 9145;Antibiotic 32232RP;RP 32232; Sinefungin; Adenosylornithine; Antibiotic A 9145
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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) |
H2O : ~100 mg/mL (~262.20 mM)
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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 | 2.6220 mL | 13.1099 mL | 26.2199 mL | |
| 5 mM | 0.5244 mL | 2.6220 mL | 5.2440 mL | |
| 10 mM | 0.2622 mL | 1.3110 mL | 2.6220 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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