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Framycetin sulfate (Neomycin B; Fradiomycin B) is a potent aminoglycoside class of antibiotic that works as a potent RNase P cleavage activity inhibitor with a Ki of 35 μM. It is a component of neomycin that is produced by Streptomyces fradiae. It can enhance effectiveness of topical antibacterial treatment of adenoiditis. It is also used in burn therapy.
| ln Vitro |
Framycetin suLfate (also known as Neomycin BsuLfate or Fradiomycin BsuLfate) has an inhibitory impact on RNase P RNA that is sensitive to pH value; hence, lowering pH will reduce the inhibitory effect of other systems [1]. The novel antibiotics 5-Azide Framycetin Sulfate B and Sulfate specifically prevent the synthesis of mature miRNAs, interact with cytokines, and effectively inhibit HCC cell lines [2]. The primary homologous target of framycetin suLfate is the decoding site of 16S rRNA; however, it also binds to the Rev response element, group I intron, and hammerhead ribozyme in HIV-1, inhibiting their biological functions [sulfate new Mycin induces misreading of genetic codes during translation and inhibits various ribozymes]. Framycetin suLfate is related to the structural motif of RNA and the DNA sequence motif of it. The 16 S rRNA region spanning from 1400 to 1500 is the ribosome target location [4].
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| References |
[1]. N E Mikkelsen, et al. Inhibition of RNase P RNA Cleavage by Aminoglycosides. Proc Natl Acad Sci U S A. 1999 May 25;96(11):6155-60.
[2]. Childs-Disney JL, et al. Small Molecule Targeting of a MicroRNA Associated with Hepatocellular Carcinoma. ACS Chem Biol. 2016 Feb 19;11(2):375-80. [3]. Stampfl S, et al. Monovalent ion dependence of neomycin B binding to an RNA aptamer characterized by spectroscopic methods. Chembiochem. 2007 Jul 9;8(10):1137-45. [4]. Hoch I, et al. Antibiotic inhibition of RNA catalysis: neomycin B binds to the catalytic core of the td group I intron displacing essential metal ions. J Mol Biol. 1998 Sep 25;282(3):557-69. |
| Additional Infomation |
Neomycin B sulfate is the aminoglycoside sulfate salt that is the sulfate salt of neomycin B; a component of neomycin sulfate. It contains a framycetin.
Neomycin Sulfate is the sulfate salt form of neomycin, a broad spectrum aminoglycoside antibiotic derived from Streptomyces fradiae with antibacterial activity. Neomycin is an antibiotic complex consisting of 3 components: the two isomeric components B and C are the active components, and neomycin A is the minor component. Neomycin irreversibly binds to the 16S rRNA and S12 protein of the bacterial 30S ribosomal subunit. As a result, this agent interferes with the assembly of initiation complex between mRNA and the bacterial ribosome, thereby inhibiting the initiation of protein synthesis. In addition, neomycin induces misreading of the mRNA template and causes translational frameshift, thereby results in premature termination. This eventually leads to bacterial cell death. Framycetin Sulfate is the sulfate salt form of framycetin, an aminoglycoside antibiotic isolated from Streptomyces lavendulae (decaris), mainly containing neomycin B, with broad-spectrum antibacterial activity. Framycetin is used mostly as a topical preparation and is poorly absorbed. Upon parenteral administration, this agent can cause nephrotoxicity and ototoxicity. A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed) |
| Molecular Formula |
C23H48N6O17S
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|---|---|
| Molecular Weight |
712.72
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| Exact Mass |
712.28
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| CAS # |
4146-30-9
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| Related CAS # |
Framycetin;119-04-0
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| PubChem CID |
197162
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| Appearance |
White to off-white solid powder
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| Boiling Point |
927.1ºC at 760 mmHg
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| Flash Point |
514.5ºC
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| Hydrogen Bond Donor Count |
15
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| Hydrogen Bond Acceptor Count |
23
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
47
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| Complexity |
953
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| Defined Atom Stereocenter Count |
19
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| SMILES |
C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CN)O2)O)O)N)O[C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](CN)O4)O)O)N)O)O)N.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
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| InChi Key |
KWBUARAINLGYMG-JGMIRXPNSA-N
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| InChi Code |
InChI=1S/C23H46N6O13.3H2O4S/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22;3*1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;3*(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;;;/m1.../s1
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| Chemical Name |
(2R,3R,4S,5S,6S)-5-amino-2-(aminomethyl)-6-(((2R,3S,4R,5S)-5-(((1R,2R,3S,5R,6S)-3,5-diamino-2-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-hydroxycyclohexyl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)tetrahydro-2H-pyran-3,4-diol sulfate
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| Synonyms |
Neomycin sulphate B Framycetin sulphate
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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 : ~250 mg/mL (~275.06 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (55.01 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4031 mL | 7.0154 mL | 14.0308 mL | |
| 5 mM | 0.2806 mL | 1.4031 mL | 2.8062 mL | |
| 10 mM | 0.1403 mL | 0.7015 mL | 1.4031 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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