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Neomycin sulfate

CAS# 1405-10-3

Neomycin sulfate

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Chemical structure

Neomycin sulfate

3D structure

Chemical Properties of Neomycin sulfate

Cas No. 1405-10-3 SDF Download SDF
PubChem ID 62403 Appearance Powder
Formula C23H48N6O17S M.Wt 712.72
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : ≥ 31 mg/mL (34.11 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid
SMILES C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N.OS(=O)(=O)O
Standard InChIKey OIXVKQDWLFHVGR-GQTDVWSESA-N
Standard InChI InChI=1S/C23H46N6O13.H2O4S/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;1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;(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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Neomycin sulfate

DescriptionNeomycin sulfate is an aminoglycoside antibiotic and calcium channel inhibitor.In Vitro:Neomycin inhibits thrombin-stimulated release of inositol 1,4,5-trisphosphate (IP3), by selectively binding PIP2, but does not inhibit 32P incorporation into PI or initiation of DNA synthesis[1]. Neomycin (10 μM-1 mM) induces considerable release of [3H]arachidonic acid from phosphatidylinositol, phosphatidylcholine and phosphatidylethanolamine in saponin-permeabilized human platelets prelabeled with [3H]arachidonic acid. Moreover, neomycin enhances arachidonic acid release induced by thrombin. Addition of neomycin (100 μM) to 45Ca2+-preloaded platelets elicits 45Ca2+ mobilizatioin from intracellular stores[2]. Neomycin (0-10 mM) inhibits guanosine 5'-[gamma-thio]triphosphate-stimulated PLD activity in digitonin-permeabilized NG108-15 cells in a concentration-dependent manner (50% inhibition at 100 μM). Neomycin similarly inhibits PLD activity present in rat brain membranes and assayed in vitro with [3H]phosphatidylcholine as substrate (50% inhibition at 65 μM)[3]. Neomycin (5 mM) causes reversible reductions in the level of intracellular Ca2+, but PtdIns(4,5)P2 is not required for the channel activity[4].

References:
[1]. Carney, D.H., et al. Phosphoinositides in mitogenesis: neomycin inhibits thrombin-stimulated phosphoinositide turnover and initiation of cell proliferation. Cell, 1985. 42(2): p. 479-88. [2]. Nakashima, S., et al. Neomycin is a potent agent for arachidonic acid release in human platelets. Biochem Biophys Res Commun, 1987. 146(2): p. 820-6. [3]. Liscovitch, M., et al., Inhibition of neural phospholipase D activity by aminoglycoside antibiotics. Biochem J, 1991. 279 ( Pt 1): p. 319-21. [4]. Huang K, et al. CRAC channel is inhibited by neomycin in a Ptdlns(4,5)P2-independent manner. Cell Biochem Funct. 2015 Mar;33(2):97-100.

Neomycin sulfate Dilution Calculator

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Neomycin sulfate Molarity Calculator

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Preparing Stock Solutions of Neomycin sulfate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4031 mL 7.0154 mL 14.0308 mL 28.0615 mL 35.0769 mL
5 mM 0.2806 mL 1.4031 mL 2.8062 mL 5.6123 mL 7.0154 mL
10 mM 0.1403 mL 0.7015 mL 1.4031 mL 2.8062 mL 3.5077 mL
50 mM 0.0281 mL 0.1403 mL 0.2806 mL 0.5612 mL 0.7015 mL
100 mM 0.014 mL 0.0702 mL 0.1403 mL 0.2806 mL 0.3508 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Neomycin sulfate

Characterization of the binding of neomycin/paromomycin sulfate with DNA using acridine orange as fluorescence probe and molecular docking technique.[Pubmed:27392082]

J Biomol Struct Dyn. 2017 Aug;35(10):2077-2089.

The binding of Neomycin sulfate (NS)/paromomycin sulfate (PS) with DNA was investigated by fluorescence quenching using acridine orange (AO) as a fluorescence probe. Fluorescence lifetime, FT-IR, circular dichroism (CD), relative viscosity, ionic strength, DNA melting temperature, and molecular docking were performed to explore the binding mechanism. The binding constant of NS/PS and DNA was 6.70 x 10(3)/1.44 x 10(3) L mol(-1) at 291 K. The values of DeltaH(theta), DeltaS(theta), and DeltaG(theta) suggested that van der Waals force or hydrogen bond might be the main binding force between NS/PS and DNA. The results of Stern-Volmer plots and fluorescence lifetime measurements all revealed that NS/PS quenching the fluorescence of DNA-AO was static in nature. FT-IR indicated that the interaction between DNA and NS/PS did occur. The relative viscosity and melting temperature of DNA were almost unchanged when NS/PS was introduced to the solution. The fluorescence intensity of NS/PS-DNA-AO was decreased with the increase in the ionic strength. For CD spectra of DNA, the intensity of positive band at nearly 275 nm was decreased and that of negative band at nearly 245 nm was increased with the increase in the concentration of NS/PS. The binding constant of NS/PS with double-stranded DNA (dsDNA) was larger than that of NS/PS with single-stranded DNA (ssDNA). From these studies, the binding mode of NS/PS with DNA was evaluated to be groove binding. The results of molecular docking further indicated that NS/PS could enter into the minor groove in the A-T rich region of DNA.

Development of a novel pH sensitive silane crosslinked injectable hydrogel for controlled release of neomycin sulfate.[Pubmed:28064050]

Int J Biol Macromol. 2017 Apr;97:218-227.

Silane crosslinked biopolymer based novel pH-responsive hydrogels were fabricated by blending the cationic (chitosan) and anionic (alginate) polymers with poly(vinyl alcohol). Tetraethoxysilane (TEOS) was used, as a crosslinker in different amounts due to its nonhazardous nature, to study its impact on physical and chemical properties of the prepared injectable hydrogels along with the controlled release of drug. The swelling response of the prepared hydrogels was examined in different solvent media which exhibited decreased swelling ratio with increase in the amount of TEOS. All the fabricated hydrogels represented highest swelling at acidic pH while low swelling at basic and neutral pH. This specific pH sensitive behavior at pH 7 made them an appropriate candidate for the injectable controlled drug delivery in which Neomycin sulfate (NMS) was successfully loaded on suitable hydrogel (comprising 50muL TEOS) to study its release mechanism. The results revealed that in simulated gastric fluid (SGF), hydrogel released the entire drug (NMS) in initial 30min while in simulated intestinal fluid (SIF), NMS was released in a controlled way up to 83% in 80min. These results endorsed that the hydrogels could be practiced as a smart intelligent material for injectable controlled drug delivery as well as for other biomedical applications at physiological pH.

Neomycin Sulfate Improves the Antimicrobial Activity of Mupirocin-Based Antibacterial Ointments.[Pubmed:26596945]

Antimicrob Agents Chemother. 2015 Nov 23;60(2):862-72.

In the midst of the current antimicrobial pipeline void, alternative approaches are needed to reduce the incidence of infection and decrease reliance on last-resort antibiotics for the therapeutic intervention of bacterial pathogens. In that regard, mupirocin ointment-based decolonization and wound maintenance practices have proven effective in reducing Staphylococcus aureus transmission and mitigating invasive disease. However, the emergence of mupirocin-resistant strains has compromised the agent's efficacy, necessitating new strategies for the prevention of staphylococcal infections. Herein, we set out to improve the performance of mupirocin-based ointments. A screen of a Food and Drug Administration (FDA)-approved drug library revealed that the antibiotic Neomycin sulfate potentiates the antimicrobial activity of mupirocin, whereas other library antibiotics did not. Preliminary mechanism of action studies indicate that neomycin's potentiating activity may be mediated by inhibition of the organism's RNase P function, an enzyme that is believed to participate in the tRNA processing pathway immediately upstream of the primary target of mupirocin. The improved antimicrobial activity of neomycin and mupirocin was maintained in ointment formulations and reduced S. aureus bacterial burden in murine models of nasal colonization and wound site infections. Combination therapy improved upon the effects of either agent alone and was effective in the treatment of contemporary methicillin-susceptible, methicillin-resistant, and high-level mupirocin-resistant S. aureus strains. From these perspectives, combination mupirocin-and-neomycin ointments appear to be superior to that of mupirocin alone and warrant further development.

Novel neomycin sulfate-loaded hydrogel dressing with enhanced physical dressing properties and wound-curing effect.[Pubmed:26394193]

Drug Deliv. 2016 Oct;23(8):2806-2812.

To develop a novel Neomycin sulfate-loaded hydrogel dressing (HD), numerous Neomycin sulfate-loaded HDs were prepared with various amounts of polyvinyl alcohol (PVA), polyvinyl pyrrolidone (PVP) and sodium alginate (SA) using freeze-thawing technique, and their physical dressing properties, drug release, in vivo wound curing and histopathology in diabetic-induced rats were assessed. SA had a positive effect on a swelling capacity, but a negative effect on the physical dressing properties and drug release of HD. However, PVP did the opposite. In particular, the Neomycin sulfate-loaded HD composed of drug, PVA, PVP and SA at the weight ratio of 1/10/0.8/0.8 had excellent swelling and bioadhesive capacity, good elasticity and fast drug release. Moreover, this HD gave more improved wound curing effect compared to the commercial product, ensured the disappearance of granulation tissue and recovered the wound tissue to normal. Therefore, this novel Neomycin sulfate-loaded HD could be an effective pharmaceutical product for the treatment of wounds.

Description

Neomycin sulfate is an aminoglycoside antibiotic used for preventing or treating bacterial infections.

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