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Nourseothricin sulfate (streptothricin sulfate) 96736-11-7

Nourseothricin sulfate (streptothricin sulfate) 96736-11-7

CAS No.: 96736-11-7

Nourseothricin sulfate (Streptothricin sulfate) is a broad-spectrum antibiotic that disrupts the outer membrane of Gram-
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Nourseothricin sulfate (Streptothricin sulfate) is a broad-spectrum antibiotic that disrupts the outer membrane of Gram-negative (Gram+) bacteria and is the primary selective marker for Fonsecaea pedrosoi. Nourseothricin sulfate inhibits protein biosynthesis in prokaryotic cells and strongly suppresses the growth of eukaryotic organisms such as fungi. It can also be used as a selective marker for a variety of organisms such as bacteria, yeast, filamentous fungi and plant cells.

Physicochemical Properties


Molecular Formula C50H94N20O22S
Molecular Weight 1359.47
Exact Mass 502.249
CAS # 96736-11-7
PubChem CID 131668562
Appearance White to off-white solid powder
Density 1.9±0.1 g/cm3
Index of Refraction 1.790
LogP -5.12
Hydrogen Bond Donor Count 12
Hydrogen Bond Acceptor Count 15
Rotatable Bond Count 11
Heavy Atom Count 40
Complexity 897
Defined Atom Stereocenter Count 9
SMILES

C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCN)N)O.OS(=O)(=O)O

InChi Key UDVWKDBCMFLRQW-TWRCRAKCSA-N
InChi Code

InChI=1S/C19H34N8O8.H2O4S/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19;1-5(2,3)4/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27);(H2,1,2,3,4)/t7-,8+,9+,11+,12-,13+,14-,15-,17+;/m0./s1
Chemical Name

[(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3,6-diaminohexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate;sulfuric acid
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro Nourseothricin sulfate resistance in E. coli can make resistant bacteria susceptible by removing their outer membrane resistance. Nourseothricin sulfate can enter the cell through porin pores and cross the outer membrane. Previous research had demonstrated that nourseothricin sulfate may open up specific channels in the outer membrane that allowed the drug to enter the cell wall. Nonetheless, there are signs that resistant strains with inactivated Nourseothricin sulfate acetyltransferase may have an extra defense mechanism in the form of a weakened outer membrane.
ln Vivo Nephrotoxicity symptoms may appear after the administration of nourseothricin sulfate, as the kidneys are the organs that preferentially eliminate the medication. Using renal cortical slices, tests were conducted under different experimental settings to assess the renal processing of Nourseothricin sulfate. Nourseothricin has no effect on the renal tubular transport system of the organic anion (para-aminohippurate, PAH) following in vivo administration. Renal cortical sections had a significant concentration of nourseothricin sulfate accumulation. Nourseothricin sulfate buildup was unaffected by probenecid, trihydroxyaminomethane, or simultaneous administration of PAH or nitrogen atmosphere, in contrast to PAH accumulation. There are no age-related variations in the buildup of Nourseothricin sulfate [4].
References

[1]. Resistance of Escherichia coli to nourseothricin (streptothricin): sensitization of resistant strains by abolition of its outer membrane resistance. Zentralbl Bakteriol. 1992 Jan;276(2):143-51.

[2]. Genetic manipulation of Fonsecaea pedrosoi using particles bombardment and Agrobacterium mediated transformation. Microbiol Res. 2018 Mar;207:269-279.

[3]. Plant-Growth Promotion and Biocontrol Properties of Three Streptomyces spp. Isolates to Control Bacterial Rice Pathogens. Front Microbiol. 2019 Feb 25;10:290.

[4]. Renal handling of nourseothricin. Pharmazie. 1988 Mar;43(3):200-2.


Solubility Data


Solubility (In Vitro) H2O : 250 mg/mL (183.90 mM)
Solubility (In Vivo) Solubility in Formulation 1: 100 mg/mL (73.56 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 0.7356 mL 3.6779 mL 7.3558 mL
5 mM 0.1471 mL 0.7356 mL 1.4712 mL
10 mM 0.0736 mL 0.3678 mL 0.7356 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.