Nourseothricin sulfate

Names

[ Name ]:
Nourseothricin sulfate

[Synonym ]:
4-O-Carbamoyl-2-deoxy-2-{[(3S)-3,6-diaminohexanoyl]amino}-N-[(7R)-7-hydroxy-4-oxooctahydro-2H-imidazo[4,5-c]pyridin-2-ylidene]-α-L-glycero-hexopyranosylamine
MFCD00165013
α-L-glycero-Hexopyranosylamine, 2-deoxy-2-[[(3S)-3,6-diamino-1-oxohexyl]amino]-N-[(7R)-octahydro-7-hydroxy-4-oxo-2H-imidazo[4,5-c]pyridin-2-ylidene]-, 4-carbamate

Biological Activity

[Description]:

Nourseothricin sulfate (Streptothricin sulfate) is a broad-spectrum antibiotic that destroys the outer membrane of Gram-negative bacteria and is a dominant selective marker for Fonsecaea pedrosoi[1][2]. Nourseothricin sulfate inhibits protein biosynthesis in prokaryotic cells and strongly inhibits the growth of eukaryotes like fungi and can also be used as a elective marker for a wide range of organisms including bacteria, yeast, filamentous fungi, and plant cells[3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Escherichia coli resistance to neurosporin can be sensitive to resistant strains by eliminating their outer membrane resistance. The polycationic antibiotic, Nourseothricin, represents a mixture of several Streptothricins, mainly D and F. Obviously, although very slowly, it can pass the outer membrane via the porin pores. It has been shown earlier that Nourseothricin is able to generate some kind of channels into the outer membrane through which it can pass the cell wall. On the other hand, there are indications that resistant strains containing a Nourseothricin-inactivating acetyl transferase possess an additional protecting system, namely a reduced penetrability of the outer membrane[1].

[In Vivo]

Nourseothricin is preferentially excreted via kidney and signs of nephrotoxicity can be observed after its administration. Renal handling of Nourseothricin is characterized in experiments on renal cortical slices under various experimental conditions. Following administration in vivo the renal tubular transport system for organic anions (p-aminohippurate, PAH) is not influenced by Nourseothricin. There is a high degree of accumulation of Nourseothricin in renal cortical slices. In contrast to PAH accumulation there is no influence of nitrogen atmosphere, simultaneous administration of PAH, probenecid or trishydroxyaminomethane on Nourseothricin accumulation. Age dependent differences in Nourseothricin accumulation does not exist[4].

[References]

[1]. Seltmann G. et al. 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]. Florencio CS, et al. Genetic manipulation of Fonsecaea pedrosoi using particles bombardment and Agrobacterium mediated transformation. Microbiol Res. 2018 Mar;207:269-279.

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

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

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Molecular Formula ]:
C₅₀H₉₄N₂₀O₂₂S

[ Molecular Weight ]:
502.522

[ Exact Mass ]:
502.249969

[ PSA ]:
276.87000

[ LogP ]:
-5.12

[ Index of Refraction ]:
1.790

[ Storage condition ]:
-20C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RD4240000

CHEMICAL NAME :: Nourseothricin, sulfate (salt)

CAS REGISTRY NUMBER :: 96736-11-7

LAST UPDATED :: 198812

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1185 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AXVMAW Archiv fuer Experimentelle Veterinaermedizin. (S. Hirzel Verlag, Postfach 506, Leipzig DDR-7010, Ger. Dem. Rep.) V.6- 1952- Volume(issue)/page/year: 40,727,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 20800 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea

REFERENCE :: AXVMAW Archiv fuer Experimentelle Veterinaermedizin. (S. Hirzel Verlag, Postfach 506, Leipzig DDR-7010, Ger. Dem. Rep.) V.6- 1952- Volume(issue)/page/year: 40,727,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RD4240000

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Related Compounds

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