SPARSOMYCIN
SPARSOMYCIN Basic information
- Product Name:
- SPARSOMYCIN
- Synonyms:
-
- Aids-012106
- B 120121L19
- nsc59729
- sparsomycin
- Sparsomycin from Streptomyces sparsogenes
- (E)-N-[(S)-1-(Hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxopyrimidine-5-yl)propenamide
- U-19183
- 2-Propenamide, N-[(1S)-1-(hydroxymethyl)-2-[(R)-[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (2E)-
- CAS:
- 1404-64-4
- MF:
- C13H19N3O5S2
- MW:
- 361.44
- Mol File:
- 1404-64-4.mol
SPARSOMYCIN Chemical Properties
- Melting point:
- 208-209° (dec)
- alpha
- D25 +69° (c = 0.5 in water)
- Density
- 1.3893 (rough estimate)
- refractive index
- 1.6390 (estimate)
- storage temp.
- 2-8°C
- solubility
- DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble
- form
- A solid
- pka
- 8.67 in water, 9.05 in 40% ethanol
- color
- White to off-white
Safety Information
- Hazard Codes
- T+
- Risk Statements
- 28
- Safety Statements
- 28-36/37-45
- RIDADR
- UN 2811 6.1/PG 2
- RTECS
- WG5850000
- Toxicity
- LD50 in dogs, rats, mice (mg/kg): 0.5-1.0, 2.25, 4.32 i.v. (Ottenheijm, 1986); LD50 i.p. in mice: 2.4 mg/kg (Owen)
SPARSOMYCIN Usage And Synthesis
Description
Sparsomycin is a bacterial metabolite and a nucleoside analog of uracil that has been found in S. sparsogenes and has diverse biological activities. It is active against KB carcinoma cells, Gram-positive and Gram-negative bacteria, and fungi. Sparsomycin is an inhibitor of peptidyl transferase that interferes with tRNA binding to the A-site of the peptidyl transfer center and increases the binding of peptidyl-tRNA to the P-site. It inhibits protein synthesis in bacteria, archaea, and eukaryotes. Sparsomycin reduces tumor growth in a P388 mouse leukemia model and in a Walker 256 carcinosarcoma rat model.
Uses
Research tool for studying protein biosynthesis.
Uses
Sparsomycin is an antibiotic that binds to active site and exit tunnel hydrophobic crevices of peptidyltransferase center of Haloarcula marismortui large ribosomal subunit.
References
[1] H C OTTENHEIJM. Chemical and biological aspects of sparsomycin, an antibiotic from Streptomyces.[J]. Progress in medicinal chemistry, 1986, 23: 219-268. DOI: 10.1016/s0079-6468(08)70344-8
[2] E. LAZARO . Chemical, biochemical and genetic endeavours characterizing the interaction of sparsomycin with the ribosome[J]. Biochimie, 1991, 73 7: Pages 1137-1143. DOI: 10.1016/0300-9084(91)90157-v
[3] D J MASON R M S A DIETZ. Actinospectacin, a new antibiotic. I. Discovery and biological properties.[J]. Antibiotics & chemotherapy (Northfield, Ill.), 1961, 11: 118-122.
[4] Z ZYLICZ. In vivo antitumor activity of sparsomycin and its analogues in eight murine tumor models.[J]. Investigational New Drugs, 1988, 6 4: 285-292. DOI: 10.1007/bf00173646
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