| Identification | Back Directory | [Name]
SPARSOMYCIN | [CAS]
1404-64-4 | [Synonyms]
U-19183
nsc59729
Aids012106
sparsomycin
Aids-012106
B 120121L19
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
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)- | [Molecular Formula]
C13H19N3O5S2 | [MDL Number]
MFCD01684112 | [MOL File]
1404-64-4.mol | [Molecular Weight]
361.44 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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) |
| Hazard Information | Back Directory | [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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BOC Sciences
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16314854226 |
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www.bocsci.com |
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