Sapurimycin
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| Category | Antibiotics |
| Catalog number | BBF-02877 |
| CAS | 133021-37-1 |
| Molecular Weight | 462.40 |
| Molecular Formula | C25H18O9 |
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Description
It is produced by the strain of Str. sp. DO-116. It has anti-gram-positive bacteria effect. In vivo, it has the effect of anti-leukemia P388 and sarcoma 180 cells. Determination in vitro, it has the effect of causing single strand breaks in superhelical plasmid DNA.
Specification
| Related CAS | 132609-35-9 |
| Synonyms | Antibiotic DC 116; 4H-Anthra(1,2-b)pyran-5-acetic acid, 7,12-dihydro-8,11-dihydroxy-2-(2-methyl-3-(1-propenyl)oxiranyl)-4,7,12-trioxo-, (2-alpha,3-alpha(Z))-(+)- |
| IUPAC Name | 2-[8,11-dihydroxy-2-[(2S,3S)-2-methyl-3-[(Z)-prop-1-enyl]oxiran-2-yl]-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]acetic acid |
| Canonical SMILES | CC=CC1C(O1)(C)C2=CC(=O)C3=C(O2)C4=C(C=C3CC(=O)O)C(=O)C5=C(C=CC(=C5C4=O)O)O |
| InChI | InChI=1S/C25H18O9/c1-3-4-15-25(2,34-15)16-9-14(28)18-10(8-17(29)30)7-11-19(24(18)33-16)23(32)21-13(27)6-5-12(26)20(21)22(11)31/h3-7,9,15,26-27H,8H2,1-2H3,(H,29,30)/b4-3-/t15-,25-/m0/s1 |
| InChI Key | MAUMGBVGKFVQCP-NAVFIMFESA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Boiling Point | 796.9°C at 760 mmHg |
| Melting Point | 145-149°C |
| Density | 1.643 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Sapurimycin, new antitumor antibiotic produced by Streptomyces. Producing organism, fermentation, isolation and biological properties
M Hara, T Takiguchi, T Ashizawa, K Gomi, H Nakano J Antibiot (Tokyo). 1991 Jan;44(1):33-9. doi: 10.7164/antibiotics.44.33.
In screening actinomycetes for antitumor compounds, Streptomyces sp. DO-116 was found to produce a new antitumor antibiotic sapurimycin. It is structurally related to, but distinct from, kapurimycins. The antibiotic was produced in a fermentation medium supplemented with high porous polymer resin which adsorbs antibiotic in the culture and results in an increase of titer. Active material was separated from the polymer resin by a solvent extraction procedure and isolated by repeated solvent extraction, adsorption chromatography and HPLC. Sapurimycin was active against bacteria, particularly Gram-positive organisms. It exhibited antitumor activity against leukemia P388 and sarcoma 180 in mice. Sapurimycin caused single strand breaks in supercoiled plasmid DNA in vitro. These results are discussed in comparison with data for kapurimycins.
2. Sapurimycin, new antitumor antibiotic produced by Streptomyces. Structure determination
Y Uosaki, T Yasuzawa, M Hara, Y Saitoh, H Sano J Antibiot (Tokyo). 1991 Jan;44(1):40-4. doi: 10.7164/antibiotics.44.40.
The structure of a new anthra-gamma-pyrone antitumor antibiotic sapurimycin was determined by the spectral studies of its methyl ester. Sapurimycin has the same anthra-gamma-pyrone skeleton as pluramycin, but is distinctly different because of the absence of sugars on the D ring and possessing a carboxylmethyl group on C-5.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
