Sapurimycin

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Sapurimycin
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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