OA-7653 Substance

Drug – bio-affecting and body treating compositions – Fermentate of unknown chemical structure – Having a known elemental analysis

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A61K 3500

Patent

active

043783481

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a novel antibiotic prepared from a novel strain belonging to Streptomyces hygroscopicus and to antibacterial compositions comprising the antibiotic.


BACKGROUND ART

While we have found that the strain of this invention belongs to Streptomyces hygroscopicus as will be described later, the strain is clearly distinct from Streptomyces hygroscopicus (Jensen) and Streptomyces hygroscopicus ISP 5578 which are typical of the species and is also distinct from the strains belonging to any known species or subspecies. Further the substance of this invention can not be isolated from the strains of any of known species or subspecies.


DISCLOSURE OF INVENTION

The substance of the invention is characterized by the following physicochemical properties.


(1) Appearance

White particulate crystals.


(2) Solubility

Sparingly soluble in 0.1 N aqueous solution of hydrochloric acid.
Insoluble in methanol, ethanol, butanol, acetone and ethyl acetate.
Soluble in 0.1 N aqueous solution of sodium hydroxide.


(3) Specific rotatory power

[.alpha]sub.D.sup.23.5 =+76.5.degree. (C=0.463, water)


(4) Elementary analysis

C: 46.10%, H: 4.47%, N: 7.18%.


(5) Molecular weight determined by ultra-centrifugal analysis About 2000



(6) Isoelectric point determined by electrophoresis pH 5-6

The isoelectric point is determined by the following method. In 1 liter of distilled water are dissolved 6.008 g of citric acid, 3.893 g of KH.sub.2 PO.sub.4, 1.769 g of H.sub.3 PO.sub.4 and 5.266 g of 5,5-diethylbarbituric acid. One-liter quantities of such solution are adjusted to pH 3, 4, 5, 6, 7 and 8 with 0.2 N aqueous sodium hydroxide solution to obtain buffer solutions. Using the buffer solutions and Whatman filter paper No. 1 (product of W. and R. Balston Ltd.) spotted with an aqueous solution of the substance of the invention, the substance is subjected to electrophoresis at 300 V for 4 hours to obtain an analysis diagram. The result is represented by Curve 1, FIG. 3, which shows that the isoelectric point is at pH 5 to 6.


(7) IR absorption spectrum

FIG. 4 shows an IR absorption spectrum obtained with use of a KBr disk, indicating main absorption peaks at 3280 (s), 1660 (s), 1640 (s), 1515 (s), 1490 (s), 1395 (s), 1235 (s), 1150 (m), 1062 (s) and 1020 (s) cm.sup.-1.


(8) UV absorption spectra

(i) The substance of the invention (1 mg/10 ml) is subjected to UV analysis at a cell length of 1 cm, using 0.1 N aqueous solution of hydrochloric acid as a solvent. FIG. 5 showing the result reveals an absorption maximum at 278 m.mu. (E.sub.1%.sup.1 cm =56).
(ii) FIG. 6 shows the result of UV analysis similarly conducted with use of distilled water as a solvent. The spectrum reveals an absorption maximum also at 278 m.mu. (E.sub.1%.sup.1 cm =56).
(iii) The substance of the invention (0.5 mg/10 ml) is subjected to UV analysis at a cell length of 1 cm, using 0.1 N aqueous solution of sodium hydroxide as a solvent. FIG. 7 showing the result reveals an absorption maximum at 298 m.mu. (E.sub.1%.sup.1 cm =100.8).


(9) .sup.1 H-NMR spectrum

FIG. 8 shows a .sup.1 H-HMR spectrum of the present substance in dimethyl sulfoxide substituted with deuterium (d.sup.6 -DMSO). Table 1 below shows the shifts (ppm) of peaks.


TABLE 1 ______________________________________ No. ppm No. ppm No. ppm ______________________________________ 1 1.05-1.35 5 3.0-4.1 9 6.6-7.0 2 1.60-2.0 6 4.2-4.9 10 7.0-7.55 3 2.2 7 5.05-5.6 11 7.6-8.0 4 2.50 8 6.3-6.5 ______________________________________


(10) .sup.13 C-NMR spectrum

FIG. 10 shows a .sup.13 C-NMR spectrum of the present substance in d.sup.6 -DMSO. Table 2 below shows the shifts (ppm) of peaks.


TABLE 2 ______________________________________ No. ppm No. ppm No. ppm ______________________________________ 1 173.2 14 148.7 27 105.9 2 173.0 15 146.8 28 104.6 3 172.4 16 138.3 29 102.3 4 172.2 17 136.5 30 96.3 5 170.8 18 135.5 31 73.6 6 169.7 19 134.1 32 69.3 7 169.0 20 131.6 33 62.5 8 167.1 21 129.7 34 60.6 9 157.0 22 128

REFERENCES:
McCormick et al., Antibiotics Annual, 1955-1956, 1956, pp. 606-611.

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