DESCRIPTIONS OF ANTIBIOTICS 



345 



positive bacteria. Certain gram-negative l)acteria 

 and certain fungi inhibited by 100 ng per ml. Ac- 

 tive on Endamoebn histoh/tii-a at 10 ng per ml (1). 

 References: 



1. Arcamone, F. et al. Oiorn. microl)iol. 1: 



77-88, 1957. 



2. Nicolaus, R. A. el al. Ricerca sci. 28: 



2314-2317, 1958. 



Proloci<liii 



Produced by: Streptomyces .sp. 



Method of extraction: Mycelivun e.xtracted with 

 methanol. Extract concentrated in vacuo; proto- 

 cidin and impurities are precipitated. Extraction 

 with methanol and concentration of extract 

 precipitate the antibiotic. Recrystallized from 

 methanol. 



Chemical and physical properties: Tetraene. 

 Ultraviolet absorption spectrum maxima at 277, 

 290, 303, and 318 m^. Very soluble in 0.01 .V HCl or 

 NaOH, glacial acetic acid, or pyridine. Soluble in 

 water, methanol, and benzaldehyde. Slightly 

 soluble in ethanol, butanol, and acetone. Infrared 

 spectrum given in reference 1. Stable to acid and 

 alkali, but not to ultraviolet light. Browns at 

 aliout 120°C. No clear-cut melting point. Negative 

 liiuret, Sakaguchi, IVIolisch, ninhydrin, anthrone, 

 and FeCla tests. Reduces KMn04 . Green reaction 

 with Fehling's solution. Becomes brownish l^lack 

 in concentrated H2SO4 . Differentiated from other 

 polyenic antibiotics on the basis of paper chroma- 

 tography (water-saturated butanol), Fehling reac- 

 tion, infrared spectrum, stability, and solubility. 



Biological activity: Not active on bacteria. Ac- 

 tive on fungi and yeasts. Inhibits Trichoutonus 

 vaginalis at 50 /ug per ml. 



Toxicity: Mice tolerate 30 mg i)er kg intrave- 

 nously. 



Reference: 1. Sakamoto, J.M.J. J. Antilnotics 

 (Japan) lOA: 128-131, 1957. 



Protoiiiyciii 



Produced by: Streptomyces sp., strain S-300. 



Chemical and physical properties: Stable, oily 

 substance. Most soluble in 5 per cent aqueous ac- 

 etone. 



Biological activity: No activity against bacteria. 

 Active against Endamoeba histolytica in vitro and 

 in vivo. 



Toxicity: No toxic effect if 50 mg per kg ad- 

 ministered orallj' to guinea pigs. 



Reference: 1. Hirabayashi, A. J. Antibiotics 

 (Jai)an) 12A: 298-309, 1959. 



Pseiidoslreptoinycin 



Produced by: Streptomyces griseus. 



Method of extraction: Extracted from broths 

 along with streptomycin. Separated from the 

 latter by fractional precipitation from a 90 per 

 cent methanol-10 per cent water solution of 

 streptomycin trihydrochloride on addition of 10 

 per cent of the quantity of triethylamine sulfate in 

 methanol calculated to completely precipitate the 

 streptomycin as the sulfate. Converted to the 

 trihydrochloride, washed with methanol, and 

 crystallized as the reineckate from water. Can be 

 converted to streptomycin in the presence of acid 

 at pH 2.5 at 50°C. 



Chemical and physical properties: Colorless 

 substance. Condensation product of two strepto- 

 mycin molecules linked at their carbonyl groups 

 \)y an amine bridge. Cannot be hydrogenated 

 catalj^tically under conditions which give a di- 

 hydro derivative of streptomycin. 



Biological activity: Has about one tenth the 

 activity of streptomycin by weight. 



Toxicity: LDo (mice) 12.5 jug per kg intrave- 

 nously (sulfate). 



Reference: 1. Solomons, I. A., Ill U. S. Patent 

 2,565,402, August 21, 1951. 



Psicofuraniiie 



Produced by: Streptomyces hygroscopicus var. 

 decoyicus. 



Synonym: Closely related to august mycin C. 



Method of extraction: Culture adjusted to pH 2.0 

 and filtered. Filtrate adjusted to pH 9.7 to 10.0 

 and adsorbed on Nuchar C-190 (1 per cent). 

 Elution with 80 per cent acetone at pH 9.7 to 10.0. 

 The eluate is adjusted to pH 7.0 to 8.0 and concen- 

 trated to an aqueous solution. Upon standing at 

 2°C, crystallization takes place. Further purifica- 

 tion by countercurrent distribution in /i-butanol 

 and water. Psicofuranine has a K value of 0.28 to 

 0.35 in that system. 



Chemical and physical properties: White crystals ; 

 m.p. 212-214°C (decomposition). CuHisN-.Oo • 

 Very soluble in dimethylformamide, dimethyl 

 sulfoxide, and hot water. Soluble as follows at 

 room temperature: water and methanol, 8 mg per 

 ml; ethanol, 6 mg per ml; n-butanol, 2 mg per ml; 

 ethyl acetate, 0.23 mg per ml. [aJn = — 53.7° (c = 

 1 per cent in dimethyl sulfoxide) and —68° (c = 

 1 per cent in dimethylformamide). Half-life 18 

 hours at pH 2.0 and 30°C; more stable at neutral 

 and alkaline pH. Maximal light absorption at 

 259 m/x (E'l'L 508) in 0.01 A' acid, and at 261 m/x 

 {EClm 527) in 0.01 .V l)ase. Infrared al)sorption 



