346 



DESCRIPTIONS OF ANTIBIOTICS 



spectrum given in reference 1. Paper chromatog- 

 raphy and ultraviolet light -absorption assay given 

 in reference 5. 



Biological activity: Activity in vitro difficult to 

 demonstrate. Active against some gram-positive 

 and gram-negative bacteria when a special semi- 

 synthetic medium is used: KH2PO4 , 3.0 gm; 

 NaaHPOj , 3.0 gm; MgS04-7HoO, 0.11 gm; 

 NH4CI, 1.0 gm; deionized water, 1 liter; liver 

 extract (3, 4). Active in mice, orally and sub- 

 cutaneously, against infections caused by Staph, 

 aureus, Streptococcus hemolyticus, and E. culi (2). 

 Active orally in rats against Walker adenocarci- 

 noma, Murphy-Sturm lymphosarcoma, Jensen 

 sarcoma, and Guerin tumor. No activity in mice 

 with either the ascitic or solid forms of Ehrlich 

 carcinoma, sarcoma 180, leukemia L-r210, or 

 spontaneous mammary adenocarcinoma (6). Psico- 

 furanine caTi be determined by a chemical method 

 in plasma and .serum (7). 



References : 



1. Eble, T. E. et al. Antibiotics & Chemo- 



therapy 9:419-420,1959. 



2. Lewis, C. e/ a/. Antibiotics & Chemotherapy 



9:421-126, 1959. 



3. Vavra, J. J. et al. Antibiotics <t Chemother- 



apy 9:427-431, 1959. 



4. Hanka, L. G. et al. Antibiotics & Chemo- 



therapy 9:432-435, 1959. 



5. Sokolski, W. T. et al. Antibiotics & Chemo- 



therapy 9:436-438,1959. 



6. Evans, J. S. and Gray, J. E. Antibiotics & 



Chemot herapy 9 : 675-684 , 1 959 . 



7. Forist, A. A. et al. Antibiotics & Chemo- 



therapy 9:685-689,1959. 



Piilvomycin 



Produced by: Streptomyces sp. 



Synonym: Closely related to mycolutein; also 

 produced by same culture. 



Method of extraction: Mycelium, containing most 

 of the active substance, extracted with methanol. 

 Extract concentrated in vacuo below 50°C, filtered, 

 and extracted with chloroform. Addition of pe- 

 troleum ether to the chloroform concentrate 

 precipitates pulvomycin. Chromatographed on 

 alumina from a methanolic solution and eluted 

 with methanol. Active fractions concentrated to 

 dryness in vacuo. Residue extracted with chloro- 

 form and precipitated with petroleum ether. 



Chemical and physical properties: Amorphous 

 powder; m.p. 94-97°C. Soluble in chloroform, ace- 

 tone, lower alcohols, benzene, dioxane, pyridine, 

 glacial acetic acid, and ethyl acetate. Insoluble in 

 carbon tetrachloride, ethyl ether, petroleum ether. 



water, dilute HCl, NajCOs solution, and 0.5 A'' 

 NaOH. Black color with concentrated H2SO4- 

 Positive test for aromatic nucleus (AICI3 and 

 CHCl.-i). Negative ninhydrin, Sakaguchi, maltol, 

 creatinine, FeCIs , Elson-Morgan, Molisch, biuret, 

 and Br 2 in CCI4 tests. C = 65.69%; H = 7.45%; 

 N = 1.85% (Kjeldahl). Rf = 0.94 on paper chro- 

 matography using water-saturated butanol con- 

 taining 2 per cent toluenesulfonic acid. Ultraviolet 

 absorption spectrum has maxima at 275 and 316 

 m/j. Infrared data given in reference 1. [ajo^ = 

 -82° (c = 1 per cent in CHCI3) and -183° (c = 1 

 per cent in methanol ) . 



Biological activity: Active on gram-positive 

 bacteria, including mycobacteria. Not active in 

 vivo. 



Toxicity: Mice tolerate 250 mg per kg intra- 

 peritoneally. 



Reference: 1. Zief, M. et al. Antibiotics & 

 Chemotherapy 7: 384-386, 1957. 



Puroniycin 



Produced by: Streptomyces alboniger (10). 



Synonyms: Achromycin (this now is a trade 

 name for tetracycline); stylomycin. 



Chemical and physical properties: Diacidic base. 

 White crystals; m.p. 175.5-177°C. Sparingly solu- 

 t)le in water and organic solvents (33). [a]o = —11° 

 (ethanol). Ultraviolet absorption spectrvmi maxi- 

 mum at 275 m/x IE\"L 203) (0.1 X NaOH) or 267.5 

 niM iSTcm 195) (0.1 N HCl). Stable pKa = 6.8 and 

 7.2. Dikydrochloride: m.p. 174°C (decomposition). 

 Sulfate: White crystals; m.p. 180-187°C (decom- 

 position). Picrate: m.p. 217.5-218°C. On acid 

 hydrolysis, the idtraviolet absorption maxima are 

 shifted 5 to 10 m^i to the longer wave length and 

 biological activity is destroyed (1, 3, 32). Infrared 

 spectrum given in reference 1. The biologically 

 inactive alcoholysis products include: the am- 

 photeric, water-soluble, acidic 6-dimethyladenine 

 (CTHgN.^), m.p. 257-258°C; the ester of p-methoxy- 

 L-phenylalanine; and 3-amino-D-ribose (9, 24). 

 C = 56.55%; H = 0.35%; N = 20.88%. C22H29N7O, 

 (1, 3, 12, 24). Puromycin is 6-dimethylamino-9- 

 (3'-p-methoxy - L - phenylalanylamino -3' - desoxy - 

 (3,l)-ribofuranosyl)purine (4, 12, 26). Structural 

 formula given in Chapter 6. 



Biological activity: Active on gram-positive 

 bacteria; less active on gram -negative bacteria 

 (1). Active on protozoa (2, 18). Active on Chlorella 

 pyrenoidosa at lO"^ ,1/ (31). Some protective or 

 curative effect on T r ypanosoma infections of mice 

 and rablnts (2, 8, 20). Prolongs survival time of 

 mice infected with Toxoplasma gondii (6) . Protects 

 against Endamoeba histolytica infections in rats 



