Of streptomycin

Dihydrostreptomycin, in which the CHO group in the middle ring is replaced by CH2OH, is made by the catalytic reduction of streptomycin, and has similar antibacterial properties. 

Before the discovery of streptomycin, pyrazinamide (126) was one of the front runners in the treatment of tuberculosis. A broad spectrum of biological activity has been associated with pyrazine derivatives, ranging from the herbicidal activity of (127) to antibiotic activity... 

Fig. 28. Effect of degree of swelling on diffusion coefficient of streptomycin in carboxylic cation exchangers /) KB-4, 2) KFA, J) KB-2, 4) KMDM-6...

The initial phase must contain three or more of the following drugp isoniazid, rifampin, and pyrazin-amide, along with either ethambutol or streptomycin. The CDC recommends treatment to begin as soon as possible after the diagnosis of tuberculosis. The treatment recommendation regimen is for the administration of rifampin, isoniazid, and pyrazinamide for a minimum of 2 months (8 weeks), followed by rifampin and isoniazid for 4 months (16 weeks) in areas with a low incidence of tuberculosis. In areas of high incidence of tuberculosis, the CDC recommends the addition of streptomycin or ethambutol for the first 2 months. 

Effect of Streptomycin on Various Enzymes Responsible for Syntheses and Degradation of Higher Saccharides, S. A. Barker, E. J. Bourne, M. Stacey, and R. B. Ward, Nature, 175 (1955) 203 -204. 

Details of the manufacture of streptomycin and griseoflilvin are to be found in previous editions of this book. 

There has been isolated an analog of streptomycin which contains one more hydroxyl group67 68 and is called hydroxystreptomycin. The biological properties of this compound are closely similar to, or identical with, those of streptomycin.69... 

The mechanism involved in the formation of maltol (XXXIX) from the streptose residue of streptomycin, a mechanism which also applies to 5-hydroxystreptose, has been outlined by Lemieux and Wolfrom.1 An alternative theory has been suggested63 this is based on the supposed formation of an intermediate acyloin compound, as shown by the following formulas. However, this theory is unacceptable since one of the require-... 

Fig. 3.7 Transgenic rapeseeds were sprouted in an airlift tank with (lane 1) and without (lane 2) of streptomycin at 100 mg L-1. Total proteins were extracted, separated by SDS-PAGE and stained with Coomassie blue. The synthesis of Rubisco large and small subunits was inhibited as clearly shown in lane 2.

The answer is a. (Hardman, pp 1105-1108.) The activity of streptomycin is bactericidal for the tubercle bacillus organism. Other aminoglycosides (e.g., gentamicin, tobramycin, neomycin, amikacin, and kanamycin) have activity against this organism but are seldom used clinically because of toxicity or development of resistance. 

The answer is d. (Hardman, pp 1105-1108.) The bactericidal activity of streptomycin and other aminoglycosides involves a direct action on the 305 ribosomal subunit, the site at which these agents both inhibit protein... 

Impairment of eighth cranial nerve function is the most important adverse effect of streptomycin. Vestibular function is most frequently affected, but hearing may also be impaired. Audiometric testing should be performed in patients who must receive streptomycin for more than 2 months. Streptomycin occasionally causes nephrotoxicity. 

The addition of streptomycin is indicated if acute pneumonia and sputum studies suggests plague. 

Reductive desulfurization with Raney nickel of the mercaptolysis products of streptomycin has supplied one of the keys to the elucidation of the structure and configuration of that antibiotic. Since the chemistry of streptomycin has recently been reviewed37 the reactions discussed here will be considered solely as examples of hydrogenolysis and their bearing upon the problem of the structure and configuration of streptomycin will be ignored. 

Kuehl, Flynn, Brink and Folkers38 in 1946 showed that mercaptolysis of streptomycin leads to the formation of an ethyl thiostreptobios-aminide diethyl thioacetal hydrochloride (XXX). The same substance... 

Karl MyrbAck, Products of the Enzymic Degradation of Starch and Glycogen 252 M. Stacey and P. W. Kent, The Polysaccharides of Mycobacterium tuberculosis 311 R. U. Lemieux and M. L. Wolfrom, The Chemistry of Streptomycin. 337... 

McCormick, B. A., Stocker, B. A., Laux, D. C., and Cohen, P. S. (1988). Roles of motility, chemotaxis, and penetration through and growth in intestinal mucus in the ability of an avirulent strain of Salmonella typhimurium to colonize the large intestine of streptomycin-treated mice. Infect. Immun. 56, 2209-2217. 

Li, Y. M., Debremaeker, D., Van Schepdael, A., Roets, E., and Hoogmartens, J. (2000). Simultaneous analysis of streptomycin, dihydrostreptomycin and their related substances by capillary zone electrophoresis. J. Liq. Chromatogr. Relat. Technol. 23, 2979—2990. 

The other component parts of streptomycin, namely L-streptose and the aminosugar 2-deoxy-2-methylamino-L-glucose (A -methyl-L-glucosamine), are also ultimately derived from o-glucose. Gentamicin Ci contains two aminosugars, L-garosamine and D-purpurosamine. 

Numerous cases of the use of antibiotics(especially cycloheximide, ohyamycin, streptomycin, tetracyclines, penicillin, griseofulvin, and polymyxin) against several bacterial and fungal diseases are now known(33-35). In the United States of America, Merck sells preparations of streptomycin and Upjohn sells that of cycloheximide for the control of the diseases of ornamental plants(R.Burg,... 

Tomato canker caused by Xanthomonas can be controlled by the application of tetracycline(52-53). Streptomycin resistant strains of bacteria have Been found on peach, tomato and peppers(54), and the mixture of two antibiotics has helped to stop tHe build-up of resistance in the patho -gens in some cases(55-56). The silvery disease of sugar-beet caused by Coryn 5actferium is insufficiently controlled by mercurial compounds, but is completely eliminated when seeds are dipped for several hours in a solution of streptomycin. 

Figure 1.1. The founders of the antibiotic era Sehnan Waksman (discoverer of streptomycin) and Alexander Fleming (discoverer of penicillin).

Selman Waksman s commitment to the isolation and screening of soil bacteria in the search for bioactive small molecules, especially potential antibiotics, was validated by the discovery of streptomycin. This led to the creation of the modem biopharmaceutical industry and the subsequent isolation of tens of thousands of bioactive small molecules from soil bacteria and other environments. A proportion of these compounds have become highly successfnl therapeutics, not only for all types of infectious diseases, but also in the treatment of many other human and animal ailments and as anticancer, immnno-modnlatory, and cardiovascular agents. Waksman and Fleming could be considered the fathers of chemical biology (Figure 1.1). 

Following on the discovery of streptomycin and its streptamine-based relatives (Figure 1.2), a new generation of the aminoglycosides derived from 2-deoxy-streptamine (DOS) was not long in coming (Figure 1.3). For a variety of reasons, many of these compounds have not been employed as hnman therapeutics for... 

The biochemical mode of action of the aminoglycosides as antibacterials has long been a topic of great interest. Early experiments carried out soon after the introduction of streptomycin suggested a variety of modes of action, but these conclusions were based largely on symptomatic analyses of antibiotic-treated bacterial cultures. One important experiment done in 1948 showed that streptomycin blocks enzyme indnction in susceptible bacteria this was the closest that anyone came to identifying the mechanism of action at the time. 

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