Streptomyces nodosus Amphotericin

Streptomyces mycarofaciens Midecamycin Streptomyces nodosus Amphotericin B Streptomyces noursei Nystatin... 

Amphotericin A and are antifungal antibiotics produced by Streptomyces nodosus. Amphotericin A is not in clinical use. 

Amphotericin B is the most important clinically and best defined chemically of the macrolide heptaene antibiotics. A fermentation product of the soil actinomycetes Streptomyces nodosus, amphotericin B binds selectively to ergosterol in the cell membrane of susceptible fungi, inducing changes in permeability that can produce lethal cell injury [50]. 

Amphotericin B Streptomyces nodosus Fungi Cell membrane... 

Amphotericin B (Fungizone), a polyene antifungal drug produced by the actinomycete Streptomyces nodosus, consists of a large ring structure with both hydrophilic... 

Streptomyces nodosus produces natural products such as amphotericin A and B. These are macrocyclic (large-ring) compounds containing numerous (three to seven) double bonds and multiple hydroxyl groups which are usually located on one side of the molecule. Amphotericin B (9.103) and the very similar nystatin (9.104) are antifungal... 

Amphotericin B is obtained from Streptomyces nodosus. It is fungistatic and administered intravenously as an infusion in the treatment of severe systemic fungal infections. It also is used for the local treatment of superficial candidiasis. Test-dose administration is advised to confirm adverse reactions. The amphotericin infusion should be slow to prevent the risk of irritation and infusion-related adverse effects. The drug is used in pregnancy without any adverse side effects.66... 

Amphotericin B [am foe TER i sin] is a naturally occurring polyene macrolide antibiotic, produced by Streptomyces nodosus. In spite of its toxic potential, amphotericin B is the drug of choice used in the treatment of the systemic mycoses. It is sometimes used in combination with flucytosine so that lower (less toxic) levels of amphotericin are possible. 

Perhaps the best known clinical agent is the heptaene polyene, amphotericin B 50, isolated from Streptomyces nodosus and first reported in 1956. The full structure was not elucidated until 1970 when it was determined by X-ray crystallography,56 closely followed by a description of the absolute configuration determined by utilising the iodo-derivative for X-ray and by mass spectroscopy.57 Quite recently, 50 years after its initial discovery, a full review giving the highlights of the chemistry around the compound was published by Cereghetti and Carreira.58... 

Amphotericin B is produced by a strain of bacteria, Streptomyces nodosus. Please refer to the general pharmacology section for antifungal drugs. 

Amphotericin B, USP. The isolation of amphotericin B (Fungizone) was reported in 1956 by Cold et al. The compound was purified from the fermentation beer of a soil culture of the actinomycete Streptomyces nodosus, which was isolated in Venezuela. The first isolate from the strepto-mycete was a separable mixture of two compounds, designated amphotericins A and B. In test cultures, compound B proved to be more active, and this is the one used clinically.- The structure and absolute stereochemi.siiy are as shown. 

The principal polyenes are amphotericin B and nystatin. Amphotericin B is produced by the bacterium Streptomyces nodosus and its activity is due to the ability to bind ergosterol, which is the dominant sterol in fungal cell membranes, and consequently increases membrane permeability by the formation of pores (Fig. 4.4). The action of ampho-... 

Amphotericin B (15) is an antifungal macrolide antibiotic produced by Streptomyces nodosus that has been used as an alternative, albeit more toxic, drug to the antimonials- It acts as a leishmanicide against the visceral and mucocutaneous forms of the disease. To overcome its potentially severe nephrotoxicity, the drug must be administered over an extended period of time. 

Caffrey, R, Lynch, S., Flood, E., Finnan, S., and Oliynyk, M. (2001). Amphotericin biosynthesis in Streptomyces nodosus Deductions from analysis of polyketide synthase and late genes. Chem. Biol. 8, 713-723. 

A convergent total synthesis of amphotericin B (517), with a jS-linked mycosamine at the C-19 hydroxyl position, a clinically useful antifungal agent isolated from Streptomyces nodosus, and its aglycon, amphoteronolide B (518), relies upon the stereocontrolled construction of enantiomerically pure (homochiral) structural units. Retrosynthetic analysis of 517 uncovers certain stereochemical features that allow construction of two of the essential chiral building blocks from 514, the chiral antipode of 503 and readily available from lb, by utilizing similar reaction conditions to those available for the synthesis of 503. Thus, chiral... 

For a long time, amphotericin B, la [17] (Fig. 1), a vastly used antifungal agent produced by Streptomyces nodosus was the only stereodefined substance known... 

Amphotericin B was first isolated from the soil bacterium Streptomyces nodosus obtained from the bed of the Orinoco river in 1955 [140, 141], Its full stereostructure 147 was elucidated in 1970 when an X-ray structure of the A-iodoacetyl derivative was obtained [142],... 

Amphotericin B Antifungal CYP161A3 (AmphL)and CYP105H4 (AmphN) Streptomyces nodosus Likely polyketide oxidative tailoring reactions [161, 788]... 

Linkc HAB, Mcchltnski W, Scbaffrier CP. Production of amphotericin B- C by Streptomyces nodosus. Fermentation and pieparation of amphotericin B- KZ-methyl-esteE. J Antibiot 1974 27 155-160. 

Polyenes. These antifimgal macrolides differ from antibacterial macrolides in the size of the lactone ring, ranging from 26 to 38 atoms, and with the presence of a series of conjugated double bonds. The only member systemically used is amphotericin B, produced by Streptomyces nodosus. Antifungal activity is due to interference with membrane sterols, resulting in permeability alteration (O Fig. 9.5). 

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