Polyenes antibiotic

Amphotericin B. Amphotericin B (3), an important polyene antibiotic, is administered almost exclusively via the intravenous route and is therefore discussed in more detail under the systemic antimycotics. The vaginal tablets contain 50 mg amphotericin B, and 100 mg tetracycline base per tablet (see also Antibiotics, tetracyclines). The tablets for oral use contain 50 mg amphotericin B, 250 mg tetracycline base, and 125 mg sodium hexametaphosphate. A combination ointment contains 1 mg fludrocortisone acetate, 2.5 mg neomycin, 0.25 mg gramicidin, and 1 g plastibase in addition to 30 mg amphotericin B (see also Antibiotics, peptides). 

Amphotericin B, is a polyene antibiotic, used in the therapy of systemic fungal infections. Its mode of action exploits differences in membrane composition between the pathogen and the human host. Ergosterol, the predominant sterol of fungi, plants, and some protozoan parasites, interacts with Amphotericin B, resulting in an increased ion permeability of the membrane. Humans contain cholesterol, which has a low affinity for amphotericin B. 

AOIABI6 DOIAAO6 G01AA09 polyene antibiotic (for treatment of candidal and trichomonal gynaecological infections, treatment of benign prostatic hypertrophy)... 

Cass A., Finklestein A. Krespi V. (1970) The ion permeability induced in thin lipid membranes by the polyene antibiotics nystatin and amphotericin B. J Gen Physiol, 56, 100-124. 

Norman A.W, Demel R.A., DeKmyff B., Geiuts Van Kessel W.S.M. Van Deenen L.L.M. (1972) Studies on the biological properties of polyene antibiotics comparison of the other polyenes widi filipin in their ability to interact specifically with sterol. Biochim BiophysActa, 290, 1-14. 

Some substances form pores in the membrane that do not exhibit ion selectivity and permit flow of the solution through the membrane. These include the polyene antibiotics amphotericin B,... 

Many of these materials form voltage-gated transmembrane ion channels, i.e. they exhibit non-linear current voltage curves, unlike the polyene antibiotics and gramicidin A which have linear current voltage curves. Of the peptaibol antibiotics the most thoroughly investigated substance to date is alamethicin 201 203>. 

The mixing of nematogenic compounds with chiral solutes has been shown to lead to cholesteric phases without any chemical interactions.147 Milhaud and Michels describe the interactions of multilamellar vesicles formed from dilauryl-phosphotidylcholine (DLPC) with chiral polyene antibiotics amphotericin B (amB) and nystatin (Ny).148 Even at low concentrations of antibiotic (molar ratio of DLPC to antibiotic >130) twisted ribbons are seen to form just as the CD signals start to strengthen. The results support the concept that chiral solutes can induce chiral order in these lyotropic liquid crystalline systems and are consistent with the observations for thermotropic liquid crystal systems. Clearly the lipid membrane can be chirally influenced by the addition of appropriate solutes. 

Rochet and Lancelin50 reported revised 1H and 13C NMR assignments of the polyene antibiotic Filipin m (83). This macrolide which was isolated from Streptomyces filipinensis was reinvestigated in DMSO-dg solution using homonuclear and heteronuclear correlation spectroscopy. In addition to several corrections to previous 1H NMR... 

Bolard J, Seigneuret M, Boudet G. Interaction between phospholipid bilayer membranes and the polyene antibiotic amphotericin B lipid state and cholesterol content dependence. Biochim Biophys Acta 1980 599 280. 

The polyene antibiotic nystatin (5 25pg/mL, 10 minutes) and the cardiac glycoside digitoxin (5 pg/mL, 10 minutes) bind cholesterol and can remove it from cell membranes, which leads to inhibition of caveolae uptake (60). Regarding its effect on clathrin uptake, no comment can be given at this time. 

Patrician A (160) Polyene antibiotic SPK-843 (161) Antifungal (systemic mycosis) Destabilizes fungal cell membrane Phase n Kaken Pharmaceuticals 828-834... 

Mozzi G Benelli P, Bruzzese T, Gahnozzi MR, Bonabello A. (2002) The use of lipid emulsions for the iv administration of a new water soluble polyene antibiotic, SPK-843. J Antimicrob Chemother 49 321-325. 

The polyene antibiotics, amphotericin B and nystatin, are of bacterial origin. They insert themselves into fun-LiJIlmann, Color Atlas of Pharmacology 2000 Thieme All rights reserved. Usage subject to terms and conditions of license. 

Natamycin Natamycin, a mixture of stereoisomeric 22-[(3-amino-3,6-dideoxy-p-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl- lO-oxo-6,11,28-trioxatricy-clo[22.3.1.0. ]-octacosa-8,14,16,18,20,penten-25-carboxylic acid (35.1.3), like amphotericin and nystatin, is a polyene antibiotic that is isolated from the products of the vital activity of the actinomycete Streptomyces natalensis [15-17]. 

Pharmacology Natamycin, a tetraene polyene antibiotic, is derived from Streptomyces natalensis. 

Some microorganisms produce compounds that can become incorporated into lipid membranes and will facilitate the transmembrane transport of ions, notably K+. These natural products are antibacterial, killing bacteria by lethally altering the transmembrane ion flux. Such antibacterial molecules are called ionophores, or ion carriers, in contrast to other antibacterials, such as polyene antibiotics, which simply produce leakage through the cell membrane. 

Enantioselective Synthesis of the Polyene Antibiotic Aglycone Rimocidinolide Methyl Ester... 

Amphotericin B, a polyene antibiotic, is the most suitable remedy, despite the nephrotoxicity that may occur, for treating systemic mycoses such as coccidio-mycoses, histoplasmosis, and blastomycosis in animals. It is not effective against dermatophytes and has no activity against bacteria. It is only available in form of a colloidal dispersion for intravenous injection since its poor absorption from the gastrointestinal tract obviates oral administration. 

Natamycin is another polyene antibiotic effective against dermatophytes. The name originally proposed for the compound was pimaricin, which has been used in some of the earlier literature studies and reports. It has been used as topical therapeutic in animals and humans for over 30 years, and it is also used as an antifungal agent in food processing. 

Antifungal polyene antibiotic obtained from a strain of Streptomyces nodosus... 

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