The structure of salinomycin, a new member of the polyether antibiotics

Kinashi, Haruyasu; Ōtake, Noboru; Yonehara, Hiroshi; Sato, Shôichi; Saito, Yoshihiko

doi:10.1016/s0040-4039(01)87382-2

Cited by 127 publications

(36 citation statements)

References 8 publications

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“…1). It is a lipophilic, anionic and weakly acidic compound with the molecular formula c 42 H 70 o 11 (1,2). Salinomycin acts in different biological membranes, including cytoplasmic and mitochondrial membranes, as a ionophore with strict selectivity for alkali ions and a strong preference for potassium, thereby promoting mitochondrial and cellular potassium efflux and inhibiting mitochondrial oxidative phosphorylation (3)(4)(5).…”

Section: Introductionmentioning

confidence: 99%

Salinomycin in cancer: A new mission for an old agent

Naujokat

Fuchs²,

Opelz³

2010

Mol Med Rep

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Abstract. Salinomycin is a monocarboxylic polyether ionophore isolated from Streptomyces albus that has been used for more than 30 years as an agricultural antibiotic to prevent coccidiosis in poultry and to improve nutrient absorption and feed efficiency in ruminants and swine. As a inonophore with strict selectivety for alkali ions and a strong preference for potassium, salinomycin interferes with transmembrane potassium potential and promotes the efflux of K

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Section: Introductionmentioning

confidence: 99%

Salinomycin in cancer: A new mission for an old agent

Naujokat

Fuchs²,

Opelz³

2010

Mol Med Rep

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“…Salinomycin is a monocarboxylic polyether antibiotic with antimicrobial and anticoccidial properties (14,22). Salinomycin shows great preferential complexation with monovalent over divalent cations in a two-phase system and mediates their transport across a CC14 bulk phase (23).…”

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confidence: 99%

Salinomycin Effects on Mitochondrial Ion Translocation and Respiration

Mitani

Yamanishi

Miyazaki

et al. 1976

Antimicrob Agents Chemother

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The effects of salinomycin on alkali cation transport and membrane functions in rat liver mitochondria have been investigated. After potassium uptake, stimulated by valinomycin or monazomycin in the presence of adenosine 5'-triphosphate, salinomycin caused rapid release of K+ from mitochondria. Salinomycin reversed valinomycin-or monazomycin-induced oscillatory swelling of mitochondria preloaded with K+, Rb+, and Na+ but was without effect on Li+ or Cs+ preloaded mitochondria. Salinomycin blocked the retention of K+ more effectively than the retention of Rb+ or Na+. Salinomycin inhibited both coupled and uncoupled respiration with strict substrate specificity in medium of low but not in high K+ concentration. The oxidation of glutamate, a-ketoglutarate, and malate plus pyruvate was inhibited by salinomycin, but that of 3-hydroxybutyrate or succinate was not significantly affected. Salinomycin inhibited adenosine triphosphatase activity of mitochondria induced by valinomycin or monazomycin in K+ and Rb+ medium without significantly affecting adenosine triphosphatase activity in Li+, Na+, or Cs+ medium. Oxidative phosphorylation in mitochondria was inhibited by sklinomycin but the inhibitory effect of salinomycin lacked the substrate specificity observed for respiration. It is proposed that salinomycin perturbs mitochondrial functions by acting as a mobile carrier for alkali cations through membranes.

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“…Our first example of this approach [4] was the assembly of the unsaturated 6,6,5-bis-spiroacetal ring system present in the polyether antibiotics salinomycin (1, [5]), narasin A (2, [6]), epi-deoxysalinomycin (3, [7]) and antibiotic CP44,161 (4, [8] The four possible stereoisomers of the 1,6,8-trioxadispiro[4.1.5.3]pentadec-13-ene ring system present in the salinomycin family of polyether antibiotics are depicted in Figure 1. Diastereomer A represents the stereochemistry adopted by salinomycin (1) and CP44,161 (4) and has three stabilizing anomeric effects but exhibits unfavourable 1,3-dipole-dipole interactions.…”

Section: Resultsmentioning

confidence: 99%

Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview

Brimble

2004

Molecules

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Abstract:The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal containing natural products such as the polyether antibiotics salinomycin and CP44,161 and the shellfish toxins, the spirolides.

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The structure of salinomycin, a new member of the polyether antibiotics

Cited by 127 publications

References 8 publications

Salinomycin in cancer: A new mission for an old agent

Salinomycin in cancer: A new mission for an old agent

Salinomycin Effects on Mitochondrial Ion Translocation and Respiration

Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview

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