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Monactin Sale

(Synonyms: 单活菌素) 目录号 : GC40613

A non-selective monovalent cation ionophore

Monactin Chemical Structure

Cas No.:7182-54-9

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产品描述

Monactin is a mactrotetralide antibiotic originally isolated from Streptomyces and a non-selective ionophore for monovalent cations, including potassium, sodium, and lithium. It has low antimicrobial activity but is more active than its homolog nonactin . Monactin induces swelling of rat liver mitochondria in medium containing either potassium or sodium, stimulates respiration, and uncouples oxidative phosphorylation. It also inhibits Wnt signaling via inhibition of TCF-β-catenin transcriptional activity.

Chemical Properties

Cas No. 7182-54-9 SDF
别名 单活菌素
Canonical SMILES O=C(O[C@H](C)C[C@]1([H])O[C@@]([C@@H]2C)([H])CC1)[C@H](C)[C@@]3([H])CC[C@](C[C@H](C)OC([C@H]([C@@]4([H])O[C@](C[C@H](OC([C@H](C)[C@]5([H])O[C@](CC5)([H])C[C@H](C)OC2=O)=O)CC)([H])CC4)C)=O)([H])O3
分子式 C41H66O12 分子量 751
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1 mM 1.3316 mL 6.6578 mL 13.3156 mL
5 mM 0.2663 mL 1.3316 mL 2.6631 mL
10 mM 0.1332 mL 0.6658 mL 1.3316 mL
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Research Update

Effects of nigericin and Monactin on cation permeability of Streptococcus faecalis and metabolic capacities of potassium-depleted cells

J Bacteriol 1968 Mar;95(3):816-23.PMID:4966827DOI:10.1128/jb.95.3.816-823.1968.

At a concentration of 10(-6)m, nigericin and Monactin inhibited growth of Streptococcus faecalis, and the inhibition was reversed by addition of excess K(+). In the presence of certain antibiotics, the cells exhibited increased permeability to certain cations; internal Rb(+) was rapidly lost by exchange with external H(+), K(+) Rb(+), and, more slowly, with Na(+) and Li(+). No effect was observed on the penetration of other small molecules. Cation exchanges induced by nigericin and Monactin were metabolically passive and apparently did not involve the energy-dependent K(+) pump. When the cells were washed, the cytoplasmic membrane recovered its original impermeability to cations. By use of Monactin, we prepared cells whose K(+) content had been completely replaced by other cations, and the metabolic characteristics of K(+)-depleted cells were studied. Cells containing only Na(+) glycolyzed almost as well as did normal ones and, under proper conditions, could accumulate amino acids and orthophosphate. These cells also incorporated (14)C-uracil into ribonucleic acid but incorporation of (14)C-leucine into protein was strictly dependent upon the addition of K(+). When K(+) or Rb(+) was added to sodium-loaded cells undergoing glycolysis, these ions were accumulated by stoichiometric exchange for Na(+). From concurrent measurements of the rate of glycolysis, it was calculated that one mole-pair of cations was exchanged for each mole of adenosine triphosphate produced.

The transport of potassium through lipid bilayer membranes by the neutral carriers valinomycin and Monactin : Experimental studies to a previously proposed model

J Membr Biol 1971 Jun;5(2):133-53.PMID:24173097DOI:10.1007/BF02107720.

Stationary conductance experiments on neutral and negatively charged bilayer membranes in the presence of valinomycin or Monactin agree with a recently proposed carrier transport model, which is common to both carrier types. This model assumes an interface reaction between a cation from the aqueous solution and a carrier molecule from the membrane phase to establish charge transport across the interface. The transport across the membrane interior is described by some kind of "Eyring model". The discussion of the current-voltage characteristic, the dependence of membrane conductance on the carrier and K(+) concentrations, and the comparison with appropriate experiments allow correlation of the different rate constants of the transport model. The results show that the rate constants partly depend on the surface charge of the membranes. This dependency can be described by introducing the Gouy-Chapman theory for charged surfaces into the transport model.It was found that the carrier molecules could be added either to the aqueous phase or to the membrane-forming solution. The quantitative treatment of this phenomenon gives an evaluation of the partition coefficient of the carrier molecules between the membrane bulk phase and water.

NH4+ ion-selective microelectrode based on the antibiotics nonactin/Monactin

Pflugers Arch 1988 Sep;412(4):359-62.PMID:3174392DOI:10.1007/BF01907552.

A liquid-membrane microelectrode (less than or equal to 1 micron tip diameter) using macrotetrolide antibiotics as ion-selective components is described. The electrode shows selectivities of NH4+ over K+, Na+ and H+ of 3.8, 100 and 150, respectively. The stability and reproducibility of the sensor signal and the response time are determined in solutions with a typical intracellular ion background. The microelectrode does not suffer from significant interference by inorganic and organic inhibitors and lipophilic cations, but high concentrations of lipophilic anions may interfere considerably.

Antiproliferative and antiplasmodial compounds from selected Streptomyces species

Bioorg Med Chem Lett 2015 Dec 1;25(23):5646-9.PMID:26508548DOI:10.1016/j.bmcl.2015.07.103.

In continuation of our ongoing search for bioactive compounds from microbial extracts, we performed antiproliferative and/or antimalarial assays on extracts of 806 microbial species isolated from Madagascan marine organisms, on 1317 species isolated from Madagascan soil samples and on a Streptomyces species (S.4) from a marine sponge collected from the Florida Keys. This work identified active extracts from four Streptomyces isolates (S.1, S.2, S.3 and S.4). The extracts of Streptomyces S.1 and S.2 showed antiproliferative activity against the A2780 ovarian cancer cell line, while those of S.3 and S.4 displayed both antiproliferative and antimalarial activity. Bioassay-guided fractionation coupled with dereplication of the active extracts led to the identification and isolation of nonactin (1), Monactin (2), dinactin (3), ±-nonactic acid (4), toyocamycin (5), piperafizine A (6) and a new dipeptide named xestostreptin (7). The structures of all isolated compounds 1-7 were elucidated by analyses of their NMR spectroscopic and mass spectrometric data, and were confirmed by comparison with the data reported in the literature. Compound 6 was crystallized and subjected to X-ray diffraction analysis to confirm its structure as piperafizine A (6). Compounds 1-3 displayed strong antiproliferative activity against A2780 ovarian cancer cells (IC50 values of 0.1, 0.13 and 0.2 μM, respectively), A2058 melanoma cells (IC50 values of 0.2, 0.02 and 0.02 μM, respectively), and H522-T1 non small-cell cancer lung cells (IC50 values of 0.1, 0.01 and 0.01 μM, respectively), while compounds 4 and 7 exhibited weak antiplasmodial activity against the Dd2 strain of Plasmodium falciparum, with IC50 values of 6.5 and 50 μM, respectively.

Macrotetrolide antibiotics produced by Streptomyces globisporus

Folia Microbiol (Praha) 1991;36(5):437-43.PMID:1821868DOI:10.1007/BF02884062.

Macrotetrolides isolated from a new producer, Streptomyces globisporus, were identified as nonactin, Monactin, dinactin and trinactin. Spectroscopic characterization of these compounds was extended by 13NMR spectra. Chemical ionization with ammonia as reactive gas was proposed for mass-spectroscopic characterization of their mixtures. Their biological activity was confirmed by using larvae of the Colorado potato beetle (Leptinotarsa decemlineata) as a new test model.